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Stock Purchase Agreement - Akamai Technologies Inc. and Straight Arrow Publishers Co. LP

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                           AKAMAI TECHNOLOGIES, INC.



                      Series B Convertible Preferred Stock
                                       and
                      Series C Convertible Preferred Stock
                               PURCHASE AGREEMENT





                           Dated as of April 16, 1999
<PAGE>   2
                                TABLE OF CONTENTS


<TABLE>
<CAPTION>
                                                                                  Page
<S>                                                                               <C>
PURCHASE AGREEMENT .............................................................    1
ARTICLE I - PURCHASE, SALE AND TERMS OF SHARES .................................    1
1.01 The Preferred Shares ......................................................    1
1.02 The Converted Shares ......................................................    1
1.03 The Shares ................................................................    1
1.04 Purchase Price and Closing ................................................    2
1.05 Use of Proceeds ...........................................................    4
1.06 Representations and Warranties by the Purchasers ..........................    5
ARTICLE II - CONDITIONS TO THE PURCHASERS' OBLIGATION ..........................    5
2.01 Representations and Warranties ............................................    5
2.02 Documentation at Closing ..................................................    6
2.03 Additional Closing Conditions .............................................    6
2.04 Consents, Waivers, Etc ....................................................    7
2.05 Bring-Down Certificate ....................................................    7
ARTICLE III - REPRESENTATIONS AND WARRANTIES OF THE COMPANY ....................    7
3.01 Organization and Standing .................................................    8
3.02 Corporate Action ..........................................................    8
3.03 Governmental Approvals ....................................................    8
3.04 Litigation ................................................................    9
3.05 Certain Agreements of Officers and Key Employees ..........................    9
3.06 Compliance with Other Instruments .........................................    9
3.07 Material Contracts ........................................................   10
3.08 ERISA .....................................................................   10
3.09 Transactions with Affiliates ..............................................   10
3.10 Assumptions or Guaranties of Indebtedness of Other Persons ................   11
3.11 Investments in Other Persons; Subsidiaries ................................   11
3.12 Securities Laws ...........................................................   11
3.13 Disclosure ................................................................   11
3.14 Brokers or Finders ........................................................   11
3.15 Capitalization; Status of Capital Stock ...................................   12
3.16 Registration Rights .......................................................   12
3.17 Books and Records .........................................................   12
3.18 Title to Assets; Patents ..................................................   12
3.19 The Year 2000 .............................................................   13
3.20 Financial Statements ......................................................   13
3.21 No Undisclosed Liabilities ................................................   14
3.22 Technology ................................................................   14
ARTICLE IV - COVENANTS OF THE COMPANY ..........................................   14
4.01 Affirmative Covenants of the Company Other Than Reporting Requirements ....   14
4.02 Negative Covenants of the Company .........................................   17
4.03 Reporting Requirements ....................................................   19
</TABLE>
<PAGE>   3
<TABLE>
<S>                                                                                <C>
ARTICLE V - DEFINITIONS AND ACCOUNTING TERMS ...................................   21
5.01 Certain Defined Terms .....................................................   21
5.02 Accounting Terms ..........................................................   24
5.03 Knowledge .................................................................   24
ARTICLE VI - MISCELLANEOUS .....................................................   24
6.01 No Waiver; Cumulative Remedies ............................................   24
6.02 Amendments, Waivers and Consents ..........................................   25
6.03 Addresses for Notices .....................................................   25
6.04 Costs, Expenses and Taxes .................................................   26
6.05 Binding Effect; Assignment ................................................   26
6.06 Survival of Representations and Warranties ................................   26
6.07 Prior Agreements ..........................................................   26
6.08 Severability ..............................................................   26
6.09 Governing Law .............................................................   26
6.10 Headings ..................................................................   26
6.11 Counterparts ..............................................................   27
6.12 Further Assurances ........................................................   27
6.13 Indemnification ...........................................................   27
</TABLE>


                                       ii
<PAGE>   4
<TABLE>
<CAPTION>
EXHIBITS
--------
<S>           <C>
1.01          List of Purchasers of Preferred Stock
1.01A         Designation of Series B Convertible Preferred Stock
1.01B         Designation of Series C Convertible Preferred Stock
1.04(d)(i)    List of Purchasers of Debt Securities
1.04(d)(ii)   Terms of Debt Securities
1.04(e)       Second Closing
2.02B         Opinion of Counsel
2.03B         Amended and Restated Stockholders Agreement
2.03E         Amended and Restated Registration Rights Agreement
2.03GA        Form of Noncompetition and Nonsolicitation Agreement
2.03GB        Form of Invention and Nondisclosure Agreement
2.03HA        Form of Stock Restriction Agreement
2.03HB        Form of Right of First Refusal Agreement
3.01          Foreign Qualifications
3.04          Litigation
3.07          Material Contracts
3.08          ERISA
3.09          Transactions with Affiliates
3.11          Investments in Other Persons; Subsidiaries
3.15          Capitalization; Status of Capital Stock
3.16          Registration Rights
3.18(a)       Title to Assets
3.18(b)       Intellectual Property
3.18(c)       Compensation for use of Intellectual Property Rights
3.20          Financial Statements
3.21          Undisclosed Liabilities
3.22          Technology
</TABLE>


                                      iii
<PAGE>   5
                            AKAMAI TECHNOLOGIES, INC.
                               One Kendall Square
                         Cambridge, Massachusetts 02139




                                                            As of April 16, 1999


TO: The Persons listed on Exhibit 1.01 hereto

Re: Series B Convertible Preferred Stock and Series C Convertible Preferred
    Stock

Ladies and Gentlemen:

     Akamai Technologies, Inc., a Delaware corporation (the "Company"), agrees
with each of you as follows:

                                    ARTICLE I

                       PURCHASE, SALE AND TERMS OF SHARES


     1.01 The Preferred Shares. The Company has authorized the issuance and sale
of up to 1,327,500 shares of its previously authorized but unissued shares of
Series B Convertible Preferred Stock, par value $.01 per share (the "Series B
Preferred Stock"), at a purchase price of $15.066 per share to the Persons
(collectively, the "Purchasers" and, individually, a "Purchaser") and in the
respective amounts set forth in Exhibit 1.01 hereto. The designation, rights,
preferences and other terms and conditions relating to the Series B Preferred
Stock are as set forth on Exhibit 1.01A hereto. The Company has authorized the
issuance and sale of up to 145,195 shares of its previously authorized but
unissued shares of Series C Convertible Preferred Stock, par value $.01 per
share (the "Series C Preferred Stock"), at a purchase price of $34.436 per share
to the Purchasers and in the respective amounts set forth in Exhibit 1.01
hereto. The designation, rights, preferences and other terms and conditions
relating to the Series C Preferred Stock are as set forth on Exhibit 1.01B
hereto. The Series B Preferred Stock and the Series C Preferred Stock are
sometimes referred to herein as the "Preferred Shares."

     1.02 The Converted Shares. The Company has authorized and has reserved and
covenants to continue to reserve, free of preemptive rights and other
preferential rights, a sufficient number of its previously authorized but
unissued shares of Common Stock to satisfy the rights of conversion of the
holders of the Preferred Shares. Any shares of Common Stock issuable upon
conversion of the Preferred Shares, and such shares when issued, are herein
referred to as the "Converted Shares."

     1.03 The Shares. The Preferred Shares and the Converted Shares are
sometimes collectively referred to herein as the "Shares."
<PAGE>   6
     1.04 Purchase Price and Closing.

          (a) The Closing. The Company agrees to issue and sell to the
Purchasers and, subject to and in reliance upon the representations, warranties,
covenants, terms and conditions of this Agreement, the Purchasers, severally but
not jointly, agree to purchase that number of the shares of Series B Preferred
Stock set forth opposite their respective names in Exhibit 1.01. The aggregate
purchase price of the shares of Series B Preferred Stock being purchased by each
Purchaser is set forth opposite such Purchaser's name in Exhibit 1.01. The
purchase and sale shall take place at a closing (the "Closing") to be held on or
before April 16, 1999, at 10:00 A.M., at such location and at such time as may
be mutually agreed upon, subject to the satisfaction of all of the conditions to
the Closing specified in Article II herein. At the Closing the Company will
issue and deliver certificates evidencing the shares of Series B Preferred Stock
to be sold at the Closing to each of the Purchasers (or its nominee) against
payment of the full purchase price therefor by (i) wire transfer of immediately
available funds to an account designated by the Company, (ii) check payable to
the order of the Company or its designee, or (iii) any combination of (i) and
(ii) above.

          (b) Option. The Baker Fund shall have the option (the "Option"),
exercisable in whole or in part in its sole discretion, to purchase from the
Company up to a maximum of 145,195 shares of Series C Preferred Stock (the
"Option Shares") at a subsequent closing (the "Subsequent Closing") at a
purchase price of $34.436 per share, under the terms and conditions of this
Agreement. The Baker Fund shall exercise the Option by giving notice (the
"Option Notice") to the Company of its intent to exercise its Option. The Option
Notice shall indicate the number of Option Shares to be purchased by the Baker
Fund at the Subsequent Closing and shall fix the date for the Subsequent
Closing, which shall be any date no earlier than the date of the Closing and no
later than the earlier of (i) December 31, 1999 and (ii) the date immediately
prior to the consummation of a Qualified Public Offering.

          (c) Subsequent Closing. The Subsequent Closing shall be held at such
location and at such time as shall be specified by the Company and the
respective Purchaser. At the Subsequent Closing, the Company will issue and
deliver certificates evidencing the shares of Series C Preferred Stock to be
sold at such Subsequent Closing against payment of the full purchase price by
(i) wire transfer of immediately available funds to an account designated by the
Company, or (ii) check payable to the order of the Company or its designee, or
(iii) any combination of (i) and (ii) above. At the Subsequent Closing, the
Purchaser purchasing shares of Series C Preferred Stock shall have received a
certificate from the President of the Company stating that the representations
and warranties of the Company contained in Article III hereof and otherwise made
by the Company in writing in connection with the transactions contemplated
hereby are true and correct (giving effect to updates, if any, to the exhibits
setting forth exceptions to the representations and warranties of the Company)
and that all conditions required to be performed prior to or at the Subsequent
Closing have been performed as of the Subsequent Closing (such certificate
referred to herein as a "Bring-Down Certificate") and shall be entitled to
receive such other certificates, opinions and other documents as shall be
reasonably requested.


                                       2
<PAGE>   7
          (d) Debt Securities.

              (i) In the event that the Board of Directors so determines, the
Company may require each of the Purchasers to purchase, severally and not
jointly, a new issue of senior subordinated notes and warrants (the "Debt
Securities") of the Company in the respective amounts set forth in Exhibit
1.4(d)(i), and having the terms substantially as set forth in Exhibit
1.4(d)(ii). The Company may exercise such right one time only on at least five
(5) business days' prior notice to the Purchasers, and the closing of the sale
and purchase of the Debt Securities (the "Debt Closing") shall occur no earlier
than the purchase and sale of all of the Series B Preferred Stock to be sold
hereunder and no later than thirty-five (35) days from the date of the Closing
hereunder; provided, however, that the date of the Debt Closing may be extended
with the consent of the Company and the affirmative vote or consent of the
Purchasers having 60% of the commitments set forth in Exhibit 1.4(d)(i). The
obligation of any Purchaser to purchase its respective portion of Debt
Securities shall be subject to the preparation, execution and delivery of
definitive documentation, including a Purchase Agreement, Forms of Senior Note
and Warrant, based on this Agreement (to the extent applicable) and reasonably
satisfactory to the parties, which documentation shall contain (i)
representations and warranties substantially the same as contained in Article
III herein (with appropriate adjustments to reflect the terms of the Debt
Securities) and (ii) conditions substantially equivalent to those contained in
Article II herein, and shall be subject to the further condition of there having
been no material adverse change in the business, operations, affairs or
condition of the Company or in its properties or assets taken as a whole, from
that as of the date hereof.

              (ii) If, for any reason other than the Company's unwillingness to
sell or other material breach of this Agreement or the Amended and Restated
Stockholders Agreement, any Purchaser does not purchase its respective portion
of Debt Securities as contemplated by Section 1.04(d)(i) (including due to a
material adverse change in the business, operations, affairs or condition of the
Company or in its properties or assets), the Company shall have the right to
repurchase, and, if the Company so elects, the Purchaser not purchasing its
respective portion of Debt Securities shall be obligated to sell to the Company,
such Purchaser's shares of Series B Preferred Stock at the price per share paid
for such shares by such Purchaser hereunder. The Company may exercise its right
to repurchase such shares by delivering written notice (the "Repurchase Notice")
to the Purchaser within sixty (60) days after such Purchaser's failure to
purchase its respective portion of Debt Securities. Such Purchaser shall be
obligated to sell such shares to the Company within ten (10) days after receipt
of the Repurchase Notice.

          (e) Second Closing.


              (i) In the event that the Company shall not have sold all
1,327,500 shares of the Series B Preferred Stock at the Closing, the Company and
the Purchasers agree that at a second closing (the "Second Closing"), the
Company may issue and sell any of the unsold shares of the Series B Preferred
Stock ("Additional Shares") to one or more of the Persons listed on Exhibit
1.04(e) (the "Additional Purchasers"). The Company and the Purchasers further
agree that (i) the Company shall amend this Agreement solely to provide for the
issuance of the Additional Shares to the Additional Purchasers at the same price
and under the terms and conditions of this Agreement and (ii) the Additional
Purchasers shall become


                                       3
<PAGE>   8
parties to this Agreement as amended by executing counterparts hereof. The terms
"Series B Preferred Stock", "Preferred Shares", "Purchaser" and "Purchasers",
when used in this Agreement, shall respectively be deemed to include such
Additional Shares as are issued and such Additional Purchaser and Additional
Purchasers as exist from time to time and the term "Closing" shall include the
Second Closing where appropriate.

              (ii) The Second Closing shall be held at such location and at such
times and dates, but on or before May 14, 1999, as shall be specified by the
Company and the Additional Purchasers. At the Second Closing, the Company will
issue and deliver certificates evidencing the Additional Shares to be sold at
the Second Closing against payment of the full purchase price by (i) wire
transfer of immediately available funds to an account designated by the Company,
(ii) check payable to the order of the Company or its designee, or (iii) any
combination of (i) and (ii) above. At the Second Closing, the Additional
Purchasers purchasing Additional Shares at the Second Closing shall have
received a certificate from the President of the Company stating that the
representations and warranties of the Company contained in Article III hereof
and otherwise made by the Company in writing in connection with the transactions
contemplated hereby are true and correct (giving effect to updates, if any, to
the exhibits setting forth exceptions to the representations and warranties of
the Company) and that all conditions required to be performed prior to or at the
Second Closing have been performed as of such Subsequent Closing.

          (f) Special Option. The Baker Fund shall have the option (the "Special
Option"), exercisable in whole or in part in its sole discretion, to purchase up
to five percent (5%) of the total number of shares of Common Stock or other
securities (the "Special Option Shares") offered in the initial public offering
of the Company (including in respect of the Special Option Shares) at a purchase
price per share equal to the price per share at which such shares are offered to
the public and on the same settlement and other terms as offered to the public.
The Baker Fund shall exercise the Special Option by giving notice to the Company
of its intent to exercise its Special Option no later than the pricing of the
initial public offering, specifying the number of Special Option Shares in
respect of which the Special Option is being exercised. All of the Special
Option Shares in respect of which the Special Option is exercised shall be fully
registered under the Securities Act. The Company agrees to cause each
underwriter of the Company's initial public offering to abide by the terms of
the Baker Fund's Special Option. The Baker Fund agrees not to offer, sell,
contract to sell, grant any option for the sale of or otherwise transfer or
dispose of any Special Option Shares for the period of the "lock-up" applicable
to other existing investors generally (not to exceed one hundred eighty (180)
days following the date of such initial public offering) without the prior
written consent of the managing underwriter of such initial public offering.

     1.05 Use of Proceeds. The Company shall use the proceeds from the sale of
the Preferred Shares under this Agreement for working capital purposes,
including Capital Expenditures, and general corporate purposes.


     1.06 Representations and Warranties by the Purchasers. Each of the
Purchasers represents and warrants, severally, but not jointly, that (a) it will
acquire the Preferred Shares and, if applicable, any Option Shares to be
acquired by it for its own account and that the


                                       4
<PAGE>   9
Preferred Shares and, if applicable, any Option Shares are being and will be
acquired by it for the purpose of investment and not with a view to distribution
or resale thereof; (b) the execution of this Agreement and the consummation of
the transactions contemplated hereby have been duly authorized by all necessary
action on the part of such Purchaser, and this Agreement has been duly executed
and delivered, and constitutes a valid, legal, binding and enforceable agreement
of such Purchaser; (c) it has taken no action which would give rise to any claim
by any other person for any brokerage commissions, finders' fees or the like
relating to this Agreement or the transactions contemplated hereby; (d) such
Purchaser has had the opportunity to ask questions of and receive answers from
representatives of the Company concerning the terms of the offering of the
Preferred Shares and the Option Shares and to obtain additional information
concerning the Company and its business; and (e) such Purchaser has the ability
to evaluate the merits and risks of an investment in the Preferred Shares and
the Option Shares and can bear the economic risks of such investment. The
acquisition by each Purchaser of the Preferred Shares and the Option Shares
acquired by it shall constitute a confirmation of the representations and
warranties made by each such Purchaser as at the date of such acquisition. Each
of the Purchasers further represents that it understands and agrees that, until
registered under the Securities Act or transferred pursuant to the provisions of
Rule 144 as promulgated by the Commission, all certificates evidencing any of
the Shares, whether upon initial issuance or upon any transfer thereof, shall
bear a legend, prominently stamped or printed thereon, reading substantially as
follows:

     "THE SECURITIES REPRESENTED BY THIS CERTIFICATE HAVE NOT BEEN REGISTERED
     UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR APPLICABLE STATE
     SECURITIES LAWS. THESE SECURITIES MAY NOT BE SOLD, MORTGAGED, PLEDGED,
     HYPOTHECATED OR OTHERWISE TRANSFERRED WITHOUT AN EFFECTIVE REGISTRATION
     STATEMENT FOR SUCH SECURITIES UNDER THE SECURITIES ACT OF 1933, AS AMENDED,
     AND APPLICABLE STATE SECURITIES LAWS, OR THE AVAILABILITY OF AN EXEMPTION
     FROM THE REGISTRATION PROVISIONS OF THE SECURITIES ACT OF 1933, AS AMENDED,
     AND APPLICABLE STATE SECURITIES LAWS."


                                   ARTICLE II

                    CONDITIONS TO THE PURCHASERS' OBLIGATION

     The obligation of any Purchaser to purchase and pay for the Preferred
Shares to be purchased by it at the Closing or, if it exercises the Option, to
purchase and pay for the Option Shares at the Subsequent Closing, is subject to
the satisfaction of the following conditions:

     2.01 Representations and Warranties. Each of the representations and
warranties of the Company set forth in Article III hereof shall be true and
correct on the date of the Closing.


                                       5
<PAGE>   10
     2.02 Documentation at Closing. The Purchasers shall have received prior to
or at the Closing all of the following documents or instruments, or evidence of
completion thereof, each in form and substance satisfactory to the Purchasers
and their counsel:

          (a) A copy of the Certificate of Incorporation of the Company (the
"Certificate of Incorporation"), certified by the Secretary of State of the
State of Delaware together with a certified copy of the Certificate of
Designation of the Series B Preferred Stock and the Certificate of Designation
of the Series C Preferred Stock, a copy of the resolutions of the Board of
Directors and, if required, the stockholders of the Company evidencing the
adoption of the Company's Certificate of Designation of the Series B Preferred
Stock and the Certificate of Designation of the Series C Preferred Stock, the
approval of this Agreement, the issuance of the Preferred Shares and the Option
Shares and the other matters contemplated hereby, and a copy of the By-laws of
the Company, all of which shall have been certified by the Secretary of the
Company to be true, complete and correct in every particular, and certified
copies of all documents evidencing other necessary corporate or other action and
governmental approvals, if any, with respect to this Agreement and the Shares.

          (b) The opinion of Hale and Dorr LLP, counsel to the Company, in the
form of Exhibit 2.02B attached hereto.

          (c) A certificate of the Secretary of the Company which shall certify
the names of the officers of the Company authorized to sign this Agreement, the
certificates for the Preferred Shares and the Option Shares and the other
documents, instruments or certificates to be delivered pursuant to this
Agreement by the Company or any of its officers, together with the true
signatures of such officers. The Purchasers may conclusively rely on such
certificate until they shall receive a further certificate of the Secretary or
an Assistant Secretary of the Company canceling or amending the prior
certificate and submitting the signatures of the officers named in such further
certificate.

          (d) A certificate of the President of the Company stating that the
representations and warranties of the Company contained in Article III hereof
and otherwise made by the Company in writing in connection with the transactions
contemplated hereby are true and correct and that all conditions required to be
performed prior to or at the Closing have been performed as of the Closing.

          (e) Certificates of Good Standing for the Company from the Secretaries
of State of the States of Delaware and California, and the Commonwealth of
Massachusetts shall have been provided to counsel to the Purchasers.

     2.03 Additional Closing Conditions. The Purchasers shall have received
prior to or at the Closing evidence of satisfaction or completion of the
following, in form and substance satisfactory to the Purchasers and their
counsel:

          (a) The Certificate of Designation of the Series B Preferred Stock and
the Certificate of Designation of the Series C Preferred Stock shall provide for
the designation of the rights and preferences of the Series B Preferred Stock
and the Series C Preferred Stock, respectively, in the forms set forth in
Exhibit 1.01A attached hereto (the "Series B Certificate of


                                       6
<PAGE>   11
Designation") and set forth in Exhibit 1.01B attached hereto (the "Series C
Certificate of Designation").

          (b) An Amended and Restated Stockholders Agreement in the form set
forth in Exhibit 2.03B (the "Amended and Restated Stockholders Agreement") shall
have been executed by the parties named therein.

          (c) The Company shall have paid the costs, expenses, taxes and filing
fees identified in Section 6.04.

          (d) The Company, the Purchasers and the other parties named therein
shall have entered into an Amended and Restated Registration Rights Agreement in
the form set forth in Exhibit 2.03E (the "Amended and Restated Registration
Rights Agreement").

          (e) The Company's By-laws shall be in form and substance reasonably
satisfactory to the Purchasers and their counsel; and not in limitation of the
foregoing, shall provide that the Chief Executive Officer shall be designated
and elected by the Board of Directors.

          (f) Each of the Founders and Key Employees shall have entered into a
non-competition and non-solicitation agreement and an invention and
non-disclosure agreement in the forms attached hereto as Exhibit 2.03GA and
Exhibit 2.03GB, respectively.

     2.04 Consents, Waivers, Etc. Prior to the Closing, the Company shall have
obtained all consents or waivers, if any, necessary to execute and deliver this
Agreement, issue the Preferred Shares and the Option Shares and to carry out the
transactions contemplated hereby and thereby, including without limitation the
waivers and/or consents of the holders of Series A Convertible Preferred Stock
of the Company in connection with the transactions contemplated hereby, and all
such consents and waivers shall be in full force and effect. All corporate and
other action and governmental filings necessary to effectuate the terms of this
Agreement, the Preferred Shares and the Option Shares and other agreements and
instruments executed and delivered by the Company in connection herewith shall
have been made or taken, except for any post-sale filing that may be required
under federal or state securities laws. In addition to the documents set forth
above, the Company shall have provided to the Purchasers any other information
or copies of documents that they may reasonably request.

     2.05 Bring-Down Certificate. At each of the Second Closing and the
Subsequent Closing, the Baker Fund and/or the Purchaser(s) purchasing shares of
Series B Preferred Stock or Series C Preferred Stock (as the case may be) at the
applicable closing shall have received a Bring-Down Certificate and shall be
entitled to receive such other certificates, opinions and other documents as
shall be reasonably requested.


                                   ARTICLE III

                  REPRESENTATIONS AND WARRANTIES OF THE COMPANY

     The Company hereby represents and warrants as follows as of the date hereof
and as of


                                       7
<PAGE>   12
the date of the Closing:

     3.01 Organization and Standing. The Company is a duly organized and validly
existing corporation in good standing under the corporate laws of the State of
Delaware and has all requisite corporate power and authority for the ownership
and operation of its properties and for the carrying on of its business as now
conducted or as now proposed to be conducted. The Company is duly licensed or
qualified and in good standing as a foreign corporation authorized to do
business in all jurisdictions wherein the character of the property owned or
leased, or the nature of the activities conducted, by it makes such licensing or
qualification necessary as set forth in Exhibit 3.01, except where the failure
to so qualify would not have a material adverse effect on the business,
operations, affairs or condition of the Company or in its properties or assets
taken as a whole, or which might call into question the validity of this
Agreement, any of the Shares, or any action taken or to be taken pursuant hereto
or thereto (a "Material Adverse Effect").

     3.02 Corporate Action. The Company has all necessary corporate power and
has taken all corporate action required to enter into and perform this
Agreement, the Amended and Restated Registration Rights Agreement, the Amended
and Restated Stockholders Agreement and any other agreements and instruments
executed in connection herewith (collectively, the "Financing Documents"). The
Financing Documents are valid and binding obligations of the Company,
enforceable in accordance with their terms. The issuance, sale and delivery of
the Preferred Shares in accordance with this Agreement, the issuance, sale and
delivery of the Option Shares have been duly authorized and reserved for
issuance, and the issuance, sale and delivery of the Converted Shares have been
duly authorized and reserved for issuance, as the case may be, by all necessary
corporate action on the part of the Company. Sufficient authorized but unissued
shares of Common Stock have been reserved by appropriate corporate action in
connection with the prospective conversion of the Preferred Shares and the
Option Shares at the initial conversion price, and the issuance of the Preferred
Shares and the Option Shares is not, and the issuance of the Converted Shares
upon the conversion of the Preferred Shares and the Option Shares will not be,
subject to preemptive rights or other preferential rights in any present
stockholders of the Company and will not conflict with any provision of any
agreement or instrument to which the Company is a party or by which it or its
property is bound.

     3.03 Governmental Approvals. Except for the filing of any notice subsequent
to the Closing that may be required under applicable state and/or federal
securities laws (which, if required, shall be filed on a timely basis and a copy
of which shall be provided to the Purchasers and their counsel), no
authorization, consent, approval, license, exemption of or filing or
registration with any court or governmental department, commission, board,
bureau, agency or instrumentality, domestic or foreign, is or will be necessary
for the execution and delivery by the Company of this Agreement, for the offer,
issue, sale and delivery of the Preferred Shares and the Option Shares, or for
the performance by the Company of its obligations under this Agreement or the
Shares.

     3.04 Litigation. Except as set forth in Exhibit 3.04, there is no
litigation or governmental proceeding or investigation pending or, to the
knowledge of the Company, threatened against the Company affecting any of its
respective properties or assets, or against any


                                       8
<PAGE>   13
officer or Key Employee relating to such person's performance of duties for the
Company or relating to his stock ownership in the Company or otherwise relating
to the business of the Company, nor to the knowledge of the Company has there
occurred any event or does there exist any condition on the basis of which any
such litigation, proceeding or investigation might properly be instituted.
Neither the Company nor, to the knowledge of the Company, any officer, Key
Employee or holder of more than 5% of the Common Stock of the Company (other
than any Purchaser) is in default with respect to any order, writ, injunction,
decree, ruling or decision of any court, commission, board or other governmental
agency specifically naming the Company, such officer, Key Employee or holder of
more than 5% of the Common Stock of the Company. Except as set forth in Exhibit
3.04, there are no actions or proceedings pending or, to the knowledge of the
Company, threatened against the Company or against any officer or Key Employee
which could reasonably be expected to result, either in any case or in the
aggregate, in any Material Adverse Effect. The foregoing sentences include,
without limiting their generality, actions pending or, to the knowledge of the
Company, threatened (or any basis therefor), involving the prior employment of
any of the Company's officers or employees (including any Key Employees) or
their use in connection with the Company's business of any information or
techniques allegedly proprietary to any of their former employers.

     3.05 Certain Agreements of Officers and Key Employees.

          (a) To the knowledge of the Company, no officer or Key Employee of
the Company is in violation of any term of any employment contract, patent
disclosure agreement, proprietary information agreement, noncompetition
agreement, or any other contract or agreement or any restrictive covenant
relating to the employment of any such officer or Key Employee by the Company,
the nature of the business conducted or to be conducted by the Company or
relating to the use of trade secrets or proprietary or confidential information
of others. The Company has no reason to believe that the employment of the
Company's officers and Key Employees will subject the Company or any Purchaser
to any liability to third-parties. The Company has entered into Noncompetition
and Nonsolicitation Agreements and Invention and Nondisclosure Agreements with
each of its employees.

          (b) To the knowledge of the Company, no officer of the Company nor
any Key Employee of the Company whose termination, either individually or in the
aggregate, would have a Material Adverse Effect, has expressed any present
intention of terminating his employment with the Company.

     3.06 Compliance with Other Instruments. The Company is in compliance in all
respects with the terms and provisions of this Agreement and of its Certificate
of Incorporation and By-laws, and in all material respects with the terms and
provisions of all mortgages, indentures, leases, agreements and other
instruments by which it is bound or to which it or any of its respective
properties or assets are subject. The Company is in compliance with all
judgments specifically naming the Company or any of the Founders, decrees,
governmental orders specifically naming the Company or any of the Founders,
statutes, rules or regulations by which it is bound or to which any of its
properties or assets are subject. Neither the execution and delivery of this
Agreement or the issuance of the Shares, nor the consummation of any transaction
contemplated by this Agreement, has constituted or resulted in or will
constitute or


                                       9
<PAGE>   14
result in a default or violation of any term or provision of any of the
foregoing documents, instruments, judgments, agreements, decrees, orders,
statutes, rules and regulations.

     3.07 Material Contracts.

          (a) Except as set forth on Exhibit 3.07, neither the Company nor any
of its properties or assets is a party to or bound by any (i) contract not made
in the ordinary course of business, or involving a commitment or payment by the
Company in excess of $50,000 or, in the Company's belief, otherwise material to
the business of the Company; (ii) contract among stockholders or granting a
right of first refusal or for a partnership or a joint venture or for the
acquisition, sale or lease of any assets or capital stock of the Company or any
other Person or involving a sharing of profits; (iii) mortgage, pledge,
conditional sales contract, security agreement, factoring agreement or other
similar contract with respect to any real or tangible personal property of the
Company; (iv) loan agreement, credit agreement, promissory note, guarantee,
subordination agreement, letter of credit or any other similar type of contract;
(v) contract with any governmental agency; or (vi) binding commitment or
agreement to enter into any of the foregoing. The Company has delivered or
otherwise made available to the Purchasers true, correct and complete copies of
the contracts listed on Exhibit 3.07 (except as noted thereon), together with
all amendments, modifications, supplements or side letters affecting the
obligations of any party thereunder.

          (b) (i) Each of the contracts listed on Exhibit 3.07 is valid and
enforceable in accordance with its terms, and there is no default under any
contract listed on Exhibit 3.07 by the Company or, to the knowledge of the
Company, by any other party thereto, and no event has occurred that with the
lapse of time or the giving of notice or both would constitute a default
thereunder except where such default is not reasonably expected to have a
Material Adverse Effect and (ii) no previous or current party to any contract
has given written notice to the Company of or made a written claim with respect
to any breach or default thereunder and the Company has no knowledge of any
notice of or claim with respect to any such breach or default.

          (c) With respect to the contracts listed on Exhibit 3.07 that were
assigned to the Company by a third party, all necessary consents to such
assignment have been obtained.

     3.08 ERISA. Except as set forth on Exhibit 3.08, the Company does not make
and has no present intentions to make any contributions to any employee pension
benefit plans for its employees that are subject to ERISA.

     3.09 Transactions with Affiliates. Except as set forth on Exhibit 3.09, as
contemplated hereby or consented to by the Purchasers in accordance with this
Agreement, there are no loans, leases, royalty agreements or other continuing
transactions between any Founder, officer, employee or director of the Company
or any Person owning 5% or more of any class of capital stock of the Company or
any member of the immediate family of such Founder, officer, employee, director
or stockholder or any corporation or other entity controlled by such officer,
employee, director or stockholder or a member of the immediate family of such
officer, employee, director or stockholder.


                                       10
<PAGE>   15
     3.10 Assumptions or Guaranties of Indebtedness of Other Persons. Except as
contemplated hereby or consented to by the Purchasers in accordance with this
Agreement, the Company has not assumed, guaranteed, endorsed or otherwise become
directly or contingently liable on (including, without limitation, liability by
way of agreement, contingent or otherwise, to purchase, to provide funds for
payment, to supply funds to or otherwise invest in the debtor or otherwise to
assure the creditor against loss), any Indebtedness of any other Person.

     3.11 Investments in Other Persons; Subsidiaries. Except as set forth on
Exhibit 3.11 or consented to by the Purchasers in accordance with this
Agreement, the Company has not made any loan or advance to any Person which is
outstanding on the date of this Agreement, nor is it committed or obligated to
make any such loan or advance, nor does the Company own any capital stock,
assets comprising the business of, obligations of, or any interest in, any
Person except as disclosed in this Agreement. The Company has no Subsidiaries.

     3.12 Securities Laws. The Company has complied with all applicable federal
and state securities laws in connection with the offer, issuance and sale of the
Shares. Prior to the Closing, neither the Company nor anyone acting on its
behalf has sold, offered to sell or solicited offers to buy the Shares or
similar securities to, or solicit offers with respect thereto from, or entered
into any preliminary conversations or negotiations relating thereto with, any
Person, so as to bring the issuance and sale of the Shares under the
registration provisions of the Securities Act, and applicable state securities
laws.

     3.13 Disclosure. Neither this Agreement nor any other agreement, document,
certificate or written statement furnished to the Purchasers or their counsel by
or on behalf of the Company in connection with the transactions contemplated
hereby contains any untrue statement of a material fact or omits to state a
material fact relating directly to the Company necessary in order to make the
statements contained herein or therein not misleading. There is no fact within
the knowledge of the Company which has not been disclosed herein or in writing
to the Purchasers and which taken by itself would constitute a circumstance
having a Material Adverse Effect. Without limiting the generality of the
foregoing, the Company does not have any knowledge that there exists, or there
is pending or planned, any statute, rule, law, regulation, standard or code
which would have a Material Adverse Effect on the Company's business.

     3.14 Brokers or Finders. No Person has or will have, as a result of the
transactions contemplated by this Agreement, any right, interest or valid claim
against or upon the Company for any commission, fee or other compensation as a
finder or broker because of any act or omission by the Company or any of their
respective agents.

     3.15 Capitalization; Status of Capital Stock. The Company has a total
authorized capitalization consisting of (i) 22,000,000 shares of Common Stock,
par value $.01 per share, of which 7,080,885 shares are issued and outstanding
and (ii) 5,000,000 shares of Preferred Stock, par value $.01 per share, of which
(A) 3,300,000 shares are designated as Series A Convertible Preferred Stock, (B)
1,327,500 shares are designated as Series B Convertible Preferred Stock, of
which no shares are issued and outstanding on the date hereof, prior to giving
effect to the transactions contemplated hereby, and (C) 145,195 shares are
designated as Series C Convertible Preferred Stock, of which no shares are
issued and outstanding on the date hereof, prior to giving


                                       11
<PAGE>   16
effect to the transactions contemplated hereby. A complete list of the capital
stock of the Company that has been previously issued and the names in which such
capital stock is registered on the stock transfer books of the Company is set
forth in Exhibit 3.15 hereto. All the outstanding shares of capital stock of the
Company have been duly authorized, and are validly issued, fully paid and
non-assessable. The Preferred Shares, when issued and delivered in accordance
with the terms hereof and after payment of the purchase price therefor, the
Option Shares, when issued and delivered in accordance with the terms hereof and
after payment of the purchase price therefor and the Converted Shares, when
issued and delivered upon conversion of the Preferred Shares and the Option
Shares, will be duly authorized, validly issued, fully-paid and non-assessable.
Except as otherwise set forth in Exhibit 3.15, no options, warrants,
subscriptions or purchase rights of any nature to acquire from the Company
shares of capital stock or other securities are authorized, issued or
outstanding, nor is the Company obligated in any other manner to issue shares of
its capital stock or other securities except as contemplated by this Agreement.
Except as set forth in Exhibit 3.15, there are no restrictions on the transfer
of shares of capital stock of the Company other than those imposed by relevant
federal and state securities laws and as otherwise contemplated by this
Agreement, the Amended and Restated Stockholders Agreement referred to in
Section 2.03(b), the Amended and Restated Registration Rights Agreement referred
to in Section 2.03(e), the Series B Certificate of Designation referred to in
Section 2.03(a), the Series C Certificate of Designation referred to in Section
2.03(a) and the Stock Restriction and Right of First Refusal Agreements referred
to in Section 2.03(h). Other than as provided in this Section and in the Amended
and Restated Stockholders Agreement, there are no agreements, understandings,
trusts or other collaborative arrangements or understandings concerning the
voting of the capital stock of the Company. The offer and sale of all capital
stock and other securities of the Company issued before the Closing complied
with or were exempt from all applicable federal and state securities laws and no
stockholder has a right of rescission with respect thereto.

     3.16 Registration Rights. Except as set forth in Exhibit 3.16 and except
for the rights granted to the Purchasers and certain other parties pursuant to
the Amended and Restated Registration Rights Agreement referred to in Section
2.03(e) hereof, no Person has demand or other rights to cause the Company to
file any registration statement under the Securities Act relating to any
securities of the Company or any right to participate in any such registration
statement.

     3.17 Books and Records. The books of account, ledgers, order books, records
and documents of the Company accurately and completely reflect all material
information relating to the business of the Company, the location and collection
of its assets, and the nature of all transactions giving rise to the obligations
or accounts receivable of the Company.

     3.18 Title to Assets; Patents.

          (a) The Company has good and marketable title in fee to such of its
fixed assets, if any, as are real property, and good and marketable title to all
of its other assets and properties, free of any mortgages, pledges, charges,
liens, security interests or other encumbrances, except those occurring in the
ordinary course of business and those indicated on Exhibit 3.18(a). The Company
enjoys peaceful and undisturbed possession under all leases


                                       12
<PAGE>   17
under which it is operating, and all said leases are valid and subsisting and in
full force and effect.

          (b) The Company does not know of any claim, previously asserted,
pending, threatened or which may otherwise be asserted ("Claim") that would
interfere with, or adversely impact upon, the Company's unencumbered right to
use, make, sell, license, distribute, promote, apply, develop and make
derivative works of ("Use"), the patents, patent rights, permits, licenses,
trade secrets, trademarks (registered or unregistered), trademark rights, trade
names, trade name rights, franchises, copyrights (registered or unregistered),
inventions (regardless of whether patentable or not), software, confidential
information, innovations and other intellectual property rights being used to
conduct its business as now operated and as now proposed to be operated, or in
the development, manufacture, use, distribution or licensing of the Company's
proprietary technology, information, products, processes, or services
(collectively, the "Intellectual Property Rights") (a list of all patents,
trademarks, trade names, permits, and licenses Used by the Company is attached
hereto as Exhibit 3.18(b)); and the Company does not have any reason to believe
that the Use of the Intellectual Property Rights infringes, conflicts or will
conflict with valid rights of any other Person. No claim is known by the Company
to be pending or threatened to the effect that, and the Company has no reason to
believe that, any such Intellectual Property Right is invalid or unenforceable
by the Company or its licensor. Except as set forth in Exhibit 3.18(c), the
Company has no obligation known by the Company to compensate any Person for the
use of any such Intellectual Property Rights, and the Company has not granted
any Person any license or other rights to use in any manner any of the
Intellectual Property Rights of the Company, whether requiring the payment of
royalties or not.

     3.19 The Year 2000. Each item of hardware, software, information
technology, embedded, or processor based system and/or any combination thereof,
used, developed, manufactured, distributed, licensed, transferred or delivered,
by the Company (collectively, the "System"), shall be able to correctly
function, operate, process data or perform date related calculations, including,
but not limited to, calculating, comparing and sequencing, from, into and
between the years 1999 and 2000, accurately process, provide and/or receive date
data, including leap year calculations, into and between the years 1999, 2000
and beyond, shall otherwise function as per the specifications thereof both
before, during and following January 1, 2000. Neither performance nor
functionality of the System shall be affected by dates prior to, during and
after January 1, 2000. A System containing or calling on a calendar function
including, without limitation, any function indexed to the CPU clock, and any
function providing specific dates or days, or calculating spans of dates or days
shall record, store, process, provide and, where appropriate, insert, true and
accurate dates and calculations for dates and spans, before, during and
following January 1, 2000. The System shall have no lesser functionality or
operability with respect to records containing dates, before, during or after
January 1, 2000 than heretofore with respect to dates prior to January 1, 2000.
The System shall be fully interoperable and interface with any and all other
system, software and/or hardware used by the Company before, during or after
January 1, 2000, and/or otherwise exchange data, including date related data
therewith.

     3.20 Financial Statements. Attached hereto as Exhibit 3.20 are copies of
the unaudited balance sheet of the Company as of December 31, 1998, the
statements of income and retained


                                       13
<PAGE>   18
earnings of the Company for the period ended December 31, 1998, and the
statements of cash flows of the Company for the period ended December 31, 1998
(the "Financial Statements"). Each of the Financial Statements was prepared in
good faith, is complete and correct in all material respects, has been prepared
in accordance with generally accepted accounting principles and in conformity
with the practices consistently applied by the Company and presents fairly the
financial position, results of operations and cash flows of the Company as of
the dates and for the periods indicated.

     3.21 No Undisclosed Liabilities. Except as set forth on Exhibit 3.21, the
Company has no liabilities (whether accrued, absolute, contingent or otherwise,
and whether due or to become due or asserted or unasserted), except (a)
obligations under contracts described in Exhibit 3.07 or under contracts that
are not required to be disclosed thereon as a result of dollar thresholds
therein; (b) liabilities provided for in the Financial Statements (other than
liabilities which, in accordance with generally accepted accounting principles,
need not be disclosed); (c) liabilities (other than accounts payable) incurred
since the Audited Financial Statements, in the ordinary course of business
consistent with past practice, the sum of which is, in the aggregate, no greater
than $200,000; and (d) accounts payable in excess of those shown on the
Financial Statements, incurred in the ordinary course of business consistent
with past practice, the sum of which is, in the aggregate, not greater than
$200,000.

     3.22 Technology. Except as set forth in Exhibit 3.22 and other than the
Intellectual Property Rights licensed to the Company pursuant to the License
Agreement, the products, processes, proprietary technology and other proprietary
know-how owned or used by the Company were completely developed by the Company's
full-time employees only; the concepts, inventions and original works of
authorship owned or used by the Company were developed or conceived by employees
within the scope of their employment by the Company and are connected with
Company's underlying products, processes and proprietary technology. No
independent contractors or consultants were used or employed by the Company in
the development of the products, processes, proprietary technology and other
proprietary know-how owned or used by the Company.


                                   ARTICLE IV

                            COVENANTS OF THE COMPANY

     4.01 Affirmative Covenants of the Company Other Than Reporting
Requirements. Without limiting any other covenants and provisions hereof, the
Company covenants and agrees that until the consummation of a Qualified Public
Offering, it will perform and observe the following covenants and provisions,
and will cause each Subsidiary, if and when such Subsidiary exists, to perform
and observe such of the following covenants and provisions as are applicable to
such Subsidiary:

          (a) Payment of Taxes and Trade Debt. Pay and discharge, and cause
each Subsidiary to pay and discharge, all taxes, assessments and governmental
charges or levies imposed upon it or upon its income, profits or business, or
upon any properties belonging to it, prior to the date on which penalties attach
thereto, and all lawful claims which, if unpaid, might


                                       14
<PAGE>   19
become a lien or charge upon any properties of the Company or any Subsidiary,
provided that neither the Company nor any Subsidiary shall be required to pay
any such tax, assessment, charge, levy or claim which is being contested in good
faith and by appropriate proceedings if the Company or any Subsidiary shall have
set aside on its books sufficient reserves, if any, with respect thereto. Pay
and cause each Subsidiary to pay, when due, or in conformity with customary
trade terms, all lease obligations, all trade debt, and all other Indebtedness
incident to the operations of the Company or its Subsidiaries, except such as
are being contested in good faith and by proper proceedings if the Company or
Subsidiary concerned shall have set aside on its books sufficient reserves, if
any, with respect thereto.

          (b) Maintenance of Insurance. Obtain and maintain from reputable
insurance companies or associations a term life insurance policy on the lives of
each of F. Thomson Leighton and Daniel Lewin the face amount equal to $2,000,000
each (so long as each remains an employee of the Company), which proceeds will
be payable to the order of the Company, and maintain insurance with a reputable
insurance company or association in such amount and covering such risks as is
customary coverage covering its properties and businesses customarily carried by
companies engaged in similar businesses and owning similar properties in the
same general areas in which the Company or any Subsidiary operates for the type
and scope of its properties and businesses and maintain, and cause each
Subsidiary to maintain, such insurance. The Company will not cause or permit any
assignment of the proceeds of the life insurance policies specified in the first
sentence of this paragraph and will not borrow against such policies. The
Company will add the Baker Fund as a notice party to such policies and will
request that the issuer(s) of such policies provide such designee with at least
ten (10) days' notice before either such policy is terminated (for failure to
pay premiums or otherwise) or assigned, or before any change is made in the
designation of a beneficiary thereof.

          (c) Preservation of Corporate Existence. Preserve and maintain, and,
unless the Company deems it not to be in its best interests, cause each
Subsidiary to preserve and maintain, its corporate existence, rights, franchises
and privileges in the jurisdiction of its incorporation, and qualify and remain
qualified, and cause each Subsidiary to qualify and remain qualified, as a
foreign corporation in each jurisdiction in which such qualification is
necessary or desirable in view of its business and operations or the ownership
or lease of its properties. Use commercially reasonable best efforts to secure,
preserve and maintain, and cause each Subsidiary to use commercially reasonable
best efforts to secure, preserve and maintain, all licenses and other rights to
use patents, processes, licenses, permits, trademarks, trade names, inventions,
intellectual property rights or copyrights owned or possessed by it and deemed
by the Company to be material to the conduct of its business or the business of
any Subsidiary.

          (d) Compliance with Laws. Comply, and cause each Subsidiary to
comply, with the requirements of all applicable laws, rules, regulations and
orders of any governmental authority, where noncompliance would have a Material
Adverse Effect.

          (e) Inspection. Permit, upon reasonable request and notice, each of
the Purchasers who holds at least 35,000 shares of the outstanding Preferred
Shares (as equitably adjusted for stock splits, stock dividends and the like) or
any authorized agents or representatives thereof to examine and make copies of
and extracts from the records and books of account of,


                                       15
<PAGE>   20
and visit and inspect the properties of the Company and any Subsidiary, to
discuss the affairs, finances and accounts of the Company and any Subsidiary
with any of its officers, directors or Key Employees and independent
accountants, and consult with and advise the management of the Company and any
Subsidiary as to their affairs, finances and accounts, all at reasonable times
and upon reasonable notice. Each Purchaser agrees that it will maintain the
confidentiality of any information so obtained by it which is not otherwise
available from other sources, subject to the disclosure of information of a
non-technical nature, including financial information, which such Purchaser
discloses to its partners and/or shareholders generally.

          (f) Keeping of Records and Books of Account. Keep, and cause each
Subsidiary to keep, adequate records and books of account in which complete
entries will be made in accordance with generally accepted accounting principles
consistently applied, reflecting all financial transactions of the Company and
any Subsidiary, and in which, for each fiscal year, all proper reserves for
depreciation, depletion, returns of merchandise, obsolescence, amortization,
taxes, bad debts and other purposes in connection with its business shall be
made.

          (g) Maintenance of Properties; Material Assets. Use commercially
reasonable best efforts to maintain and preserve, and cause each Subsidiary to
use commercially reasonable best efforts to maintain and preserve, all of its
properties and assets, necessary for the proper conduct of its business, in good
repair, working order and condition, ordinary wear and tear excepted, including,
without limitation, the maintenance and preservation of any material patents,
licenses, permits or agreements being used by the Company in its business as now
operated and as now proposed to be operated, including that certain patent and
license agreement dated October 26, 1998 by and between the Massachusetts
Institute of Technology ("MIT") and the Company (the "License Agreement"). The
Company shall continue to use its best efforts to seek to obtain the assignment
of all rights (including any and all patent rights and copyrights) of those
individuals known to be authors of the Program as such term is defined in the
License Agreement.

          (h) Compliance with ERISA. Comply, and cause each Subsidiary to
comply, with all minimum funding requirements applicable to any pension,
employee benefit plans or employee contribution plans which are subject to ERISA
or to the Internal Revenue Code of 1986, as amended (the "Code"), and comply,
and cause each Subsidiary to comply, in all other material respects with the
provisions of ERISA and the Code, and the rules and regulations thereunder,
which are applicable to any such plan. Neither the Company nor any Subsidiary
will permit any event or condition to exist which could permit any such plan to
be terminated under circumstances which would cause the lien provided for in
Section 4068 of ERISA to attach to the assets of the Company or any Subsidiary.

          (i) Budgets Approval. Not later than 45 days prior to the commencement
of each fiscal year, prepare and submit to, and obtain the approval of a
majority of the Board of Directors of, a business plan and monthly operating
budgets in reasonable detail for the next fiscal year, including capital and
operating expense budgets, cash flow projections and profit and loss
projections, all itemized in reasonable detail (including itemization of
provisions for officers' compensation). The budget and business plan shall be
reviewed by the Company periodically, and all changes therein and all material
deviations therefrom shall be resubmitted to


                                       16
<PAGE>   21
the Board of Directors. The Company shall not enter into any activity not in the
ordinary course of business and not envisioned by the budget and business plan,
unless approved by the affirmative vote of a majority of the members of the
Board of Directors.

          (j) Financings. Promptly, fully and in detail, inform the Board of
Directors of any substantive discussions, offers or contracts relating to
possible financings of any nature for the Company, whether initiated by the
Company or any other Person, except for (i) arrangements with trade creditors,
and (ii) utilization by the Company or any Subsidiary of commercial lending
arrangements with financial institutions.

          (k) By-laws. The Company shall at all times cause its By-laws to
provide that, unless otherwise required by the laws of the State of Delaware,
(i) any two directors or (ii) any holder or holders of at least 25% of the
outstanding Series A Preferred Stock or Series B Preferred Stock, shall have the
right to call a meeting of the stockholders. The Company shall at all times
maintain provisions in its By-laws or Certificate of Incorporation indemnifying
all directors against liability to the maximum extent permitted under the laws
of the State of Delaware.

          (l) Noncompetition and Nonsolicitation Agreements; Invention and
Nondisclosure Agreements. The Company shall obtain a Noncompetition and
Nonsolicitation Agreement ("Noncompetition and Nonsolicitation Agreement"), and
Invention and Nondisclosure Agreement ("Invention and Nondisclosure Agreement")
in the form attached hereto as Exhibits 2.03HA and 2.03HB, respectively, from
each Key Employee of the Company.

          (m) The Board of Directors. Call, and to the extent a quorum can be
maintained, hold meetings of the Board of Directors as determined by a majority
of the Board of Directors (which majority shall include at least one
representative designated by holders of Preferred Stock of the Company), but in
any event not less than on a quarterly basis. Promptly pay all direct
out-of-pocket expenses reasonably incurred by each non-management director of
the Company in attending each meeting of the Board of Directors or any committee
thereof.

     4.02 Negative Covenants of the Company. Without limiting any other
covenants and provisions hereof, the Company covenants and agrees that, for so
long as at least 50% of the shares of Series A Preferred Stock outstanding as of
the date hereof or 50% of the shares of Series B Preferred Stock which were
issued pursuant to this Agreement remain outstanding, it will comply with and
observe the following covenants and provisions, and will cause each Subsidiary,
if and when such Subsidiary exists, to comply with and observe such of the
following covenants and provisions as are applicable to such Subsidiary, and
will not, without the consent of at least 50% in interest of the holders of the
Series A Preferred Stock, Series B Preferred Stock and Series C Preferred Stock,
voting together as a single class on a Common Stock equivalent basis:

          (a) Restrictions on Indebtedness. Create, incur, assume or suffer to
exist, or permit any Subsidiary to create, incur, assume or suffer to exist, any
liability with respect to any Indebtedness for money borrowed except the
following:


                                       17
<PAGE>   22
              (i) Indebtedness for money borrowed by the Company, not to exceed,
in the aggregate, $25,000,000; and

              (ii) Indebtedness of the Company in respect of Capital
Expenditures subject to Section 4.02(i) herein.

          (b) Merger or Sale. Merge with or into any other entity (except a
Subsidiary or merger in which the Company is the surviving Company and the
holders of Company voting stock outstanding immediately prior to the transaction
constitute a majority of the holders of voting stock outstanding immediately
following the transaction or a consolidation or merger pursuant to which the
aggregate consideration definitively and unconditionally payable to all of the
stockholders of the Company is greater than $400 million), sell to any person or
entity any assets constituting all or substantially all of the assets of the
Company, or agree to do or permit any Subsidiary to do any of the foregoing
(unless the aggregate consideration definitively and unconditionally payable to
the Company or all of the stockholders as a result of any such transaction is
greater than $400 million).

          (c) Assumptions or Guaranties of Indebtedness of Other Persons.
Assume, guarantee, endorse or otherwise become directly or contingently liable
on, or permit any Subsidiary to assume, guarantee, endorse or otherwise become
directly or contingently liable on (including, without limitation, liability by
way of agreement, contingent or otherwise, to purchase, to provide funds for
payment, to supply funds to or otherwise invest in the debtor or otherwise to
assure the creditor against loss) any Indebtedness of any other Person, except
for guaranties by endorsement of negotiable instruments for deposit or
collection in the ordinary course of business, and except for the guaranties of
the permitted obligations of any wholly-owned Subsidiary.

          (d) Distributions. Declare or pay any dividends, purchase, redeem,
retire, or otherwise acquire for value any of its capital stock (or rights,
options or warrants to purchase such shares) now or hereafter outstanding,
return any capital to its stockholders as such, or make any distribution of
assets to its stockholders as such, or permit any Subsidiary to do any of the
foregoing (such transactions being hereinafter referred to as "Distributions"),
except that any such Subsidiary may declare and make payment of cash and stock
dividends, return capital and make distributions of assets to the Company, and
except as specifically provided for in the Company's Certificate of
Incorporation, the Series B Certificate of Designation or the Series C
Certificate of Designation; provided, however, that nothing herein contained
shall prevent the Company from:

               (i) effecting a stock split (except for a reverse stock split) or
declaring or paying any dividend consisting of shares of any class of capital
stock to the holders of shares of such class of capital stock, or

               (ii) redeeming any stock of a deceased stockholder out of
insurance held by the Company on that stockholder's life, or

               (iii) repurchasing the shares of Common Stock at the original
cost thereof (in accordance with the Stock Restriction and Right of First
Refusal Agreements substantially in


                                       18
<PAGE>   23
the form of Exhibits 2.03HA and 2.03HB, respectively, attached hereto or similar
agreement) held by officers, employees, directors or consultants of the Company
which are subject to restrictive stock purchase agreements under which the
Company has the option to repurchase such shares upon the occurrence of certain
events, including the termination of employment,

if in the case of any such transaction the payment can be made in compliance
with the other terms of this Agreement.

          (e) Change in Nature of Business. Make or permit any Subsidiary to
make, any material change in the nature of its business as contemplated in
written materials delivered to the Purchasers prior to the date hereof.

          (f) Ownership of Subsidiaries. Purchase or hold beneficially any
stock, other securities or evidences of Indebtedness in, or make any investment
in any other Person, excluding a wholly-owned subsidiary of the Company.

          (g) Issuance of Reserved Employee Shares. Grant to any of its
employees awards, options or other rights to purchase Reserved Employee Shares
unless authorized by vote of a majority of the Board of Directors which shall
include at least two members designated by holders of Preferred Stock of the
Company.

          (h) Dealings with Affiliates and Others. Other than as contemplated by
this Agreement, and other than transactions in the ordinary course of business
involving less than $50,000, enter into any transaction, including, without
limitation, any loans or extensions of credit or royalty agreements, with any
officer or director of the Company or any Subsidiary or holder of any class of
capital stock of the Company, or any member of their respective immediate
families or any corporation or other entity directly or indirectly affiliated
with one or more of such officers, directors or stockholders or members of their
immediate families unless such transaction is approved in advance by a majority
of disinterested members of the Board of Directors, or absent such Board of
Directors approval, by a majority in interest of the Purchasers.

          (i) Capital Expenditures. Incur any Capital Expenditures in any fiscal
year in excess of the agreed upon budget therefor.

          (j) Chief Executive Officer. Elect a Chief Executive Officer unless
such person has received the prior approval of those members of the Board of
Directors specified in Sections 4(i) and (ii) of the Amended and Restated
Stockholders Agreement.

     4.03 Reporting Requirements. For as long as any of the Preferred Shares
remain outstanding, the Company will furnish the following to each Purchaser who
holds at least 35,000 shares (as equitably adjusted for stock splits, stock
dividends and the like) of the Series B Preferred Stock which were issued
pursuant to this Agreement (provided, that any notice required to be delivered
pursuant to Section 4.03(e) shall be deemed delivered by providing such notice
to the director elected by the holders of the Series B Preferred Stock):

          (a) Monthly Reports: as soon as available and in any event within 30
days after the end of each calendar month, unaudited consolidated and
consolidating balance sheets of


                                       19
<PAGE>   24
the Company and its Subsidiaries as of the end of such month and consolidated
and consolidating statements of income and retained earnings of the Company and
its Subsidiaries for such month and for the period commencing at the end of the
previous fiscal year and ending with the end of such month, setting forth in
each case in comparative form the corresponding figures for the corresponding
period of the preceding fiscal year, and including comparisons to monthly
budgets, a cash flow analysis for such month, a schedule showing each
expenditure of a capital nature during such month, and a summary discussion of
the Company's principal functional areas, all in reasonable detail and duly
certified (subject to year-end audit adjustments) by the chief financial officer
of the Company as having been prepared in accordance with generally accepted
accounting principles consistently applied;

          (b) Quarterly Reports: to the extent not otherwise provided to any
Person, as soon as available and in any event within 45 days after the end of
each of the first three quarters of each fiscal year of the Company, unaudited
consolidated balance sheets of the Company and its Subsidiaries as of the end of
such quarter and consolidated statements of income and cash flows of the Company
and its Subsidiaries for such quarter and for the period commencing at the end
of the previous fiscal year and ending with the end of such quarter, setting
forth in each case in comparative form the corresponding figures for the
corresponding period of the preceding fiscal year, and including comparisons to
quarterly budgets and a summary discussion of the Company's principal functional
areas, all in reasonable detail and duly certified (subject to year-end audit
adjustments) by the chief financial officer of the Company as having been
prepared in accordance with generally accepted accounting principles
consistently applied;

          (c) Annual Reports: as soon as available and in any event within 120
days after the end of each fiscal year of the Company, a copy of the annual
audit report for such year for the Company and its Subsidiaries, including
therein consolidated balance sheets of the Company and its Subsidiaries as of
the end of such fiscal year and consolidated statements of income of the Company
and its Subsidiaries for such fiscal year, setting forth in each case in
comparative form the corresponding figures for the preceding fiscal year, all
such consolidated statements to be duly certified by the chief financial officer
of the Company and by such independent public accountants of recognized national
standing approved by a majority of the Board of Directors;

          (d) Budgets: as soon as available after approval by the Board of
Directors, a business plan and monthly operating budgets for the forthcoming
fiscal year;

          (e) Notice of Adverse Changes: promptly after the occurrence thereof
and in any event within 10 days after each occurrence, notice of any material
adverse change in the operations or financial condition of the Company or any
material default in any other material agreement to which the Company is a
party;

          (f) Written Reports: promptly upon receipt or publication thereof, any
written reports submitted to the Company by independent public accountants in
connection with an annual or interim audit of the books of the Company and its
Subsidiaries made by such accountants or by consultants or other experts in
connection with such consultant's or other


                                       20
<PAGE>   25
expert's review of the Company's operations or industry, and written reports
prepared by the Company to comply with other investment or loan agreements;

          (g) Notice of Proceedings: promptly after the commencement thereof,
notice of all material actions, suits and proceedings of the type described in
Section 3.04 before any court or governmental department, commission, board,
bureau, agency or instrumentality, domestic or foreign, affecting the Company or
any Subsidiary; and

          (h) Stockholders' and Commission Reports: promptly upon sending,
making available, or filing the same, such reports and financial statements as
the Company or any Subsidiary shall send or make available to the stockholders
of the Company or file with the Commission.


                                    ARTICLE V

                        DEFINITIONS AND ACCOUNTING TERMS

     5.01 Certain Defined Terms. As used in this Agreement, the following terms
shall have the following meanings (such meanings to be equally applicable to
both the singular and plural forms of the terms defined):

     "Agreement" means this Series B Convertible Preferred Stock and Series C
Convertible Preferred Stock Purchase Agreement as from time to time amended and
in effect between the parties, including all Exhibits hereto.

     "Baker Fund" means Baker Communications Fund, L.P., a Delaware limited
partnership, and its and its successors and assigns holding at least 2,000
shares of Series B Preferred Stock and/or Series C Preferred Stock.

     "Board of Directors" means the board of directors of the Company as
constituted from time to time.

     "Capital Expenditures" for any period shall mean all amounts debited or
required to be debited to the fixed asset accounts on the balance sheet of the
Company during such period in accordance with generally accepted accounting
principles in respect of (a) the acquisition, construction, improvement,
replacement or betterment of land, buildings, machinery, equipment or of any
other fixed assets or leaseholds, and (b) to the extent related to and not
included in (a) above, materials, contract labor and direct labor (excluding
expenditures properly chargeable to repairs or maintenance in accordance with
generally accepted accounting principles).

     "Closing" shall have the meaning attributable to it in Section 1.04 of this
Agreement.

     "Commission" means the Securities and Exchange Commission (or any other
federal agency administering the securities laws).

     "Common Stock" includes (a) the Company's Common Stock, par value $.01 per
share,


                                       21
<PAGE>   26
as authorized on the date of this Agreement, (b) any other capital stock of any
class or classes (however designated) of the Company, authorized on or after the
date hereof, the holders of which shall have the right, without limitation as to
amount, either to all or to a share of the balance of current dividends and
liquidating dividends after the payment of dividends and distributions on any
shares entitled to preference, and the holders of which shall ordinarily, in the
absence of contingencies or in the absence of any provision to the contrary in
the Company's Certificate of Incorporation, be entitled to vote for the election
of a majority of directors of the Company (even though the right so to vote has
been suspended by the happening of such a contingency or provision), and (c) any
other securities into which or for which any of the securities described in (a)
or (b) may be converted or exchanged pursuant to a plan of recapitalization,
reorganization, merger, sale of assets or otherwise.

     "Company" means and shall include Akamai Technologies, Inc., a Delaware
corporation, and its successors and assigns.

     "Consolidated" and "consolidating" when used with reference to any term
defined herein mean that term as applied to the accounts of the Company and its
Subsidiaries consolidated in accordance with generally accepted accounting
principles.

     "Converted Shares" shall have that meaning attributable to it in Section
1.02 of this Agreement.

     "ERISA" means the Employee Retirement Income Security Act of 1974, as
amended.

     "Founders" shall mean F. Thomson Leighton, Daniel Lewin, Jonathan Seelig,
Randall Kaplan, Gilbert Friesen and David Karger.

     "Indebtedness" means all obligations, contingent and otherwise, for
borrowed money which should, in accordance with generally accepted accounting
principles, be classified upon the obligor's balance sheet (or the notes
thereto) as liabilities, but in any event including liabilities secured by any
mortgage on property owned or acquired subject to such mortgage, whether or not
the liability secured thereby shall have been assumed, and also including (a)
all guaranties, endorsements and other contingent obligations, in respect of
Indebtedness of others, whether or not the same are or should be so reflected in
said balance sheet (or the notes thereto), except guaranties by endorsement of
negotiable instruments for deposit or collection or similar transactions in the
ordinary course of business and (b) the present value of any lease payments due
under leases required to be capitalized in accordance with applicable Statements
of Financial Accounting Standards, determined by discounting all such payments
at the interest rate determined in accordance with applicable Statements of
Financial Accounting Standards.

     "Key Employee" means and includes any Founder, the President, chief
executive officer, chief financial officer, chief operating officer, vice
president of operations, research, development, sales or marketing, or any other
individual who performs a significant role in the operations of the Company or a
Subsidiary as may be reasonably designated by the Board of Directors.


                                       22
<PAGE>   27
     "Option" shall have the meaning attributable to it in Section 1.04(b) of
this Agreement.

     "Option Shares" shall have the meaning attributable to it in Section
1.04(b) of this Agreement.

     "Person" means an individual, corporation, partnership, joint venture,
trust, or unincorporated organization, or a government or any agency or
political subdivision thereof.

     "Preferred Shares" shall have the meaning attributable to it in Section
1.01 of this Agreement.

     "Preferred Stock" means the Series A Preferred Stock, the Series B
Preferred Stock and the Series C Preferred Stock.

     "Purchaser" and "Purchasers" shall have that meaning attributable to those
words in Section 1.01 of this Agreement and shall include the Purchasers and
also any other holder of the Shares who holds at least 2,000 shares of Series B
Preferred Stock and/or Series C Preferred Stock.

     "Qualified Public Offering" means a fully underwritten, firm commitment
public offering pursuant to an effective registration under the Securities Act
covering the offer and sale by the Company of its Common Stock in which (i) the
aggregate gross proceeds from such offering to the Company shall be at least
$20,000,000; and (ii) the price paid by the public for such shares shall be at
least (x) 2.0 times the then Series B Conversion Price if the public offering
occurs prior to the 18 month anniversary of the date of the Closing, or (y) 3.0
times the then Series B Conversion Price if the public offering occurs on or
after the 18 month anniversary of the date of the Closing.

     "Reserved Employee Shares" means shares of Common Stock, not to exceed in
the aggregate 3,450,000 shares (appropriately adjusted to reflect stock splits,
stock dividends, combinations of shares and the like with respect to the Common
Stock and subject to the provisions of the Section 4.02(g) hereof), reserved by
the Company for issuance pursuant to the Company's 1998 Stock Incentive Plan,
provided that such number may be increased by up to 2,519,742 additional shares
of Common Stock (the "Founders' Shares") (appropriately adjusted to reflect
stock splits, stock dividends, combinations of shares and the like with respect
to the Common Stock and subject to the provisions of the Section 4.02(g) hereof
and including 710,700 shares previously issued or subject to options prior to
the date hereof) held by the Founders upon the repurchase of such Founders
Shares by the Company from the Founders pursuant to contractual rights held by
the Company. The foregoing numbers of Reserved Employee Shares may be increased
by the affirmative vote or written consent of a majority of the directors
elected solely by the holders of Series A Preferred Stock and Series B Preferred
Stock or the affirmative vote or written consent of the holders of at least 50%
of the then outstanding shares of Series A Preferred Stock, Series B Preferred
Stock and Series C Preferred Stock, voting together as a single class on a
Common Stock equivalent basis.

     "Securities Act" means the Securities Act of 1933, or any similar federal
statute, and the


                                       23
<PAGE>   28
rules and regulations of the Commission thereunder, all as the same shall be in
effect at the time.

     "Series B Conversion Price" shall have the meaning attributable to it in
the Series B Certificate of Designation.

     "Series C Conversion Price" shall have the meaning attributable to it in
the Series C Certificate of Designation.

     "Series A Preferred Stock" means the Series A Convertible Preferred Stock
of the Company, par value $.01 per share.

     "Series B Preferred Stock" means the Series B Convertible Preferred Stock
of the Company, par value $.01 per share, having the rights, powers, privileges
and preferences set forth in Exhibit 1.01A hereto.

     "Series C Preferred Stock" means the Series C Convertible Preferred Stock
of the Company, par value $.01 per share, having the rights, powers, privileges
and preferences set forth in Exhibit 1.01B hereto.

     "Shares" shall have that meaning attributable to it in Section 1.03 of this
Agreement.

     "Subsidiary" or "Subsidiaries" means any corporation, partnership, trust or
other entity of which the Company and/or any of its other Subsidiaries (as
herein defined) directly or indirectly owns at the time a majority of the
outstanding shares of every class of equity securities of such corporation,
partnership, trust or other entity.

     5.02 Accounting Terms. All accounting terms not specifically defined herein
shall be construed in accordance with generally accepted accounting principles
consistently applied, and all financial data submitted pursuant to this
Agreement shall be prepared in accordance with such principles.

     5.03 Knowledge. All references to the knowledge or awareness of the Company
shall mean the knowledge of any director or Key Employee of the Company.


                                   ARTICLE VI

                                  MISCELLANEOUS

     6.01 No Waiver; Cumulative Remedies. No failure or delay on the part of any
party to this Agreement in exercising any right, power or remedy hereunder shall
operate as a waiver thereof; nor shall any single or partial exercise of any
such right, power or remedy preclude any other or further exercise thereof or
the exercise of any other right, power or remedy hereunder. The remedies herein
provided are cumulative and not exclusive of any remedies provided by law.

     6.02 Amendments, Waivers and Consents. Any provision in this Agreement to
the contrary notwithstanding, and except as hereinafter provided changes in or
additions to this


                                       24
<PAGE>   29
Agreement may be made, and compliance with any covenant or provision set forth
herein may be omitted or waived, if the Company (i) shall obtain consent thereto
in writing from the holder or holders of at least 60% of the then outstanding
shares of Series B Preferred Stock, and (ii) shall deliver copies of such
consent in writing to any holders who did not execute such consent; provided,
however, that any provision set forth in Section 4.02 of this Agreement (except
for Section 4.02(b) and 4.02(h), the waiver or amendment of which shall require
consent thereto in writing from the holder or holders of at least 60% of the
then outstanding shares of Series B Preferred Stock) may be amended or waived
with the written consent of more than 50% in interest of the holders of Series A
Preferred Stock, Series B Preferred Stock and Series C Preferred Stock, voting
together as a single class on a Common Stock equivalent basis. Any waiver or
consent may be given subject to satisfaction of conditions stated therein and
any waiver or consent shall be effective only in the specific instance and for
the specific purpose for which given. The Company shall not offer, or agree to
pay, any fee or other consideration to any Purchaser in connection with any
amendment, modification or waiver of any provision of this Agreement, the Series
B Certificate of Designation, the Series C Certificate of Designation, the
Amended and Restated Stockholders Agreement or the Amended and Restated
Registration Rights Agreement unless such amendment, modification or waiver
relates solely to the rights and remedies of such Purchaser and does not
adversely affect any rights or remedies of any other holder of the Series B
Preferred Stock or of the Series C Preferred Stock or such fee or other
consideration is offered and paid to all Purchasers pro rata to their holdings
of Series B Preferred Stock and Series C Preferred Stock. In addition, the
Company shall not directly or indirectly repurchase or retire any Series B
Preferred Stock or Series C Preferred Stock (other through the conversion
thereof in accordance with the terms of the Series B Certificate of Designation
or the Series C Certificate of Designation, as the case may be).

     6.03 Addresses for Notices. All notices, requests, demands and other
communications provided for hereunder shall be in writing and mailed, faxed or
delivered to each applicable party at the address set forth in Exhibit 1.01
hereto or at such other address as to which such party may inform the other
parties in writing in compliance with the terms of this Section.

     If to any other holder of the Shares: at such holder's address for notice
as set forth in the register maintained by the Company, or, as to each of the
foregoing, at the addresses set forth on Exhibit 1.01 hereto or at such other
address as shall be designated by such Person in a written notice to the other
parties complying as to delivery with the terms of this Section 6.03.

     If to the Company: at the address set forth on page 1 hereof, or at such
other address as shall be designated by the Company in a written notice to the
other parties complying as to delivery with the terms of this Section, with a
copy to: Hale and Dorr LLP, 60 State Street, Boston, MA 02109, Attention: John
H. Chory, Esq.

     All such notices, requests, demands and other communications shall, when
mailed (which mailing must be accomplished by first class mail, postage prepaid;
express overnight courier service; or registered mail, return receipt requested)
or transmitted by facsimile, be effective three days after deposited in the
mails or upon transmission by facsimile, respectively, addressed as aforesaid,
unless otherwise provided herein.


                                       25
<PAGE>   30
     6.04 Costs, Expenses and Taxes. The Company agrees to pay in connection
with the preparation, execution and delivery of this Agreement and the issuance
of the Preferred Shares, the reasonable out-of-pocket expenses of the Baker Fund
(including legal, accounting and other expenses), up to a maximum of $30,000. In
addition, the Company shall pay any and all stamp and other taxes payable or
determined to be payable in connection with the execution and delivery of this
Agreement, the issuance of the Preferred Shares and the other instruments and
documents to be delivered hereunder or thereunder, and agrees to save the
Purchasers harmless from and against any and all liabilities with respect to or
resulting from any delay in paying or omission to pay such taxes.

     6.05 Binding Effect; Assignment. This Agreement shall be binding upon and
inure to the benefit of the Company and the Purchasers and their respective
heirs, successors and assigns, except that the Company shall not have the right
to delegate any of its respective obligations hereunder or to assign its
respective rights hereunder or any interest herein without the prior written
consent of the holders of at least a majority in interest of the Shares.

     6.06 Survival of Representations and Warranties. All representations and
warranties made in this Agreement, the Shares, or any other instrument or
document delivered in connection herewith or therewith, shall survive the
execution and delivery hereof or thereof.

     6.07 Prior Agreements. This Agreement constitutes the entire agreement
between the parties and supersedes any prior understandings or agreements
concerning the purchase and sale of the Shares.

     6.08 Severability. The provisions of this Agreement and the terms of the
Series B Preferred Stock and the Series C Preferred Stock are severable and, in
the event that any court of competent jurisdiction shall determine that any one
or more of the provisions or part of a provision contained in this Agreement or
the Series B Preferred Stock or the Series C Preferred Stock shall, for any
reason, be held to be invalid, illegal or unenforceable in any respect, such
invalidity, illegality or unenforceability shall not affect any other provision
or part of a provision of this Agreement or the terms of the Series B Preferred
Stock or the Series C Preferred Stock; but this Agreement and the terms of the
Series B Preferred Stock and the Series C Preferred Stock, as the case may be,
shall be reformed and construed as if such invalid or illegal or unenforceable
provision, or part of a provision, had never been contained herein, and such
provisions or part reformed so that it would be valid, legal and enforceable to
the maximum extent possible.

     6.09 Governing Law. This Agreement shall be construed and enforced in
accordance with and governed by the General Corporation Law of the State of
Delaware as to matters within the scope thereof, and as to all other matters
shall be governed by and construed in accordance with the internal laws of the
Commonwealth of Massachusetts.

     6.10 Headings. Article, Section and subsection headings in this Agreement
are included herein for convenience of reference only and shall not constitute a
part of this Agreement for any other purpose.


                                       26
<PAGE>   31
     6.11 Counterparts. This Agreement may be executed in any number of
counterparts, all of which taken together shall constitute one and the same
instrument, and any of the parties hereto may execute this Agreement by signing
any such counterpart.

     6.12 Further Assurances. From and after the date of this Agreement, upon
the request of any Purchaser or the Company, the Company and the Purchasers
shall execute and deliver such instruments, documents and other writings as may
be reasonably necessary or desirable to confirm and carry out and to effectuate
fully the intent and purposes of this Agreement and the Shares.

     6.13 Indemnification.

          (a) The Company shall, with respect to the representations, warranties
and agreements made by it herein, indemnify, defend and hold the Purchasers
harmless against all liability, loss or damage, together with all reasonable
costs and expenses related thereto (including legal and accounting fees and
expenses (collectively, "Losses" and individually, a "Loss")), arising from the
untruth, inaccuracy or breach of any such representations, warranties or
agreements of the Company. Without limiting the generality of the foregoing, the
Purchasers shall be deemed to have suffered a Loss as a result of the untruth,
inaccuracy or breach of any such representations or warranties if such Loss
shall be suffered by the Company as a result of, or in connection with, such
untruth, inaccuracy or breach of any facts or circumstances constituting such
untruth, inaccuracy or breach. To claim a Loss, one or more Purchasers shall
deliver to the Company a notice (the "Loss Notice") specifying in reasonable
detail the nature and estimated amount of the Loss. At the time of delivery of
the Loss Notice to the Company, a duplicate copy of the Loss Notice shall be
delivered to the other Purchasers. A determination as to the existence and
amount of the Loss claimed in the Loss Notice shall be made in accordance with
Section 6.13(c) below. Any dispute regarding a Loss shall be determined as set
forth in Section 6.13(c) herein.

          (b) The representations and warranties of the Company set forth in
this Agreement shall survive the Closing until April 16, 2001 and be of no
further force or effect as of such date, except that (i) the representations and
warranties set forth in Sections 3.13 and 3.18 shall survive the Closing until
April 16, 2000, and (ii) the representations and warranties set forth in Section
3.15 shall survive the Closing forever and shall not terminate.

          (c) Within 10 days after delivery of the Loss Notice, the Purchasers
shall designate a representative (the "Purchaser Representative"). The Company
and the Purchaser Representative shall thereafter attempt in good faith for 30
days to agree upon the amount of the Loss claimed in the Loss Notice (the "Loss
Amount") and the then fair market value of one share of Series B Preferred Stock
and one share of Series C Preferred Stock after giving effect to the Loss
(respectively, the "Current Series B Value" and the "Current Series C Value").
If no such agreement can be reached, the Company and the Purchaser
Representative shall each promptly select an arbitrator and thereafter the two
arbitrators shall select a third arbitrator. The three arbitrators shall
thereafter determine, by majority vote and pursuant to the then rules of the
American Arbitration Association, the Loss Amount, the Current Series B Value
and the Current Series C Value. Each of the arbitrators shall be a member in
good standing of the American


                                       27
<PAGE>   32
Arbitration Association. The Company and the Purchaser Representative shall each
be permitted to submit written positions and arguments to the arbitrators
concerning the matters at issue before the arbitrators. The fees and expenses of
the arbitrators shall be borne (i) 100% by the Company, if the Loss Amount as
determined by the arbitrators is greater than or equal to 50% of the estimated
amount of the Loss as set forth in the Loss Notice, or (ii) 100% by the
Purchaser or Purchasers submitting the Loss Notice, if the Loss Amount as
determined by the arbitrators is less than 50% of the estimated amount of the
Loss as set forth in the Loss Notice.


                                       28
<PAGE>   33
           IN WITNESS WHEREOF, the parties hereto have caused this Agreement to
be executed as of the date first above written.


THE COMPANY:                                   AKAMAI TECHNOLOGIES, INC.



                                               By:    /s/ Daniel Lewin
                                                      ----------------
                                               Name:  Daniel Lewin
                                               Title: President

PURCHASERS:                                    BAKER COMMUNICATIONS FUND, L.P.



                                               By:    /s/ Edward W. Scott
                                                      -------------------
                                               Name:  Edward W. Scott
                                               Title: General Partner


                                       29
<PAGE>   34
                       ADDITIONAL PURCHASER SIGNATURE PAGE


     By his, her or its execution and delivery of this signature page, the
undersigned hereby (i) joins in and agrees to be an "Additional Purchaser" under
that certain Series B Convertible Preferred Stock and Series C Convertible
Preferred Stock Purchase Agreement dated as of April 16, 1999 among Akamai
Technologies, Inc. (the "Company") and the individuals and entities named
therein (the "Purchase Agreement"), (ii) joins in and agrees to be a "Series B
Purchaser" under that certain Amended and Restated Registration Rights Agreement
dated as of April 16, 1999 among the Company and the individuals and entities
named therein (the "Registration Rights Agreement"), (iii) joins in and agrees
to be a "Series B Investor" under that certain Amended and Restated
Stockholders' Agreement dated as of April 16, 1999 among the Company and the
individuals and entities named therein (the "Stockholders' Agreement") and (iv)
authorizes this signature page to be attached to the Purchase Agreement, the
Registration Rights Agreement and the Stockholders' Agreement.


                                   Name of Purchaser:

                                   AT Investors LLC

                                   Authorized Signature:

                                   /s/ Arthur Bilger
                                   --------------------

                                   Address:
                                   480 Bel Air Road
                                   Los Angeles, CA  90077

                                   Number of Shares of Series B Convertible
                                   Preferred Stock Being Purchased:

                                   9,610 Shares

                                   Aggregate Purchase Price ($15.066 per Share):

                                   $144,784.26

Agreed to and accepted this
30th day of April, 1999.

AKAMAI TECHNOLOGIES, INC.
By: /s/ Daniel Lewin
    ----------------
<PAGE>   35
                       ADDITIONAL PURCHASER SIGNATURE PAGE


     By his, her or its execution and delivery of this signature page, the
undersigned hereby (i) joins in and agrees to be an "Additional Purchaser" under
that certain Series B Convertible Preferred Stock and Series C Convertible
Preferred Stock Purchase Agreement dated as of April 16, 1999 among Akamai
Technologies, Inc. (the "Company") and the individuals and entities named
therein (the "Purchase Agreement"), (ii) joins in and agrees to be a "Series B
Purchaser" under that certain Amended and Restated Registration Rights Agreement
dated as of April 16, 1999 among the Company and the individuals and entities
named therein (the "Registration Rights Agreement"), (iii) joins in and agrees
to be a "Series B Investor" under that certain Amended and Restated
Stockholders' Agreement dated as of April 16, 1999 among the Company and the
individuals and entities named therein (the "Stockholders' Agreement") and (iv)
authorizes this signature page to be attached to the Purchase Agreement, the
Registration Rights Agreement and the Stockholders' Agreement.


                                   Name of Purchaser:

                                   Battery Investment Partners IV, LLC

                                   Authorized Signature:

                                   /s/ Todd Dagres
                                   ----------------

                                   Address:
                                   20 Williams Street
                                   Wellesley, MA  02481

                                   Number of Shares of Series B Convertible
                                   Preferred Stock Being Purchased:

                                   969 Shares

                                   Aggregate Purchase Price ($15.066 per Share):

                                   $14,598.95

Agreed to and accepted this
30th day of April, 1999.

AKAMAI TECHNOLOGIES, INC.

By: /s/ Daniel Lewin
    ----------------
<PAGE>   36
                       ADDITIONAL PURCHASER SIGNATURE PAGE


     By his, her or its execution and delivery of this signature page, the
undersigned hereby (i) joins in and agrees to be an "Additional Purchaser" under
that certain Series B Convertible Preferred Stock and Series C Convertible
Preferred Stock Purchase Agreement dated as of April 16, 1999 among Akamai
Technologies, Inc. (the "Company") and the individuals and entities named
therein (the "Purchase Agreement"), (ii) joins in and agrees to be a "Series B
Purchaser" under that certain Amended and Restated Registration Rights Agreement
dated as of April 16, 1999 among the Company and the individuals and entities
named therein (the "Registration Rights Agreement"), (iii) joins in and agrees
to be a "Series B Investor" under that certain Amended and Restated
Stockholders' Agreement dated as of April 16, 1999 among the Company and the
individuals and entities named therein (the "Stockholders' Agreement") and (iv)
authorizes this signature page to be attached to the Purchase Agreement, the
Registration Rights Agreement and the Stockholders' Agreement.

                                  Name of Purchaser:

                                  Battery Ventures IV, L.P.

                                  Authorized Signature:

                                  /s/ Todd Dagres
                                  ----------------

                                  Address:
                                  20 Williams Street
                                  Wellesley, MA  02481

                                  Number of Shares of Series B Convertible
                                  Preferred Stock Being Purchased:

                                  62,087 Shares

                                  Aggregate Purchase Price ($15.066 per Share):

                                  $935,402.74

Agreed to and accepted this
30th day of April, 1999.

AKAMAI TECHNOLOGIES, INC.

By: /s/ Daniel Lewin
    ----------------
<PAGE>   37
                       ADDITIONAL PURCHASER SIGNATURE PAGE


     By his, her or its execution and delivery of this signature page, the
undersigned hereby (i) joins in and agrees to be an "Additional Purchaser" under
that certain Series B Convertible Preferred Stock and Series C Convertible
Preferred Stock Purchase Agreement dated as of April 16, 1999 among Akamai
Technologies, Inc. (the "Company") and the individuals and entities named
therein (the "Purchase Agreement"), (ii) joins in and agrees to be a "Series B
Purchaser" under that certain Amended and Restated Registration Rights Agreement
dated as of April 16, 1999 among the Company and the individuals and entities
named therein (the "Registration Rights Agreement"), (iii) joins in and agrees
to be a "Series B Investor" under that certain Amended and Restated
Stockholders' Agreement dated as of April 16, 1999 among the Company and the
individuals and entities named therein (the "Stockholders' Agreement") and (iv)
authorizes this signature page to be attached to the Purchase Agreement, the
Registration Rights Agreement and the Stockholders' Agreement.


                                  Name of Purchaser:

                                  Brian T. Bedol

                                  Authorized Signature:

                                  /s/ Brian T. Bedol
                                  ------------------

                                  Address:
                                  31 Eagle Rock Way
                                  Montclair, NJ  07042

                                  Number of Shares of Series B Convertible

                                  Preferred Stock Being Purchased:

                                  5,766 Shares

                                  Aggregate Purchase Price ($15.066 per Share):

                                  $86,870.56

Agreed to and accepted this
30th day of April, 1999.

AKAMAI TECHNOLOGIES, INC.

By: /s/ Daniel Lewin
    ----------------
<PAGE>   38
                       ADDITIONAL PURCHASER SIGNATURE PAGE


     By his, her or its execution and delivery of this signature page, the
undersigned hereby (i) joins in and agrees to be an "Additional Purchaser" under
that certain Series B Convertible Preferred Stock and Series C Convertible
Preferred Stock Purchase Agreement dated as of April 16, 1999 among Akamai
Technologies, Inc. (the "Company") and the individuals and entities named
therein (the "Purchase Agreement"), (ii) joins in and agrees to be a "Series B
Purchaser" under that certain Amended and Restated Registration Rights Agreement
dated as of April 16, 1999 among the Company and the individuals and entities
named therein (the "Registration Rights Agreement"), (iii) joins in and agrees
to be a "Series B Investor" under that certain Amended and Restated
Stockholders' Agreement dated as of April 16, 1999 among the Company and the
individuals and entities named therein (the "Stockholders' Agreement") and (iv)
authorizes this signature page to be attached to the Purchase Agreement, the
Registration Rights Agreement and the Stockholders' Agreement.


                                  Name of Purchaser:

                                  David F. Callan

                                  Authorized Signature:

                                  /s/ David F. Callan
                                  -------------------

                                  Address:
                                  300 Commercial Street
                                  #806
                                  Boston, MA  02109

                                  Number of Shares of Series B Convertible
                                  Preferred Stock Being Purchased:

                                  1,922 Shares

                                  Aggregate Purchase Price ($15.066 per Share):

                                  $28,956.85

Agreed to and accepted this
30th day of April, 1999.

AKAMAI TECHNOLOGIES, INC.

By: /s/ Daniel Lewin
    ----------------
<PAGE>   39
                       ADDITIONAL PURCHASER SIGNATURE PAGE


     By his, her or its execution and delivery of this signature page, the
undersigned hereby (i) joins in and agrees to be an "Additional Purchaser" under
that certain Series B Convertible Preferred Stock and Series C Convertible
Preferred Stock Purchase Agreement dated as of April 16, 1999 among Akamai
Technologies, Inc. (the "Company") and the individuals and entities named
therein (the "Purchase Agreement"), (ii) joins in and agrees to be a "Series B
Purchaser" under that certain Amended and Restated Registration Rights Agreement
dated as of April 16, 1999 among the Company and the individuals and entities
named therein (the "Registration Rights Agreement"), (iii) joins in and agrees
to be a "Series B Investor" under that certain Amended and Restated
Stockholders' Agreement dated as of April 16, 1999 among the Company and the
individuals and entities named therein (the "Stockholders' Agreement") and (iv)
authorizes this signature page to be attached to the Purchase Agreement, the
Registration Rights Agreement and the Stockholders' Agreement.


                                  Name of Purchaser:

                                  George Conrades

                                  Authorized Signature:


                                  /s/ George H. Conrades
                                  ----------------------

                                  Address:
                                  3 Channing Place
                                  Cambridge, MA  02138

                                  Number of Shares of Series B Convertible
                                  Preferred Stock Being Purchased:

                                  8,649 Shares

                                  Aggregate Purchase Price ($15.066 per Share):

                                  $130,305.83

Agreed to and accepted this
30th day of April, 1999.

AKAMAI TECHNOLOGIES, INC.

By: /s/ Daniel Lewin
    ----------------
<PAGE>   40
                       ADDITIONAL PURCHASER SIGNATURE PAGE


     By his, her or its execution and delivery of this signature page, the
undersigned hereby (i) joins in and agrees to be an "Additional Purchaser" under
that certain Series B Convertible Preferred Stock and Series C Convertible
Preferred Stock Purchase Agreement dated as of April 16, 1999 among Akamai
Technologies, Inc. (the "Company") and the individuals and entities named
therein (the "Purchase Agreement"), (ii) joins in and agrees to be a "Series B
Purchaser" under that certain Amended and Restated Registration Rights Agreement
dated as of April 16, 1999 among the Company and the individuals and entities
named therein (the "Registration Rights Agreement"), (iii) joins in and agrees
to be a "Series B Investor" under that certain Amended and Restated
Stockholders' Agreement dated as of April 16, 1999 among the Company and the
individuals and entities named therein (the "Stockholders' Agreement") and (iv)
authorizes this signature page to be attached to the Purchase Agreement, the
Registration Rights Agreement and the Stockholders' Agreement.


                                  Name of Purchaser:

                                  David Allan Kaplan Revocable Trust
                                     dated December 19, 1980

                                  Authorized Signature:


                                  /s/ David Allan Kaplan
                                  ----------------------

                                  Address:
                                  30833 Northwestern
                                  Suite 204
                                  Farmington Hills, MI  48334

                                  Number of Shares of Series B Convertible
                                  Preferred Stock Being Purchased:

                                  3,844 Shares

                                  Aggregate Purchase Price ($15.066 per Share):

                                  $57,913.70

Agreed to and accepted this
30th day of April, 1999.

AKAMAI TECHNOLOGIES, INC.

By: /s/ Daniel Lewin
    ----------------
<PAGE>   41
                       ADDITIONAL PURCHASER SIGNATURE PAGE


     By his, her or its execution and delivery of this signature page, the
undersigned hereby (i) joins in and agrees to be an "Additional Purchaser" under
that certain Series B Convertible Preferred Stock and Series C Convertible
Preferred Stock Purchase Agreement dated as of April 16, 1999 among Akamai
Technologies, Inc. (the "Company") and the individuals and entities named
therein (the "Purchase Agreement"), (ii) joins in and agrees to be a "Series B
Purchaser" under that certain Amended and Restated Registration Rights Agreement
dated as of April 16, 1999 among the Company and the individuals and entities
named therein (the "Registration Rights Agreement"), (iii) joins in and agrees
to be a "Series B Investor" under that certain Amended and Restated
Stockholders' Agreement dated as of April 16, 1999 among the Company and the
individuals and entities named therein (the "Stockholders' Agreement") and (iv)
authorizes this signature page to be attached to the Purchase Agreement, the
Registration Rights Agreement and the Stockholders' Agreement.


                                   Name of Purchaser:

                                   James Dolce

                                   Authorized Signature:

                                   /s/ James A. Dolce Jr.
                                   ----------------------

                                   Address:
                                   9 Stonegale Road
                                   Hopkinton, MA  01748

                                   Number of Shares of Series B Convertible
                                   Preferred Stock Being Purchased:

                                   3,319 Shares

                                   Aggregate Purchase Price ($15.066 per Share):

                                   $50,004.05
Agreed to and accepted this
30th day of April, 1999.

AKAMAI TECHNOLOGIES, INC.

By: /s/ Daniel Lewin
    ----------------
<PAGE>   42
                       ADDITIONAL PURCHASER SIGNATURE PAGE


     By his, her or its execution and delivery of this signature page, the
undersigned hereby (i) joins in and agrees to be an "Additional Purchaser" under
that certain Series B Convertible Preferred Stock and Series C Convertible
Preferred Stock Purchase Agreement dated as of April 16, 1999 among Akamai
Technologies, Inc. (the "Company") and the individuals and entities named
therein (the "Purchase Agreement"), (ii) joins in and agrees to be a "Series B
Purchaser" under that certain Amended and Restated Registration Rights Agreement
dated as of April 16, 1999 among the Company and the individuals and entities
named therein (the "Registration Rights Agreement"), (iii) joins in and agrees
to be a "Series B Investor" under that certain Amended and Restated
Stockholders' Agreement dated as of April 16, 1999 among the Company and the
individuals and entities named therein (the "Stockholders' Agreement") and (iv)
authorizes this signature page to be attached to the Purchase Agreement, the
Registration Rights Agreement and the Stockholders' Agreement.


                                  Name of Purchaser:

                                  Ehrenkranz & Ehrenkranz LLP

                                  Authorized Signature:

                                  /s/ Joel S. Ehrenkranz, General Partner
                                  ---------------------------------------

                                  Address:
                                  375 Park Avenue
                                  New York, NY  10152

                                  Number of Shares of Series B Convertible

                                  Preferred Stock Being Purchased:

                                  9,610 Shares

                                  Aggregate Purchase Price ($15.066 per Share):

                                  $144,784.26

Agreed to and accepted this
30th day of April, 1999.

AKAMAI TECHNOLOGIES, INC.

By: /s/ Daniel Lewin
    ----------------
<PAGE>   43
                       ADDITIONAL PURCHASER SIGNATURE PAGE


     By his, her or its execution and delivery of this signature page, the
undersigned hereby (i) joins in and agrees to be an "Additional Purchaser" under
that certain Series B Convertible Preferred Stock and Series C Convertible
Preferred Stock Purchase Agreement dated as of April 16, 1999 among Akamai
Technologies, Inc. (the "Company") and the individuals and entities named
therein (the "Purchase Agreement"), (ii) joins in and agrees to be a "Series B
Purchaser" under that certain Amended and Restated Registration Rights Agreement
dated as of April 16, 1999 among the Company and the individuals and entities
named therein (the "Registration Rights Agreement"), (iii) joins in and agrees
to be a "Series B Investor" under that certain Amended and Restated
Stockholders' Agreement dated as of April 16, 1999 among the Company and the
individuals and entities named therein (the "Stockholders' Agreement") and (iv)
authorizes this signature page to be attached to the Purchase Agreement, the
Registration Rights Agreement and the Stockholders' Agreement.


                                  Name of Purchaser:

                                  Gilbert B. Friesen

                                  Authorized Signature:

                                  /s/ Gilbert B. Friesen
                                  ----------------------

                                  Address:
                                  770 BonHill Road
                                  Los Angeles, CA  90049

                                  Number of Shares of Series B Convertible

                                  Preferred Stock Being Purchased:

                                  19,221 Shares

                                  Aggregate Purchase Price ($15.066 per Share):

                                  $289,583.56

Agreed to and accepted this
30th day of April, 1999.

AKAMAI TECHNOLOGIES, INC.

By: /s/ Daniel Lewin
    ----------------
<PAGE>   44
                       ADDITIONAL PURCHASER SIGNATURE PAGE


     By his, her or its execution and delivery of this signature page, the
undersigned hereby (i) joins in and agrees to be an "Additional Purchaser" under
that certain Series B Convertible Preferred Stock and Series C Convertible
Preferred Stock Purchase Agreement dated as of April 16, 1999 among Akamai
Technologies, Inc. (the "Company") and the individuals and entities named
therein (the "Purchase Agreement"), (ii) joins in and agrees to be a "Series B
Purchaser" under that certain Amended and Restated Registration Rights Agreement
dated as of April 16, 1999 among the Company and the individuals and entities
named therein (the "Registration Rights Agreement"), (iii) joins in and agrees
to be a "Series B Investor" under that certain Amended and Restated
Stockholders' Agreement dated as of April 16, 1999 among the Company and the
individuals and entities named therein (the "Stockholders' Agreement") and (iv)
authorizes this signature page to be attached to the Purchase Agreement, the
Registration Rights Agreement and the Stockholders' Agreement.


                                  Name of Purchaser:

                                  Earl P. Galleher III

                                  Authorized Signature:

                                  /s/ Earl P. Galleher III
                                  ------------------------

                                  Address:
                                  5910 Cranston Road
                                  Bethesda, MD  20816

                                  Number of Shares of Series B Convertible

                                  Preferred Stock Being Purchased:

                                  961 Shares

                                  Aggregate Purchase Price ($15.066 per Share):

                                  $14,478.43

Agreed to and accepted this
30th day of April, 1999.

AKAMAI TECHNOLOGIES, INC.

By: /s/ Daniel Lewin
    ----------------
<PAGE>   45
                       ADDITIONAL PURCHASER SIGNATURE PAGE


     By his, her or its execution and delivery of this signature page, the
undersigned hereby (i) joins in and agrees to be an "Additional Purchaser" under
that certain Series B Convertible Preferred Stock and Series C Convertible
Preferred Stock Purchase Agreement dated as of April 16, 1999 among Akamai
Technologies, Inc. (the "Company") and the individuals and entities named
therein (the "Purchase Agreement"), (ii) joins in and agrees to be a "Series B
Purchaser" under that certain Amended and Restated Registration Rights Agreement
dated as of April 16, 1999 among the Company and the individuals and entities
named therein (the "Registration Rights Agreement"), (iii) joins in and agrees
to be a "Series B Investor" under that certain Amended and Restated
Stockholders' Agreement dated as of April 16, 1999 among the Company and the
individuals and entities named therein (the "Stockholders' Agreement") and (iv)
authorizes this signature page to be attached to the Purchase Agreement, the
Registration Rights Agreement and the Stockholders' Agreement.


                                  Name of Purchaser:

                                  Thomas A. Herring

                                  Authorized Signature:

                                  /s/ Thomas A. Herring
                                  ---------------------

                                  Address:
                                  2305 Barton Creek Blvd.
                                  #44
                                  Austin, TX  78735

                                  Number of Shares of Series B Convertible
                                  Preferred Stock Being Purchased:

                                  961 Shares

                                  Aggregate Purchase Price ($15.066 per Share):

                                  $14,478.43

Agreed to and accepted this
30th day of April, 1999.

AKAMAI TECHNOLOGIES, INC.

By: /s/ Daniel Lewin
    ----------------
<PAGE>   46
                       ADDITIONAL PURCHASER SIGNATURE PAGE


     By his, her or its execution and delivery of this signature page, the
undersigned hereby (i) joins in and agrees to be an "Additional Purchaser" under
that certain Series B Convertible Preferred Stock and Series C Convertible
Preferred Stock Purchase Agreement dated as of April 16, 1999 among Akamai
Technologies, Inc. (the "Company") and the individuals and entities named
therein (the "Purchase Agreement"), (ii) joins in and agrees to be a "Series B
Purchaser" under that certain Amended and Restated Registration Rights Agreement
dated as of April 16, 1999 among the Company and the individuals and entities
named therein (the "Registration Rights Agreement"), (iii) joins in and agrees
to be a "Series B Investor" under that certain Amended and Restated
Stockholders' Agreement dated as of April 16, 1999 among the Company and the
individuals and entities named therein (the "Stockholders' Agreement") and (iv)
authorizes this signature page to be attached to the Purchase Agreement, the
Registration Rights Agreement and the Stockholders' Agreement.


                                  Name of Purchaser:

                                  Randall Kaplan

                                  Authorized Signature:

                                  /s/ Randall Kaplan
                                  ------------------

                                  Address:
                                  1657 Veteran Avenue
                                  #203
                                  Los Angeles, CA  90024

                                  Number of Shares of Series B Convertible
                                  Preferred Stock Being Purchased:

                                  3,844 Shares

                                  Aggregate Purchase Price ($15.066 per Share):

                                  $57,913.70

Agreed to and accepted this
30th day of April, 1999.

AKAMAI TECHNOLOGIES, INC.

By: /s/ Daniel Lewin
    ----------------

<PAGE>   47
                       ADDITIONAL PURCHASER SIGNATURE PAGE



         By his, her or its execution and delivery of this signature page, the
undersigned hereby (i) joins in and agrees to be an "Additional Purchaser" under
that certain Series B Convertible Preferred Stock and Series C Convertible
Preferred Stock Purchase Agreement dated as of April 16, 1999 among Akamai
Technologies, Inc. (the "Company") and the individuals and entities named
therein (the "Purchase Agreement"), (ii) joins in and agrees to be a "Series B
Purchaser" under that certain Amended and Restated Registration Rights Agreement
dated as of April 16, 1999 among the Company and the individuals and entities
named therein (the "Registration Rights Agreement"), (iii) joins in and agrees
to be a "Series B Investor" under that certain Amended and Restated
Stockholders' Agreement dated as of April 16, 1999 among the Company and the
individuals and entities named therein (the "Stockholders' Agreement") and (iv)
authorizes this signature page to be attached to the Purchase Agreement, the
Registration Rights Agreement and the Stockholders' Agreement.


                                   Name of Purchaser:

                                   Scott Morrisee

                                   Authorized Signature:

                                   /s/ Scott Morrisse
                                   ----------------------------------

                                   Address:

                                   69 Spinnakers Way
                                   ----------------------------------
                                   Portsmouth, NH  03801
                                   ----------------------------------

                                   Number of Shares of Series B Convertible
                                   Preferred Stock Being Purchased:

                                   1,922 Shares

                                   Aggregate Purchase Price ($15.066 per Share):
                                   $28,956.85

Agreed to and accepted this 30th
day of April, 1999.

AKAMAI TECHNOLOGIES, INC.

By: /s/  Daniel Lewin
    ----------------------------------
<PAGE>   48
                       ADDITIONAL PURCHASER SIGNATURE PAGE



         By his, her or its execution and delivery of this signature page, the
undersigned hereby (i) joins in and agrees to be an "Additional Purchaser" under
that certain Series B Convertible Preferred Stock and Series C Convertible
Preferred Stock Purchase Agreement dated as of April 16, 1999 among Akamai
Technologies, Inc. (the "Company") and the individuals and entities named
therein (the "Purchase Agreement"), (ii) joins in and agrees to be a "Series B
Purchaser" under that certain Amended and Restated Registration Rights Agreement
dated as of April 16, 1999 among the Company and the individuals and entities
named therein (the "Registration Rights Agreement"), (iii) joins in and agrees
to be a "Series B Investor" under that certain Amended and Restated
Stockholders' Agreement dated as of April 16, 1999 among the Company and the
individuals and entities named therein (the "Stockholders' Agreement") and (iv)
authorizes this signature page to be attached to the Purchase Agreement, the
Registration Rights Agreement and the Stockholders' Agreement.


                                   Name of Purchaser:
                                   Peter Morton Lifetime Trust

                                   Authorized Signature:

                                   /s/ [Illegible]
                                   ----------------------------------

                                   Address:

                                   510 N. Robertson Blvd.
                                   ----------------------------------

                                   Los Angeles, CA  90048
                                   ----------------------------------

                                   Number of Shares of Series B Convertible
                                   Preferred Stock Being Purchases:

                                   9,610 Shares

                                   Aggregate Purchase Price ($15.066 per Share):

                                   $144,784.26


Agreed to and accepted this
30th day of April, 1999.

AKAMAI TECHNOLOGIES, INC.

By:/s/  Daniel Lewin
   ----------------------------------
<PAGE>   49
                       ADDITIONAL PURCHASER SIGNATURE PAGE



         By his, her or its execution and delivery of this signature page, the
undersigned hereby (i) joins in and agrees to be an "Additional Purchaser" under
that certain Series B Convertible Preferred Stock and Series C Convertible
Preferred Stock Purchase Agreement dated as of April 16, 1999 among Akamai
Technologies, Inc. (the "Company") and the individuals and entities named
therein (the "Purchase Agreement"), (ii) joins in and agrees to be a "Series B
Purchaser" under that certain Amended and Restated Registration Rights Agreement
dated as of April 16, 1999 among the Company and the individuals and entities
named therein (the "Registration Rights Agreement"), (iii) joins in and agrees
to be a "Series B Investor" under that certain Amended and Restated
Stockholders' Agreement dated as of April 16, 1999 among the Company and the
individuals and entities named therein (the "Stockholders' Agreement") and (iv)
authorizes this signature page to be attached to the Purchase Agreement, the
Registration Rights Agreement and the Stockholders' Agreement.


                                  Name of Purchaser:

                                  Polaris Venture Partners Founders Fund II L.P.

                                  By:  Polaris Venture Management Co. II LLC,
                                       its General Partner

                                  Authorized Signature:

                                  /s/ Terrence McGuire
                                  ----------------------------------

                                  Address:

                                  1000 Winter Street, Suite 3350
                                  ----------------------------------

                                  Waltham, MA  02451
                                  ----------------------------------

                                  Number of Shares of Series B Convertible
                                  Preferred Stock Being Purchases:

                                  Preferred Stock Being Purchased:

                                  5,631 Shares

                                  Aggregate Purchase Price ($15.066 per Share):

                                  $84,836.65

Agreed to and accepted this
30th day of April, 1999.

AKAMAI TECHNOLOGIES, INC.

By: /s/  Daniel Lewin
    ----------------------------------
<PAGE>   50
                       ADDITIONAL PURCHASER SIGNATURE PAGE



         By his, her or its execution and delivery of this signature page, the
undersigned hereby (i) joins in and agrees to be an "Additional Purchaser" under
that certain Series B Convertible Preferred Stock and Series C Convertible
Preferred Stock Purchase Agreement dated as of April 16, 1999 among Akamai
Technologies, Inc. (the "Company") and the individuals and entities named
therein (the "Purchase Agreement"), (ii) joins in and agrees to be a "Series B
Purchaser" under that certain Amended and Restated Registration Rights Agreement
dated as of April 16, 1999 among the Company and the individuals and entities
named therein (the "Registration Rights Agreement"), (iii) joins in and agrees
to be a "Series B Investor" under that certain Amended and Restated
Stockholders' Agreement dated as of April 16, 1999 among the Company and the
individuals and entities named therein (the "Stockholders' Agreement") and (iv)
authorizes this signature page to be attached to the Purchase Agreement, the
Registration Rights Agreement and the Stockholders' Agreement.


                                   Name of Purchaser:

                                   Polaris Venture Partners II L.P.

                                   By:  Polaris Venture Management Co. II LLC,
                                        its General Partner

                                   Authorized Signature

                                   /s/ Terrance McGuire
                                   ----------------------------------

                                   Address:

                                   1000 Winter Street, Suite 3350
                                   ----------------------------------

                                   Watham, MA  02451
                                   ----------------------------------

                                   Number of Shares of Series B Convertible
                                   Preferred Stock Being Purchases:

                                   231,687 Shares

                                   Aggregate Purchase Price ($15.066 per Share):

                                   $3,490,596.30

Agreed to and accepted this
30th day of April, 1999.

AKAMAI TECHNOLOGIES, INC.

By: /s/  Daniel Lewin
    ----------------------------------
<PAGE>   51
                       ADDITIONAL PURCHASER SIGNATURE PAGE



         By his, her or its execution and delivery of this signature page, the
undersigned hereby (i) joins in and agrees to be an "Additional Purchaser" under
that certain Series B Convertible Preferred Stock and Series C Convertible
Preferred Stock Purchase Agreement dated as of April 16, 1999 among Akamai
Technologies, Inc. (the "Company") and the individuals and entities named
therein (the "Purchase Agreement"), (ii) joins in and agrees to be a "Series B
Purchaser" under that certain Amended and Restated Registration Rights Agreement
dated as of April 16, 1999 among the Company and the individuals and entities
named therein (the "Registration Rights Agreement"), (iii) joins in and agrees
to be a "Series B Investor" under that certain Amended and Restated
Stockholders' Agreement dated as of April 16, 1999 among the Company and the
individuals and entities named therein (the "Stockholders' Agreement") and (iv)
authorizes this signature page to be attached to the Purchase Agreement, the
Registration Rights Agreement and the Stockholders' Agreement.

                                   Name of Purchaser:
                                   Richard Donner & Lauren Shuler Donner
                                    as trustees of the R&L Donner Trust under
                                    the amended and restated trust agreement
                                    dated 12/15/95

                                   Authorized Signature

                                   /s/      [Illegible]
                                   ----------------------------------

                                   Address:

                                   ----------------------------------

                                   ----------------------------------

                                   Number of Shares of Series B Convertible
                                   Preferred Stock Being Purchases:

                                   4,805 Shares

                                   Aggregate Purchase Price ($15.066 per Share):

                                   $72,392.13


Agreed to and accepted this
30th day of April, 1999.

AKAMAI TECHNOLOGIES, INC.

By: /s/  Daniel Lewin
    ----------------------------------
<PAGE>   52
                       ADDITIONAL PURCHASER SIGNATURE PAGE



         By his, her or its execution and delivery of this signature page, the
undersigned hereby (i) joins in and agrees to be an "Additional Purchaser" under
that certain Series B Convertible Preferred Stock and Series C Convertible
Preferred Stock Purchase Agreement dated as of April 16, 1999 among Akamai
Technologies, Inc. (the "Company") and the individuals and entities named
therein (the "Purchase Agreement"), (ii) joins in and agrees to be a "Series B
Purchaser" under that certain Amended and Restated Registration Rights Agreement
dated as of April 16, 1999 among the Company and the individuals and entities
named therein (the "Registration Rights Agreement"), (iii) joins in and agrees
to be a "Series B Investor" under that certain Amended and Restated
Stockholders' Agreement dated as of April 16, 1999 among the Company and the
individuals and entities named therein (the "Stockholders' Agreement") and (iv)
authorizes this signature page to be attached to the Purchase Agreement, the
Registration Rights Agreement and the Stockholders' Agreement.


                                   Name of Purchaser:

                                   Linda Eder Ross

                                   Authorized Signature

                                   /s/ Linda Eder Ross
                                   ----------------------------------

                                   Address:

                                   24650 North Cromwell
                                   ----------------------------------
                                   Franklin, Michigan  48025
                                   ----------------------------------

                                   Number of Shares of Series B Convertible
                                   Preferred Stock Being Purchases:

                                   961 Shares

                                   Aggregate Purchase Price ($15.066 per Share):

                                   $14,478.43

Agreed to and accepted this
30th day of April, 1999.

AKAMAI TECHNOLOGIES, INC.

By: /s/  Daniel Lewin
    ----------------------------------
<PAGE>   53
                       ADDITIONAL PURCHASER SIGNATURE PAGE



         By his, her or its execution and delivery of this signature page, the
undersigned hereby (i) joins in and agrees to be an "Additional Purchaser" under
that certain Series B Convertible Preferred Stock and Series C Convertible
Preferred Stock Purchase Agreement dated as of April 16, 1999 among Akamai
Technologies, Inc. (the "Company") and the individuals and entities named
therein (the "Purchase Agreement"), (ii) joins in and agrees to be a "Series B
Purchaser" under that certain Amended and Restated Registration Rights Agreement
dated as of April 16, 1999 among the Company and the individuals and entities
named therein (the "Registration Rights Agreement"), (iii) joins in and agrees
to be a "Series B Investor" under that certain Amended and Restated
Stockholders' Agreement dated as of April 16, 1999 among the Company and the
individuals and entities named therein (the "Stockholders' Agreement") and (iv)
authorizes this signature page to be attached to the Purchase Agreement, the
Registration Rights Agreement and the Stockholders' Agreement.


                                   Name of Purchaser:

                                   Paul Sagan

                                   Authorized Signature

                                   /s/ Paul Sagan
                                   ----------------------------------

                                   Address:

                                   5 Sunset Ridge
                                   ----------------------------------

                                   Lexington, MA  02421
                                   ----------------------------------

                                   Number of Shares of Series B Convertible
                                   Preferred Stock Being Purchases:

                                   1,922 Shares

                                   Aggregate Purchase Price ($15.066 per Share):

                                   $28,956.85

Agreed to and accepted this
30th day of April, 1999.

AKAMAI TECHNOLOGIES, INC.

By: /s/  Daniel Lewin
    ----------------------------------
<PAGE>   54
                       ADDITIONAL PURCHASER SIGNATURE PAGE



         By his, her or its execution and delivery of this signature page, the
undersigned hereby (i) joins in and agrees to be an "Additional Purchaser" under
that certain Series B Convertible Preferred Stock and Series C Convertible
Preferred Stock Purchase Agreement dated as of April 16, 1999 among Akamai
Technologies, Inc. (the "Company") and the individuals and entities named
therein (the "Purchase Agreement"), (ii) joins in and agrees to be a "Series B
Purchaser" under that certain Amended and Restated Registration Rights Agreement
dated as of April 16, 1999 among the Company and the individuals and entities
named therein (the "Registration Rights Agreement"), (iii) joins in and agrees
to be a "Series B Investor" under that certain Amended and Restated
Stockholders' Agreement dated as of April 16, 1999 among the Company and the
individuals and entities named therein (the "Stockholders' Agreement") and (iv)
authorizes this signature page to be attached to the Purchase Agreement, the
Registration Rights Agreement and the Stockholders' Agreement.


                                   Name of Purchaser:

                                   Jonathan Seelig

                                   Authorized Signature

                                   /s/ Jonathan Seelig
                                   ----------------------------------

                                   Address:

                                   334 Harvard St.
                                   ----------------------------------

                                   Cambridge, MA  02139
                                   ----------------------------------

                                   Number of Shares of Series B Convertible
                                   Preferred Stock Being Purchases:

                                   4,228 Shares

                                   Aggregate Purchase Price ($15.066 per Share):

                                   $63,699.05

Agreed to and accepted this
30th day of April, 1999.

AKAMAI TECHNOLOGIES, INC.

By: /s/  Daniel Lewin
    ----------------------------------
<PAGE>   55
                       ADDITIONAL PURCHASER SIGNATURE PAGE



         By his, her or its execution and delivery of this signature page, the
undersigned hereby (i) joins in and agrees to be an "Additional Purchaser" under
that certain Series B Convertible Preferred Stock and Series C Convertible
Preferred Stock Purchase Agreement dated as of April 16, 1999 among Akamai
Technologies, Inc. (the "Company") and the individuals and entities named
therein (the "Purchase Agreement"), (ii) joins in and agrees to be a "Series B
Purchaser" under that certain Amended and Restated Registration Rights Agreement
dated as of April 16, 1999 among the Company and the individuals and entities
named therein (the "Registration Rights Agreement"), (iii) joins in and agrees
to be a "Series B Investor" under that certain Amended and Restated
Stockholders' Agreement dated as of April 16, 1999 among the Company and the
individuals and entities named therein (the "Stockholders' Agreement") and (iv)
authorizes this signature page to be attached to the Purchase Agreement, the
Registration Rights Agreement and the Stockholders' Agreement.


                                   Name of Purchaser:

                                   Michael and Julie Seelig

                                   Authorized Signature

                                   /s/ Michael Seelig
                                   ----------------------------------

                                   /s/ Julie Seelig
                                   ----------------------------------

                                   Address:

                                   6049 Hudson St.
                                   ----------------------------------

                                   Vancouver, BC
                                   ----------------------------------

                                   V6M 2Z4 Canada
                                   ----------------------------------

                                   Number of Shares of Series B Convertible
                                   Preferred Stock Being Purchases:

                                   1,922 Shares

                                   Aggregate Purchase Price ($15.066 per Share):

                                   $28,956.85

Agreed to and accepted this
30th day of April, 1999.

AKAMAI TECHNOLOGIES, INC.

By: /s/  Daniel Lewin
    ----------------------------------
<PAGE>   56
                       ADDITIONAL PURCHASER SIGNATURE PAGE



         By his, her or its execution and delivery of this signature page, the
undersigned hereby (i) joins in and agrees to be an "Additional Purchaser" under
that certain Series B Convertible Preferred Stock and Series C Convertible
Preferred Stock Purchase Agreement dated as of April 16, 1999 among Akamai
Technologies, Inc. (the "Company") and the individuals and entities named
therein (the "Purchase Agreement"), (ii) joins in and agrees to be a "Series B
Purchaser" under that certain Amended and Restated Registration Rights Agreement
dated as of April 16, 1999 among the Company and the individuals and entities
named therein (the "Registration Rights Agreement"), (iii) joins in and agrees
to be a "Series B Investor" under that certain Amended and Restated
Stockholders' Agreement dated as of April 16, 1999 among the Company and the
individuals and entities named therein (the "Stockholders' Agreement") and (iv)
authorizes this signature page to be attached to the Purchase Agreement, the
Registration Rights Agreement and the Stockholders' Agreement.


                                   Name of Purchaser:

                                   Straight Arrow Publishers Company, L.P.

                                   Authorized Signature

                                   /s/ John M. Logana
                                   ----------------------------------
                                   Vice President and CFO

                                   Address:

                                   1290 Ave. of the Americas
                                   ----------------------------------

                                   NY, NY  10104
                                   ----------------------------------

                                   Number of Shares of Series B Convertible
                                   Preferred Stock Being Purchases:

                                   4,805 Shares

                                   Aggregate Purchase Price ($15.066 per Share):

                                   $72,392.13

Agreed to and accepted this
30th day of April, 1999.

AKAMAI TECHNOLOGIES, INC.

By: /s/  Daniel Lewin
    ----------------------------------