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Sample Business Contracts

Stock Purchase Agreement - Akamai Technologies Inc. and Cisco Systems Inc.

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                            AKAMAI TECHNOLOGIES, INC.



                      SERIES E CONVERTIBLE PREFERRED STOCK

                               PURCHASE AGREEMENT



                           DATED AS OF AUGUST 6, 1999

<PAGE>   2

                                TABLE OF CONTENTS



<TABLE>
<S>                                                                                                              <C>
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.................................................................... 1
         1.05     Restrictions on Transfer and Standstill Agreement............................................. 3
         1.06     Use of Proceeds............................................................................... 4
         1.07     Representations and Warranties by the Purchaser............................................... 4

ARTICLE II - CONDITIONS TO THE PURCHASER'S OBLIGATION........................................................... 5
         2.01     Representations and Warranties................................................................ 5
         2.02     Documentation at Closing...................................................................... 5
         2.03     Additional Closing Conditions................................................................. 6
         2.04     Consents, Waivers, Etc.........................................................................7
         2.05     Performance....................................................................................7

ARTICLE III - REPRESENTATIONS AND WARRANTIES OF THE COMPANY..................................................... 7
         3.01     Organization and Standing..................................................................... 7
         3.02     Corporate Action.............................................................................. 7
         3.03     Governmental Approvals........................................................................ 8
         3.04     Litigation.................................................................................... 8
         3.05     Certain Agreements of Officers, Founders and Key Employees.................................... 8
         3.06     Compliance with Other Instruments............................................................. 9
         3.07     Material Contracts............................................................................ 9
         3.08     ERISA........................................................................................ 10
         3.09     Transactions with Affiliates................................................................. 10
         3.10     Assumptions or Guaranties of Indebtedness of Other Persons................................... 10
         3.11     Investments in Other Persons; Subsidiaries................................................... 10
         3.12     Securities Laws.............................................................................. 10
         3.13     Disclosure................................................................................... 10
         3.14     Brokers or Finders........................................................................... 11
         3.15     Capitalization; Status of Capital Stock...................................................... 11
         3.16     Registration Rights.......................................................................... 11
         3.17     Books and Records............................................................................ 11
         3.18     Title to Assets; Patents..................................................................... 12
         3.19     The Year 2000................................................................................ 12
         3.20     Financial Statements......................................................................... 13
         3.21     Changes.......................................................................................13
         3.22     No Undisclosed Liabilities................................................................... 13
         3.23     Technology................................................................................... 13
         3.24     Permits.......................................................................................13
         3.25     Environmental and Safety Laws.................................................................13
</TABLE>


                                      - i -
<PAGE>   3


<TABLE>
<S>                                                                                                             <C>
         3.26     Corporate Documents; Minute Books.............................................................13
         3.27     Labor Agreements and Actions..................................................................13

ARTICLE IV - COVENANTS OF THE COMPANY.......................................................................... 13
         4.01     Affirmative Covenants of the Company Other Than Reporting
                  Requirements................................................................................. 13
         4.02     Negative Covenants of the Company............................................................ 15
         4.03     Reporting Requirements....................................................................... 17

ARTICLE V - DEFINITIONS AND ACCOUNTING TERMS................................................................... 19
         5.01     Certain Defined Terms........................................................................ 19

ARTICLE VI - MISCELLANEOUS..................................................................................... 22
         6.01     No Waiver; Cumulative Remedies............................................................... 22
         6.02     Amendments, Waivers and Consents............................................................. 22
         6.03     Addresses for Notices........................................................................ 22
         6.04     Costs, Expenses and Taxes.................................................................... 23
         6.05     Binding Effect; Assignment................................................................... 23
         6.06     Survival of Representations and Warranties................................................... 23
         6.07     Prior Agreements............................................................................. 23
         6.08     Severability................................................................................. 23
         6.09     Governing Law................................................................................ 23
         6.10     Headings..................................................................................... 24
         6.11     Counterparts................................................................................. 24
         6.12     Further Assurances........................................................................... 24
         6.13     Indemnification.............................................................................. 24
</TABLE>


                                     - ii -
<PAGE>   4

EXHIBITS

1.01               Designation of Series E Convertible Preferred Stock
2.02B              Opinion of Counsel
2.03B              Third Amended and Restated Stockholders Agreement
2.03D              Third Amended and Restated Registration Rights 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               Changes
3.22               Undisclosed Liabilities
3.23               Technology
3.27               Labor Agreements and Actions


                                     - iii -
<PAGE>   5

                            AKAMAI TECHNOLOGIES, INC.
                                  201 Broadway
                         Cambridge, Massachusetts 02139


                                             As of August 6, 1999


TO:      Cisco Systems, Inc.

Re:      Series E Convertible Preferred Stock

Ladies and Gentlemen:

         Akamai Technologies, Inc., a Delaware corporation (the "Company"),
agrees with 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 1,867,480 shares of its previously authorized but unissued shares
of Series E Convertible Preferred Stock, par value $.01 per share (the "Series E
Preferred Stock"), at a purchase price of $26.239 per share to Cisco Systems,
Inc. (the "Purchaser"). The designation, rights, preferences and other terms and
conditions relating to the Series E Preferred Stock are as set forth on Exhibit
1.01 hereto. The Series E Preferred Stock is 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."

         1.04 Purchase Price and Closing. The Company agrees to issue and sell
to the Purchaser and, subject to and in reliance upon the representations,
warranties, covenants, terms and conditions of this Agreement, the Purchaser
agrees to purchase 1,867,480 shares of Series E Preferred Stock for an aggregate
purchase price of $49,000,807.72. The purchase and sale shall take place at a
closing (the "Closing") to be held on or before August 6, 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 E Preferred Stock to be sold at the Closing to
the Purchaser (or its nominee) against payment of the full purchase price
therefor
<PAGE>   6

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.

         1.05 Restrictions on Transfer and Standstill Agreement.

                  (a) Transfer Restrictions. Without the prior written
permission of the Company, no more than 25% of the Shares may be sold or
transferred by the Purchaser (except to a wholly-owned subsidiary or a
wholly-owned subsidiary of a wholly-owned subsidiary of the Purchaser, or the
like); provided, however, that if the Purchaser wishes to sell or transfer any
of such 25% of the Shares to a third party, it shall first submit a written
offer to sell such Shares to the Company on terms and conditions, including
price, not less favorable to the Company than those on which it proposes to sell
such Shares to such third party (the "Offer"). The Offer shall disclose the
identity of the proposed purchaser or transferee, the Shares proposed to be sold
or transferred and the agreed terms of the sale or transfer. If the Offer
provides that the purchase price for the Shares shall be paid other than in
cash, then the per-Share purchase price for the Shares subject to the Offer
shall be deemed to be the Market Price (as defined below). Within five days
after receipt of the Offer, the Company shall give written notice to the
Purchaser of its intent to purchase all or none of the offered Shares on the
same terms and conditions as set forth in the Offer. The Company can pay the
cash equivalent of any non-cash consideration based on the Market Price. If the
Company does not purchase all of the Shares offered by the Purchaser pursuant to
the Offer, such Shares may be sold by the Purchaser at any time within 90 days
after the date of the Offer at not less than the price and upon other terms and
conditions, if any, not more favorable to such proposed purchaser or transferee
than those specified in the Offer. All restrictions set forth in this Section
1.05(a) shall terminate upon the earlier of the date one year after the date of
(i) closing of a Qualified Public Offering (as defined in Section 5.01 of the
Agreement) or (ii) registration of a class of the Company's securities under the
Securities Exchange Act of 1934, as amended (the "1934 Act"). For purposes of
this Section 1.05(a), the "Market Price" shall be determined as follows:

                           (i) If the Company's Common Stock is listed on a
national securities exchange, the NASDAQ National Market System, the NASDAQ
system, or another nationally recognized exchange or trading system (an
"Exchange") as of the date of the Offer, then the Market Price shall be deemed
to be the average closing price per share of the Company's Common Stock on such
Exchange for the 20 trading days ending on the trading day prior to the date of
the Offer; provided that if the Company's Common Stock has been listed on an
Exchange for fewer than 21 trading days, the Market Price shall be deemed to be
the average closing price per share of the Company's Common Stock since it has
been listed on such Exchange.

                           (ii) If the Company's Common Stock is not listed on
an Exchange as of the date of the Offer, then the Market Price shall be the fair
market value per share of the Shares as of the date of the Offer as determined
in good faith by the Purchaser's Board of Directors; provided, however, that the
Company shall have the right to contest such determination by giving notice
thereof to the Purchaser within ten days of such determination, and in such
event the Market Price shall be the fair market value per share of the Shares as
of the date of the Offer as determined by an independent appraiser to be
selected by the Purchaser and approved by the Company, which approval shall not
be unreasonably withheld. The independent appraiser's fees and expenses shall be
paid as follows:


                                        2
<PAGE>   7

                                    (A) If the Market Price as determined by the
independent appraiser is less than or equal to 110% of the Market Price
determined by the Purchaser's Board of Directors, then the independent
appraiser's fees and expenses shall be paid by the Company.

                                    (B) If the Market Price as determined by the
independent appraiser is greater than 110% of the Market Price determined by the
Purchaser's Board of Directors, then the independent appraiser's fees and
expenses shall be paid by the Purchaser.

                  (b) Standstill Agreement. The Purchaser hereby agrees that
from and after the date hereof until the earlier of the date one year after the
date of (i) closing of a Qualified Public Offering (as defined in Section 5.01
of this Agreement) or (ii) registration of a class of the Company's securities
under the 1934 Act, unless such shall have been specifically invited in writing
by the Company, neither Purchaser nor any of its affiliates (as such term is
defined under the 1934 Act) or agents will in any manner, directly or
indirectly, (a) effect or seek, offer or propose (whether publicly or otherwise)
to effect, or cause or participate in or in any way assist any other Person to
effect or seek, offer or propose (whether publicly or otherwise) to effect or
participate in, (i) any acquisition of any securities (or beneficial ownership
thereof) or assets of the Company, except that during the one-year period from
and after a Qualified Public Offering, the Purchaser may acquire capital stock
of the Company provided that after any such acquisition, the Purchaser and its
affiliates shall beneficially own no more than 10% of each class of the
Company's voting securities; (ii) any tender or exchange offer, merger or other
business combination involving the Company; (iii) any recapitalization,
restructuring, liquidation, dissolution or other extraordinary transaction with
respect to the Company; or (iv) any "solicitation" of "proxies" (as such terms
are used in the proxy rules of the Commission) or consents to vote any voting
securities of the Company; (b) otherwise act, alone or in concert with others,
to seek control of the Company's Board of Directors; or (c) take any action
which might require the Company to make a public announcement regarding any of
the types of matters set forth in (a) above. Notwithstanding the above in this
Section 1.05(b), if (i) following the Company's initial public offering a bona
fide tender offer that seeks to acquire more than 50% of the outstanding voting
securities of the Company is commenced by a third party unaffiliated with the
Purchaser, or (ii) prior to the Company's initial public offering any
individual, entity or group (within the meaning of Section 13(d)(3) or 14(d)(2)
of the 1934 Act) other than the Purchaser and its affiliates acquires more than
50% of the Company's outstanding voting securities, then any above restriction
contained in this Section 1.05(b) imposed on the Purchaser will immediately
terminate, and the Purchaser shall be free to acquire or offer to acquire any or
all outstanding shares of the Company. Prior to the Company's initial public
offering, the Company will provide written notice to the Purchaser immediately
after the Company learns of any such individual, entity or group acquiring more
than 25% of the Company's outstanding voting securities. Notwithstanding
anything to the contrary in this Section, the Purchaser shall be entitled to
acquire securities of the Company pursuant to Section 4.1 of the Amended and
Restated Stockholders' Agreement (as defined in Section 2.03(b) below).

                  (c) "Most Favored Nation". If (i) the Company sells securities
to a Strategic Investor (as defined in Section 4.6(l) of the Amended and
Restated Stockholders' Agreement) and (ii) in connection with its purchase of
such securities, such Strategic Investor is subject to provisions less
restrictive than those set forth in Sections 1.05(a) or 1.05(b) above to
purchase and/or sell securities of the Company, then the Company shall amend
such sections, and/or


                                        3
<PAGE>   8

take such other actions as may be required (including releasing restrictions
imposed by Sections 1.05(a) or 1.05(b)), in order that the Purchaser obtains
rights no less favorable than those obtained by such Strategic Investor to
purchase and/or sell securities of the Company.

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

         1.07 Representations and Warranties by the Purchaser. The Purchaser
represents and warrants that (a) it will acquire the Preferred Shares for its
own account and that the Preferred Shares are being 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 the Purchaser, and this Agreement has been duly executed and delivered,
and constitutes a valid, legal, binding and enforceable agreement of the
Purchaser, except (i) as limited by applicable bankruptcy, insolvency,
reorganization, moratorium and other laws of general application affecting
enforcement of creditors' rights generally, (ii) as limited by laws relating to
the availability of specific performance, injunctive relief or other equitable
remedies and (iii) to the extent the indemnification provisions contained in the
Third Amended and Restated Registration Rights Agreement (as defined in Section
2.04(b)) may be limited by applicable federal or state securities laws; (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) the 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 to
obtain additional information concerning the Company and its business; and (e)
the Purchaser has the ability to evaluate the merits and risks of an investment
in the Preferred Shares and can bear the economic risks of such investment. The
acquisition by the Purchaser of the Preferred Shares shall constitute a
confirmation of the representations and warranties made by the Purchaser as at
the date of such acquisition. The Purchaser 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."

The Purchaser further represents that it understands and agrees that all
certificates evidencing any of the Shares, whether upon initial issuance or upon
any transfer thereof, shall bear legends, prominently stamped or printed
thereon, reading substantially as follows:


                                        4
<PAGE>   9

         "THE SECURITIES REPRESENTED BY THIS CERTIFICATE ARE SUBJECT TO
         RESTRICTIONS ON TRANSFER UNDER A SERIES E CONVERTIBLE PREFERRED
         STOCK PURCHASE AGREEMENT."


                                   ARTICLE II

                    CONDITIONS TO THE PURCHASER'S OBLIGATION

         The obligation of the Purchaser to purchase and pay for the Preferred
Shares at the 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.

         2.02 Documentation at Closing. The Purchaser 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 Purchaser:

                  (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 E 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 E
Preferred Stock, the approval of this Agreement, the issuance of the Preferred
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 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 Purchaser may conclusively rely on such certificate until it 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 covenants and
conditions required to be performed prior to or at the Closing have been
performed as of the Closing.


                                        5
<PAGE>   10

                  (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 the Purchaser.

                  (f) The Company and the Purchaser shall have entered into a
Strategic Alliance and Joint Development Agreement relating to the integration
of the Purchaser's router and switch hardware and equipment technologies with
the Company's Internet content distribution technologies.

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

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

                  (b) A Third 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, the Purchaser and the other parties named
therein shall have entered into a Third Amended and Restated Registration Rights
Agreement in the form set forth in Exhibit 2.03D (the "Amended and Restated
Registration Rights Agreement").

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

         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 to carry out the transactions
contemplated hereby and thereby, including without limitation the waivers and/or
consents of the holders of 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
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
Purchaser any other information or copies of documents that they may reasonably
request.

         2.05 Performance. The Company shall have performed and complied with
all agreements, obligations and conditions contained in this Agreement that are
required to be performed or complied with by it on or before the Closing.


                                        6
<PAGE>   11

                                   ARTICLE III

                  REPRESENTATIONS AND WARRANTIES OF THE COMPANY

         The Company hereby represents and warrants as follows as of the date
hereof and as of 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 legally 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, and the issuance, sale
and delivery of the Converted Shares, have been duly authorized 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 at the
initial conversion price, and the issuance of the Preferred Shares is not, and
the issuance of the Converted Shares upon the conversion of the Preferred 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 Purchaser), 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, 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


                                        7
<PAGE>   12

any 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 or Key
Employee of the Company 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 or an officer or Key
Employee 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. Except as set forth in Exhibit
3.04, there is no action, suit, proceeding or investigation by the Company
currently pending or that the Company intends to initiate.

         3.05 Certain Agreements of Officers, Founders 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 the 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


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<PAGE>   13

constitute or 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, there are no (i)
contracts not made in the ordinary course of business, or involving a commitment
or payment by the Company in excess of $100,000 or, in the Company's belief,
otherwise material to the business of the Company; (ii) contracts 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) mortgages, pledges, conditional sales contracts, security agreements,
factoring agreements or other similar contracts with respect to any real or
tangible personal property of the Company; (iv) loan agreements, credit
agreements, promissory notes, guarantees, subordination agreements, letters of
credit or any other similar type of contracts; (v) contracts with any
governmental agency; (vi) licenses of any patent, copyright, trade secret or
other proprietary right to or from the Company, other than licenses arising from
the purchase of "off the shelf" or other standard products; (vii) provisions
restricting or affecting the development, manufacture or distribution of the
Company's products or services; or (viii) binding commitments or agreements to
enter into any of the foregoing (collectively, the "Material Contracts"). The
Company has delivered or otherwise made available to the Purchaser true, correct
and complete copies of the Material Contracts, other than those specifically
agreed upon by the Company and the Purchaser to not be delivered, together with
all amendments, modifications, supplements or side letters affecting the
obligations of any party thereunder.

                  (b) (i) Each of the Material Contracts is valid and
enforceable in accordance with its terms, and there is no default under any
Material Contract by the Company or, to the knowledge of the Company by any
other party thereto, and no event has occurred with respect to any of the
Material Contracts that with the lapse of time or the giving of notice or both
would constitute a default by the Company thereunder except where such default
is not reasonably expected to have a Material Adverse Effect and (ii) no
previous or current party to any Material 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 Material Contracts that were assigned
to the Company by a third party, all necessary consents to such assignment have
been obtained.

                  (d) The Company has not engaged in the past three (3) months
in any discussion (i) with any representative of any corporation or corporations
regarding the consolidation or merger of the Company with or into any such
corporation or corporations, (ii) with any corporation, partnership, association
or other business entity or any individual regarding the sale, conveyance or
disposition of all or substantially all of the assets of the Company or a
transaction or series of related transactions in which more than fifty percent
(50%) of the voting power of the Company is disposed of, or (iii) regarding any
other form of acquisition, liquidation, dissolution or winding up of the
Company.


                                        9
<PAGE>   14

         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 Purchaser 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.

         3.10 Assumptions or Guaranties of Indebtedness of Other Persons. Except
as contemplated hereby or consented to by the Purchaser 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 Purchaser 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 solicited 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 Purchaser 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


                                       10
<PAGE>   15

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) 300,000,000 shares of Common Stock,
par value $.01 per share, of which 19,222,655 shares are issued and outstanding
and (ii) 10,000,000 shares of Preferred Stock, par value $.01 per share, of
which (A) 1,100,000 shares are designated as Series A Convertible Preferred
Stock, all of which shares are issued and outstanding on the date hereof, (B)
1,327,500 shares are designated as Series B Convertible Preferred Stock, all of
which shares are issued and outstanding on the date hereof, (C) 145,195 shares
are designated as Series C Convertible Preferred Stock, of which no shares are
issued and outstanding on the date hereof, (D) 685,194 shares are designated as
Series D Convertible Preferred Stock, all of which shares are issued and
outstanding on the date hereof, and (D) 1,867,480 shares are designated as
Series E Convertible Preferred Stock, of which no shares are issued and
outstanding on the date hereof, prior to giving effect to the transactions
contemplated hereby. Set forth on Exhibit 3.15 is the number of issued and
outstanding shares of the capital stock of the Company. 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 and the Converted Shares, when issued and delivered upon
conversion of the Preferred 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, the Amended and
Restated Registration Rights Agreement, the Certificate of Incorporation and
stock restriction and right of first refusal agreements between the Company and
certain of its employees. 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 Purchaser and certain other parties
pursuant to the Amended and Restated Registration Rights Agreement, 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.


                                       11
<PAGE>   16

         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 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. The Company has taken all reasonable and
customary actions to maintain and protect its Intellectual Property Rights.
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, or processor based
system and/or any combination thereof, developed, manufactured, distributed,
licensed or delivered, by the Company (collectively, the "System"), shall in all
material respects 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,


                                       12
<PAGE>   17

before, during or after January 1, 2000 than heretofore with respect to dates
prior to January 1, 2000.

         3.20 Financial Statements. Attached hereto as Exhibit 3.20 are copies
of the unaudited balance sheets of the Company as of December 31, 1998 and May
31, 1999, the statements of income and retained earnings of the Company for the
period ended December 31, 1998 and for the five months ended May 31, 1999, and
the statements of cash flows of the Company for the period ended December 31,
1998 and for the five months ended May 31, 1999 (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 Changes. Except as set forth in Exhibit 3.21, since May 31, 1999,
there has not been:

                  (a) any adverse change in the assets, liabilities, financial
condition or operating results of the Company from that reflected in the
Financial Statements, except changes in the ordinary course of business that
have not been, in the aggregate, materially adverse;

                  (b) any damage, destruction or loss, whether or not covered by
insurance, materially and adversely affecting the assets, properties, financial
condition, operating results or business of the Company;

                  (c) any waiver by the Company of any valuable right or of a
debt owed to it;

                  (d) any satisfaction or discharge of any lien, claim or
encumbrance or payment of any obligation by the Company, except in the ordinary
course of business and that is not material to the assets, properties, financial
condition, operating results or business of the Company;

                  (e) any change or amendment to a material contract or
arrangement by which the Company or any of its assets or properties is bound or
subject;

                  (f) any change in any compensation arrangement or agreement
with any employee;

                  (g) any sale, assignment or transfer of any patents or patent
applications, trademarks or trademark applications, service marks, trade names,
corporate names, copyrights or copyright registrations, trade secrets or other
intangible assets, or disclosure of any proprietary information to any person;

                  (h) any resignation or termination of employment of any key
officer of the Company; and the Company, to the best of its knowledge, does not
know of the impending resignation or termination of employment of any such
officer;


                                       13
<PAGE>   18

                  (i) any declaration, payment, setting aside or other
distribution of cash or other property to its holders with respect to its
capital stock or other equity securities (including without limitation any
warrants, options or other rights to acquire its capital stock or other equity
securities;

                  (j) any mortgage, pledge, transfer of a security interest in,
or lien, created by the Company, with respect to any of its properties or
assets, except liens for taxes not yet due or payable;

                  (k) receipt of notice that there has been a loss of, or order
cancellation by, any major customer of the Company;

                  (l) made any charitable contributions or pledges;

                  (m) make capital expenditures or commitments (other than with
respect to the deployment of servers) therefor that aggregate in excess of
$100,000;

                  (n) make any loans or advances to, guarantees for the benefit
of, or any investments in, any person (including but not limited to any of the
Company's employees, officers or directors, or any members of their immediate
families), corporation, partnership, joint venture or other entity;

                  (o) to the best of the Company's knowledge, any other event or
condition of any character that might materially and adversely affect the
assets, properties, financial condition, operating results or business of the
Company; or any agreement or commitment by the Company to do any of the things
described in this Section 3.21.

         3.22 No Undisclosed Liabilities. Except as set forth on Exhibit 3.22,
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 Financial Statements, in the ordinary course of business consistent
with past practice, the sum of which is, in the aggregate, no greater than
$300,000; 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 $300,000.

         3.23 Technology. Except as set forth in Exhibit 3.23, the proprietary
technology, information, products, processes and services 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 proprietary products, processes and technology. No
independent contractors or consultants were used or employed by the Company in
the development of proprietary technology and other proprietary know-how owned
or used by the Company.


                                       14
<PAGE>   19

         3.24 Permits. The Company has all franchises, permits, licenses and any
similar authority necessary for the conduct of its business, and the Company
believes it can obtain, without undue burden or expense, any similar authority
for the conduct of its business as planned to be conducted. The Company is not
in default in any material respect under any of such franchises, permits,
licenses or any other similar authority.

         3.25 Environmental and Safety Laws. The Company, the operation of its
business and any real property that the Company owns or has owned, leases or has
leased or otherwise occupies or uses or has occupied or used (the "Premises")
are, to the best of the Company's knowledge, in compliance with all applicable
Environmental Laws (as defined below) and orders or directives of any
governmental authorities having jurisdiction over such Environmental Laws. The
Company has not received any citation, directive, letter or other communication,
written or oral, or any notice of any proceeding, claim or lawsuit, from any
person arising out of the ownership or occupation of the Premises, or the
conduct of its operations, and the Company is not aware of any basis therefor.
To the best of the Company's knowledge, no material expenditures are or will be
required in order to comply with any Environmental Laws. For purposes of this
Agreement, the term "Environmental Laws" shall mean any Federal, state, local or
foreign law, ordinance, rule, regulation, permit and authorization pertaining to
the protection of human health or the environment.

         3.26 Corporate Documents; Minute Books. Except for amendments necessary
to satisfy representations and warranties or conditions contained herein (the
forms of which amendments have been approved by the Purchaser or its counsel),
the Company's Certificate of Incorporation, as amended, and By-laws, as amended,
are in the forms previously provided to counsel to the Purchaser. The minute
books of the Company provided to the Purchaser or its counsel contain a summary
of all meetings of directors and stockholders since the time of incorporation
and reflect all transactions referred to in such minutes accurately in all
material respects.

         3.27 Labor Agreements and Actions. Except as set forth in Exhibit 3.27,
the Company is not aware that any officer or key employee, or that any group of
employees of the Company, intends to terminate their employment with the
Company, nor does the Company have a present intention to terminate the
employment of any of the foregoing. The employment of each officer and employee
of the Company is terminable at the will of the Company. The Company has
complied in all material respects with all applicable state and federal equal
employment opportunity and other laws related to employment (including without
limitation provisions thereof relating to wages, hours, equal opportunity,
collective bargaining and the payment of social security and other taxes), and
the Company is not aware that it has any labor relations problems (including
without limitation any union organization activities, threatened or actual
strikes or work stoppages or material grievances). The Company is not bound by
or subject to (and none of its assets or properties is bound by or subject to)
any written or oral, express or implied, contract, commitment or arrangement
with any labor union.


                                       15
<PAGE>   20

                                   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 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.

                  (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,


                                       16
<PAGE>   21

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 to
the President of the Company, the Purchaser (provided the Purchaser 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
financial and employment records and books of the Company, to visit and inspect
the properties of the Company and any Subsidiary, to discuss the finances and
other matters of the Company and any Subsidiary not related to the Company's
customers, licensees, licensors, strategic partners and suppliers with any of
its officers, directors or Key Employees and independent accountants, and to
consult with and advise the management of the Company and any Subsidiary as to
their finances and other matters not related to the Company's customers,
licensees, licensors, strategic partners and suppliers, all at reasonable times
and upon reasonable notice to the President of the Company. The Purchaser agrees
that it will maintain the confidentiality of any information so obtained by it
which is not otherwise available from other sources.

                  (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.

                  (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.


                                       17
<PAGE>   22

                  (i) Public Announcements. Subject to applicable laws that may
require disclosure by the Company, any public announcements by the Company
relating to this Series E Preferred Stock financing shall be mutually agreed
upon by the Company and the Purchaser.

         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 E 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, Series C Preferred Stock, Series D
Preferred Stock and Series E 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:

                           (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 merger with a Subsidiary or a consolidation 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 $1.2 billion), 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 $1.2
billion).

                  (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


                                       18
<PAGE>   23

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 or the Series E 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 stock restriction and right of first
refusal agreements or similar agreements) 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 Purchaser 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 the Purchaser.

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


                                       19
<PAGE>   24

         4.03 Reporting Requirements. For as long as at least 35,000 of the
Preferred Shares remain outstanding (as equitably adjusted for stock splits,
stock dividends and the like), the Company will furnish the Purchaser:

                  (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 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: 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 for the forthcoming fiscal year: as soon as
available after approval by the Board of Directors;

                  (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;


                                       20
<PAGE>   25

                  (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 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 E Convertible Preferred Stock Purchase
Agreement as from time to time amended and in effect between the parties,
including all Exhibits hereto.

         "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, 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


                                       21
<PAGE>   26

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.

         "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.


                                       22
<PAGE>   27

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

         "Purchaser" shall have that meaning attributable to it in Section 1.01
of this Agreement.

         "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 October 16, 2000, or (y) 3.0 times the then Series B Conversion
Price if the public offering occurs on or after October 16, 2000.

         "Reserved Employee Shares" means shares of Common Stock, not to exceed
in the aggregate 11,377,800 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 7,559,226
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 2,132,100 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, Series C Preferred Stock, Series D Preferred
Stock and Series E 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 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 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.

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

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


                                       23
<PAGE>   28

         "Series E Preferred Stock" means the Series E Convertible Preferred
Stock of the Company, par value $.01 per share, having the rights, powers,
privileges and preferences set forth in Exhibit 1.01 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 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 E 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 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,
Series C Preferred Stock, Series D Preferred Stock and Series E Preferred Stock,
voting together as a single class on a Common Stock equivalent basis.
Notwithstanding the foregoing proviso, no amendment or waiver approved in
accordance herewith shall be effective if and to the extent such amendment or
waiver treats the holders of any series of preferred stock of the Company
differently than the holders of any other series of preferred stock of the
Company, unless the written consent of a majority of such series shall have been
obtained. 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.


                                       24
<PAGE>   29

         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 below 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 the Purchaser: at 170 West Tasman Drive, San Jose, California
95134 or at such other address as shall be designated by the Purchaser in a
written notice to the Company 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 Purchaser 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.

         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 Purchaser,
including legal, accounting and other expenses, up to a maximum of $20,000. 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 Purchaser 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 Purchaser 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. Any
transfer of Shares by the Purchaser shall be in accordance with Section 1.05(a)
and shall be subject to the concurrent assumption by the transferee of all the
rights and obligations of the Purchaser hereunder. The rights and obligations of
the parties hereunder (including without limitation the rights and obligations
under Section 1.05) shall remain in effect indefinitely unless terminated in
accordance with their terms or upon written agreement of the Company and the
Purchaser.

         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 and the documents referred to
herein constitute the entire agreement between the parties and supersedes any
prior understandings or agreements concerning the purchase and sale of the
Shares.


                                       25
<PAGE>   30

         6.08 Severability. The provisions of this Agreement and the terms of
the Series E 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 E 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 E Preferred Stock; but this Agreement and the terms of the Series E
Preferred Stock, 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.

         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 the Purchaser or the Company, the Company and the Purchaser
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
Purchaser 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 Purchaser shall be deemed to have suffered a Loss as a result of the
untruth, inaccuracy or breach of any such representations or warranties if a
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, the Purchaser shall deliver
to the Company a notice (the "Loss Notice") specifying in reasonable detail the
nature and estimated amount of the Loss. 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.


                                       26
<PAGE>   31

                  (b) The representations and warranties of the Company set
forth in this Agreement shall survive the Closing until August 6, 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 August 6, 2000, and (ii) the representations and warranties set forth in
Section 3.15 shall survive the Closing forever and shall not terminate.

                  (c) Beginning 10 days after delivery of the Loss Notice, the
Company and the Purchaser shall 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 E Preferred Stock after giving
effect to the Loss (the "Current Series E Value"). If no such agreement can be
reached, the Company and the Purchaser 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 and the
Current Series E Value. Each of the arbitrators shall be a member in good
standing of the American Arbitration Association. The Company and the Purchaser
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 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.


                                       27
<PAGE>   32

         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/ Paul Sagan
                                                  ----------------------------
                                                  Paul Sagan
                                                  President

PURCHASER:                                   CISCO SYSTEMS, INC.


                                             By:  /s/ John Chambers
                                                  -----------------------------
                                             Name: John Chambers
                                             Title:


                                       28