Document:

Severance Agreement dated June 4, 2008

 Exhibit 10.1 
 SEVERANCE AGREEMENT 
 This Severance Agreement (“Agreement”) is made as of June 4,
2008 by and between I-many, Inc., a Delaware corporation having its principal place of business at 399 Thornall Street Edison, New Jersey 08837 (the “Company”), and Lawrence Lindsey, a resident of Livermore, California
(“Executive”). 
 WHEREAS, Executive is employed by the Company, the Company desires to continue receiving the services of
Executive, and Executive desires to continue his employment with the Company, and 
 WHEREAS, the Board of Directors of the Company
(the “Board of the Directors”) has determined that it is in the best interest of the Company and its shareholders to formalize the circumstances under which Executive will receive certain payments and/or benefits upon the separation of his
employment with the Company. 
 NOW, THEREFORE, in consideration of the mutual covenants and promises contained herein and other good
and valuable consideration, the receipt and sufficiency of which are acknowledged by the parties, the Company and Executive agree to the follows: 
 1. Employment Term. Executive’s employment with the Company shall be at-will and Executive expressly acknowledges that his employment may be terminated at the discretion of either party at any time and for any reason.
During the course of Executive’s employment with the Company, Executive agrees to devote his full business time, energy, attention, and skill to such employment and agrees not to, directly or indirectly, engage or participate in, or become
employed by, or become a director, officer, or partner of, or provide services for compensation to or in connection with, any business activity that would be considered competitive with the business of the Company or which conflicts or interferes
with the performance of Executive’s obligations under this Agreement without the express written consent of the Board of Directors. 
 2. Termination of Employment. 
 2.1 Effects of Termination. 
 (a) Termination by the Company - Other than For Cause. Subject to the terms and conditions hereof, if: (1) Executive’s employment is
terminated solely upon the discretion of the Company pursuant to any reason other than for Cause or due to Death or Permanent Disability, as those terms are defined below; (2) Executive resigns his employment no more than ninety (90) days
after a fundamental reduction in Executive’s duties and responsibilities or a material failure to pay Executive compensation when it is due; (3) Executive resigns his employment no more than ninety (90) days after the Company requires
him to relocate his principal work location more 

 
than 75 miles from its current location of Redwood Shores, CA, or more than ninety (90) miles from Executive’s current home which is located in
Livermore, CA; or (4) Executive resigns his employment no more than ninety (90) days after Executive’s annual salary is reduced by 20% (except a temporary reduction that is imposed proportionately on all members of the Company’s
executive management team (EMT)), Executive shall be entitled to the following: 
 (i) Salary and Accrued Vacation. Salary through the
date of termination, accrued vacation earned but not yet paid through the date of termination, and any earned but unpaid bonus and commissions, the availability and pro rata calculation of which shall be determined solely at the discretion of the
Board of Directors. 
 (ii) Severance. The Company shall pay Executive severance equal to six (6) months of Executive’s
annualized base salary in effect as of the date of termination (or, if applicable, Executive’s greatest annualized base salary in effect within 90 days prior to his resignation), less applicable deductions and withholdings, payable in
accordance with the Company’s usual payroll practices. 
 (iii) Medical Benefits. The Company shall continue to maintain
Executive as a participant in its health insurance plan as required and/or permitted under the Consolidated Omnibus Budget Reconciliation Act of 1985 (often referred to as “COBRA”) and insofar as elected by Executive; for up to six
(6) months following termination of employment, but only until Executive accepts subsequent employment that offers health insurance, the Company shall reimburse Executive, on a monthly basis, for the difference between his COBRA expense and the
amount paid by a Company employee for the same coverage. 
 (b) Termination by the Company following Change in Control. Subject to
the terms and conditions hereof, if during the 180-day period following a Change in Control of the Company (regardless of Executive’s length of service as an employee of the Company at such time), Executive’s employment is terminated
pursuant to subsections 2.1(a)(1), 2.1(a)(2), 2.1(a)(3) or 2.1(a)(4) above, then Executive shall be entitled to the following: 
 (i)
Salary and Accrued Vacation. Salary through the date of termination, accrued vacation earned but not yet paid through the date of termination, and any earned but unpaid bonus and commissions, the availability and pro rata calculation of which
shall be determined solely at the discretion of the Board of Directors. 
 (ii) Severance. The Company shall pay Executive severance
equal to twelve (12) months of Executive’s annualized base salary in effect as of the date of termination (or, if applicable, Executive’s greatest annualized base salary in effect within 90 days prior to his resignation), less
applicable deductions and withholdings, payable in accordance with the Company’s usual payroll practices. 

 (iii) Medical Benefits. The Company shall continue to maintain Executive as a participant in its
health insurance plan as required and/or permitted under COBRA and insofar as elected by Executive; for up to twelve (12) months following termination of employment, but only until Executive accepts subsequent employment that offers health
insurance, the Company shall reimburse Executive, on a monthly basis, for the difference between his COBRA expense and the amount paid by a Company employee for the same coverage. 
 (iv) The benefits contained in this subsection 2.1(b) are intended as a replacement for the benefits contained in subsection 2.1(a), and not
supplemental thereto. 
 For purposes of this Agreement, a “Change in Control” is defined as the consummation of any of the following transactions:
(i) any merger or consolidation which results in the voting securities of the Company outstanding immediately prior thereto representing immediately thereafter (either by remaining outstanding or by being converted into voting securities of the
surviving or acquiring entity) less than a majority of the combined voting power of the voting securities of the Company or such surviving or acquiring entity outstanding immediately after such merger or consolidation; (ii) any sale of all or
substantially all of the assets of the Company; or (iii) the complete liquidation of the Company. 
 (c) General Release. The
Company or its successor shall not become obligated to make any severance payment or supplemental medical benefits payment under Sections 2.1(a)(ii) and (iii) or Sections 2.1(b)(ii) and (iii) unless Executive signs a general release of
claims against the Company or its successor substantially in the form of the agreement and general release attached at Exhibit A and continues to comply with the terms and conditions of agreement and general release. Such agreement and general
release shall include a mutual non-disparagement covenant and a re-affirmation of Executive’s obligations under his Nondisclosure and Developments Agreement with the Company dated April 2007. 
 (d) Termination by the Company – For Cause. The Company may terminate Executive’s employment for Cause: (i) at any time upon ten
(10) days’ written notice without cure by the Executive, or pay of an equivalent amount without such notice, in the case of (A) or (B) of this paragraph below; and (ii) without prior written notice, in the case of
(C) and (D) of this paragraph below. If the Company terminates Executive’s employment for Cause, it shall have no further obligations to Executive under this Agreement except for the payment of: (i) accrued and unpaid salary and
unused vacation time, through the effective date of termination; (ii) unpaid expenses reasonably incurred by the Executive and submitted in compliance with Company policies; and (iii) earned but not yet paid bonus and commissions, the
availability and pro rata calculation of which shall be determined solely at the discretion of the Board of Directors. Executive acknowledges and agrees that he will not be entitled to receive severance pay or supplemental medical benefits pay if
terminated for Cause. 

 For the purposes of this Agreement, “Cause” for termination shall be deemed to exist upon: (A) a good
faith finding by the Company that Executive refused to perform his/her assigned duties for the Company, consistent with the terms of this Agreement and the Company’s code of conduct; (B) a good faith finding by the Company that Executive
has engaged in gross negligence or gross misconduct in a matter that materially interferes with Executive’s job performance; (C) material dishonesty; or (D) the conviction of Executive of, or the entry of pleading of guilty or nolo
contendre by Executive to, any crime involving moral turpitude or any felony. 
 (e) Termination through Death or Permanent
Disability. The Company may also terminate Executive’s employment in the event of the Executive’s Death or Permanent Disability, as defined below. In the event of Executive’s Death or Permanent Disability while employed hereunder,
Employer shall have no further obligations to Executive under this Agreement except for the payment of: (i) accrued and unpaid salary and unused vacation time, through the effective date of termination; (ii) unpaid expenses reasonably
incurred by the Executive and submitted in compliance with Company policies; and (iii) earned but not yet paid bonus and commissions, the availability and pro rata calculation of which shall be determined solely at the discretion of the Board
of Directors. In addition, Executive will be eligible to participate in the benefit plans of the Company, at Executive’s cost and as long as continued participation is permitted under the terms and conditions of such plans and the requirements
of COBRA, for a period of up to six (6) months after the date of termination, or longer if required by applicable law. Executive acknowledges and agrees that he will not be entitled to receive severance pay if terminated due to Death or
Permanent Disability. 
 For purposes of this Agreement, the term “Permanent Disability” shall mean the inability of the Executive, due to a
physical or mental disability, for a period of 90 days (exclusive of time off pursuant to state or federal leave laws), whether or not consecutive, during any 360-day period to perform the essential functions of the job, including the services
contemplated under this Agreement, with or without reasonable accommodations. A determination of Permanent Disability shall be made at the sole discretion of the Company. 
 (f) No Other Benefits. No benefits other than those specifically enumerated in this section 2.1 shall be owed to the Executive upon termination
of employment. 
 2.2 Acknowledgement. Executive acknowledges and agrees that the compensation and benefits provided in this
Section 2 have been negotiated with the Company and shall be deemed to fully satisfy any notice requirements that may be required by any jurisdiction. Executive further acknowledges that the severance and medical benefits continuation benefits
provided in Section 2.1 are adequate consideration for the non-competition promises contained in Executive’s Nondisclosure, Developments and Noncompete Agreement with the Company. 

 2.3 Expense Reimbursement. The Company shall reimburse all legitimate business expenses submitted
by Executive within thirty (30) days of termination of his employment, whether for Cause or not for Cause, in accordance with the Company’s normal expense reimbursement policies. 
 3. Stock Option and Restricted Stock Vesting Acceleration. Notwithstanding any conflicting terms contained in a stock option agreement
between the Company and the Executive, upon a Change in Control of the Company, all of the Executive’s remaining unvested stock options and restricted stock (whether granted before or after the date of this Agreement) shall become vested in
full. Such acceleration shall not become effective until Executive signs a general release of claims against the Company substantially in the form of the agreement and general release attached at Exhibit A as well as signs any other documents
necessary to properly effectuate the vesting of the stock options and/or restricted stock. 
 4. Miscellaneous. 
 4.1 Successors and Assigns. This Agreement shall be binding upon and shall inure to the benefit of the Company’s successors in interest,
including, without limitation, successors through merger, consolidation, or sale of substantially all of the Company’s stock or assets, and shall be binding upon Executive. The Employee’s Nondisclosure, Developments and Noncompete
Agreement and Section 2.1 of this Agreement shall survive the cessation of Executive’s employment with the Company, regardless of who causes the cessation and regardless of the circumstances surrounding the cessation of employment.

 4.2 Notice. All notices required or permitted to be given under this Agreement shall be giving in writing and shall be deemed
sufficiently given if hand delivered by hand or mailed by registered mail, return receipt requested, to Executive’s respective address and the principal offices of the Company, as listed above. By giving notice to the other party in accordance
with this Paragraph, each party may change the address at which it is to receive notices hereunder. 
 4.3 Applicable Law;
Jurisdiction. This Agreement shall be governed by, construed in, interpreted and enforced in accordance with the laws of the State of New Jersey. In the event that any action is commenced concerning the parties’ obligations and rights under
this Agreement, and such action is for whatever reason not subject to arbitration, each of the Company and Executive agrees to submit itself to the personal jurisdiction of a competent court sitting within the State of New Jersey. 
 4.4 Independent Advice. Executive acknowledges that Executive has had the opportunity to evaluate this Agreement independently and with
Executive’s own professional advisors, and has not received and is not relying upon legal, tax or other professional advice from or on behalf of the Company in connection with entering into this Agreement. 

 4.5 Severability. In the event any provisions of this Agreement is found to be invalid or
unenforceable, such provisions shall be severable from the Agreement and shall not affect the validity or enforceability of any other provision of this Agreement, which shall remain in full force and effect. 
 4.6 Waiver. No failure or delay by either party in exercising any right, power or privilege under this Agreement shall operate as a waiver of the
right, power or privilege. A single or partial exercise of any right, power or privilege shall not preclude any other further exercise of the right, power or privilege. The rights and remedies provided in this Agreement shall be cumulative and not
exclusive of any rights or remedies provided by law. 
 4.7 Agreement. This Agreement, including the exhibits thereto, and the
Nondisclosure and Developments Agreement previously signed by Executive constitute the entire agreement between the parties and may only be changed by a written document signed by both parties. No agreements or representatives, oral or otherwise,
express or implied, with respect to the subject matter hereof have been made by either party which are not set forth expressly in this Agreement. 
 4.8 Prior Agreements. This Agreement revokes, replaces and supercedes any prior agreements and understandings, whether written or oral relating to the subject matter of this Agreement between the Company and Executive, except for
Executive’s Nondisclosure and Developments Agreement dated April 2007. 
 IN WITNESS WHEREOF, the parties have executed this Agreement
under seal as of the date set forth above, the Company acting herein by its duly authorized officer. 
  

							
	Executive:	 		 	I-many, Inc.
				
	 /s/ Lawrence Lindsey
	 		 	By:	 	 /s/ John A. Rade

	Lawrence Lindsey	 		 	Name:	 	John A. Rade
		 		 	Title:	 	President and Chief Executive OfficerFrom of Incentive Stock Option Agreement

 Exhibit 10.3 
 I-MANY, INC. 
 Incentive Stock Option Agreement 
 Granted Under the 2008 Stock Incentive Plan 
  

	1.	Grant of Option. 

 This agreement evidences the
grant by I-many, Inc., a Delaware corporation (the “Company”), on                     , 2008 (the “Grant Date”) to
[PARTICIPANT] (the “Participant”) of an option to purchase, in whole or in part, on the terms provided herein and in the Company’s 2008 Stock Incentive Plan (the “Plan”), a total of
                     shares (the “Shares”) of common stock, $.0001 par value per share, of the Company (“Common Stock”) at
$             per share. Unless earlier terminated, this option shall expire on
                    , 201     (the “Final Exercise Date”). 
 It is intended that the option evidenced by this agreement shall be an incentive stock option as defined in Section 422 of the Internal Revenue Code
of 1986, as amended, and any regulations promulgated thereunder (the “Code”). Except as otherwise indicated by the context, the term “Participant”, as used in this option, shall be deemed to include any person who acquires the
right to exercise this option validly under its terms. 
  

	2.	Vesting Schedule. 

 This option will become
exercisable (“vest”) in installments for not more than the number of shares set forth opposite such applicable date: 
  

			
	 June 1, 2007 [example]
	  	25% of the Shares
	 September 1, 2007
	  	an additional 6.25% of the Shares
	 December 1, 2007
	  	an additional 6.25% of the Shares
	 March 1, 2008
	  	an additional 6.25% of the Shares
	 June 1, 2008
	  	an additional 6.25% of the Shares
	 September 1, 2008
	  	an additional 6.25% of the Shares
	 December 1, 2008
	  	an additional 6.25% of the Shares
	 March 1, 2009
	  	an additional 6.25% of the Shares
	 June 1, 2009
	  	an additional 6.25% of the Shares
	 September 1, 2009
	  	an additional 6.25% of the Shares
	 December 1, 2009
	  	an additional 6.25% of the Shares
	 March 1, 2010
	  	an additional 6.25% of the Shares
	 June 1, 2010
	  	an additional 6.25% of the Shares

 The right of exercise shall be cumulative so that to the extent the option is not exercised in any
period to the maximum extent permissible it shall continue to be exercisable, in whole or in part, with respect to all shares for which it is vested until the earlier of the Final Exercise Date or the termination of this option under Section 3
hereof or the Plan. 

	3.	Exercise of Option. 

 (a) Form of Exercise.
Each election to exercise this option shall be in writing, signed by the Participant, and received by the Company at its principal office, accompanied by this agreement and payment in full. The Participant may make payment in the following manners:

 (1) in cash or by check, payable to the order of the Company; 
 (2) by (i) delivery of an irrevocable and unconditional undertaking by a creditworthy broker to deliver promptly to the Company sufficient funds to
pay the exercise price and any required tax withholding or (ii) delivery by the Participant to the Company of a copy of irrevocable and unconditional instructions to a creditworthy broker to deliver promptly to the Company cash or a check
sufficient to pay the exercise price and any required tax withholding; or 
 (3) by any combination of the above permitted forms of payment.

 The Participant may purchase less than the number of shares covered hereby, provided that no partial exercise of this option may be for
any fractional share. 
 (b) Continuous Employment with the Company Required. Except as otherwise provided in this Section 3,
this option may not be exercised unless the Participant, at the time he or she exercises this option, is, and has been at all times since the Grant Date, an employee of the Company or any parent or subsidiary of the Company as defined in
Section 424(e) or (f) of the Code (an “Eligible Participant”). 
 (c) Termination of Relationship with the
Company. If the Participant ceases to be an Eligible Participant for any reason, then, except as provided in paragraphs (d) and (e) below, the right to exercise this option shall terminate three months after such cessation (but in no
event after the Final Exercise Date). Notwithstanding the foregoing, if the Participant, prior to the Final Exercise Date, violates the non-competition or confidentiality provisions of any employment contract, confidentiality and nondisclosure
agreement or other agreement between the Participant and the Company, the right to exercise this option shall terminate immediately upon such violation. 
 (d) Exercise Period Upon Death or Disability. If the Participant dies or becomes disabled (within the meaning of Section 22(e)(3) of the Code) prior to the Final Exercise Date while he or she is an
Eligible Participant and the Company has not terminated such relationship for “cause” as specified in paragraph (e) below, this option shall be exercisable, within the period of one year following the date of death or disability of
the Participant by the Participant, provided that this option shall not be exercisable after the Final Exercise Date. 
 (e)
Discharge for Cause. If the Participant, prior to the Final Exercise Date, is discharged by the Company for “cause” (as defined below), the right to exercise this option shall terminate immediately upon the effective date of such
discharge. “Cause” shall mean willful misconduct by the Participant or willful failure by the Participant to perform his or her responsibilities to the Company (including, without limitation, breach by the Participant of any provision of
any employment, consulting, advisory, nondisclosure, non-competition or other 

  

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similar agreement between the Participant and the Company), as determined by the Company, which determination shall be conclusive. The Participant shall be
considered to have been discharged for “Cause” if the Company determines, within 30 days after the Participant’s resignation, that discharge for cause was warranted. 
  

	4.	Withholding. 

 No Shares will be issued pursuant to
the exercise of this option unless and until the Participant pays to the Company, or makes provision satisfactory to the Company for payment of, any federal, state or local withholding taxes required by law to be withheld in respect of this option.

  

	5.	Nontransferability of Option. 

 This option may not
be sold, assigned, transferred, pledged or otherwise encumbered by the Participant, either voluntarily or by operation of law, except by will or the laws of descent and distribution, and, during the lifetime of the Participant, this option shall be
exercisable only by the Participant. 
  

	6.	Disqualifying Disposition. 

 If the Participant
disposes of Shares acquired upon exercise of this option within two years from the Grant Date or one year after such Shares were acquired pursuant to exercise of this option, the Participant shall notify the Company in writing of such disposition.

  

	7.	Provisions of the Plan. 

 This option is subject to
the provisions of the Plan, a copy of which is furnished to the Participant with this option. 
 IN WITNESS WHEREOF, the Company has caused
this option to be executed under its corporate seal by its duly authorized officer. This option shall take effect as a sealed instrument. 
  

							
	 	 	 	 	I-MANY, INC.
	Dated:                     	 		 		 	
				
		 		 	By:	 	  

		 		 	Name:	 	Kevin M. Harris
		 		 	Title:	 	Chief Financial Officer

 PARTICIPANT’S ACCEPTANCE 
 The undersigned hereby accepts the foregoing option and agrees to the terms and conditions thereof. The undersigned hereby acknowledges receipt of a copy
of the Company’s 2008 Stock Incentive Plan. 
  

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	PARTICIPANT:
	  

	[PARTICIPANT]
		
	Address:	 	  

		
		 	  

  

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