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Employment Agreement - IntraLinks Inc. and James Dougherty

Employment Forms

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                                                                  EXECUTION COPY


                             EMPLOYMENT AGREEMENT

          This Agreement is made as of this 10th day of January, 2000 by and
between IntraLinks, Inc., a Delaware corporation (the "Company") and James
Dougherty (the "Executive"), an individual residing at [Address].

     1.   Term. Executive shall be employed by the Company for a period
          ----
commencing on January 10, 2000 and, except as provided herein, ending two (2)
years from such date (the "Initial Term"). The Initial Term and each successive
term thereafter shall automatically renew for successive one (1) year periods
unless either party provides one hundred and twenty (120) days prior written
notice of its intention not to renew (the Initial Term and any subsequent
renewal term, the "Term"). A failure not to renew this Agreement shall not
constitute a termination of Executive's employment.

     2.   Position; Duties. Executive shall serve as the President and Chief
          ----------------
Operating Officer of the Company, reporting to the Chief Executive Officer of
the Company, and shall perform such duties as requested by the Chief Executive
Officer of the Company and as are normally assigned to a person of the
Executive's title and position at a corporation of the size and nature of the
Company. During the Term hereof, Executive shall devote substantially all of his
business time and attention to the business and affairs of the Company and use
his best efforts to promote the business, affairs and reputation of the Company.
Executive may serve as a Director of other companies that do not in any way
compete with the business of the Company provided that serving on such board(s)
does not interfere with the performance of his duties hereunder. Executive shall
also be entitled to observer status at regularly called meetings of the Board of
Directors of the Company.

     3.   Compensation.
          ------------

          (a)  Base Salary. For services rendered to the Company hereunder, the
               -----------
Company shall pay Executive a salary equal to $275,000 per year (the "Base
Salary"). The Board of Directors of the Company shall annually review the Base
Salary for increases.

          (b)  Bonus Plan. Executive shall work with Senior Management and the
               ----------
Board of Directors of the Company to establish a Company bonus plan which the
Company intends shall have a commencement date of January 1, 2000. Executive,
together with all other eligible executives and employees of the Company shall
be eligible to participate in such bonus plan and receive up to fifty percent
(50%) of his salary as part of such plan. In the event such a bonus plan is not
adopted in calendar year 2000 and Executive is terminated without Cause (as
defined in Section 7(a) hereof) during calendar year 2000, Executive shall be
eligible for a bonus for calendar year 2000 of up to fifty percent (50%) of his
base salary, to be paid in conformity with any other
<PAGE>

bonuses awarded to Senior Officers of the Company, based on the achievement of
mutually agreed upon objectives.

     4.   Stock Options. In conjunction with the execution of this Agreement,
          -------------
the Executive shall be issued 338,722 Incentive Stock Options (constituting, as
of the date hereof, 3.2% of the Company's outstanding shares of Common Stock on
a fully diluted basis) pursuant to the Company's Stock Option Plan at an
exercise price of $10.40 per share. Such Incentive Stock Options shall vest in
accordance with Schedule A hereto, subject to Section 7(d) below.

     5.   Benefits. Executive shall be eligible to participate in all benefit
          --------
plans, on the same terms and conditions, as those benefit plans available to
other senior executives of the Company including, without limitation, retirement
and savings plans, medical/dental and hospitalization plans and life insurance.
Executive shall become eligible to participate in the Company's 401(k)
retirement plan as of the first designated plan entry date following the
completion of one year's employment with the Company. Executive shall also be
entitled to four (4) weeks per annum vacation with full pay.

     6.   Expense Reimbursement. The Company shall reimburse Executive for all
          ---------------------
reasonable out-of-pocket expenses incurred in the performance of his services
hereunder in accordance with the Company's applicable expense reimbursement and
related policies and procedures as in effect from time to time and subject to
submission by Executive of appropriate documentation reflecting the incurrence
of such expenses.

     7.   Termination of Employment.
          -------------------------

          (a)  Termination for Cause. Executive's employment under this
               ---------------------
Agreement may be terminated For Cause at any time, effective upon written notice
from the Chief Executive Officer of the Company after formal action by the Chief
Executive Officer and the Board of Directors at a special meeting duly called
for the purpose of considering the termination of Executive. "For Cause" shall
be deemed to mean one or more of the following: (i) Executive's embezzlement or
misappropriation of funds, (ii) Executive's conviction of a felony involving
moral turpitude, (iii) Executive's commission of material acts of dishonesty,
fraud, or deceit, or (iv) Executive's habitual or willful neglect of duties
(after notice and 30 days' opportunity to cure) or breach of the terms and
provisions of this Agreement, the Agreements to be executed in connection
herewith attached as Exhibit 7(a) hereto, or the policies of the Company known
to Executive. In the event that Executive is terminated For Cause, Executive
shall (i) be paid all Base Salary earned, accrued or owing to him under this
Agreement through the date of termination but not yet paid, (ii) forfeit all
rights to all unvested stock options granted to Executive, and (iii) no longer
be entitled to receive any other compensation or benefits thereafter.

                                       2
<PAGE>

          (b)  Termination without Cause; Termination Upon Expiration and Non-
               ---------------------------------------------------------------
Renewal.
-------

               (i)     The Company may, at any time, terminate this Agreement
without Cause on written notice to Executive. For purposes hereof, the
termination of this Agreement by Executive at his initiative following the date
on which he learns of the occurrence of any of the following events shall
constitute termination without Cause:

                       (A)    a reduction in Executive's then current Base
Salary, which reduction is not the result of across-the-board Company action
reducing current Base Salary;

                       (B)    the removal of Executive as President and Chief
Operating Officer of the Company;

                       (C)    a material diminution in Executive's duties or the
assignment to Executive of duties that materially impair his ability to perform
the duties normally assigned to a person of his title and position at a
corporation of the size and nature of the Company; and

                       (D)    the failure of the Company to obtain by operation
of law or otherwise the assumption of its obligations to perform this Agreement
from any successor to all or substantially all of the assets of the Company
within forty-five (45) days after a merger, consolidation, sale or similar
transaction; and

                       (E)    the relocation of the Company's principal office
to a location more than fifty (50) miles from New York, New York.

               (ii)    If Executive's employment is terminated without Cause
(for any reason other than termination following Change of Control as defined in
Section 7(d) hereof),

                       (A)    the Company shall pay to Executive as liquidated
damages an amount equal to two (2) years of Executive's Base Salary and a pro-
rata portion of any bonus earned by Executive (and not yet paid) provided that
any targets or other requirements set by the Board of Directors in connection
with the grant of such bonus have been met on a pro-rata basis;

                       (B)    the Company shall pay to Executive any other
amount (including any portion of Base Salary) earned, accrued or owing to
Executive through the date of termination but not yet paid; and

                       (C)    vested stock options shall remain exercisable for
the remainder of their terms and granted but unvested options which would vest
by their

                                       3
<PAGE>

terms within 12 months of any such termination without Cause shall automatically
vest and shall remain exercisable for the remainder of their terms.

          Amounts payable hereunder shall be paid in monthly installments or, at
the option of the Company, in a lump sum.

          (c)  Termination Upon Death or Disability. This Agreement shall
terminate automatically upon Executive's death. In the event of termination of
Executive's employment as a result of death, the Company shall (i) continue to
pay to Executive's estate, on a monthly basis, his Base Salary for a period of
six (6) months from the date of death and (ii) any other amounts earned, accrued
or owing to Executive under this Agreement through the date of death but not yet
paid. Furthermore, all stock options vested at the time of death shall remain
exercisable for the remainder of the terms relating to such stock options.

          This Agreement shall terminate at the option of the Company if
Executive shall suffer "disability." For purpose hereof, "disability" shall be
defined to mean Executive's inability, due to physical or mental incapacity, to
substantially perform his duties and responsibilities under this Agreement for a
period of sixty (60) days from the date of such disability as determined by an
approved medical doctor selected by the mutual agreement of the parties hereto.
In the event that the parties hereto cannot agree on an approved medical doctor,
each party shall select a medical doctor and the two doctors shall select a
third medical doctor who shall serve as the approved medical doctor hereunder.
The Company shall notify Executive in writing of its decision to terminate this
Agreement due to Executive's disability. In the event of termination of
Executive's employment as a result of "disability," the Company shall (i) pay to
Executive, on a monthly basis, for a period of six (6) months from the date of
disability, an amount equal to his monthly Base Salary minus any monthly payment
received by Executive from any Company purchased disability policy and (ii)
continue Executive's participation in Company benefit plans in which he
participated immediately prior to such termination for a period equal to the
lessor of (A) twelve (12) months or (B) the remainder of the term of this
Agreement. Furthermore, upon any such termination by reason of "disability," all
vested stock options shall remain exercisable for the remainder of their
respective terms.

          (d)  Change of Control. If, within twelve (12) months after a Change
               -----------------
of Control of the Company (as hereinafter defined) (i) Executive is no longer
President and Chief Operating Officer of the Company, or the surviving entity of
such transaction (without regard to any parent/subsidiary relationship) for any
reason other than expiration of the Term of this Agreement, (ii) Executive's
duties or responsibilities are substantially and materially diminished, or (iii)
Executive's current position in the chain of command of the Company or surviving
entity of such transactions (without regard to any parent/subsidiary
relationship) is materially diminished, Executive may be conclusively deemed, in
the sole discretion of Executive, to have been terminated without cause and
shall therefore be entitled to the benefits set forth in Sections 7(b)(ii)(B)
and 7(b)(ii)(C)

                                       4
<PAGE>

hereof. Furthermore, upon any such termination, stock options granted but not
yet vested which would vest by their terms within 12 months of such termination
without Cause shall automatically vest and shall remain exercisable for the
remainder of their terms. Executive shall give the Board of Directors of the
Company or any surviving entity, written notice of his termination without cause
hereunder and exercise of his rights under Section 7(b) hereof.

          For purposes of this Agreement, "Change of Control" shall be deemed to
occur if any of the following have occurred:

               (i)     any "person," as such term is currently used in Section
13(d) of the Securities Exchange Act of 1934, becomes a "beneficial owner," as
such term is currently used in Rule 13d-3 promulgated under that Act of fifty
percent (50%) or more of the Voting Stock of the Company. For purposes of this
Agreement, Voting Stock shall mean the issued and outstanding capital stock or
other securities of any class or classes having general voting power under
ordinary circumstances, in the absence of contingencies, to elect the directors
of a corporation.

               (ii)    a majority of the Board of Directors of the Company
consists of individuals other than Incumbent Directors, which term means the
members of the Board on the date hereof; provided that any individual becoming a
director subsequent to such date whose election or nomination for election was
supported by two-thirds of the directors who then comprised the Incumbent
Directors shall be considered to be an Incumbent Director;

               (iii)   the Board of Directors of the Company adopts any plan of
liquidation providing for the distribution of all or substantially all of the
Company's assets;

               (iv)    all or substantially all of the assets or business of the
Company are disposed of in any one or more transactions pursuant to a merger,
consolidation or other transaction (unless the shareholders of the Company
immediately prior to such merger, consolidation or other transaction
beneficially own, directly or indirectly, in substantially the same proportion
as they owned the Voting Stock of the Company, all of the Voting Stock or other
ownership interests of the entity or entities, if any, that succeed to the
business of the Company); or

               (v)     the Company combines with another company and is the
surviving corporation but, immediately after the combination, the shareholders
of the Company immediately prior to the combination hold, directly or
indirectly, fifty percent (50%) or less of the Voting Stock of the combined
company, (there being excluded from the number of shares held by such
shareholders, but not from the Voting Stock of the combined company, any shares
received by affiliates of such other company in exchange for securities of such
other company).

                                       5
<PAGE>

     8.   Non-Competition, etc.
          --------------------

          (a)  Executive covenants and agrees that during the Term plus two (2)
years after termination or expiration hereof, he will not, either directly or
indirectly (as agent, employee, advisor (whether or not paid), director,
officer, stockholder, partner or individual proprietor, or as an investor who
has made an advance, loan or contribution to capital), compete in the geographic
area of North America with the Company or with any subsidiary affiliated company
or division of the Company in the Company's business of providing services that
allow companies to manage, through the internet, business processes generally
characterized by multiple collaborating parties, volumes of information,
repeated cycles of revision or review of documents or information and a need for
high levels of security, or any other commercially viable product developed
during Executive's employment with the Company.

          (b)  Executive covenants and agrees that during the Term plus two (2)
years after any termination under this Agreement, he will not contact or solicit
business that competes with the Company's business from persons who, during the
Term, were customers of the Company or its subsidiaries, affiliated companies or
divisions, or induce such persons to do business with any person other than the
Company or its affiliated subsidiaries, companies or divisions. Executive also
agrees that during the Term plus two (2) years after any termination under this
Agreement, he will not solicit or encourage any person who, on the date of the
end of the Term or the date of termination under this Agreement, was an employee
of the Company (or its subsidiaries, affiliated companies or divisions) to:

               (i)     terminate his employment with the Company (or any of its
subsidiaries, affiliated companies or divisions); or

               (ii)    become affiliated with any company or business which is
in a similar business to that of the Company (or any of its subsidiaries,
affiliated companies or divisions) or in which Executive, either directly or
indirectly (as an agent, employee, director, officer, stockholder, partner or
individual proprietor, or as an investor who has made advances on loans or
contributions to capital), has an interest.

     9.   Indemnification. The Company will indemnify Executive to the fullest
          ---------------
extent permitted (including payment of legal expenses as incurred) by law or the
Company's by-laws. Executive shall be entitled to the protection of any
insurance policies the Company may elect to maintain generally for the benefit
of its directors and officers.

     10.  Compliance with Laws. Executive hereby covenants and agrees to comply
          --------------------
with all federal and state laws and regulations relating to or arising out of
his employment hereunder, including, without limitation, any and all federal and
state securities laws.

                                       6
<PAGE>

     11.  Confidentiality and Other Agreements. As a condition to the Company's
          ------------------------------------
performance of its obligations hereunder, Executive shall enter into and execute
contemporaneously with the execution hereof, those agreements attached hereto as
Exhibit 7(a).

     12.  Remedies for Breach. Executive acknowledges that his violation of any
          -------------------
of the provisions of Section 8 of this Agreement or of the provisions of any of
the related agreements set out in Schedule 7.1(a) hereof will cause irreparable
injury to the Company and that Executive agrees that, in any case, the Company
shall be entitled to seek, in addition to any other rights and remedies the
Company may have at law or in equity, an injunction enjoining and restraining
Executive from doing or continuing to do any act which violates any provision of
this Agreement.

     13.  Miscellaneous. This Agreement shall be governed by and construed in
          -------------
accordance with the laws of the State of New York without regard to any conflict
of laws provisions thereof.

          (a)  Any notices required shall be in writing and shall be deemed to
be duly made or given when mailed by registered or certified mail, return
receipt requested to:

               Mr. James Dougherty
               33 Wilton Road
               Pleasantville, NY 10570

               IntraLinks, Inc.
               1372 Broadway, Suite 12A
               New York, New York 10018
               Attn: Mr. Mark Adams

          (b)  This Agreement shall not be amended except by a writing signed by
both parties hereof. This Agreement may be executed in counterpart signature
pages, which when taken together with signature of all parties, shall constitute
a complete original.

          (c)  In the event of a Change of Control, the Company will require the
successor to the Company as Executive's employer to expressly assume and agree
to perform this Agreement in the same manner and to the same extent that the
Company would have been required to perform. This Agreement shall inure to the
benefit of Executive's personal or legal representatives, executors,
administrators, heirs, and successors. This Agreement shall not be assignable by
Executive. The Company may, at its sole option, transfer the Company's business
to a subsidiary or similar entity and assign this Agreement in its entirety to
such entity, which shall thereafter have the rights and obligations of the
Company hereunder. Such an assignment shall not constitute a

                                       7
<PAGE>

termination of Executive's employment or trigger any other rights or remedies of
Executive. Each of the parties hereto agrees to execute all documents and
instruments and to take or cause to be taken all actions which are necessary or
appropriate to facilitate such an assignment by the Company.

          (d)  Each party shall pay its own expenses in connection with the
negotiation, preparation and execution of this Agreement.

          (e)  Each party hereto represents and warrants that they are not party
to any other agreement which would conflict with or interfere with the terms and
conditions of this Agreement.

          (f)  No waiver of any breach of any terms hereof shall be effective
unless made in writing signed by the party against whom enforcement of the
waiver is sought, and such waiver shall not be construed as a waiver of any
subsequent breach of that term or of any other term of the same or different
nature.

          (g)  The parties agree to submit all controversies, claims and matters
of difference in any way related to this Agreement or the performance or breach
of the whole or any part hereof, to arbitration in New York, New York, according
to the rules and practices of the American Arbitration Association. Any such
dispute shall be decided by three (3) arbitrators. Arbitration of any such
controversy, claim or matter of difference shall be a condition precedent to any
legal action thereon. Awards shall be final and binding on all parties to the
extent and in the manner provided by the laws of the State of New York.

                                       8
<PAGE>

          IN WITNESS WHEREOF, the undersigned have executed this Agreement as of
the first date above written.


                                        _______________________________
                                        James Dougherty



                                        INTRALINKS, INC.



                                        By: ____________________________
                                              Name:
                                              Title:

                                       9
<PAGE>

                                  Schedule A

                      Vesting of Incentive Stock Options



     84,681 Incentive Stock Options shall vest upon execution of this Agreement.

     50,809 Incentive Stock Options shall vest upon the consummation of the
     Company's Initial Public Offering of Common Stock.

     67,744 Incentive Stock Options shall vest at the end of the Company's
     fiscal year 2000.

     67,744 Incentive Stock Options shall vest at the end of the Company's
     fiscal year 2001.

     67,744 Incentive Stock Options shall vest at the end of the Company's
     fiscal year 2002.