INTRALINKS HOLDINGS, INC.


SEPARATION AND INDEPENDENT CONTRACTOR
SERVICES AGREEMENT


This Separation
and Independent Contractor Services Agreement (the “Agreement”) is made and entered into this 30th
day of August, 2012 by and between IntraLinks Holdings, Inc. and/or one or more of its subsidiaries (the “Company”),
and Anthony Plesner, residing at XXXXXXXXXXXXXXXXXXXX (“Contractor”).
Upon termination of Contractor’s employment with the Company, the Company desires to retain Contractor as an independent
contractor to perform consulting services for the Company and Contractor is willing to perform such services, on terms set forth
more fully below. In consideration of the mutual promises contained herein, the parties agree as follows:


1.EMPLOYMENT STATUS


(a)Effective
as of September 1, 2012 (the “Separation Date”), Contractor hereby resigns from his position of Chief Financial
Officer and Chief Administrative Officer of the Company, and as a Section 16 Officer of the Company, as well as any other officer
titles or senior executive roles he currently holds with the Company or any of its subsidiaries. In addition, Contractor hereby
irrevocably resigns as an employee of the Company effective as of the Separation Date. The Company hereby acknowledges and accepts
the foregoing resignations of Contractor. Prior to the Separation Date, Contractor will sign all reports required to be filed
by Section 13 or 15(d) of the Securities Exchange Act of 1934 and related documents.


(b)On the first
regular payroll date following the Separation Date, the Company will pay Contractor a lump sum (less applicable taxes and withholding)
equal to all accrued but unpaid salary, and accrued but unused vacation or PTO time as of the Separation Date. The Company will
also reimburse Contractor for all business-related expenses that he incurred prior to the Separation Date so long as such expenses
are accompanied by supporting receipts and are submitted and approved in accordance with the Company’s regular practices.
The Separation Date shall be the date of the “qualifying event” under the Consolidated Omnibus Budget Reconciliation
Act of 1985 (“COBRA”).


(c)Other than
as specified herein and as otherwise required by law, Contractor affirms that any entitlement Contractor has or has had as an employee
of the Company under any Company benefit plan, program contract or policy, including the employment Agreement, dated as of March
18, 2005, by and between Intralinks, Inc. and the Contractor (the “Employment Agreement”), terminates as of
the Separation Date.


(d)Contractor
represents and warrants that he is not aware of any violation of law or Company policy by the Company or anyone acting on its behalf
or of any matter required to be disclosed by or on behalf of the Company to any local, state or federal governmental agency or
entity or self-regulatory agency that has not been so disclosed as required.


2.SERVICES AND COMPENSATION


(a)Contractor
agrees to perform the services (the “Services”) described in Exhibit A, attached hereto, for the
Company. Contractor shall provide the Services during the period beginning on the Separation Date and ending on June 30, 2013 (the
“Work Period”) unless sooner terminated in accordance with Section 10.


(b)During the
Work Period, the Company agrees to pay Contractor the compensation set forth in Exhibit A for the Services. Except
as noted on Exhibit A, all payments set forth in this Section 2 and on Exhibit A shall be subject to all applicable federal,
state and/or local taxes, and the Company may withhold from any amounts payable to Contractor (including any amounts payable pursuant
to this Agreement) in order to comply with such withholding obligations.






    	 



    	 	



    
(c)On the Separation
Date, Contractor agrees to sign the Release set forth in Exhibit B.


3.CONFIDENTIALITY


(a)“Confidential
Information” means any Company proprietary information, technical data, trade secrets or know-how, including, but not
limited to, all Work Product as defined in Section 3(a) below, research, product plans, products, services, customers, customer
lists, markets, source code, algorithms, software, developments, techniques, improvements, invention (whether patentable or not),
works of authorship, processes, formulas, technology, designs, drawings, engineering, hardware configuration information, marketing,
finances or other business information disclosed by the Company either directly or indirectly in writing, orally or by drawings
or inspection of parts or equipment. Without limiting the generality of the foregoing, Confidential Information shall include the
terms of this Agreement and any information relating to any Company employee, customer or supplier obtained in connection with
Contractor's relationship with the Company.


(b)Contractor
will not, during or subsequent to the term of this Agreement, use the Company's Confidential Information for any purpose whatsoever
other than the performance of the Services on behalf of the Company or disclose the Company's Confidential Information to any third
party except to the extent disclosure is required by law or legal process, or to enforce Contractor’s rights under this Agreement.
It is understood that said Confidential Information shall remain the sole property of the Company. Contractor further agrees to
take all reasonable precautions to prevent any unauthorized disclosure of such Confidential Information. Confidential Information
does not include information which: (i) is known to Contractor at the time of disclosure to Contractor by the Company as evidenced
by written records of Contractor, other than as a result of any prior services rendered by Contractor to the Company; (ii) has
become publicly known and made generally available through no wrongful act of Contractor; or (iii) has been rightfully received
by Contractor from a third party who, to Contractor’s knowledge, is authorized to make such disclosure. Contractor agrees
that Contractor will not, during the term of this Agreement, use for or disclose to the Company any proprietary information (including
but not limited to any trade secret) of any former or current employer of Contractor or other person or entity to the extent such
use or disclosure would violate any agreement, duty, law or regulation to which Contractor, or, to Contractor's knowledge, the
Company, is subject, unless consented to in writing by such employer, person or entity. Contractor will indemnify the Company and
hold it harmless from and against all claims, liabilities, damages and expenses, including reasonable attorney’s fees and
costs of suit, arising out of or in connection with any violation or claimed violation of any law, regulation or third party's
rights resulting in whole or in part from the Company's use of information or Work Product furnished by Contractor under this Agreement.


(c)Contractor
recognizes that the Company has received and in the future will receive from third parties their confidential or proprietary information
subject to a duty on the Company's part to maintain the confidentiality of such information and to use it only for certain limited
purposes. Contractor agrees that Contractor owes the Company and such third parties, during the term of this Agreement, a duty
to hold all such confidential or proprietary information in the strictest confidence and not to disclose it to any person, firm
or corporation or to use it except as necessary in carrying out the Services for the Company consistent with the Company's agreement
with such third party or as required by law or legal process.


(d)Upon the termination
of this Agreement, or upon the Company's earlier request, Contractor will deliver to the Company all of the Company's property
or tangible Confidential Information that Contractor may have in Contractor's possession or control.


4.OWNERSHIP


(a)Contractor
agrees that all works of authorship, notes, records, drawings, designs, inventions, improvements, developments, discoveries, ideas,
techniques, know-how and trade secrets, whether or not patentable, conceived, made or discovered by Contractor, solely or in collaboration
with others, during the period of this Agreement which relate in any manner to the business of the Company that Contractor may
be directed to undertake, investigate or experiment with, or which Contractor may become associated with in work, investigation
or experimentation in the line of business of the Company in performing the Services hereunder (collectively, “Work Product”),
are the sole property of the Company. In addition, any Work Product that constitute works of authorship shall be considered "works
made for hire" as that term is defined in the United States Copyright Act. Contractor further agrees to assign (or cause to
be assigned) and does hereby assign fully to the Company all Work Product and any copyrights, patents, mask work rights or other
intellectual property rights relating thereto.






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(b)Contractor
agrees to assist the Company, or its designee, at the Company's expense, in every proper and reasonable way to secure the Company's
rights in the Work Product and any copyrights, patents, mask work rights or other intellectual property rights relating thereto
in any and all countries, including the disclosure to the Company of all pertinent information and data with respect thereto, the
execution of all applications, specifications, oaths, assignments and all other instruments which the Company shall deem necessary
in order to apply for and obtain such rights and in order to assign and convey to the Company, its successors, assigns and nominees
the sole and exclusive right, title and interest in and to such Work Product, and any copyrights, patents, mask work rights or
other intellectual property rights relating thereto. Contractor further agrees that Contractor's obligation to execute or cause
to be executed, when it is in Contractor's power to do so, any such instrument or papers shall continue after the termination of
this Agreement.


(c)Contractor
agrees that if in the course of performing the Services, Contractor incorporates into any Work Product developed hereunder any
invention, improvement, development, concept, discovery, work or other proprietary information owned by Contractor or in which
Contractor has an interest, the Company is hereby granted and shall have a nonexclusive, royalty-free, perpetual, irrevocable,
worldwide license to make, have made, modify, use and sell such item as part of or in connection with such Work Product.


(d)Contractor
agrees that if the Company is unable because of Contractor's unavailability, dissolution, mental or physical incapacity, or for
any other reason, to secure Contractor's signature to apply for or to pursue any application for any United States or foreign patents
or mask work or copyright registrations covering the Work Product assigned to the Company above, then Contractor hereby irrevocably
designates and appoints the Company and its duly authorized officers and agents as Contractor's agent and attorney in fact, to
act for and in Contractor's behalf and stead to execute and file any such applications and to do all other lawfully permitted acts
to further the prosecution and issuance of patents, copyright and mask work registrations thereon with the same legal force and
effect as if executed by Contractor.


5.DISCLOSURE AND REPORTS


Contractor agrees
that Contractor will (i) promptly disclose in writing to the Company all Work Product, (ii) from time to time during the term of
this Agreement or any extension thereof keep the Company advised as to Contractor's progress in performing the Services hereunder,
and (iii) as requested by the Company, prepare written reports with respect thereto. It is understood that the time required in
the preparation of such written reports shall be considered time devoted to the performance of Contractor's Services.


6.NON-DISPARAGEMENT


(a)Contractor
agrees not to make disparaging, critical or otherwise detrimental comments to any person or entity concerning (i) the Company,
its officers, directors and employees; (ii) the products, services or programs provided or to be provided by the Company; (iii)
the business affairs or the financial condition of the Company; or (iv) the circumstances surrounding Contractor’s employment
or consulting relationship with the Company. Notwithstanding the foregoing, nothing in this Agreement shall prevent Contractor
from providing truthful testimony in the context of legal, investigative or related proceedings.


(b)The Company
agrees to instruct its officers, directors and senior managers not to make disparaging, critical or otherwise detrimental comments
to any person or entity concerning Contractor. Subject to compliance by Contractor with his obligations under this Agreement, the
Company agrees to provide Contractor with a favorable oral reference to a prospective employer or other third party. The Company
will direct all employer and other third party inquiries regarding Contractor’s relationship with the Company, including
his prior employment relationship, to the Company’s Chief Executive Officer or General Counsel. 






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7. FUTURE
COOPERATION



			Contractor agrees to cooperate reasonably with the Company and all of its affiliates (including
its and their outside counsel) in connection with the contemplation, prosecution and defense of all phases of existing, past and
future litigation or regulatory investigation about which the Company believes Contractor may have knowledge or information. Contractor
further agrees to make himself available at mutually convenient times during and outside of regular business hours as reasonably
deemed necessary by the Company’s counsel in connection with such litigation or regulatory investigation. Contractor agrees
to appear without the necessity of a subpoena to testify truthfully in any legal or regulatory proceedings in which the Company
calls Contractor as a witness or where the Company believes that his testimony is necessary to the Company’s defense in such
proceedings. The Company will endeavor to provide Contractor reasonable notice when requesting Contractor’s services under
this Section 7.




8. Sections
of the Employment Agreement, Stock and Option Agreements and Insider Trading Policy Still in Effect.




Contractor is a
party to the Employment Agreement, certain restricted stock and stock option agreements under the TA Indigo Holding Corporation
2007 Stock Option and Grant Plan, the IntraLinks Holdings, Inc. 2007 Stock Option and Grant Plan and the IntraLinks Holdings, Inc.
2010 Equity Incentive Plan (collectively, as modified herein, the “Stock and Option Agreements”) and is subject
to the IntraLinks Holdings, Inc. Statement of Company Policy on Insider Trading and Disclosure (the “Insider Trading Policy”).
Contractor acknowledges that certain of Contractor’s obligations under the Employment Agreement, the Stock and Option Agreements
and the Insider Trading Policy were intended to, and do in fact, survive the termination of Contractor’s employment with
the Company. Contractor hereby reaffirms Contractor’s obligations existing under the Employment Agreement, including with
respect to noncompetition, non-solicitation and nondisclosure as set forth in Section 6 thereof, the Stock and Option Agreements
and the Insider Trading Policy all of which are incorporated by reference into this Section 8 and shall remain in full force and
effect. Contractor further agrees and acknowledges that nothing contained in this General Release shall be construed to relieve
Contractor of such ongoing obligations including, without limitation, those set forth in Section 6 of the Employment Agreement.
Contractor further acknowledges that the payments and benefits provided under this Agreement are contingent upon Contractor’s
continued compliance with any ongoing obligations under the Employment Agreement, the Stock and Option Agreements and the Insider
Trading Policy and that such payments and benefits shall cease in the event Contractor breaches any of Contractor’s contractual
obligations set forth in the Employment Agreement, the Stock and Option Agreements or the Insider Trading Policy.


9.STANDARD OF PERFORMANCE


Contractor’s
performance under this Agreement shall be conducted with due diligence and in full compliance with the highest professional standards
of practice in the industry and all results will be Contractor’s independent work. Contractor shall comply with all applicable
laws and Company safety rules in the course of performing the Services. If Contractor’s work requires a license or permit,
Contractor has obtained that license or permit and it is in full force and effect.


10.CONFLICTING OBLIGATIONS


Contractor certifies that Contractor
has no outstanding agreement or obligation that is in conflict with any of the provisions of this Agreement, or that would preclude
Contractor from complying with the provisions hereof, and further certifies that Contractor will not enter into any such conflicting
Agreement during the term of this Agreement.


11.TERM AND TERMINATION


(a)This Agreement will commence on
the date first written above and will continue until the end of the Work Period, or until sooner terminated as provided below.






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(b)Notwithstanding
anything herein to the contrary, the Company may terminate this Agreement upon 30 days’ prior written notice if Contractor
refuses to or is unable to perform the Services (other than as a result of a medical disability) or is in breach of any material
provision of this Agreement, and Contractor fails to cure such failure of performance or breach within such notice period. The
parties agree to discuss any dispute giving rise to a notice of breach.


(c)Upon such termination
all rights and duties of the parties toward each other shall cease except:


(i)that the
Company shall be obliged to pay, within thirty (30) days of the effective date of termination, all amounts owing to Contractor
for Services completed and accepted by the Company prior to the termination date and related expenses, if any, in accordance with
the provisions of Section 1 (Services and Compensation) hereof; and


(ii)Sections 3,
4, 6, 7, 8, 11(c), 12, 13, 14, 15 and 16 shall survive termination of this Agreement. Both Contractor and the Company agree that
either of them is entitled to communicate Contractor’s obligations under this Agreement to any future or potential client
or employer of Contractor, and that Contractor is entitled to communicate with his advisors and family about the terms of this
Agreement.


12.SUBCONTRACTING; ASSIGNMENT


Contractor shall not
subcontract or assign any obligations hereunder to any third party without the express prior written consent of the Company. Neither
this Agreement nor any right hereunder or interest herein may be assigned or transferred by Contractor without the express written
consent of the Company.


13.INDEPENDENT
CONTRACTOR


Nothing in this Agreement
shall be construed in any way to constitute Contractor as an agent, employee or representative of the Company, but Contractor shall
perform the Services hereunder as an independent contractor. Contractor agrees to furnish (or reimburse the Company for) all tools
and materials necessary to accomplish this contract, and shall incur all expenses associated with performance, except as expressly
provided on Exhibit A of this Agreement. Contractor acknowledges and agrees that Contractor is obligated to report as income
all compensation received by Contractor pursuant to this Agreement, and Contractor agrees to and acknowledges the obligation to
pay all self-employment and other taxes that may be due thereon.


14.EQUITABLE
RELIEF


Contractor agrees
that it would be impossible or inadequate to measure and calculate the Company's damages from any breach of the covenants set forth
in Sections 3, 4, 6, 7 or 8 herein. Accordingly, Contractor agrees that if Contractor breaches Sections 3, 4, 6, 7 or 8, the Company
will have available, in addition to any other right or remedy available, the right to obtain from any court of competent jurisdiction
an injunction restraining such breach or threatened breach and specific performance of any such provision. Contractor further agrees
that no bond or other security shall be required in obtaining such equitable relief and Contractor hereby consents to the issuances
of such injunction and to the ordering of such specific performance.


15.GOVERNING
LAW AND LEGAL ACTIONS


This Agreement shall
be governed by the laws of the State of New York, without regard to its conflicts of laws principles. The parties hereby consent
to the jurisdiction of the state and federal courts located in New York, New York for the adjudication of any case or controversy
arising under or relating to this Agreement, and each party hereby irrevocably waives any right to a jury trial in any such action
or proceeding.






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16.NOTICES;
ENTIRE AGREEMENT


All notices under
this Agreement shall be addressed to the other party at the address shown below or such other address as either party may notify
the other of and shall be deemed given (i) upon delivery to the party to be notified if delivered by hand or professional courier
service or confirmed fax, or (ii) three days after deposited in the United States mail, postage prepaid, registered or certified
mail, return receipt requested. This Agreement is the entire agreement of the parties and supersedes any prior agreements between
them with respect to the subject matter hereof, except that the parties agree that the terms of that certain Indemnification Agreement
between Contractor and the Company dated November 29th, 2011 (the “Indemnification Agreement”) shall
remain in full force and effect pursuant to the terms thereof as shall the benefits of the Company’s Officers and Director’s
Insurance policies and except as provided in Section 8 of this Agreement.


17.COUNTERPARTS


This
Agreement may be executed in one or more counterparts, each of which shall be an original, but all of which together shall constitute
one and the same instrument.


 






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IN WITNESS WHEREOF, the
parties hereto have executed this Agreement as of the day and year first above written.



 


	 	

COMPANY


INTRALINKS HOLDINGS, INC.



	 	 
	 	By: 	/s/ RONALD
W. HOVSEPIAN
	 	Name: Ronald W. Hovsepian
	 	Title: President and Chief Executive Officer

Address: 150 E. 42nd Street, 8th
Floor

New York, NY 10017



 


	 	CONTRACTOR
	 	 
	 	By: 	/s/ ANTHONY
PLESNER
	 	Name: Anthony Plesner


Address: XXXXXXXXXXXXXXXX


XXXXXXXXXX


 



 






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EXHIBIT A TO SEPARATION AND INDEPENDENT
CONTRACTOR SERVICES AGREEMENT DATED AUGUST 30, 2012


SERVICES AND COMPENSATION


		1.	Contact.Contractor's principal Company
contacts shall be the Chief Financial Officer and General Counsel.



		2.	Services.



(a)The
services to be provided by Contractor during the Work Period shall include assisting the Company from time to time, at the request
of Chief Financial Officer or the General Counsel, in any matter reasonably related to the duties previously performed by Contractor
as an employee of the Company and such other transition duties or cooperation as may be reasonably requested from time to time,
including cooperating with the Company and all of its affiliates (including its and their outside counsel) in connection with the
contemplation, prosecution and defense of all phases of existing, past and future litigation (collectively, the “Services”).
Contractor shall control the means by which he provides Services, but acknowledges and agrees that the Company is retaining him
to provide the Services because his skills and knowledge are exceptional and unique and, therefore, that he will provide the Services
personally. The Company will provide Contractor with reasonable notice prior to requiring him to provide Services to the Company
during the Work Period that involve more than an immaterial time commitment by Contractor.


(b)It
is understood Services are provided on a non-exclusive basis and Contractor may accept employment with or become engaged to provide
services to other entities (subject to Section 6 of the Employment Agreement). The parties will cooperate to enable Contractor
to meet such other commitments in conjunction with performance of the Services. Acceptance or performance of such other commitments
(provided Contractor complies with Section 6 of the Employment Agreement) shall not constitute a breach of this Agreement by Contractor,
nor be a basis or justification for suspension or termination of this Agreement by the Company.


		3.	Compensation.



(a)The Company shall pay Contractor
a total of $ 100,000 during the term of this Agreement, at a monthly rate of $10,000 per month for each month during the Work Period,
pro-rated for any partial month of the Work Period.


(b)If, and only if, bonuses are
paid under the Company’s 2012 Executive Incentive Bonus Plan (the “Incentive Plan”), Contractor will receive
75% of any bonus amount he would have otherwise earned under the Incentive Plan had he remained an employee of the Company.


(c)The Company shall reimburse
Contractor for reasonable travel and business expenses incurred by Contractor in performing Services pursuant to this Agreement
and authorized in advance in writing.


(d)Contractor shall provide the
Company with monthly invoices detailing the fees and expense reimbursements that Contractor believes are due under this Agreement
by the 15th of each month during the Work Period, and shall itemize and provide receipts for expenses upon request.
The Company agrees to pay Contractor his monthly fee and any expenses due under an invoice by no later than the 30th
day of each month..






    	 



    	 



    
(e)In accordance with the terms
of the IntraLinks Holdings, Inc. 2007 Stock Option and Grant Plan (the “Plan”) and stock option award agreement
relating to the award of an option to purchase 100,000 shares of the Company’s common stock (the “Option Shares”)
granted by the Company to Contractor on February 26, 2010, the Company confirms and agrees that, subject to compliance by Contractor
of the terms and conditions contained in this Agreement (including the Release attached as Exhibit B hereto), the Option
Shares will continue to vest during the Work Period according to the vesting terms of the stock option award agreement relating
to the Option Shares and, on June 30, 2013, all of the Option Shares shall vest and become fully exercisable and non-forfeitable
if Contractor remains in continuous service until the last day of the Work Period. Contractor agrees to execute, acknowledge, and
deliver to the Company all such documents and agreements reasonably necessary, in the Company’s discretion, to enable the
Company to accomplish the objectives described in this Section 3(e). Contractor acknowledges and agrees that all of his other equity
awards issued under the Plan and the Intralinks Holdings, Inc. 2010 Equity Incentive Plan other than the Option Shares shall lapse
as of the Separation Date and will not be exercisable. Subject to the terms of the Plan, all of the Option Shares that have vested
will be exercisable for 90 days after the end of the Work Period. Any portion of the Option Shares that are not exercised during
such 90-day period will be immediately forfeited and become null and void. The exercise of any Option Shares shall be subject to
the terms of the Plan.


 



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EXHIBIT B TO SEPARATION AND INDEPENDENT
CONTRACTOR SERVICES AGREEMENT DATED AUGUST 30, 2012


Release


WHEREAS, Contractor was an employee-at-will
of the Company;


WHEREAS, the Company and Contractor
have agreed to amicably resolve all issues arising out of their employment relationship, including agreeing to payment of additional
consideration, as set forth below; and


WHEREAS, Contractor, in consideration
of the Separation and Independent Contractor Services Agreement between the Company and the Contractor dated August 30, 2012 (the
“Agreement”) and the payments made and to be made thereunder, has agreed to release and forever discharge the
Company from any and all liabilities, claims or obligations arising from the employment relationship.


NOW, THEREFORE, in consideration
of the covenants contained herein, and the promises set forth above, and for other good and valuable consideration, the receipt
and sufficiency of which is hereby acknowledged, the parties agree as follows:


		1.	Contractor acknowledges that Contractor’s employment terminated effective September 1, 2012.



		2.	Nothing in this Release shall be construed to prevent Contractor from filing a charge with, or participating in an investigation
conducted by any governmental agency, including, without limitation, the United States Equal Employment Opportunity Commission
(the “EEOC”), or applicable state/city fair employment practices agency, to the extent required or permitted
by law. Nevertheless, Contractor gives up the right to receive any relief whatsoever, including but not limited to financial benefit
or monetary recovery from any lawsuit filed or settlement reached by the EEOC or anyone else with respect to any claims released
and waived in this Agreement.



		3.	Notwithstanding paragraph 5, Contractor understands and agrees that by signing this Release, Contractor is not releasing claims
that relate to: (i) any claims arising after the date Contractor signs this Agreement; (ii) any claims for enforcement of the Agreement,
the Indemnification Agreement (as defined in Section 14 of the Agreement) or this Release; (iii) any rights or claims to workers’
compensation or unemployment benefits; (iv) claims for accrued, vested benefits under any employee benefit plan of the Company
in accordance with the terms of such plans and applicable law; (v) any claims or rights which cannot be waived by law and/or (vi)
any continuing rights for indemnification under the Company’s charter or bylaws in effect as of the date hereof or under
the Indemnification Agreement.



		4.	For good and valuable consideration including but not limited to the opportunity to enter into the Agreement and this Release,
Contractor, on behalf of himself, his heirs, executors, administrators, successors and assigns, hereby voluntarily and unconditionally
releases and waives his rights to pursue any and all legal claims, rights, debts, liabilities, demands, causes of action, obligations,
complaints, grievances, losses, covenants, contracts, agreements, promises, damages, lawsuits or administrative proceedings in
United States federal or state courts or administrative agencies, known or unknown, suspected or unsuspected, arising from the
beginning of the world through the date of this Release agreement, against the Company, its employee benefits plans, parent, subsidiary
or affiliated companies, and/or their respective present or former directors, officers, employees, agents and fiduciaries, including,
without limitation, any claims, lawsuits or administrative proceedings arising out of or in any way relating to the Contractor's
employment with the Company, termination or resignation from such employment. This Release and waiver shall include, but is not
limited to, any and all claims of unlawful employment discrimination in regard to citizenship, immigration status, national origin,
gender, sexual orientation, religion, race, physical or mental disability, marital status or age, whether such claims may be brought
pursuant to state or local law or the federal equal employment, fair employment, civil or human rights laws, codes, ordinances,
or the laws of the United States, including, but not limited to, the Americans With Disabilities Act, the Worker Adjustment and
Restraining Notification Act, the Age Discrimination in Employment Act (the “ADEA”), the Older Workers' Benefit
Protection Act, Title VII of the Civil Rights Act, as amended, the Family and Medical Leave Act, the Employee Retirement Income
Security Act of 1974, as amended, the Fair Labor Standards Act, as amended, New York's Executive Laws, New York’s Labor Laws,
New York City Human Rights Laws, the California Fair Employment and Housing Act, any provisions of the California Labor Code pertaining
to hours of work or the payment of wages, including (but not limited to) California Labor Code sections 200-272, 500-558, 1171-1205,
any Wage Orders promulgated by the California Industrial Welfare Commission, and any and all claims arising out of his employment
or lack of employment with the Company. This Release and waiver shall further include, but not be limited to, all claims under
local, state and federal law, including, but not limited to, wrongful employment termination, breach of express or implied contract
of employment, defamation, intentional infliction of emotional distress, negligent infliction of emotional distress, express or
implied tort, invasion of privacy, retaliation, breach of the covenant of good faith and fair dealing, or any other tort or contract
claim, or other claims for punitive or compensatory damages relating in any manner whatsoever to Contractor’s employment
or lack of employment with the Company.



 






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		5.	With respect to any claim of age discrimination brought pursuant to the ADEA, it is expressly understood that Contractor is
hereby waiving rights or claims under the ADEA in a “knowing and voluntary” manner, in accordance with the meaning
of those terms as set forth in 29 U.S.C. §626(f)(1). In connection therewith, Contractor, by signing this Release, hereby
acknowledges and represents that:



		a.	She/he has been advised that she/he has the opportunity to consult with an attorney in connection with the execution of this
Agreement, and that she/he has a period of up to twenty one (21) days in which to consider this Agreement, including his waiver
of statutory rights for age discrimination under this Agreement; and



		b.	in accordance with the provisions of 29 U.S.C. §626(f)(1), she/he shall have a period of seven (7) days following the
execution of this Agreement (the “Revocation Period”) in which to revoke this Agreement by providing written
notice of such revocation by hand or overnight courier service (e.g. FedEx, UPS) delivery to:







IntraLinks Holdings, Inc.


150 East 42nd St.,
8th Floor


New York, NY 10017


Attention: Human Resources


		6.	In further consideration of the Company’s willingness to pay amounts provided for in the Agreement and this Release to
which Contractor is not otherwise entitled, Contractor hereby agrees:



		a.	Not to allege that the ending of Contractor’s employment relationship with the Company suggests any violation of law
or Company policy;



		b.	Not to engage in actions contrary to the interests of the Company except: (i) to enforce the terms of the Agreement, the Indemnification
Agreement or this Release; (ii) pursue any rights to indemnification under the Company’s charter or bylaws in effect as of
the date hereof or the Indemnification Agreement; or (iii) to the extent required by law; provided, however, that if Contractor
receives a subpoena or similar demand relating in any way to the Company, Contractor shall promptly notify the Company so that
the Company shall have the ability to seek an appropriate protective order prior to Contractor making any disclosure in response
to such subpoena or demand;



		c.	Except as necessary or appropriate in connection with performing Services under the Agreement, not to remove from the custody
of the Company, any documents, facsimiles, computer tapes, disks or printouts, or other written or electronically-produced information
of a confidential nature;



 



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		d.	To return to the Company any Company property in the Contractor’s possession or otherwise given to Contractor for his
use, including but not limited to, credit cards, keys, identification badges, Company property, assets, manuals, notes, reports,
agreements of any kind or nature belonging to or pertaining to the Company, except that Contractor may retain his Company laptop
and iPhone provided all Confidential Information (as defined in the Agreement) has been removed from such devices, following expiration
of the Agreement;



		e.	To pay in full any outstanding balance on any corporate credit card issued to Contractor; and



		f.	To give to the Company all passwords/encryption keys for Company-related files which are password protected/encrypted.







		7.	Contractor represents and warrants that he : (i) is not aware of any violation of law or Company policy by the Company or anyone
acting on its behalf; (ii) is not aware of any matter required to be disclosed by or on behalf of the Company to any local, state
or federal governmental agency or entity or self-regulatory agency (each, a “Regulatory Entity”), including
but not limited to the U.S. Department of Labor, New York Department of Labor and/or the California Division of Labor Standards
Enforcement, California Department of Fair Employment and Housing, the U.S. Securities and Exchange Commission, the New York Stock
Exchange or the Equal Employment Opportunity Commission, that has not been so disclosed as required; or (iii) has not made or filed
any complaint, charge, or grievance against the Company with any Regulatory Entity.



		8.	This Release covers and includes all claims that Contractor has against the Company, whether actually known or not, despite
the fact that California Civil Code Section 1542 may provide otherwise. Each party expressly waives all rights and benefits available
to him / it in any capacity under the provisions of Section 1542, which provides as follows:







A general release does not extend
to claims which the creditor does not know or suspect to exist in his or her favor at the time of executing the release, which
if known must materially affect the settlement with the debtor.


		9.	Contractor affirms that, in making this Release, he is not relying on, and has not relied on, any representation or statement
by the Company or its attorneys with respect to any facts surrounding the termination of his employment or rights he may have or
assert in connection therewith. Contractor fully understands and warrants that, if any fact on which he relied in executing this
Release be found thereafter to be other than, or different from, the facts now believed by him to be true, Contractor expressly
accepts and assumes the risk of such possible difference in fact and acknowledges that this Release shall be and remains effective
notwithstanding any such difference in fact.



		10.	In the event Contractor so notifies the Company in writing of his decision to revoke this Release within the Revocation Period,
he will waive and forfeit any entitlement to the amounts identified in the Agreement, and the Company shall have no further obligation
to make said payments to Contractor. Both parties understand that Contractor’s decision to terminate this Release operates
to terminate Contractor’s employment effective as of September 1, 2012.



		11.	This Release shall be binding upon and shall inure to the benefit of the parties hereto and their heirs, administrators, executors,
representatives, successors, and assigns. Contractor represents and warrants that no person other than Contractor has any interest
or right in the matters referred to herein, that Contractor has the sole right and exclusive authority to execute this Release,
and that Contractor has not sold, assigned, transferred, conveyed, or otherwise disposed of any claim or demand relating to any
matter covered by this Release .



		12.	Should any of the provisions set forth herein be determined to be invalid by any court, agency or any other tribunal of competent
jurisdiction, such determination shall not affect the enforceability of the other provisions herein and, to this end, the provisions
of this Release are declared to be severable.



 



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		13.	No other consideration has or will be furnished or paid other than the consideration herein recited. Contractor acknowledges
and agrees that the payments set forth in the Agreement: (i) are in lieu of any termination benefits that Contractor may have been
entitled to under the IntraLinks, Inc. Senior Executive Severance Plan or other agreement, policy or plan of the Company in connection
with the termination of his employment with the Company; (ii) represent payments to which Contractor would not otherwise be entitled
to but for his agreement to and execution of the Agreement and this Release; and (iii) exceed any payment, benefit, or other thing
of value to which Contractor might otherwise be entitled under any policy, procedure or plan of the Company and/or any other agreement
between Contractor and the Company in connection with the termination of his employment with the Company.



		14.	Contractor and the Company agree that this Release may be executed in multiple counterparts, including a facsimile copy, and
that it is the intent of Contractor and the Company that a copy of this Release signed by either Contractor or the Company shall
be deemed to constitute an original, and shall be fully enforceable against such party.



		15.	The Agreement and Release embody the entire understanding and agreement of the parties hereto in relation to the subject matter
hereof and, with exception to the promises, agreements, and covenants referenced in paragraph 16, no promise, condition, representation
or warranty, express or implied, not set forth herein shall bind any party hereto. No provision of this Release may be modified,
waived or discharged, unless such modification or discharge is agreed to in a written document signed by both parties to this Release.
No waiver by either party hereto of any breach by the other party of any provision of this Release shall be deemed a waiver of
similar or dissimilar provisions at the same or at any prior or subsequent time. No such waiver by the Company shall be effective
unless it shall be set forth in writing and signed by the Chief Executive Officer of the Company.



		16.	Notwithstanding any provision hereof to the contrary, nothing in this Release shall supersede, cancel, or otherwise affect
any provisions of any confidentiality, non-competition and/or non-solicitation agreement and restrictive covenants in effect between
Contractor and the Company which survive the termination of Contractor’s employment with the Company. Contractor further
acknowledges the Company is and shall remain the sole owner of all rights, title, and ownership, intellectual property, and other
interests in and to any and all inventions, original works of authorship, developments, discoveries, improvements, derivative works,
algorithms, file layouts, formulas, computer programs, source or object code, compositions, trade secrets, designs, processes,
techniques, know-how and data, innovations and ideas, whether or not patentable, including, but not limited to, information regarding
products, procedures, methods, equipment, compositions, technology, formulas, research and development programs, sales methods,
cost of production and overhead, customer lists, customer usages and requirements, and other confidential technical or business
information, which Contractor has solely or jointly conceived or developed or reduced to practice within the scope of his employment
with the Company. Contractor acknowledges that all original works of authorship which have been made by him (solely or jointly
with others) within the scope of employment and which are protectable by copyright are "works made for hire," as that
term is defined in the United States Copyright Act of 1976, as amended.



		17.	The interpretation, construction and performance of this Release shall be governed by the laws of the State of New York, without
giving effect to the choice of law provisions of such jurisdiction. New York courts shall be the forum for resolving any dispute
relating to or arising under this Agreement. Contractor irrevocably submits to the exclusive jurisdiction of the federal and state
courts for the State of New York for purposes of any action, suit, or other proceeding arising out of or relating to this Release.







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EMPLOYEE:


 


	/s/ Anthony Plesner	 	Date:	August 30, 2012
	Anthony Plesner	 	 	 


 


IntraLinks Holdings,
Inc.


 


	By:	/s/ RONALD W. HOVSEPIAN	 	Date:	August 30, 2012
	 	Ronald W. Hovsepian	 	 	 
	 	President and Chief Executive Officer	 	 	 


 








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