Document:

INTRALINKS HOLDINGS,
INC.

SEPARATION AND
INDEPENDENT CONTRACTOR SERVICES AGREEMENT

(Individual)

This Separation
and Independent Contractor Services Agreement (the "Agreement") is made and entered into as of January 27, 2012
by and between IntraLinks Holdings, Inc. and/or one or more of it subsidiaries ("Company"), and David G. Curran,
residing at xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx ("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 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 January 27, 2012, Contractor hereby resigns from his position of Executive Vice President, Business and Legal
Affairs 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 March 31, 2012 (the “Separation Date”). Company hereby acknowledges and accepts
the foregoing resignations of Contractor.

(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. 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 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 Company. Contractor shall provide the Services during the period beginning on the Separation Date and ending on January
31, 2013 (the “Work Period”) unless sooner terminated in accordance with Section 9.

(b)          
During the Work Period, 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 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.

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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 4(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 Company.

(b)          
Contractor will not, during or subsequent to the term of this Agreement, use Company's Confidential Information for any
purpose whatsoever other than the performance of the Services on behalf of Company or disclose 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 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 Company
as evidenced by written records of Contractor, other than as a result of any prior services rendered by Contractor to 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 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 Company and
hold it harmless from and against all claims, liabilities, damages and expenses, including reasonable attorneys 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 Company has received and in the future will receive from third parties their confidential or
proprietary information subject to a duty on Company's part to maintain the confidentiality of such information and to use it only
for certain limited purposes. Contractor agrees that Contractor owes 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 Company consistent with Company's agreement
with such third party or as required by law or legal process.

(d)          
Upon the termination of this Agreement, or upon Company's earlier request, Contractor will deliver to Company all of 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 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 Company in performing the Services hereunder (collectively, "Work
Product"), are the sole property of Company. In addition, any Work Product which 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 Company, or its designee, at Company's expense, in every proper and reasonable way to secure
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 Company of all pertinent information and data with respect thereto,
the execution of all applications, specifications, oaths, assignments and all other instruments which Company shall deem necessary
in order to apply for and obtain such rights and in order to assign and convey to 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, 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 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 Company above, then Contractor hereby irrevocably
designates and appoints 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 Company all Work Product, (ii) from time to time during the term of this
Agreement or any extension thereof keep Company advised as to Contractor's progress in performing the Services hereunder, and
(iii) as requested by 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-SOLICITATION;
NON-DISPARAGEMENT

(a)          
Contractor agrees that during the term of this Agreement and for one (1) year thereafter, Contractor will not encourage or solicit
any employee of Company to leave the Company for any reason. Contractor also agrees not to make disparaging, critical or
otherwise detrimental comments to any person or entity concerning (i) Company, its officers, directors and employees; (ii) the
products, services or programs provided or to be provided by Company; (iii) the business affairs or the financial condition of
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. Company recognizes that Contractor cannot control the fact that he may receive unsolicited inquiries from
Company employees. 

(b)          
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. 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.

7.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.

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8.CONFLICTING
OBLIGATIONS

(a)            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.

(b)          
In view of Contractor's access to Company's trade secrets and proprietary know-how, Contractor further agrees, without limiting
any obligations set forth in Section 3 hereof, not to provide services substantially similar to the Services to or for the benefit
of any entity that competes directly with the Company for a period following the termination of this Agreement equal to (i) the
number of months this Agreement was in effect or (ii) twelve (12) months, whichever is shorter.

9.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.

(b)          
Notwithstanding anything herein to the contrary, 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 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 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, 8(b), 9(c), 10, 11, 12, 13 and 14 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.

10.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 Company.

11.INDEPENDENT
CONTRACTOR

Nothing in this Agreement
shall be construed in any way to constitute Contractor as an agent, employee or representative of Company, but Contractor shall
perform the Services hereunder as an independent contractor. Contractor agrees to furnish (or reimburse 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.

 

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12.EQUITABLE
RELIEF

Contractor agrees
that it would be impossible or inadequate to measure and calculate Company's damages from any breach of the covenants set forth
in Sections  3, 4, 6 or 8(b) herein. Accordingly, Contractor agrees that if Contractor breaches Sections 3, 4, 6 or 8(b),
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.

13.GOVERNING
LAW AND LEGAL ACTIONS

This Agreement shall
be governed by the laws of the Commonwealth of Massachusetts, without regard to its conflicts of laws principles. The parties hereby
consent to the jurisdiction of the state and federal courts located in Suffolk County, Massachusetts 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.

14.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 entered into in September 2010 and ratified through a Board of Directors Unanimous Written Consent
dated November 29, 2012 (collectively 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.

15.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
	 	150 E. 42nd Street
	 	8th Floor
	 	New York, NY 10017
	 	 
	 	CONTRACTOR
	 	 
	 	By: /s/ David G. Curran
	 	Name: David G. Curran
	 	Address:  xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx
	 	 

 

 

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EXHIBIT A TO SEPARATION
AND INDEPENDENT CONTRACTOR SERVICES AGREEMENT DATED JANUARY 27, 2012

SERVICES AND
COMPENSATION

1.Contact.Contractor's
principal Company contacts shall be the Chief Executive 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 Executive Officer
or the General Counsel, in any matter reasonably related to the duties previously performed by Contractor as an employee of, and
legal counsel to, 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 will not be providing legal services, advice or counsel in the provision of the Services hereunder and as of the Separation
Date, will no longer serve in the capacity of legal counsel to the Company. Contractor shall control the means by which he provides
Services, but acknowledges and agrees that 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 this is not
a fixed time based engagement. 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 8(b) of this 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 8(b) of this 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)Company shall pay Contractor
a total of $ 216,667.67 during the term of this Agreement, at a monthly rate of $21,666.67 per month for each month during the
Work Period, pro rated for any partial month of the Work Period.

(b)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.

(c)Contractor shall provide
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.
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..

(d)In accordance with the
provisions of COBRA and subject to Contractor’s election to continue COBRA coverage for his family and continued eligibility
under COBRA, the Company shall reimburse Contractor during the Work Period for premium payments to continue Contractor’s
current family dental and health coverage to the same extent and under the same available plans and rules, restrictions and regulations
applicable to active Company employees. Contractor will be responsible for the employee co-pay portion of such coverage and, following
the termination of the Work Period, Contractor will be responsible for any and all payments for the elected period of continued
health insurance coverage under COBRA.

    
	
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(e)Company confirms and agrees
that Contractor shall be eligible for any applicable cash bonus award that Contractor would have received had Contractor remained
an employee of the Company pursuant to Company’s Senior Executive Incentive Bonus Plan for fiscal year 2011 based on fiscal
2011 performance as contemplated thereunder. Any such bonus eligibility and payment shall be made under the same rules, restrictions
and regulations applicable to other participants under the Senior Executive Incentive Bonus Plan (except as modified hereby to
permit Contractor’s continued participation).

(f)In accordance with the
terms of the IntraLinks Holdings, Inc. 2010 Equity Incentive Plan (the “Plan”) and the restricted stock unit award
agreement relating to the award of 50,000 restricted stock units granted by the Company to Contractor on November 8, 2010 (the
“RSUs”), the Company confirms and agrees that for purposes of the RSUs the term “employment” shall include
Contractor’s Contractor relationship, such that the RSUs shall continue to vest until the termination of the Work Period.
In addition, subject to compliance by Contractor of the terms and conditions contained in this Agreement (including the Release
attached as Exhibit B hereto), the Company will accelerate the vesting of the entire then-remaining unvested portion of the RSUs
as of January 31, 2013 so that all 50,000 RSUs shall have vested as of that date. Contractor agrees to execute, acknowledge, and
deliver to Company all such documents and agreements reasonably necessary, in Company’s discretion, to enable Company to
accomplish the objectives described in this Section 3(f). Contractor acknowledges and agrees that all of his equity awards issued
under the Plan other than the RSUs that are not vested as of the Separation Date shall lapse on that date and will not be releasable
or exercisable. The release of any exercise of any stock options shall be subject to the terms of the Plan.

(g)In the event of Contractor’s
death or disability during the Work Period, the foregoing Compensation (payments, benefits, etc. set forth) payable to Contractor
under this Section 3 of Exhibit A shall be made to Contractor’s spouse (or other heirs in the event of such spouse’s
death).

(h)From the effective date
of this Agreement until the Separation Date, Contractor shall be permitted to continue to use the leased premises located at 12
East 86th Street, Apt. 329, New York, NY 10020. During this period and following the Separation Date, the Company shall
make timely payment of all rental and related expenses due under the lease in connection with the leased premises through the end
of the lease term. Contractor shall be permitted to remove his personal effects from the leased premises including without limitation,
art work, clothes, television and small electrical appliances.

 

 

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EXHIBIT B TO SEPARATION
AND INDEPENDENT CONTRACTOR SERVICES AGREEMENT DATED JANUARY 27, 2012

Release

WHEREAS, Employee was an employee-at-will;

WHEREAS, the Company and Employee
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, Employee, in consideration
of the Separation and Independent Contractor Services Agreement between the Company and the Employee dated January 27, 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.	Employee acknowledges that Employee’s employment terminated effective March 31, 2012.

		2.	Nothing in this Release shall be construed to prevent Employee 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
(EEOC), or applicable state/city fair employment practices agency, to the extent required or permitted by law. Nevertheless, Employee
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, Employee understands and agrees that by signing this Release, Employee is not releasing claims
that relate to: (i) any claims arising after the date Employee signs this Agreement; (ii) any claims for enforcement of the Agreement,
the Indemnification Agreement and Board Consent (as defined in Section 14 of the Agreement, hereafter collectively the “Indemnification
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,
Employee, 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 Employee'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 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 Employee’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 Employee is hereby
waiving rights or claims under this Act 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, Employee, by signing this Agreement, 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 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 Fl

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 Employee is not otherwise entitled, Employee hereby agrees:

		a.	Not to allege that the ending of Employee’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 Employee receives
a subpoena or similar demand relating in any way to the Company, Employee shall promptly notify the Company so that the Company
shall have the ability to seek an appropriate protective order prior to Employee making any disclosure in response to such subpoena
or demand;

	

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		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;

		d.	To return to the Company any Company property in the Employee’s possession or otherwise given to Employee 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 Employee 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 Employee; and

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

		7.	The Employee 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 the Employee 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.	Employee 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. The Employee 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, Employee 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 Employee 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 Employee. Both parties understand that Employee’s decision to terminate this Release operates to
terminate Employee’s employment effective as of January __, 2012.

	

    	-5-

    	 

    
		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. Employee represents and warrants that no person other than Employee has any interest
or right in the matters referred to herein, that Employee has the sole right and exclusive authority to execute this Release ,
and that Employee 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.

		13.	No other consideration has or will be furnished or paid other than the consideration herein recited. Employee acknowledges
and agrees that the payments set forth in the Agreement: (i) are in lieu of any termination benefits that Employee 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 Employee 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 the Employee might otherwise be entitled under any policy, procedure or plan of the Company and/or any other
agreement between Employee and the Company in connection with the termination of his employment with the Company.

		14.	Employee and Company agree that this Release may be executed in multiple counterparts, including a facsimile copy, and that
it is the intent of Employee and Company that a copy of this Release signed by either Employee or 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
the Employee and the Company which survive the termination of Employee’s employment with Company. Employee 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
Employee has solely or jointly conceived or developed or reduced to practice within the scope of his employment with the Company.
Employee 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. The Employee 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 .

    	-6-

    	 

    
DO NOT SIGN UNTIL
CLOSE OF BUSINESS ON MARCH 31, 2012.

	 	EMPLOYEE:	 
	 	 	 
	 	____________________________________	Date:  _______________________
	 	David G. Curran	 
	 	 	 
	 	IntraLinks Holdings, Inc.	 
	 	 	 
	 	By:  _________________________________	Date:  _______________________
	 	 	 

 

    	-7-EMPLOYMENT AGREEMENT

EMPLOYMENT AGREEMENT
dated as of January 27, 2012 (the “Effective Date”), by and between IntraLinks Holdings, Inc., a Delaware corporation
with its principal place of business at New York, New York (hereinafter referred to as the “Company”), and Scott
Semel, residing in XXXXXXXXXXXXXXXXXX (hereinafter referred to as “Executive”).

WHEREAS, the Company
desires to employ Executive as Executive Vice President and General Counsel, subject to the terms and conditions of this agreement
(this “Agreement”).

NOW, THEREFORE, in
consideration of the promises and covenants herein, the parties agree as follows:

1.Employment

Executive accepts
employment with the Company on the Effective Date in accordance with the terms and conditions of this Agreement. Executive is and
will be an employee at will, which means that either Executive or the Company may terminate the employment relationship at any
time, with or without “Cause”, as defined below, or notice, subject to the provisions of Sections 4 and 5 of this Agreement.

2.Duties

2.1Executive
shall, during the term of his employment with the Company, perform the duties of Executive Vice President and General Counsel and
shall perform such other duties as shall be specified and designated from time to time by the Chief Executive Officer (the “CEO”)
or his successor or designee. Executive shall devote his full business time and effort to the performance of his duties hereunder.
Executive shall report to the CEO or such other senior officer of the Company (without resulting in substantial diminution of Executive’s
duties) as the CEO or the Company’s board of directors (the “Board of Directors”) shall designate from
time to time. Notwithstanding the foregoing, Executive may (a) serve on the boards of the Disability Law Center and the New England
Center for the Performing Arts, the Thoracic Oncology Visiting Committee of the Dana Farber Cancer Institute, and the Overseers
Committee of Brigham and Women’s Hospital, so long as such service does not materially interfere with Executive’s performance
of his duties to the Company as provided in this Agreement, and (b) engage in or serve such civic, community, charitable, educational,
religious or non-profit organizations and boards as he may select so long as such service does not materially interfere with Executive’s
performance of his duties to the Company as provided in this Agreement.

2.2Executive’s
employment hereunder shall be subject to the rules and regulations of the Company involving the general conduct of business of
the Company in force from time to time and applicable to senior executives of the Company.

2.3The parties
hereto understand and acknowledge that the Company’s headquarters are located in New York, NY. Notwithstanding the foregoing,
the Company agrees that Executive’s principal work location shall be at the Company’s offices located in Charlestown,
MA (the “Executive’s Office Location”); provided that, the Executive may be required to
travel to other locations in the ordinary course of business or as directed by the Board of Directors.

    	 

    	 

    
3.Compensation

3.1Salary.
The Company shall pay Executive an annualized salary of $280,000 (the “Annual Salary”), in accordance with the
customary payroll practices of the Company applicable to senior executives. Executive’s performance and Annual Salary shall
be reviewed annually in accordance with the Company’s policy and his Annual Salary may be adjusted upward (but not downward)
in the sole discretion of the Compensation Committee of the Board of Directors (the “Compensation Committee”).

3.2Bonus.
Executive shall be eligible to receive an annual bonus (with a target “at plan” amount equal to 50% of the amount of
Annual Salary actually paid or accrued during the calendar year) (the “Target Bonus”), the criteria for, exact
amount and award of said Target Bonus to be determined in the discretion of the Compensation Committee; provided that, the Company
may award a bonus less than or in excess of the Target Bonus depending on the levels at which bonus plan targets are achieved.
Bonuses payable to Executive pursuant to this Section 3.2 shall be paid to Executive at the same time such bonuses are paid to
the most senior executive officers of the Company, but in no event later than March 15th of the calendar year immediately
following the calendar year in which it was earned. Except as set forth in Sections 4 and 5.3 hereof, Executive shall be eligible
to receive any such bonus if Executive is actively employed by the Company on the date bonuses, if any,
are paid and Executive has not given notice of resignation or been given notice of termination by the Company for “Cause,”
as defined in this Agreement, on or prior to that date.

3.3Equity
Grant. Subject to approval by the Compensation Committee, Executive will be granted an option (the “Option”)
to purchase 90,000 shares of the Company’s common stock (“Common Stock”) and a grant of 45,000 restricted
stock units (the “RSU Grant”). The exercise price per share of the Option will be equal to the closing trading
price of the Common Stock on the New York Stock Exchange on the date that the option is granted. The Option and RSU Grant will
be subject to the terms and conditions applicable to options and restricted stock units granted under the Company’s 2010
Equity Incentive Plan (the “Plan”), as described therein and the applicable award agreement.

3.4Benefits.
Executive shall be eligible to participate in the Company’s employee benefits plans, subject to the terms and conditions
of the applicable plan documents, and subject to the Company’s right to amend, terminate, increase costs and/or take other
similar action with respect to any or all of its benefit plans, as with all other plans and programs of the Company.

3.5Expenses.
The Company shall pay or reimburse Executive for all reasonable out-of-pocket expenses actually incurred by Executive in the performance
of Executive’s services under this Agreement, in accordance with the Company’s expense reimbursement policies in effect
from time to time (including timely submission of proof of such expenses (including, in the case of reimbursements, proof of payment)
in such form as the Company may require). If an expense reimbursement is not exempt from Section 409A of the Internal Revenue Code
of 1986, as amended (“Section 409A”), the following rules apply: (i) in no event shall any reimbursement be
paid after the last day of the taxable year following the taxable year in which the expense was incurred; (ii) the amount of reimbursable
expenses incurred in one tax year shall not affect the expenses eligible for reimbursement in any other tax year; and (iii) the
right to reimbursement for expenses is not subject to liquidation or exchange for any other benefit.

    	2

    	 

    
3.6Vacation.
Executive shall be entitled to 24 vacation and personal days per full calendar year of his employment.

3.7Delivery
of Compensation. In the event of Executive’s death, any accrued but unpaid payments by the Company hereunder shall be
made to the executors or administrators of Executive’s estate against the delivery of such tax waivers, proper letters testamentary
and other documents as the Company may reasonably request.

4.Termination
upon Death or Disability

This Agreement and
the Executive’s employment shall terminate upon Executive’s death. If Executive becomes disabled, the Company may terminate
this Agreement and Executive’s employment by written notice to Executive. For purposes 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 ninety (90) consecutive 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. Upon death or termination of employment by virtue of disability,
Executive (or Executive’s estate or beneficiaries in the case of the death of Executive) shall have no right to receive any
compensation or benefit hereunder on and after the effective date of the termination of employment other than (i) Annual Salary
earned and accrued under this Agreement prior to the effective date of termination; (ii) earned, accrued and vested benefits and
paid time off, subject to the terms of the plans applicable thereto; (iii) pro-rated bonus determined in accordance with the provisions
of Section 5.3(c); and (iv) reimbursement under this Agreement for expenses incurred prior to the effective date of termination.
The pro-rated bonus shall be paid to Executive (or Executive’s estate or beneficiaries in the case of the death of the Executive)
at such time when the Company pays bonuses to its senior executives. This Agreement shall otherwise terminate upon the effective
date of the termination of employment and Executive shall have no further rights hereunder.

5.Other Terminations
of Employment 

5.1Termination
for Cause. The Company may terminate this Agreement and Executive’s employment hereunder for Cause. For purposes of this
Agreement, “Cause” shall mean: (i) conduct by Executive constituting a material act of misconduct in connection
with the performance of his duties, including, without limitation, misappropriation of funds or property of the Company or any
of its subsidiaries or affiliates other than the occasional, customary and de minimis use of Company property for personal purposes;
(ii) the commission by Executive of any felony involving deceit, dishonesty or fraud, or any conduct by Executive that would reasonably
be expected to result in material economic injury or reputational harm to the Company or any of its subsidiaries and affiliates
if he were retained in his position; (iii) willful and continued non-performance by Executive of his duties hereunder (other than
by reason of Executive’s physical or mental illness, incapacity or disability); (iv) a breach by Executive of any of the
provisions contained in Section 7 of this Agreement; (v) a material violation by Executive of the Company’s material written
employment policies, where such violations results in material harm to the Company; or (vi) failure to cooperate with a bona fide
internal investigation or an investigation by regulatory or law enforcement authorities, after being instructed by the Board of
Directors to cooperate, or the willful destruction or failure to preserve documents or other materials known to be relevant to
such investigation or the inducement of others to fail to cooperate or to produce documents or other materials in connection with
such investigation; provided that, with respect to subsections (iii) and (v) above, Cause will only be deemed to
occur after written notice to Executive describing in reasonably specific detail the events/actions giving rise to the Cause determination,
and the failure by Executive to cure such events/actions giving rise to the Cause determination within thirty (30) days following
such written notice. Notwithstanding any other provision of this Agreement, if the Company terminates Executive’s employment
in accordance with the terms of this Section 5.1 for Cause, Executive shall have no right to receive any compensation or benefit
hereunder on and after the effective date of the termination of employment other than (w) Annual Salary earned and accrued under
this Agreement prior to the effective date of termination; (x) earned, accrued and vested benefits and paid time off under this
Agreement prior to the effective date of termination, subject to the terms of the plans applicable thereto (and any applicable
laws and regulations); and (y) reimbursement under this Agreement for expenses incurred prior to the effective date of termination.
This Agreement shall otherwise terminate upon the effective date of the termination of employment and Executive shall have no further
rights hereunder.

    	3

    	 

    
5.2Termination
by Executive. Notwithstanding any other provision of this Agreement, if Executive terminates this Agreement and his employment
under this Section 5.2, Executive shall have no right to receive any compensation or benefit hereunder on and after the effective
date of the termination of employment other than (i) Annual Salary earned and accrued under this Agreement prior to the effective
date of termination; (ii) earned, accrued and vested benefits and paid time off under this Agreement prior to the effective date
of termination, subject to the terms of the plans applicable thereto (and any applicable laws and/or regulations); and (iii) reimbursement
under this Agreement for expenses incurred prior to the effective date of termination. This Agreement shall otherwise terminate
upon the effective date of the termination of employment and Executive shall have no further rights hereunder. Executive shall
endeavor to provide thirty (30) days’ prior written notice to the Company if he terminates his employment under this Section
5.2.

5.3Termination
by the Company Without Cause. The Company may terminate this Agreement and Executive’s employment at any time for any
reason. If this Agreement and Executive’s employment with the Company is terminated pursuant to this Section 5.3 for reasons
other than Cause, Executive’s death or disability, Executive shall have no right to receive any compensation or benefit hereunder
on and after the effective date of the termination of employment other than:

    	4

    	 

    
(a)Annual Salary
earned and accrued under this Agreement prior to the effective date of termination and any earned but unpaid bonus;

(b)an additional
six (6) months of Annual Salary at the rate in effect at termination payable in the form of salary continuation, subject to applicable
withholding taxes; and

(c)an amount
equal to the bonus that Executive would have received for the year of termination if Executive had remained employed throughout
the calendar year, with such amount to be determined at the end of the calendar year based on the levels at which the bonus plan
targets are achieved, multiplied by a fraction, the numerator of which being the number of calendar days Executive is employed
in the calendar year of termination and the denominator of which being 365:

(d)payment
of the premiums for Executive’s group health insurance coverage pursuant to COBRA, if eligible and elected, for a period
of six (6) months, or until such sooner date that Executive begins employment with another employer; provided that after expiration
of the relevant COBRA payment period above, the Company will allow Executive to continue such coverage at his own expense for the
remainder of any COBRA continuation period pursuant to applicable law and Executive shall notify the Company immediately upon acceptance
of employment with another employer;

(e)accelerated
vesting of Executive’s equity awards with service vesting through the next six (6) months;

(f)earned,
accrued and vested benefits and paid time off under this Agreement prior to the effective date of termination, subject to the terms
of the plans applicable thereto; and

(g)reimbursement
under this Agreement for expenses incurred prior to the effective date of termination.

    	5

    	 

    
The amounts due under Sections 5.3(b)
and (c) shall not be paid or given unless Executive executes a customary agreement releasing all claims against the Company (in
the form attached hereto as Exhibit A) (the “Release Agreement”) and the Release Agreement becomes enforceable
and irrevocable within 60 days following the date on which the termination of Executive’s employment becomes effective. The
Annual Salary due under this Section 5.3(b) (the “Severance”) shall commence to be paid to Executive on the
first Company payroll date following the date the Release Agreement becomes enforceable
and irrevocable, provided, however, that: (x) if the 60-day period in which the Release Agreement is required to become effective
and enforceable begins in one calendar year and ends in the following calendar year, the Severance shall be paid in the second
calendar year; and (y) in all events, subject to the effectiveness of the Release Agreement, the Severance shall be paid prior
to March 15 of the year following the year in which the termination of Executive’s employment becomes effective. The pro-rated
bonus due under Section 5.3(c) shall be paid to Executive at such time when the Company pays bonuses to its senior executives,
but in no event earlier than the date provided in the preceding sentence. The Company shall pay the premiums due under Section
5.3(d) each month at the time the Company normally pays the insurer of the Company’s group health insurer on behalf of its
remaining employees.

5.4Change
in Control.

(a)Executive
shall be fully eligible to participate and receive benefits and payments under the terms of the Company’s Senior Executive
Severance Plan (the “Severance Plan”); provided that, to the extent the Company modifies the Severance Plan
or adopts a similar plan or policy that provider greater severance benefits and/or payments to the Company’s senior executives,
Executive shall be fully entitled to participate in such modified Severance Plan or newly adopted plan or policy.

(b)In addition,
the applicable award agreements for the Option and RSU Grant shall provide that upon a Sale Event (as defined in the Plan), Executive
shall receive 100% accelerated vesting of any unvested shares under the Option and RSU Grant, with such vesting to occur immediately
prior to the closing of the Sale Event.

5.5Additional
Limitation.

(a)Anything
in this Agreement to the contrary notwithstanding, in the event that the amount of any compensation, payment or distribution by
the Company to or for the benefit of Executive, whether paid or payable or distributed or distributable pursuant to the terms of
this Agreement or otherwise, calculated in a manner consistent with Section 280G of the Internal Revenue Code of 1986, as amended
(the “Code”) and the applicable regulations thereunder (the “Severance Payments”), would
be subject to the excise tax imposed by Section 4999 of the Code, the following provisions shall apply:

(i)If
the Threshold Amount is less than (x) the Severance Payments, but greater than (y) the Severance Payments reduced by the sum of
(A) the Excise Tax and (B) the total of the Federal, state, and local income and employment taxes on the amount of the Severance
Payments which are in excess of the Threshold Amount, then the Severance Payments shall be reduced (but not below zero) to the
extent necessary so that the sum of all Severance Payments shall not exceed the Threshold Amount. In such event, the Severance
Payments shall be reduced in the following order: (A) cash payments not subject to Section 409A of the Code; (B) cash payments
subject to Section 409A of the Code; (C) equity-based payments and acceleration; and (D) non-cash forms of benefits. To the extent
any payment is to be made over time (e.g., in installments, etc.), then the payments shall be reduced in reverse chronological
order.

(ii)Except
in the circumstances set forth in (i), Executive shall be entitled to receive his full Severance Payments.

(b)For the
purposes of this Section 5.5, “Threshold Amount” shall mean three times Executive’s “base amount”
within the meaning of Section 280G(b)(3) of the Code and the regulations promulgated thereunder less one dollar ($1.00); and “Excise
Tax” shall mean the excise tax imposed by Section 4999 of the Code, and any interest or penalties incurred by Executive
with respect to such excise tax.

    	6

    	 

    
(c)The determination
as to which of the alternative provisions of Section 5.5(a) shall apply to Executive shall be made by a nationally recognized accounting
firm selected by the Company (the “Accounting Firm”), which shall provide detailed supporting calculations both
to the Company and Executive within 15 business days of the Date of Termination, if applicable, or at such earlier time as is reasonably
requested by the Company or Executive. For purposes of determining which of the alternative provisions of Section 5.5(a) shall
apply, Executive shall be deemed to pay federal income taxes at the highest marginal rate of federal income taxation applicable
to individuals for the calendar year in which the determination is to be made, and state and local income taxes at the highest
marginal rates of individual taxation in the state and locality of Executive’s residence on the Date of Termination, net
of the maximum reduction in federal income taxes which could be obtained from deduction of such state and local taxes. Any determination
by the Accounting Firm shall be binding upon the Company and Executive.

6.Covenants
of Executive.

6.1Non-Competition;
Non-Solicitation. As a material inducement to the Company to enter into this Agreement, Executive hereby expressly agrees to
be bound by the following covenants, terms and conditions. Executive hereby agrees that he will have access to trade secrets, proprietary
and confidential information relating to the Company and its affiliates and their respective clients, including but not limited
to, marketing data, financial information, client and prospect lists (including without limitation, computer- and web-based compilations
(including but not limited to salesforce.com or other CRM system data) maintained by the Company or its affiliates or Executive),
and details of programs and methods, potential and actual acquisitions, divestitures and joint ventures, pricing policies, strategies,
terms of service, business and product plans, cost information and software, in each case of the Company, its affiliates and/or
their respective clients. Accordingly, Executive voluntarily enters into the following covenants to provide the Company with reasonable
protection of those interests:

(a)Executive
agrees that during the term of his employment with the Company and for a period of one year thereafter, Executive shall not, alone
or as an employee, officer, director, agent, shareholder (other than an owner of 2% or less of the outstanding shares of any publicly-traded
company), consultant, partner, member, owner or in any other capacity, directly or indirectly:

(i)engage
in any Competitive Activity (as defined below) within or with respect to any location in the United States or abroad in which Executive
performed or directed his services (including but not limited to sales and customer support calls, whether conducted in person,
by telephone or online) at any time during the 12-month period immediately preceding the termination of Executive’s employment
for any reason (the “Territories”), or assist any other person or organization in engaging in, or preparing
to engage in, any Competitive Activity in such Territories;

(ii)solicit
or provide services to any Clients, as defined below, of the Company and/or any of its affiliates, on his own behalf or on behalf
of any third party, in furtherance of any Competitive Activity. For purposes of this Section 6, “Client” shall
mean any then-current customer of the Company, former customer of the Company (who was a customer of the Company within the 12-month
period immediately preceding the termination of Executive’s employment hereunder);

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(iii)encourage,
participate in or solicit any employee or consultant of the Company and/or any affiliate to engage in Competitive Activity or to
accept employment with any third party, whether or not engaged in Competitive Activity. This subsection (iii) shall be limited
to employees and consultants who: (A) are current employees or consultants; or (B) left the employment of the Company or whose
provision of services to the Company terminated within the 12-month period prior to Executive’s termination of employment
with the Company for any reason; and

(iv)for
purposes of this Agreement, “Competitive Activity” shall mean any offering, sale, licensing or provision by
any entity of any software, application service or system, in direct competition with the Company’s offerings and including
electronic or digital document repositories for inter-enterprise exchanges designed to facilitate transactional due diligence,
mergers, acquisitions, divestitures, financings, investments, investor relations, research and development, clinical trials or
other business processes for which the Company’s products or services are or have been used during the 12-month period preceding
termination of Executive’s employment for any reason.

(b)Executive
agrees that the foregoing restrictions are reasonable and justified in light of: (i) the nature of the Company’s business
and customers; (ii) the confidential and proprietary information to which Executive has had and will have exposure and access during
the course of his employment with the Company; and (iii) the need for the adequate protection of the business and the goodwill
of the Company. In the event any restriction in this Section 6 is deemed to be invalid or unenforceable by any court of competent
jurisdiction, Executive agrees to the reduction of said restriction to such period or scope that such court deems reasonable and
enforceable.

(c)Executive
acknowledges and agrees that any breach of this Section 6 shall cause the Company immediate, substantial and irreparable harm and
therefore, in the event of any such breach, Executive agrees that, without prejudice to any other remedies which may be available
to the Company, and the Company shall have the right to seek specific performance and injunctive relief, without the need to post
a bond or other security.

(d)Without
in any way limiting the provisions of this Section 6, Executive further acknowledges and agrees that the provisions of this Section
6 shall remain applicable in accordance with their terms after the date of termination of Executive’s employment, regardless
of whether Executive’s termination or cessation of employment is voluntary or involuntary.

6.2Confidential
and Proprietary Information. During and after the term of Executive’s employment with the Company, Executive covenants
and agrees that he will not disclose to anyone without the Company’s prior written consent, any confidential materials, documents,
records or other non-public information of any type whatsoever concerning or relating to the business and affairs of the Company
which Executive may have acquired in the course of his employment hereunder, including but not limited to: (a) trade secrets of
the Company; (b) lists of and/or information concerning current, former, and/or prospective customers or clients of the Company;
and (c) information relating to methods of doing business (including information concerning operations, technology and systems)
in use or contemplated use by the Company and not generally known among the Company’s competitors (the “Confidential
Information”), except that Executive may use and disclose such Confidential Information (i) in the course of Executive’s
employment with, and for the benefit of, the Company, (ii) to enforce any rights or defend any claims hereunder or under any other
agreement to which Executive is a party with the Company, provided that such disclosure is relevant to the enforcement of such
rights or defense of such claims and is only disclosed in the formal proceedings related thereto, (iii) when required to do so
by a court of law, by any governmental agency having supervisory authority over the business of the Company or by any administrative
or legislative body (including a committee thereof) with jurisdiction to order him to divulge, disclose or make accessible such
Confidential Information; provided that Executive shall give prompt written notice to the Company of such requirement, disclose
no more information than is so required, and reasonably cooperate with any attempts by the Company to obtain a protective order
or similar treatment, (iv) as to such Confidential Information that is or becomes generally known to the public or trade without
Executive’s violation of this Section 6.2, or (v) to Executive’s spouse, attorney and/or his personal tax and financial
advisors as reasonably necessary or appropriate to advance Executive’s tax, financial and other personal planning (each an
“Exempt Person”), provided, however, that any disclosure or use of Confidential Information by
an Exempt Person shall be deemed to be a breach of this Section 6.2 by Executive.

    	8

    	 

    
6.3Rights
and Remedies upon Breach. Executive acknowledges and agrees that his breach of any provision of this Section 6 (the “Restrictive
Covenants”) would result in irreparable injury and damage for which money damages do not provide an adequate remedy.
Therefore, if Executive breaches or threatens to commit a breach of any Restrictive Covenant, the Company shall have the following
rights and remedies (in accordance with applicable law and upon compliance with any necessary prerequisites imposed by law upon
the availability of such remedies), each of which rights an remedies shall be independent of the other and severally enforceable,
and all of which right and remedies shall be in addition to, and not in lieu of, any other rights and remedies available to the
Company under law or in equity (including, without limitation, the recovery of damages):

(a) to have
the Restrictive Covenants specifically enforced (without posting bond and without the need to prove damages) by any court having
jurisdiction, including, without limitation, the right to seek an entry against Executive of restraining orders and injunctions
(preliminary, mandatory, temporary and permanent) against violations, threatened or actual, and whether or not then continuing,
of such covenants;

(b) to require
Executive to forfeit his right to receive the balance of any compensation due him which is not yet earned and accrued under this
Agreement (whether it be in the form of Annual Salary, expenses or paid time off); and

In addition, without
limiting the Company’s remedies for any breach by Executive of the Restrictive Covenants, except as required by law, if (i)
the Company files a civil action against Executive based on his alleged breach of the Restrictive Covenants, and (ii) the Company
obtains preliminary injunctive relief enjoining the Executive from breaching any of the Restrictive Covenants, or a court of competent
jurisdiction issues a final judgment (not subject to appeal, which shall include any order or judgment that finally disposes of
the action) that the Executive has breached any of the Restrictive Covenants, then the Executive shall promptly repay to the Company
any such payments he previously received pursuant to Sections 5.3(b) and (c) above and the Company will have no obligation to pay
any of the amounts that remain payable by the Company under Sections 5.3(b) and (c). If, however, a court of competent jurisdiction
either denies the Company’s motion, request or application for preliminary injunctive relief or issues a final judgment (not
subject to appeal, which shall include any order or judgment that finally disposes of the action) that the Executive has not breached
any of the Restrictive Covenants, then Executive shall not be obligated to repay, and the Company shall not be entitled to recoup,
any of the payments made to the Executive pursuant to Sections 5.3(b) and (c).

    	9

    	 

    
6.4Definition
of the Company. For this Section 6, the “Company” shall include all of the Company’s parents, subsidiaries,
and affiliates and their respective successors and assigns, and “affiliate” shall mean any entity that, directly
of indirectly, through one or more intermediaries, controls or is controlled by or is under common control with the Company. As
used in this Section 6.4, “control” shall mean the possession, directly or indirectly, of the powers to direct
or cause the direction of the management and policies of such entity, whether though the ownership of voting securities, by contract
or otherwise.

7.Section 409A
of the Code.

 

(a)The Severance payable
to Executive under Sections 5.3 of this Agreement are intended to be exempt from the coverage of Section 409A of the Code because
the payments are made to Executive within the time periods set forth in Treas. Reg. §1.409A-1(a)(4) and
each installment payment is intended to be a separate payment for purposes of Treas. Reg. §1.409A-2(b)(2)(iii). To
the extent that any payment or benefit due to Executive under this Agreement provides for the payment of non-qualified deferred
compensation benefits in connection with a termination of the Executive’s employment (regardless of the reason for such termination),
however, such termination of the Executive’s employment triggering payment of benefits under the terms of this Agreement
must also constitute a “separation from service” under Section 409A(a)(2)(A)(i) of the Code and Treas. Reg. §1.409A-1(h)
before the Company shall make payment of such benefits. To the extent that termination of the Executive’s employment does
not constitute a separation of service under Section 409A(a)(2)(A)(i) of the Code and Treas. Reg. §1.409A-1(h) (as the result
of further services that are reasonably anticipated to be provided by him to the Company or any of its affiliates or successors
at the time his employment terminates), any benefits payable under this Agreement that constitute non-qualified deferred compensation
under Section 409A of the Code shall be delayed until after the date of a subsequent event constituting a separation of service
under Section 409A(a)(2)(A)(i) of the Code and Treas. Reg. §1.409A-1(h). For purposes of clarification, this Section 7(a)
shall not cause any forfeiture of benefits on the Executive’s part, but shall only act as a delay in payment of such benefits
until such time as a separation from service occurs.

 

(b)Anything in this
Agreement to the contrary notwithstanding, if at the time of Executive’s separation from service within the meaning of Section 409A
of the Code, Executive is also a “specified employee” within the meaning of Section 409A(a)(2)(B)(i) of the
Code, then to the extent any payment or benefit that Executive becomes entitled to under this Agreement on account of Executive’s
separation from service would be considered deferred compensation subject to Section 409A of the Code, such payment shall
not be payable and such benefit shall not be provided until the date that is the earlier of (A) six months and one day after
Executive’s separation from service, or (B) Executive’s death.  If any such delayed cash payment is otherwise
payable on an installment basis, the first payment shall include a catch-up payment covering amounts that would otherwise have
been paid during the six-month period but for the application of this provision, and the balance of the installments shall be payable
in accordance with their original schedule.

 

    	10

    	 

    
(c)All in-kind benefits
provided and expenses eligible for reimbursement under this Agreement shall be provided by the Company or incurred by Executive
during the time periods set forth in this Agreement.  All reimbursements shall be paid as soon as administratively practicable,
but in no event shall any reimbursement be paid after the last day of the taxable year following the taxable year in which the
expense was incurred.  The amount of in-kind benefits provided or reimbursable expenses incurred in one taxable year shall
not affect the in-kind benefits to be provided or the expenses eligible for reimbursement in any other taxable year.  Such
right to reimbursement or in-kind benefits is not subject to liquidation or exchange for another benefit.

 

(d)The
parties intend that this Agreement will be administered in accordance with Section 409A of the Code. To the extent that any provision
of this Agreement is ambiguous as to its compliance with Section 409A of the Code, the provision shall be read in such a manner
so that all payments hereunder comply with Section 409A of the Code. The parties agree that this Agreement may be amended, as reasonably
requested by either party, and as may be necessary to fully comply with Section 409A of the Code and all related rules and regulations
in order to preserve the payments and benefits provided hereunder without additional cost to either party.

(e)The Company makes
no representation or warranty and shall have no liability to Executive or any other person if any provisions of this Agreement
are determined to constitute deferred compensation subject to Section 409A of the Code but do not satisfy an exemption from, or
the conditions of, such Section.

 

8.Other Provisions

8.1Severability.
Executive acknowledges and agrees that (i) he has had an opportunity to seek advice of counsel in connection with this Agreement;
and (ii) the Restrictive Covenants are reasonable in geographical and temporal scope and in all other respects. If it is determined
by a court of competent jurisdiction that any provision of this Agreement, including, without limitation, any Restrictive Covenant,
or any part thereof, is invalid or unenforceable, the remainder of the Agreement shall not thereby be affected and shall be given
full effect, without regard to the invalid provisions. The parties hereto will substitute for the invalid or unenforceable provision
a new, mutually acceptable, valid and enforceable provision of like economic effect.

    	11

    	 

    
8.2Blue
Penciling. If any court determines that any covenant in this Agreement, including, without limitation, any Restrictive Covenant
or any part thereof, is unenforceable because of the duration or geographical scope of such provision, the duration or scope of
such provision, as the case may be, shall be reduced so that such provision becomes enforceable and, in its reduced form, such
provision shall then be enforceable and shall be enforced.

8.3Indemnification.
Executive shall be entitled to indemnification as provided in the Company’s certificate of incorporation and bylaws, to the
fullest extent permitted under Delaware law. In addition, the Company and Executive will execute the Company’s standard indemnification
agreement for senior executive and/or directors.

8.4Notices.
Any notice or other communication required or permitted hereunder shall be in writing and shall be delivered in person, by facsimile
or electronic mail or by certified or registered mail, postage prepaid. Any such notice given by certified or registered mail shall
be deemed given five days after the date of deposit in the United States mails as follows:

		(i)	If to the Company:

150 East 42nd
Street, 8th Floor

 New York, NY 10017

 

		(ii)	If to Executive, to:

 

XXXXXXXXXXXXX

XXXXXXXXXXX

 

With
a copy to:

XXXXXXXXXXX

XXXXXXXXXX.

XXXXXXXXXXXXX

XXXXXXXXXXX

 

Any such person may
by notice given in accordance with this Section to the other party designate another address or person for receipt by such person
of notices hereunder.

8.5Entire
Agreement. This Agreement, along with exhibit attached hereto and the award agreements for the Option and RSU Grant referenced
in Section 3.3 above, constitutes the entire agreement and understanding between the parties hereto with respect to the subject
matter hereof and terminates and supersedes any and all prior agreements, understandings and representations, whether written or
oral, by or between the parties hereto or their affiliates which may have related to the subject matter hereof in any way.

8.6Waivers
and Amendments. This Agreement may be amended, superseded or canceled, and the terms hereof may be waived, only by a written
instrument singed by the parties or, in the case of a waiver, by the party waiving compliance. No delay by either party in exercising
any right, power or privilege hereunder shall operate as a waiver thereof, nor shall any waiver on the part of any party of any
such right, power or privilege nor any single or partial exercise as any such right, power or privilege, preclude any other or
further exercise thereof or the exercise of any other such right, power or privilege.

    	12

    	 

    
8.7GOVERNING
LAW. THIS AGREEMENT SHALL BE GOVERNED BY AND CONSTRUED IN ACCORDANCE WITH THE LAWS OF THE STATE OF NEW YORK WITHOUT REGARD
TO PRINCIPLES OF CONFLICTS OF LAW.

8.8Venue.
The parties agree irrevocably to submit to the exclusive jurisdiction of the federal
courts or, if no federal jurisdiction exists, the state courts, located in Boston, Massachusetts, for the purposes of any suit,
action or other proceeding brought by any party arising out of any breach of any of the provisions of this Agreement and hereby
waive, and agree not to assert by way of motion, as a defense or otherwise, in any such suit, action, or proceeding, any claim
that it is not personally subject to the jurisdiction of the above-named courts, that the suit, action or proceeding is brought
in an inconvenient forum, that the venue of the suit, action or proceeding is improper, or that the provisions of this Agreement
may not be enforced in or by such courts.

8.9Assignment.
This Agreement, and Executive’s rights and obligations hereunder, may not be assigned by Executive without the prior written
consent of the Company; any purported assignment by Executive in violation hereof shall be null and void. In the event of any sale,
transfer or other disposition of all or substantially all of the Company’s assets or business, whether by merger, consolidation
or otherwise, the Company shall assign this Agreement and its rights and obligations hereunder.

8.10Withholding.
The Company shall be entitled to withhold from any payments or deemed payments any amount of withholding required by applicable
law.

8.11Binding
Effect. This Agreement shall be binding upon and inure to the benefit of the parties and their respective successors, permitted
assigns, heirs, executors and legal representatives.

8.12Survival.
Anything in this Agreement to the contrary notwithstanding, to the extent applicable, Sections 1, 6 and 8 shall survive the termination
of this Agreement for any reason.

8.13Headings.
The headings in this Agreement are for reference only and shall not affect the interpretation of this Agreement.

8.14Legal
Fees. The Company shall reimburse the reasonable legal fees and expenses of Executive incurred in connection with the review
and negotiation of this Agreement, not to exceed $5,000.

8.15Counterparts.
This Agreement may be executed by the parties hereto in separate counterparts, each of which when so executed and delivered shall
be an original but all such counterparts together shall constitute one and the same instrument. Each counterpart may consist of
two copies hereof each signed by one of the parties hereto.

    	13

    	 

    
8.16Third-Party
Agreements and Rights. Executive represents to the Company that Executive’s execution of this Agreement, Executive’s
employment with the Company and the performance of Executive’s proposed duties for the Company will not violate any obligations
Executive may have to any previous employer or any other party. In Executive’s work for the Company, Executive will not disclose
or make use of any information in violation of any agreements with or rights of any previous employer or other party, and Executive
will not bring to the premises of the Company any copies or other tangible embodiments of non-public information belonging to or
obtained from any previous employment or other party.

8.17Clawback.
The bonus payments and equity grants made to Executive under this Agreement shall be subject to and shall be deemed amended hereby
to ensure compliance with a policy adopted by the Company in response to any statutory or regulatory mandate requiring the repayment
of compensation paid to Executive, provided, however, that unless specifically required by such statute or regulation, such policy
shall not be deemed to amend this Agreement to require diminution, reduction or repayment of any compensation paid, awarded or
promised to Executive under this Agreement prior to the effective date of such statute, regulation, mandate or order, including
without limitation any bonus payment or equity award.

[Signature Page Follows]

    	14

    	 

    
 

IN WITNESS WHEREOF,
the parties hereto have signed their names as of the day and year first above written.

	SCOTT SEMEL	 	
        INTRALINKS HOLDINGS,
INC.

	 	 	 	 	 
	 	 	 	 	 
	/s/ Scott Semel	 	By:	/s/ Ronald W.
Hovsepian
	 	 	 		Ronald W. Hovsepian

President and Chief Executive Officer

	 	 	 	 	 
	 	
        

         
	 	 	 
	Date:	January 25, 2012	 	Date:	January 27, 2012
	 		 		 

 

 

    	15

    	 

    
 

Exhibit A

Form of Release Agreement

 

 

[INTRALINKS HOLDINGS, INC. LETTERHEAD]

 

 

 

Mr. Scott Semel

XXXXXXXXXXXXX

XXXXXXXXXXX

 

Dear Scott:

 

This release agreement
(“Agreement”) is tendered to you in accordance with the terms of your January 25, 2012 Employment Agreement
(the “Employment Agreement”) and confirms the agreement that we have reached regarding your separation from
employment with IntraLinks Holdings, Inc. and any of its related and affiliated entities (the “Company”). The
purpose of this Agreement is to establish mutually agreeable arrangements for amicably ending your employment relationship and
to provide for an appropriate release of any claims by you. As you know, execution of this Agreement also is a precondition to
your eligibility for severance benefits under the Employment Agreement.

It is important
that this Agreement be entered into with several understandings between you and the Company. You are entering into this Agreement
voluntarily. You understand that you are giving up your right to bring all possible legal claims against the Company among others,
including claims relating to your employment and separation from employment.

Neither the Company
nor you want your employment relationship to end with a legal dispute. You understand that by entering into this Agreement, the
Company is not admitting in any way that it violated any legal obligation that it owed to you or to any other person. To the contrary,
the Company’s willingness to enter into this Agreement demonstrates that it is continuing to deal with you fairly and in
good faith.

With those understandings
and in exchange for the promises set forth below, you and the Company agree as follows:

1.Termination

You confirm and
agree that your employment with the Company terminated effective ________________ (the “Termination Date”).
You also hereby resign from any and all positions, offices and directorships that you may hold with the Company and its affiliates
as of the Termination Date. To the extent that the Company has not already done so, the Company shall pay to you within ten days
of the termination of your employment a lump-sum amount equal to the amounts due under Sections 5.3(a), (f) and (g) of the Employment
Agreement through the Termination Date.

    	16

    	 

    
2.Severance Benefit

Once this Agreement
becomes enforceable and irrevocable, you will receive the severance package set forth in Section 5.3 of the Employment Agreement
in accordance with the terms and conditions set forth therein.

3.Release of Claims

You voluntarily
and irrevocably release and discharge the Company, each related or affiliated entity, employee benefit plans, and the predecessors,
successors, and assigns of each of them, and each of their respective current and former officers, directors, shareholders, employees,
and agents (any and all of which are referred to as “Releasees”) generally from all charges, complaints, claims,
promises, agreements, causes of action, damages, and debts that relate in any manner to your employment with or services for the
Company, known or unknown (“Claims”), which you have, claim to have, ever had, or ever claimed to have had against
any of the Releasees through the date on which you execute this Agreement. This general release of Claims includes, without implication
of limitation, all Claims related to the compensation provided to you by the Company, your decision to resign from your employment,
your termination from the Company, your resignation from directorships, offices and other positions with the Company, or your activities
on behalf of the Company, including, without implication of limitation, any Claims of wrongful discharge, breach of contract, breach
of an implied covenant of good faith and fair dealing, tortious interference with advantageous relations, any intentional or negligent
misrepresentation, and unlawful discrimination or deprivation of rights under the common law or any statute or constitutional provision
(including, without implication of limitation, the Employee Retirement Income Security Act, Title VII of the Civil Rights Act of
1964, the Age Discrimination in Employment Act, the Americans with Disabilities Act and Chapter 151B of the Massachusetts General
Laws). You also waive any Claim for reinstatement, damages of any nature, severance pay, attorney’s fees, or costs.

You agree that you
will not hereafter pursue any Claim against any Releasee, by filing a lawsuit in any local, state or federal court for or on account
of anything which has occurred up to the present time as a result of your previous employment and you shall not seek reinstatement,
damages of any nature, severance pay, attorney’s fees, or costs, provided, however, that nothing in this general release
shall be construed to include a release of Claims that (a) arise from the Company’s obligations under this Agreement, the
Employment Agreement, any equity award/grant agreements (of whatever name or kind), and any shareholder agreements between you
and the Company, (b) relate to your status as a shareholder in the Company, (c) relate to the Company’s obligation to defend
and indemnify you under the terms of your indemnification agreement with the Company, the Company’s certificate of incorporation
and by-laws, Delaware law and any applicable directors and officers liability insurance policy, and (d) cannot be released as a
matter of law. You represent you have not assigned to any third party and you have not filed with any agency or court any Claim
released by this Agreement.

4.Confidential and Proprietary
Information

You acknowledge
your ongoing covenant under Section 6.2 of the Employment Agreement to preserve as confidential the Company’s Confidential
Information as that term is defined by Section 6.2. Your covenants under Section 6 of the Employment Agreement are incorporated
herein by this reference.

    	17

    	 

    
5.Return of Property

All documents, records,
material and all copies of any of the foregoing pertaining to Confidential Information (as defined in Section 6.2 of the Employment
Agreement), and all software, equipment, and other supplies, whether or not pertaining to Confidential Information, that have come
into your possession or been produced by you in connection with your employment (“Property”) have been and remain
the sole property of the Company and you confirm that you have returned to the Company all Property. In no event should this provision
be construed to require you to return to the Company any document or other materials concerning your remuneration and benefits
during your employment with the Company.

6.Litigation Cooperation

You agree to cooperate
fully with the Company in the defense or prosecution of any claims or actions which already have been brought or which may be brought
in the future against or on behalf of the Company which relate to events or occurrences that you were involved in or which you
gained knowledge of during your employment with the Company. Your full cooperation in connection with such claims or actions shall
include, without implication of limitation, being available to meet with counsel to prepare for discovery or trial and to testify
truthfully as a witness when reasonably requested by the Company at reasonable times designated by the Company. You agree that
you will not voluntarily disclose any information to any person or party that is adverse to the Company and that you will maintain
the confidences and privileges of the Company. The Company agrees to reimburse you for any reasonable out-of-pocket expenses that
you incur in connection with such cooperation, subject to reasonable documentation. The Company will try, in good faith, to exercise
its rights under this Section so as not to unreasonably interfere with your ability to engage in gainful employment.

7.Protective Covenants

You acknowledge
and affirm the ongoing validity of the protective covenants set forth in Section 6 of the Employment Agreement which covenants
are incorporated herein by this reference. You acknowledge and affirm the Company’s right to seek injunctive relief as provided
in Section 6 of the Employment Agreement to restrain any violations under Section 6 of the Employment Agreement.

8.Nondisparagement

You agree not to
make any disparaging statements concerning the Company or any of its affiliates, subsidiaries or current or former officers, directors,
shareholders, employees or agents. You further agree that you shall not voluntarily provide information to or otherwise cooperate
with any individual or entity that is contemplating or pursuing litigation against any of the Releasees or that is undertaking
any investigation or review of any of the Releasees’ activities or practices; provided, however, that you may participate
in or otherwise assist in any investigation or inquiry conducted by the EEOC or the Massachusetts Commission Against Discrimination.
These nondisparagement obligations shall not in any way affect your obligation to testify truthfully in any legal proceeding.

    	18

    	 

    
The Company will
instruct its officers and directors not to take any action or make any statement, orally or in writing, which disparages or criticizes
you or that would harm your reputation.

9.Notices, Acknowledgments
and Other Terms

You are advised
to consult with an attorney before signing this Agreement.

This Agreement and
the Employment Agreement set forth the entire agreement between you and the Company, and all previous agreements, or promises between
you and the Company relating to the subject matter of this Agreement and the Employment Agreement are superseded, null, and void,
with the exception of any equity grant/award agreements (of whatever name or kind), shareholder agreements, and indemnification
agreements between you and the Company, the terms of which remain in full force and effect.

You acknowledge
that you have been given the opportunity, if you so desired, to consider this Agreement for 21 days before executing it. If not
signed by you and returned to me so that I receive it by close of business on the day next following the foregoing period, this
Agreement will be invalid. In addition, if you breach any of the conditions of the Agreement within the 21-day period, the offer
of this Agreement will be withdrawn and your execution of the Agreement will not be valid. In the event that you execute and return
this Agreement in less than the 21-day period you have been provided, you acknowledge that such decision was entirely voluntary
and that you had the opportunity to consider this letter agreement for the entire period. The Company acknowledges that for a period
of seven days from the date of the execution of this Agreement, you shall retain the right to revoke this Agreement by written
notice that I actually receive before the end of such period, and that this Agreement shall not become effective or enforceable
until the expiration of such revocation period (the “Effective Date”).

By signing this
Agreement, you acknowledge that you are doing so voluntarily. You also acknowledge that you are not relying on any representations
by me or any other representative of the Company concerning the meaning of any aspect of this Agreement.

This Agreement shall
be binding upon each of the parties and upon their respective heirs, administrators, representatives, executors, successors and
assigns, and shall inure to the benefit of each party and to their heirs, administrators, representatives, executors, successors,
and assigns.

In the event of
any dispute, this Agreement will be construed as a whole, will be interpreted in accordance with its fair meaning, and will not
be construed strictly for or against either you or the Company. The law of the State of New York will govern any dispute about
this Agreement, including any interpretation or enforcement of this Agreement. The jurisdiction and venue provisions set forth
in Section 8.8 of the Employment Agreement will apply with respect to any dispute arising directly or indirectly out of this Agreement.
In the event that any provision or portion of a provision of this Agreement shall be determined to be unenforceable, the remainder
of this Agreement shall be enforced to the fullest extent possible as if such provision or portion of a provision were not included.
This Agreement may be modified only by a written agreement signed by you and an authorized representative of the Company.

    	19

    	 

    
If you agree to
these terms, please sign and date below and return this Agreement to me within the time limitation set forth above.

	 	 	
        Sincerely,

        INTRALINKS HOLDINGS, INC.

	 	 	 	 
	 	 	 	 
	 	 	By:	 
	 	 	Title:	 
	 	 	 	 
	
        Accepted and agreed to: 
	 	 	 
	 	 	 	 
	 	 	 	 
	 	 	 	 
	Scott Semel	 	Date	 

 

 

    	20

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