Document:

Exhibit 10.1

 

COOPERATION AGREEMENT

 

This Cooperation Agreement
(this “Agreement”), effective as of September 13, 2022 (the “Effective Date”), is
entered into by and between Tabula Rasa HealthCare, Inc., a Delaware corporation (the “Company”), and Indaba
Capital Management, L.P. (“Indaba”). Indaba and each of its Affiliates (as defined below) are collectively referred
to as the “Investors.” The Company and Indaba are sometimes together referred to herein as the “Parties,”
and each, a “Party.”

 

WHEREAS, the Investors
beneficially own 6,521,578 shares of the Company’s common stock, par value $0.0001 per share (the “Common Stock”),
and hold $89,728,000 aggregate principal amount of the Company’s 1.75% convertible senior subordinated notes due February 15, 2026
(the “Senior Notes”), which, subject to conditions and adjustments described in the indenture governing the
Senior Notes, the Investors have the right to convert into 1,282,805 shares of Common Stock
as of the Effective Date; and

 

WHEREAS, the Parties
have determined that it is in their respective best interests to come to an agreement with respect to the composition of the Board of
Directors of the Company (the “Board”) and certain other matters, as provided in this Agreement.

 

NOW, THEREFORE, in
consideration of the promises, representations and mutual covenants and agreements set forth herein, and for other good and valuable consideration,
the receipt and sufficiency of which are hereby acknowledged, the Parties hereby agree as follows:

 

1.             Board
Composition and Related Matters.

 

(a)      Board
Matters.

 

(i)        Effective
upon the execution of this Agreement, the Board and all applicable committees of the Board shall take all necessary actions to (A) accept
the resignations tendered by each of Dr. Calvin Knowlton and Dr. Orsula Knowlton (together, the “Knowltons”) as directors
of the Company, who the Company hereby represents have submitted, or shall no later than the date hereof submit, letters of resignation
to the Board that will become effective immediately prior to the appointment of the New Directors (as defined below) and (B) appoint
Jonathan D. Schwartz (the “Non-Indaba Designee”) to the Board as a Class III director and Derek C. Schrier
(the “Indaba Designee” and together with the Non-Indaba Designee, the “New Directors”)
to the Board as a Class III director. Notwithstanding that the New Directors will be appointed as Class III directors with terms expiring
at the 2025 annual meeting of stockholders (the “2025 Annual Meeting”), the New Directors intend to voluntarily
stand for election at the Company’s 2023 annual meeting of stockholders (the “2023 Annual Meeting”) and
2024 annual meeting of stockholders.

 

(ii)       
During the period commencing on the Effective Date through the end of the 2023 Annual Meeting, the size of the Board shall not
exceed nine (9) members without the prior written consent of Indaba (such consent not to be unreasonably withheld, conditioned or delayed).

 

     

     

    

 

(iii)      
Effective upon the execution of this Agreement, the Board and all applicable committees of the Board shall take all necessary actions
to (A) appoint Michael Purcell as the independent Chair of the Board and (B) eliminate the role of Lead Independent Director of the Board.

 

(iv)      
Following the Effective Date, Mr. A Gordon Tunstall will continue to serve on the Board as an independent director until the earlier
of (x) the appointment of a third, new independent director designated by Indaba, who is racially or ethnically diverse, subject to the
Board’s approval, which is not to be unreasonably withheld and (y) December 31, 2022, at which time he will voluntarily resign from
the Board (with such resignation not to be unreasonably withheld, conditioned or delayed).

 

(b)      Board
Committees.

 

(i)        Effective
upon the appointment of the New Directors, the Board shall take all necessary actions to form a Strategic Review Committee of the Board
(the “Strategic Committee”). The scope of the Strategic Committee will be to oversee the Company’s current
strategic process relating to the sale of non-core assets and explore other strategic alternatives and value creation opportunities with
a view toward maximizing stockholder value. The Strategic Committee shall consist of no more than three (3) directors, who shall initially
be the New Directors and Dr. Jan Berger, to serve until the 2023 Annual Meeting. The Indaba Designee shall serve as Chair of the Strategic
Committee until the 2023 Annual Meeting.

 

(ii)       
Effective upon the appointment of the New Directors, the Board shall take all necessary actions to consolidate the Corporate Governance
Committee of the Board and Nominating Committee of the Board into one committee of the Board (the “Nominating and Governance
Committee”), consisting of no more than three (3) directors, who shall initially be the Non-Indaba Designee, Kathrine O’Brien,
and Dennis Helling, to serve until the 2023 Annual Meeting. Ms. O’Brien shall serve as Chair of the Nominating and Governance Committee
until the 2023 Annual Meeting.

 

(iii)      
Effective upon the appointment of the New Directors, the Board shall take all necessary actions to reduce the size of the Compensation
Committee of the Board (the “Compensation Committee”), such that it shall consist of no more than three (3)
directors, who shall initially be the Non-Indaba Designee, Pamela Schweitzer, and Ms. O’Brien, to serve until the 2023 Annual Meeting.
The Non-Indaba Designee shall serve as Chair of the Compensation Committee until the 2023 Annual Meeting.

 

(iv)      
Effective upon the appointment of the New Directors, the Board shall take all necessary actions to reconstitute the Audit Committee
of the Board (the “Audit Committee”), such that it consists of no more than three (3) directors, who shall initially
be of Mr. Purcell, Dr. Berger, and Samira Beckwith, to serve until the 2023 Annual Meeting. Mr. Purcell shall continue to serve as Chair
of the Audit Committee until the 2023 Annual Meeting.

 

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(c)      Board
Compensation and Other Benefits. The Company agrees that each New Director (and any Replacement Director) shall receive (i) the
same benefits of director and officer insurance as all other non-management directors on the Board, (ii) the same compensation for his
or her service as a director as the compensation received by other non-management directors on the Board, and (iii) such other benefits
on the same basis as all other non-management directors on the Board.

 

(d)      Board
Policies and Procedures. Each Party acknowledges that each New Director (and any Replacement Director), shall be governed by
all the same policies, processes, procedures, codes, rules, standards and guidelines applicable to members of the Board (collectively,
the “Company Policies”), and will be required to strictly adhere to the Company’s policies on confidentiality
imposed on all members of the Board. Notwithstanding anything to the contrary contained in this Agreement or the Company Policies, the
Indaba Designee (and any Replacement Director) may provide Confidential Information (as defined below) of the Company to Indaba or legal
counsel retained by Indaba that the Indaba Designee (or any Replacement Director) learns in his or her capacity as a member of the Board;
provided, however, that prior to providing such Confidential Information, the intended recipients shall execute a customary
confidentiality agreement pursuant to which (i) they shall be informed of the confidential nature of the Confidential Information and
(ii) Indaba shall cause such intended recipients to refrain from disclosing the Confidential Information to anyone, by any means, or
from otherwise using the Confidential Information in any way other than in connection with assisting Indaba in the evaluation of its
investment in the Company.

 

(e)      Replacement
Rights. If, at any time prior to the Termination Date, either of the New Directors (or any Replacement Director) is unable to
serve as a director for any reason and ceases to be a director, Indaba shall have the right to propose to the Company a replacement director
(a “Replacement Director”) with relevant financial and business experience, who qualifies as “independent”
pursuant to Nasdaq Stock Market LLC’s listing standards and the Securities and Exchange Commission (the “SEC”) rules
and regulations; provided that Indaba’s right to propose a Replacement Director pursuant to this Section 1(e) shall
terminate when the Investors cease to beneficially own, in the aggregate, the Minimum Ownership Amount (as defined below). Any candidate
for Replacement Director shall be subject to the reasonable approval of the Nominating and Governance Committee and the Board, which
approval shall occur as soon as practicable following Indaba proposing a director and shall not be unreasonably withheld, conditioned
or delayed, and such Replacement Director shall be appointed to the Board within five (5) business days after the Board and the Nominating
Committee have approved of such candidate. Any Replacement Director appointed to the Board in accordance with this Section 1(e)
shall be appointed to any applicable committee of the Board of which the replaced director was a member immediately prior to such director’s
resignation or removal. In the event the Board or the Nominating and Governance Committee determines in good faith not to approve any
Replacement Director proposed by Indaba, Indaba shall have the right to propose additional Replacement Directors in accordance with this
Section 1(e) until a Replacement Director is appointed to the Board.

 

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(f)       Board
Declassification. The Company agrees that following the execution of this Agreement, the Board and all applicable committees
of the Board shall take all necessary actions to seek the approval of the Company’s stockholders at the 2023 Annual Meeting of
an amendment to the Certificate of Incorporation (as defined below) to declassify the structure of the Board, such that all directors
up for election beginning with the 2023 Annual Meeting will be elected for a one year term (assuming stockholder approval of the amendment
to the Certificate of Incorporation providing for such declassification), with the Board becoming fully declassified by the 2025 Annual
Meeting.

 

2.             Management Transition and Related Matters

 

(a)      Effective
upon the execution of this Agreement, the Knowltons will deliver their respective resignation notices to the Board, pursuant to which
the Knowltons will resign from any and all positions of the Company they each respectively hold (the “Resignations”),
with such Resignations to be effective as of the Effective Date. Effective upon the Resignations, Brian Adams will be appointed as interim
Chief Executive Officer (provided, however, that oversight with respect to the matters indicated on Schedule 1 attached
hereto shall be assigned to the Company’s Chief Financial Officer, who shall then report directly to both the interim Chief Executive
Officer and the Board on such matters) and the Board shall commence a search for a new Chief Executive Officer of the Company promptly
following the Resignations.

 

(b)      In connection with the Resignations, each of the Knowltons will enter into an executive separation agreement effective as of the
Effective Date in the form attached hereto as Exhibit A.

 

(c)      Effective
upon the Resignations, the Company will enter into consulting agreements with each of the Knowltons, in the form attached hereto as Exhibit
B, in order to facilitate the successful transition of his or her, as applicable, responsibilities.

 

3.              Withdrawal of Section 220 Demand And Waiver Of Inspection Rights During The Term. As
of the Effective Date, Indaba shall be deemed to have irrevocably withdrawn its stockholder inspection demand letter (the “Section
220 Demand”) that it delivered to the Company on July 27, 2022, pursuant to Section 220 of the DGCL. During the Term, Indaba and
its Affiliates irrevocably waives any and all rights to inspect the Company’s books and records pursuant to Section 220 of the DGCL
or the common law.

 

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4.              No
Litigation and General Release of Claims. During the Term, each Party hereby covenants and agrees
that it shall not, and shall not permit any of its Affiliates or Representatives to, directly or indirectly, alone or in concert with
others, encourage, pursue, or assist any other person to threaten or initiate any lawsuit, claim, or other proceeding before any court
(each, a “Legal Proceeding”) against the other Party, any of its Affiliates,
or its Representatives, except for (a) any Legal Proceeding initiated primarily to remedy a breach of or to enforce this Agreement, or
(b) counterclaims with respect to any proceeding initiated by or on behalf of one Party or its Affiliates against any other Party or
its Affiliates; provided, however, that the foregoing shall not prevent any Party or any of its Representatives from responding to oral
questions, interrogatories, requests for information or documents, subpoenas, civil investigative demands or similar processes (each,
a “Legal Requirement”) in connection with any Legal Proceeding if such Legal
Proceeding has not been initiated by, on behalf of, or at the direct or indirect suggestion of such Party or any of its Representatives;
provided, further, that in the event any Party or any of its Representatives receives such Legal Requirement, such Party shall give prompt
written notice of such Legal Requirement to the other Party (except where such notice would be legally prohibited or not practicable).
Each Party represents and warrants to each other Party that neither it nor any assignee has filed any Legal Proceeding or is aware of
any Legal Proceeding, or a Legal Requirement related thereto, against any other Party that has not been disclosed to such other Party
prior to the date hereof. It is understood and that in consideration of the mutual promises and covenants contained herein, and after
consultation with their respective counsel, the Company, on the one hand, and each other Party, on the other hand, on behalf of themselves
and for all of their past and present related, parent and subsidiary companies, joint venturers, limited liability companies, and partnerships,
successors, assigns, and the respective owners, officers, directors, nominees for election to the Board, agents, employees, shareholders,
members, consultants and attorneys, Affiliates, and other Representatives of each of them (collectively “Affiliated Persons”
and each, an “Affiliated Person”), irrevocably and unconditionally release,
acquit and forever discharge the other and all of their Affiliated Persons, from any and all causes of action, claims, actions, rights,
judgments, obligations, damages, demands, losses, controversies, contentions, complaints, promises, accountings, bonds, bills, debts,
dues, sums of money, expenses, specialties and fees and costs (whether direct, indirect or consequential, incidental or otherwise including,
without limitation, attorney’s fees or court costs, of whatever nature) incurred in connection therewith of any kind whatsoever,
whether known or unknown, suspected or unsuspected, in their own right and derivatively, in law or in equity or liabilities of whatever
kind or character (the “Claims”), which the Parties have or may have against
one another based upon events occurring prior to the date of the execution of this Agreement, including, without limitation, arising
out of or related to the Section 220 Demand, the engagement and interactions between the Investors and the Company (either directly or
through their respective Representatives) and the Parties’ communications with other investors in the Company (the “Released
Matters”). The Parties acknowledge that this general release of claims includes, but is not
limited to, any and all statutory and common law claims for, among other things, fraud and breach of fiduciary duty based upon events
occurring prior to the Effective Date. The Parties intend that the foregoing release be broad with respect to the Released Matters, provided,
however, this release and waiver of Claims does not release any rights and duties under this Agreement and shall not include any actions
or claims any Party may have for breach of, or to enforce, the terms of this Agreement.

 

Each
of the Parties to this Agreement represents and warrants that it has not heretofore transferred or assigned, or purported to transfer
or assign, to any person, firm, or corporation any claims, demands, obligations, losses, causes of action, damages, penalties, costs,
expenses, attorneys’ fees, liabilities, or indemnities herein released.

 

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The
Company, on the one hand, and the Investors, on the other hand, on behalf of themselves and their Affiliated Persons, each acknowledge
that as of the Effective Date, the Parties may have claims against an Affiliated Person that a Party does not know or suspect to exist
in his, her or its favor, including, but not limited to claims that, had they been known, might have affected the decision to enter into
this Agreement, or to provide the general release set forth in this Section 4. In connection with any such claims, the Parties
agree that they intend to waive, relinquish, and release any and all provisions, rights, and benefits any state or territory of the United
States or other jurisdiction that purports to limit the application of a release to unknown claims, or to facts unknown at the time this
Agreement was entered into. Without limiting the foregoing, the Parties expressly waive any right or protection under Section 1542 of
the California Civil Code, which provides: A GENERAL RELEASE DOES NOT EXTEND TO CLAIMS THAT THE CREDITOR OR RELEASING PARTY DOES NOT KNOW
OR SUSPECT TO EXIST IN HIS OR HER FAVOR AT THE TIME OF EXECUTING THE RELEASE AND THAT, IF KNOWN BY HIM OR HER, WOULD HAVE MATERIALLY AFFECTED
HIS OR HER SETTLEMENT WITH THE DEBTOR OR RELEASED PARTY. In connection with the foregoing waiver, the Parties acknowledge that they, or
any of them, may (including after the Effective Date) discover facts in addition to or different from those known or believed by them
to be true with respect to the subject matter of this Agreement, but it is the intention of the Parties to complete, fully, finally, and
forever compromise, settle, release, discharge, and extinguish any and all claims that they may have against each other and their Affiliated
Person, known or unknown, suspected or unsuspected, contingent or absolute, accrued or unaccrued, apparent or unapparent, that now exist
or previously existed, without regard to the subsequent discovery of additional or different facts. The Parties acknowledge that the foregoing
waiver is a key, material, bargained-for element to this Agreement and the general release that is part of it. The Parties further acknowledge
that nothing is this this Section 4, will prevent directors from carrying out in good faith their fiduciary duties as directors
of the Company.

 

5.             Mutual Non-Disparagement.

 

(a)      Subject
to Section 6, Indaba agrees that, during the Term, neither it nor any other Investor shall, and it shall cause each of its Representatives
and the other Investors’ Representatives not to, directly or indirectly, in any capacity or manner, make, transmit or otherwise
communicate in any way any remark, comment, communication or other statement of any kind, whether verbal, in writing, electronically
transferred or otherwise, that might reasonably constitute an ad hominem attack on, or otherwise defames, the Company or any of its Representatives,
or any of their businesses, products or services.

 

(b)      The Company hereby agrees that, during the Term, neither it nor any of its Representatives shall, and it shall cause each of its
Representatives not to, directly or indirectly, in any capacity or manner, make, transmit or otherwise communicate in any way any remark,
comment, communication or other statement of any kind, whether verbal, in writing, electronically transferred or otherwise, that might
reasonably be construed to be derogatory, or constitute an ad hominem attack on, or otherwise defames the reputation or good name of the
Investors or any of their Representatives, or any of their businesses, products or services.

 

(c)      Notwithstanding the foregoing, nothing in this Section 5 or elsewhere in this Agreement shall prohibit any Party from making
any factual statement, including as required under the federal securities laws or other applicable laws (including to comply with any
subpoena or other legal process from any governmental or regulatory authority with competent jurisdiction over the relevant Party hereto)
or stock exchange regulations.

 

(d)      The limitations set forth in Sections 5(a) and 5(b) shall not prevent any Party from responding to any public statement
made by the other Party of the nature described in Sections 5(a) and 5(b), if such statement by the other Party was made
in breach of this Agreement.

 

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6.            
Standstill.

 

(a)      During
the Term, Indaba shall not, and shall cause the other Investors and its and the other Investors’ respective Representatives not
to, in any way, directly or indirectly (in each case, except as expressly permitted by this Agreement):

 

(i)        
make, engage in, or in any way participate in, directly or indirectly, any “solicitation” (as such term is defined
under the Securities Exchange Act of 1934, as amended (the “Exchange Act”)) of proxies or consents with respect to the election
or removal of directors of the Company or any other matter or proposal relating to the Company or become a “participant” (as
such term is defined in Instruction 3 to Item 4 of Schedule 14A promulgated under the Exchange Act) in any such solicitation of proxies
or consents;

 

(ii)       
knowingly encourage or advise any Third Party (as defined below) or knowingly assist any Third Party in encouraging or advising
any other person (A) with respect to the giving or withholding of any proxy or consent relating to, or other authority to vote, any Voting
Securities, or (B) in conducting any type of referendum relating to the Company (other than such encouragement or advice that is consistent
with the Board’s recommendation in connection with such matter);

 

(iii)      
form, join or act in concert with any “group” as defined pursuant to Section 13(d) of the Exchange Act with respect
to any Voting Securities, other than solely with Affiliates of the Investors with respect to Voting Securities now or hereafter owned
by them or otherwise in any manner agree, attempt, seek or propose to deposit any securities of the Company in any voting trust or similar
arrangement, or subject to any securities of the Company to any arrangement or agreement with respect to the voting thereof, except as
expressly set forth in this Agreement;

 

(iv)      
make, or in any way participate in, any offer or proposal with respect to any Extraordinary Transaction (as defined below), either
publicly or in a manner that would reasonably require public disclosure by the Company or Indaba and any of the other Investors (it being
understood that the foregoing will not restrict the Indaba and the other Investors from tendering shares, receiving payment for shares
or otherwise participating in any Extraordinary Transaction initiated by a Third Party on the same basis as other stockholders of the
Company);

 

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(v)       make
any public proposal with respect to any material change in the capitalization, stock repurchase programs, dividend policy, management,
business, strategy or corporate structure of the Company or any of its subsidiaries;

 

(vi)      
enter into a voting trust, arrangement or agreement with respect to any Voting Securities, or subject any Voting Securities to
any voting trust, arrangement or agreement, in each case other than (A) this Agreement, (B) solely with Affiliates of the Investors or
(C) granting proxies in solicitations approved by the Board;

 

(vii)     
(A) seek, alone or in concert with others, election or appointment to, or representation on, the Board or nominate or propose the
nomination of, or recommend the nomination of, any candidate to the Board (including, for the avoidance of doubt, by making a change to
the size of the Board or proposing to fill any vacancies on the Board), except as set forth in this Agreement, (B) make or be the proponent
of any stockholder proposal to the Company, (C) seek, alone or in concert with others, the removal of any member of the Board; or (D)
call or seek to call, alone or in concert with others, a special meeting of stockholders of the Company; provided that nothing in this
Agreement will prevent the Investors or their Affiliates from taking actions in furtherance of identifying any Replacement New Director;

 

(viii)     
make any request for stockholder list materials or other books and records of the Company under Section 220 of the Delaware General
Corporation Law or otherwise; provided that nothing herein shall prevent either New Director (or any Replacement Director) from
making such a request solely in such New Director’s (or Replacement Director’s) capacity as a director in a manner consistent
with his or her fiduciary duties to the Company;

 

(ix)      
enter into any negotiations, agreements or understandings with any person not (A) a Party to this Agreement, (B) a member of the
Board, (C) an officer of the Company, or (D) an Affiliate of the Investors (any person not set forth in clauses (A)-(D) shall be referred
to as a “Third Party”) to take any action that any of the Investors are prohibited from taking pursuant to this
Section 6(a);

 

(x)       
sell, offer or agree to sell directly or indirectly, through swap or hedging transactions or otherwise, the securities of the Company
or any rights decoupled from the underlying securities of the Company held by Indaba or any Indaba Affiliate to any Third Party that would
knowingly result in such Third Party, together with its affiliates and associates, owning, controlling or otherwise having any beneficial
or other ownership interest in the aggregate of more than 4.9% of the shares of Common Stock outstanding at such time, except in a transaction
approved by the Board; or

 

(xi)      
request that the Company, directly or indirectly, amend or waive any provision of this Section (including this clause (xi), other
than through non-public communications with the Company that would not reasonably be expected to trigger public disclosure obligations
for any of the Parties.

 

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Notwithstanding anything
set forth herein to the contrary, nothing set forth in this Agreement shall be deemed to prevent Indaba or the other Investors from (I)
communicating privately with the Board or any of the Company’s executive officers regarding any matter, so long as such communications
are not intended to, and would not reasonably be expected to, require the Company or Indaba to make public disclosure with respect thereto,
(II) identifying potential director candidates to serve on the Board as Replacement Directors, so long as such actions do not create,
and that Indaba would not reasonably expect to create, a public disclosure obligation for Indaba or the Company, are not publicly disclosed
by Indaba or its Affiliates and are undertaken on a basis reasonably designed to be confidential; (III) making or sending private communications
to investors or prospective investors in Indaba or any of its Affiliates, provided that such statements or communications (1) are
based on publicly available information and (2) are not reasonably expected to be publicly disclosed and are understood by all parties
to be confidential communications; (IV) taking any action to the extent necessary to comply with any law, rule or regulation or any action
required by any governmental or regulatory authority or stock exchange that has, or may have, jurisdiction over Indaba; or (V) communicating
privately with stockholders of the Company when such communication is not made with an intent to otherwise violate, and would not be reasonably
expected to result in a violation of, any provision of this Agreement. Furthermore, for the avoidance of doubt, nothing in this Agreement
shall be deemed to restrict in any way either New Directors (or any Replacement Director) in the exercise of his or her fiduciary duties
under applicable law as a director of the Company.

 

(b)      Notwithstanding anything contained in this Agreement to the contrary, the provisions of Sections 4, 5 and 6
of this Agreement shall automatically terminate upon the consummation of a Change of Control transaction agreed to by the Board and involving
the Company, provided, that if the Indaba Designee (or any Replacement Director thereof) approves of any such Change of Control transaction
as a Board member, the termination provided for under this Section 6(b) shall not apply with respect to such Change of Control
transaction.

 

(c)      At any time Indaba ceases to have a Schedule 13D filed with the SEC and during the Term, upon reasonable written notice from the
Company pursuant to Section 17 hereof, Indaba shall promptly provide the Company with information regarding the amount of the securities
of the Company (i) beneficially owned by each of the Investors, (ii) with respect to which any of the Investors has (A) any direct or
indirect rights or options to acquire or (B) any economic exposure through any derivative securities or contracts or instruments in any
way related to the price of such securities, or (iii) with respect to which Indaba or any other of the Investors has hedged its position
by selling covered call options. This ownership information provided to the Company will be kept strictly confidential, unless required
to be disclosed pursuant to applicable laws and regulations, any subpoena, legal process or other legal requirement or in connection with
any litigation or similar proceedings in connection with this Agreement.

 

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7.             Representations and Warranties of the Company. The Company represents and warrants to Indaba that (b) the Company has
the corporate power and authority to execute this Agreement and to bind it thereto, (c) this Agreement has been duly and validly authorized,
executed and delivered by the Company, constitutes a valid and binding obligation and agreement of the Company, and is enforceable against
the Company in accordance with its terms, except as enforcement thereof may be limited by applicable bankruptcy, insolvency, reorganization,
moratorium, fraudulent conveyance or similar laws generally affecting the rights and remedies of creditors and subject to general equity
principles, and (d) the execution, delivery and performance of this Agreement by the Company does not and will not violate or conflict
with (i) any law, rule, regulation, order, judgment or decree applicable to it, or (ii) result in any breach or violation of or constitute
a default (or an event which with notice or lapse of time or both could become a default) under or pursuant to, or result in the loss
of a material benefit under, or give any right of termination, amendment, acceleration or cancellation of, any organizational document,
or any material agreement, contract, commitment, understanding or arrangement to which the Company is a party or by which it is bound.

 

8.              Representations and Warranties of Indaba. Indaba represents and warrants to the Company that (e) this Agreement has
been duly and validly authorized, executed and delivered by Indaba, and constitutes a valid and binding obligation and agreement of Indaba,
enforceable against Indaba in accordance with its terms, except as enforcement thereof may be limited by applicable bankruptcy, insolvency,
reorganization, moratorium, fraudulent conveyance or similar laws generally affecting the rights and remedies of creditors and subject
to general equity principles, (f) the signatory for Indaba has the power and authority to execute this Agreement and any other documents
or agreements entered into in connection with this Agreement on behalf of itself and Indaba, and to bind Indaba to the terms hereof and
thereof, (g) the execution, delivery and performance of this Agreement by Indaba and the performance of this Agreement by the other Investors
does not and will not violate or conflict with (i) any law, rule, regulation, order, judgment or decree applicable to it, or (ii) result
in any breach or violation of or constitute a default (or an event which with notice or lapse of time or both could become a default)
under or pursuant to, or result in the loss of a material benefit under, or give any right of termination, amendment, acceleration or
cancellation of, any organizational document, agreement, contract, commitment, understanding or arrangement to which any Investor is
a party or by which it is bound, (h) neither Indaba nor any of its Affiliates has provided or will provide the New Directors (or any
Replacement Director) with any compensation for his or her service as the New Directors (or any Replacement Director), and (e) any onboarding
documentation (including any director candidate questionnaire) and other information provided by the New Directors to the Company in
connection with his appointment to the Board is true, accurate and complete in all material respects. For the avoidance of doubt, any
compensation received by the Indaba Designee by virtue of his or her relationship with Indaba shall not be deemed to be compensation
for his or her service as a New Director.

 

9.             SEC
Filings.

 

(a)      No
later than four (4) business days following the Effective Date, the Company shall file with the SEC a Current Report on Form 8-K reporting
its entry into this Agreement and appending this Agreement as an exhibit thereto (the “Form 8-K”). The Form
8-K shall be consistent with the terms of this Agreement. The Company shall provide Indaba with a reasonable opportunity to review and
comment on the Form 8-K prior to it being filed with the SEC and consider in good faith any comments provided by Indaba.

 

(b)      No
later than two (2) business days following the Effective Date, Indaba shall file with the SEC an amendment to that certain Schedule 13D,
dated December 15, 2020 and as amended (the “Schedule 13D”), in compliance with Section 13 of the Exchange
Act reporting its entry into this Agreement and appending this Agreement as an exhibit thereto or incorporating this Agreement by reference
to the Company’s Form 8-K (the “Schedule 13D Amendment”). The Schedule 13D Amendment shall be consistent
with the terms of this Agreement. Indaba shall provide the Company with a reasonable opportunity to review and comment on the Schedule
13D Amendment prior to it being filed with the SEC and consider in good faith any comments of the Company.

 

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10.           Term;
Termination.  The term of this Agreement (the “Term”) shall commence on the Effective Date and shall
automatically terminate forty-five (45) days before the nomination window closes under the Bylaws for the Company’s 2023 Annual
Meeting (the “Termination Date”).

 

11.           Expenses. Each Party shall be responsible for its own fees and expenses in connection with the negotiation and
execution of this Agreement and the transactions contemplated hereby; provided, however, that the Company shall promptly reimburse Indaba
for its reasonable and documented out-of-pocket fees and expenses, including legal expenses, arising out of or related to its engagement
with the Company to date and the negotiation and execution of this Agreement and the transactions contemplated hereby in an amount not
to exceed $500,000.

 

12.           No
Other Discussions or Arrangements. Indaba represents and warrants that, as of the date of this Agreement, except as specifically
disclosed on the Schedule 13D or any Form 4 filing, (i) the Investors do not own, of record or beneficially, any Voting Securities or
any securities convertible into, or exchangeable or exercisable for, any Voting Securities and (j) the Investors have not entered into,
directly or indirectly, any agreements or understandings with any person (other than its own Representatives) with respect to any potential
transaction involving the Company or the voting or disposition of any securities of the Company.

 

13.           Governing Law; Jurisdiction. This Agreement shall be governed by and construed in accordance with the internal laws
of the State of Delaware without giving effect to any choice or conflict of law provision or rule that would cause the application of
laws of any jurisdiction other than those of the State of Delaware. Each Party agrees that it shall bring any suit, action or other proceeding
in respect of any claim arising out of or related to this Agreement (each, an “Action”) exclusively in (k) the Delaware
Court of Chancery in and for New Castle County, (l) in the event (but only in the event) that such court does not have subject matter
jurisdiction over such Action, the United States District Court for the District of Delaware or (m) in the event (but only in the event)
such courts identified in clauses (a) and (b) do not have subject matter jurisdiction over such Action, any other Delaware state court
(collectively, the “Chosen Courts”), and, solely in connection with an Action, (i) irrevocably submits to the exclusive
jurisdiction of the Chosen Courts, (ii) irrevocably submits to the exclusive venue of any such Action in the Chosen Courts and waives
any objection to laying venue in any such Action in the Chosen Courts, (iii) waives any objection that the Chosen Courts are an inconvenient
forum or do not have jurisdiction over any Party hereto and (iv) agrees that service of process upon such Party in any such Action shall
be effective if notice is given in accordance with Section 17 of this Agreement. Each Party agrees that a final judgment in any Action
brought in the Chosen Courts shall be conclusive and binding upon each of the Parties and may be enforced in any other courts, the jurisdiction
of which each of the Parties is or may be subject, by suit upon such judgment.

 

    11

     

    

 

14.           Waiver
of Jury Trial. EACH PARTY HERETO ACKNOWLEDGES AND AGREES THAT ANY CONTROVERSY WHICH MAY ARISE UNDER THIS AGREEMENT IS
LIKELY TO INVOLVE COMPLICATED AND DIFFICULT ISSUES AND, THEREFORE, EACH SUCH PARTY IRREVOCABLY AND UNCONDITIONALLY WAIVES TO THE FULLEST
EXTENT PERMITTED BY APPLICABLE LAW ANY RIGHT IT MAY HAVE TO A TRIAL BY JURY IN RESPECT OF ANY LEGAL ACTION ARISING OUT OF OR RELATING
TO THIS AGREEMENT OR THE TRANSACTIONS CONTEMPLATED BY THIS AGREEMENT. EACH PARTY TO THIS AGREEMENT CERTIFIES AND ACKNOWLEDGES THAT (A)
NO REPRESENTATIVE OF ANY OTHER PARTY HERETO HAS REPRESENTED, EXPRESSLY OR OTHERWISE, THAT SUCH OTHER PARTY WOULD NOT SEEK TO ENFORCE
THE FOREGOING WAIVER IN THE EVENT OF A LEGAL ACTION, (B) SUCH PARTY HAS CONSIDERED THE IMPLICATIONS OF THIS WAIVER, (C) SUCH PARTY MAKES
THIS WAIVER VOLUNTARILY, AND (D) SUCH PARTY HAS BEEN INDUCED TO ENTER INTO THIS AGREEMENT BY, AMONG OTHER THINGS, THE MUTUAL WAIVERS
AND CERTIFICATIONS IN THIS SECTION 14.

 

15.          
Specific Performance. Each of the Parties acknowledges and agrees that irreparable injury to the other Parties
would occur in the event any of the provisions of this Agreement are not performed in accordance with their specific terms or are otherwise
breached and that such injury would not be adequately compensable by the remedies available at law (including the payment of money damages).
It is accordingly agreed that each of the Parties (the “Moving Party”) shall be entitled to specific enforcement of,
and injunctive or other equitable relief as a remedy for any such breach or to prevent any violation or threatened violation of, the
terms hereof, and the other Parties will not take action, directly or indirectly, in opposition to the Moving Party seeking such relief
on the grounds that any other remedy or relief is available at law or in equity. The Parties further agree to waive any requirement for
the security or posting of any bond in connection with any such relief. The remedies available pursuant to this Section 15 shall not
be deemed to be the exclusive remedies for a breach of this Agreement but shall be in addition to all other remedies available at law
or equity.

 

16.          Certain Definitions. As used in this Agreement:

 

(a)      “Affiliate”
shall mean any “Affiliate” as defined in Rule 12b-2 promulgated by the SEC under the Exchange Act, including, for the avoidance
of doubt, persons who become Affiliates subsequent to the Effective Date;

 

(b)      “beneficial owner”, “beneficial ownership” and “beneficially own”
shall have the same meanings as set forth in Rule 13d-3 promulgated by the SEC under the Exchange Act;

 

    12

     

    

 

(c)      “business day” shall mean any day other than a Saturday, Sunday or day on which the commercial banks
in the State of New York are authorized or obligated to be closed by applicable law;

 

(d)      “Bylaws”
shall mean the Amended and Restated Bylaws of the Company, as currently in effect as of the Effective Date;

 

(e)      “Certificate of Incorporation” shall mean the Amended and Restated Certificate of Incorporation of the
Company, as may be amended from time to time;

 

(f)      a
 “Change of Control” transaction shall be deemed to have taken place if (i) any person is or becomes a beneficial
owner, directly or indirectly, of securities of the Company representing more than fifty percent (50%) of the equity interests and voting
power of the Company’s then-outstanding equity securities or (ii) the Company effects a merger or a stock-for-stock transaction
whereby immediately after the consummation of the transaction the Company’s stockholders retain less than fifty percent (50%) of
the equity interests and voting power of the surviving entity’s then-outstanding equity securities, or (iii) the Company sells
all or substantially all of its assets to a Third Party;

 

(g)      “Confidential
Information” shall mean all information that is understood to be confidential by a reasonable person by the context of
its disclosure and/or its content, scope or nature that is entrusted to or obtained by a director of the Company by reason of his or
her position as a director of the Company, including, but not limited to, discussions or matters considered in meetings of the Board
or Board committees; provided, however, Confidential Information shall not include information that (v) at the time of
disclosure is, or as of and at such time such disclosure thereafter becomes, generally available to the public other than as a result
of any material breach of this Agreement by Indaba or any of its Representatives or any director’s noncompliance with the Company
Policies, (vi) at the time of disclosure is, or as of and at such time such disclosure thereafter becomes, available to Indaba or its
Representatives on a non-confidential basis from a Third-Party source, provided that, to Indaba or its Representative’s
knowledge, such Third-Party is not and was not prohibited from disclosing such Confidential Information to Indaba or its Representative
by any applicable law or contractual obligation, (vii) was legally obtained by Indaba or its Representatives prior to being disclosed
by or on behalf of a director of the Company (whether or not the Indaba Designee or a Replacement Director), or (viii) was or is independently
developed by Indaba or any of its Representatives without reliance on, or reference to, any Confidential Information.

 

(h)      “Extraordinary
Transaction” shall mean any equity tender offer, equity exchange offer, merger, acquisition, joint venture, business combination,
financing, recapitalization, restructuring, disposition, distribution, spin-off, or sale or transfer of a majority of the Company’s
assets, in one or a series of transactions.

 

(i)       “Minimum
Ownership Amount” shall mean 5% of the outstanding Common Stock.

 

    13

     

    

 

(j)      
“other Party” shall mean, with respect to the Company, Indaba, and with respect to Indaba, the Company;

 

(k)      “person” or “persons” shall mean any individual, corporation (including not-for-profit),
general or limited partnership, limited liability company, joint venture, estate, trust, association, organization or other entity of
any kind, structure or nature;

 

(l)      “Representative”
shall mean a person’s Affiliates and its and their respective directors, officers, employees, partners, members, managers, consultants,
legal or other advisors, agents and other representatives; provided, that when used with respect to the Company, “Representatives”
shall not include any non-executive employees; and

 

(m)     “Voting Securities” means the Common Stock and any other securities of the Company entitled to vote in
the election of directors.

 

17.          
Notices. All notices, requests, consents, claims, demands, waivers, and other communications hereunder shall
be in writing and shall be deemed to have been given: (n) when delivered by hand (with written confirmation of receipt), (o) when received
by the addressee if sent by a nationally recognized overnight courier (receipt requested), (p) on the date sent by email if sent during
normal business hours, and on the next business day if sent after normal business hours (to the extent that no “bounce back,”
 “out of office” or similar message indicating non-delivery is received with respect thereto); or (q) on the third day after
the date mailed, by certified or registered mail, return receipt requested, postage prepaid. Such communications must be sent to the
respective Parties at the addresses set forth in this Section 17 (or to such other address that may be designated by a Party from time
to time in accordance with this Section 17).

 

If to the Company, to its address at:

Tabula Rasa HealthCare, Inc.

228 Strawbridge Drive, Suite 100

Moorestown, New Jersey 08057

	Attention:	Brian W. Adams
	Email:	BAdams@trhc.com

 

With copies (which shall not constitute notice) to:

Morgan, Lewis & Bockius LLP

1701 Market Street

Philadelphia, PA 19103

	Attention:	Justin W. Chairman
	 	Kevin M. Shmelzer
	Email:	justin.chairman@morganlewis.com
	 	kevin.shmelzer@morganlewis.com

 

    14

     

    

 

If to Indaba, to the address at:

Indaba Capital Management, L.P.

c/o Indaba Capital Management L.P.

One Letterman Drive

Building D, Suite DM700

San Francisco, CA 94129

	Attention:	Derek C. Schrier
	Email:	Derek@indabacapital.com

 

With copies (which shall not constitute notice) to:

Olshan Frome Wolosky LLP

1325 Avenue of the Americas

New York, NY 10019

	Attention:	Steve Wolosky
	 	Elizabeth Gonzalez-Sussman
	Email: 	swolosky@olshanlaw.com
	 	egonzalez@olshanlaw.com

 

18.           Entire
Agreement. This Agreement constitutes the sole and entire agreement of the Parties with respect to the subject matter
contained herein, and supersedes all prior and contemporaneous understandings, agreements, representations, and warranties, both written
and oral, with respect to such subject matter. This Agreement may only be amended, modified, or supplemented by an agreement in writing
signed by each Party.

 

19.           Severability. If any term or provision of this Agreement is invalid, illegal, or unenforceable in any jurisdiction,
such invalidity, illegality, or unenforceability shall not affect any other term or provision of this Agreement or invalidate or render
unenforceable such term or provision in any other jurisdiction.

 

20.           Counterparts.
This Agreement may be executed in counterparts, each of which shall be deemed an original, but all of which together shall be deemed
to be one and the same agreement. A signed copy of this Agreement delivered by facsimile, email, or other means of electronic transmission
shall be deemed to have the same legal effect as delivery of an original signed copy of this Agreement.

 

21.           Assignment. No Party may assign any of its rights or delegate any of its obligations hereunder without the prior
written consent of the other Parties. Any purported assignment or delegation in violation of this Section 21 shall be null and void.
No assignment or delegation shall relieve the assigning or delegating Party of any of its obligations hereunder. This Agreement is for
the sole benefit of the Parties and their respective successors and permitted assigns and nothing herein, express or implied, is intended
to or shall confer upon any other person or entity any legal or equitable right, benefit or remedy of any nature whatsoever under or
by reason of this Agreement.

 

    15

     

    

 

22.           Waivers.
No waiver by any Party of any of the provisions hereof shall be effective unless explicitly set forth in writing and signed by the
Party so waiving. No waiver by any Party shall operate or be construed as a waiver in respect of any failure, breach, or default not
expressly identified by such written waiver, whether of a similar or different character, and whether occurring before or after that
waiver. No failure to exercise, or delay in exercising, any right, remedy, power, or privilege arising from this Agreement shall operate
or be construed as a waiver thereof; nor shall any single or partial exercise of any right, remedy, power, or privilege hereunder preclude
any other or further exercise thereof or the exercise of any other right, remedy, power, or privilege.

 

23.           Public Announcement. Promptly following the execution of this Agreement, the Company shall issue a mutually
agreeable press release (the “Press Release”) substantially in the form attached hereto as Exhibit C. Prior to the
issuance of the Press Release, neither the Company nor Indaba shall, and Indaba shall cause the other Investors not to, issue any press
release or make any public announcement regarding this Agreement or take any action that would require public disclosure thereof without
the prior written consent of the other Party, except to the extent required by applicable law or the rules of any national securities
exchange.

 

[Remainder of Page Intentionally Left Blank]

 

    16

     

    

 

IN WITNESS WHEREOF,
the Parties have executed this Agreement to be effective as of the Effective Date.

 

	 	TABULA
    RASA HEALTHCARE, INC.
	 	 
	 	By:	/s/ Brian W. Adams
	 	Name:	Brian W. Adams
	 	Title: 	Co-President

 

Signature Page to

Cooperation Agreement

 

     

     

    

 

	 	INDABA CAPITAL MANAGEMENT, L.P.
	 	 
	 	By:	IC GP, LLC, its general partner
	 	 
	 	By:	/s/ Derek C. Schrier
	 	Name:	Derek C. Schrier
	 	Title:	Managing Member

 

Signature Page to

Cooperation AgreementExhibit 10.2

 

EXECUTIVE TRANSITION AND SEPARATION AGREEMENT

 

This Executive Transition
and Separation Agreement (this “Agreement”), is entered into as of the date set forth on the signature page below (the
 “Execution Date”), by and between Dr. Calvin H. Knowlton (“you”) and Tabula Rasa Healthcare, Inc.
(together with its wholly owned subsidiaries and affiliates, the “Company”).

 

BACKGROUND

 

WHEREAS, you currently serve
as Chief Executive Officer of the Company (“CEO);

 

WHEREAS, you and the Company
are parties to that certain Change-In-Control and Severance Agreement, effective January 1, 2018 (the “Severance Agreement”),
which will terminate in its entirety upon execution of this Agreement;

 

WHEREAS, you are resigning
from the Board of Directors of the Company (the “Board”) effective as of the Execution Date and the execution of this
Agreement shall constitute such resignation (the “Resignation Date”);

 

WHEREAS, you and the Company
have mutually agreed that your employment with the Company will end on the Execution Date (the “Termination Date”)
and you have agreed to enter into a consulting agreement with the Company pursuant to which the Company will engage you as an independent
contractor to provide certain advisory and transition services from the Termination Date through December 31, 2022 as set forth in such
consulting agreement, substantially in the form attached hereto as Exhibit A (the “Consulting Agreement”);

 

WHEREAS, both you and the
Company desire to enter into this Agreement to set forth the terms and conditions of the termination of your employment with the Company,
including your agreement to provide certain advisory and transition services through December 31, 2022 pursuant to the Consulting Agreement
and the severance payable to you upon the Termination Date.

 

NOW THEREFORE, in consideration
of the mutual promises set forth in this Agreement and of other good and valuable consideration, the sufficiency of which you acknowledge,
and intending to be legally bound hereby, you and the Company agree as follows:

 

1.         
Recitals. The foregoing recitals are hereby made part of this Agreement and are incorporated herein by reference.

 

2.         
General Terms of Separation. Regardless of whether you sign this Agreement, the Company will provide you with (a) any $566,500
(“Base Salary”) earned through the Termination Date that remains unpaid; (b) any accrued but unused personal time
off days; (c) reimbursement for any outstanding expenses for which you have not been reimbursed and which are authorized and (d)
any vested benefits under the Company’s employee benefit plans in accordance with the terms of such plans, as accrued through the
Termination Date (collectively, the “Accrued Obligations”). The Accrued Obligations, which are set forth on Schedule
A, shall be paid following the Termination Date at such times and in accordance with such plans and policies as would normally apply to
such amounts or benefits.

 

     

     

    

 

3.         Consideration.
If you (a) sign and do not revoke this Agreement (b) comply with the obligations set forth in this Agreement and (c) continue to comply
with the restrictive covenants in Paragraph 7 below, then the Company will provide you with the following severance payments and benefits
(collectively, the “Consideration”):

 

(i)        You
will receive continuation of your Base Salary in accordance with the Company’s regular payroll practices, less all relevant taxes
and other withholdings, for a period of eighteen (18) months starting on the first payroll date following the Termination Date.

 

(ii)       For the eighteen (18) months following the Termination Date (the “Coverage Period”), if you timely and properly
elect to receive continued health coverage under the Company’s health plan under the Consolidated Omnibus Budget Reconciliation
Act (“COBRA”), you will receive continued health (including hospitalization, medical, dental, vision, etc.) insurance
coverage (“COBRA Coverage”) that is substantially similar in all material respects to the coverage provided to other
Company employees as of the Termination Date, provided that you pay to the Company, on a monthly basis, an amount equal to the amount
active Company employees pay for such coverage. You agree to promptly notify the Company of your coverage under an alternative health
plan upon becoming covered by such alternative plan, at which time your COBRA Coverage may be reduced or eliminated, as applicable, to
the extent that continued receipt of COBRA Coverage would result in duplicative benefits. The COBRA continuation coverage period under
Section 4980B of the Internal Revenue Code of 1986, as amended (the “Code”) shall run concurrently with the Coverage
Period.

 

(iii)      You
will receive reimbursement for reasonable fees and costs you incur for outplacement services during the twelve (12) months following
the Termination Date, up to a maximum of $25,000, provided that you submit any requests for reimbursement to the Company within thirty
(30) days of the date the expense is incurred.

 

(iv)      424,707 unvested shares of restricted stock you hold pursuant to the Company’s 2016 Omnibus Incentive Compensation Plan
will vest as of the Termination Date. All other restricted stock awards, including all performance stock unit awards you hold in the
Company that are unvested as of the Termination Date will be terminated and cancelled as of the Termination Date.

 

You agree and acknowledge
that the payments described in Section 2 are the final compensation to which you are entitled and you are not owed any other money or
compensation for services performed. You will not be eligible for the Consideration described in this Paragraph 3 unless the Company
has received an executed copy of this Agreement, which has not been revoked. You further agree that the amounts described in Section 3
are the full consideration for this Agreement and are equal to or exceed the severance benefits described in the Severance Agreement and
are equal to or exceed any benefits, compensation, or other financial consideration to which Employee would be entitled absent his signing
of this Agreement.

 

4.         
General Release.

 

(a)        
In exchange for the consideration and other conditions set forth in this Agreement, you hereby generally and completely release
the Company, each of their affiliated entities, and their respective current and former directors, officers, employees, shareholders,
stockholders, partners, general partners, limited partners, managers, members, managing directors, operating affiliates, agents, attorneys,
predecessors, successors, Company and subsidiary entities, insurers, assigns and affiliated entities (collectively, the “Released
Parties”) of and from any and all claims, liabilities and obligations, both known and unknown, arising from or related to events,
acts, or omissions occurring prior to or on the date you sign this Agreement (collectively, the “Released Claims”).
The Released Claims include, but are not limited to: (a) all claims arising from or in any way related to your employment or other
participation in connection with any of the Released Parties, or the termination of that employment or participation; (b) all claims
related to compensation or benefits, including salary, bonuses, commissions, vacation pay, expense reimbursements, severance pay, change-in-control
payments, fringe benefits, or profit sharing or any claims under the Severance Agreement; (c) all claims for breach of contract,
wrongful termination, and breach of the implied covenant of good faith and fair dealing; (d) all tort claims, including claims for
fraud, defamation, emotional distress, and discharge in violation of public policy; and (e) all federal, state, and local statutory claims,
including claims for discrimination, harassment, retaliation, attorneys’ fees, or other claims arising under the federal Civil Rights
Act of 1964 (as amended), the federal Americans with Disabilities Act of 1990, the federal Age Discrimination in Employment Act of 1967
(as amended) (the “ADEA”), the Employee Retirement Income Security Act of 1974 (“ERISA”) (including,
but not limited to, claims for breach of fiduciary duty under ERISA), and the Older Workers Benefit Protection Act (the “OWBPA”).
In giving the releases set forth above, which include claims which may be unknown to you at present, you hereby expressly waive and relinquish
all rights and benefits under any law or legal principle in any jurisdiction with respect to your release of claims herein, including
but not limited to the release of unknown and unsuspected claims. Notwithstanding anything to the contrary in this Paragraph 4, you are
not prohibited from making or asserting and you are not waiving: (i) your rights under this Agreement; (ii) any claims for unemployment
compensation, workers’ compensation or state disability insurance benefits pursuant to the terms of applicable state laws; (iii)
any claim for vested benefits under any Company-sponsored retirement or welfare benefit plan; (iv) any other right that may not be released
under applicable law; and (v) your rights, if any, to indemnification pursuant to the Company’s organizational documents or any
D&O insurance policy.

 

    2

     

    

 

(b)        
In exchange for the conditions set forth in this Agreement, the Company hereby generally and completely releases you of and from
any and all claims, liabilities and obligations, both known and unknown, in law or in equity, by contract, or otherwise, arising from
or related to events, acts, or omissions occurring prior to or on the date you sign this Agreement, in each case, solely related to the
pledges and subsequent forced sales of the Company’s securities sold by you and your spouse in November 2021.

 

5.         
Reports to Government Entities. Nothing in this Agreement restricts or prohibits you from initiating communications directly
with, responding to any inquiries from, providing testimony before, providing confidential information to, reporting possible violations
of law or regulation to, or from filing a claim or assisting with an investigation directly with a self-regulatory authority or a government
agency or entity, including the U.S. Equal Employment Opportunity Commission, the Department of Labor, the National Labor Relations Board,
the Department of Justice, the Securities and Exchange Commission, the Congress, and any agency Inspector General (collectively, the “Regulators”),
or from making other disclosures that are protected under the whistleblower provisions of state or federal law or regulation. However,
to the maximum extent permitted by law, you are waiving your right to receive any individual monetary relief from the Company, or any
others covered by the Released Claims resulting from such claims or conduct, regardless of whether you or another party has filed them,
and in the event you obtain such monetary relief the Company will be entitled to an offset for the payments made pursuant to this Agreement.
This Agreement does not limit your right to receive an award from any Regulator that provides awards for providing information relating
to a potential violation of law. You do not need the prior authorization of the Company to engage in conduct protected by this paragraph,
and you do not need to notify the Company that you have engaged in such conduct. Please take notice that federal law provides criminal
and civil immunity to federal and state claims for trade secret misappropriation to individuals who disclose a trade secret to their attorney,
a court, or a government official in certain, confidential circumstances that are set forth at 18 U.S.C. §§ 1833(b)(1) and 1833(b)(2),
related to the reporting or investigation of a suspected violation of the law, or in connection with a lawsuit for retaliation for reporting
a suspected violation of the law. Pursuant to the Defend Trade Secrets Act of 2016, you will not be held criminally or civilly liable
under any federal or state trade secret law for the disclosure of the trade secrets of the Company or any of its affiliates that is made
by you (a) in confidence to a federal, state, or local government official, either directly or indirectly, or to an attorney, and solely
for the purpose of reporting or investigating a suspected violation of law, or (b) in a complaint or other document filed in a lawsuit
or other proceeding, if such filing is made under seal.

 

    3

     

    

 

6.         
No Actions Pending Against the Company. You acknowledge and agree that that: (a) you are not aware of any facts that may
constitute violations of the Company’s policies and/or legal obligations; and (b) you have not filed any discrimination, wrongful
discharge, wage and hour, or any other complaints or charges against the Released Parties in any local, state or federal court, tribunal,
or administrative agency.

 

7.         
Restrictive Covenants. You expressly acknowledge that a condition your receipt of the Consideration set forth in Paragraph
3 is your continued compliance with the restrictive covenants set forth below,

 

(a)        
Non-Competition. In consideration of the promises contained herein and the Consideration set forth in Paragraph 3, without
the prior written consent of the Company, you shall not, at any time during the period commencing on the Execution Date and terminating
on the three (3) year anniversary date of the Execution Date, (i) directly or indirectly engage in, represent in any way, be connected
with, or otherwise render any services to any Competing Business (as hereinafter defined) competing with the business of the Company or
any direct or indirect subsidiary or affiliate thereof in the United States, whether such engagement shall be as an officer, director,
owner, employee, partner, affiliate or other participant in any Competing Business, or (ii) assist others in engaging in any Competing
Business in the manner described in clause (i) above. As used herein, “Competing Business” shall mean any firm or business
organization that competes (i) with the Company in the development and/or commercialization of data-driven technology and solutions (including,
but not limited to, risk adjustment services, pharmacy benefit management solutions, cloud-based electronic health records solutions,
and third-party administration services) or pharmacy services (including, but not limited to, medication fulfillment and adherence packaging
services) to the types of entities now served or proposed to be served by the Company or (ii) in a business area discussed in writing
by the Company before the Termination Date for entry within twelve (12) months of Termination Date. Notwithstanding the foregoing restrictions,
it shall not be a violation of this Paragraph 7(a) for you to own a five (5%) percent or smaller interest in any corporation required
to file periodic reports with the United States Securities and Exchange Commission, so long as you perform no services or lend any assistance
to such corporation.

 

(b)        
Non-Solicitation. In consideration of the promises contained herein and the Consideration set forth in Paragraph 3, without
the prior written consent of the Company, you shall not, at any time during the period commencing on the Execution Date and terminating
on the three (3) year anniversary date of the Execution Date, directly or indirectly, (i) induce or solicit any employees of the
Company or any direct or indirect subsidiary or affiliate thereof to terminate their employment with the Company or any such direct or
indirect subsidiary or affiliate or to engage in any Competing Business; (ii) hire any employee of the Company or any direct or indirect
subsidiary or affiliate thereof or any person who was employed by the Company in the 12 month period prior to the hiring; or (iii) induce
any entity or person with which the Company or any direct or indirect subsidiary or any affiliate thereof has a business relationship
to terminate or alter such business relationship.

 

(c)        
You understand that the foregoing restrictions may limit your ability to earn a livelihood in a business similar to the business
of the Company or any subsidiary or affiliate thereof, but you nevertheless believes that you have received sufficient consideration and
other benefit to justify clearly such restrictions which, in any event (given your education, skills and ability), you do not believe
would prevent you from earning a living.

 

(d)        
If the duration of, the scope of or any business activity covered by any provision of this Section 7 is in excess of what is determined
to be valid and enforceable under applicable law, such provision shall be construed to cover only that duration, scope or activity that
is determined to be valid and enforceable. You hereby acknowledge that this Section 7 shall be given the construction that renders its
provisions valid and enforceable to the maximum extent, not exceeding its express terms, possible under applicable law.

 

    4

     

    

 

(e)        
Non-Disparagement.  During the period commencing on the Execution Date and terminating on the five (5) year anniversary
date of the Execution Date, you shall not disparage the Company or their respective officers, directors, investors, employees, and affiliates
or make any public statement reflecting negatively on the Company or their respective officers, directors, investors, employees, and affiliates,
including (without limitation) any matters relating to the operation or management of the Company, irrespective of the truthfulness or
falsity of such statement. The Company shall instruct and take all reasonable steps to cause its Named Executive Officers (as defined
under Item 402 of Regulation S-K) and members of the Board not to, disparage the Executive on any matters relating to the Executive’s
services to the Company, business, professional or personal reputation or standing in the pharmacy industry, irrespective of the truthfulness
or falsity of such statement. Nothing in this section shall prohibit the Parties from testifying truthfully in any forum or to any governmental
agency.

 

(f)         
Proprietary Information.  During the period commencing on the Execution Date and terminating on the three (3) year
anniversary date of the Execution Date, you shall hold in strictest confidence and will not disclose, use, lecture upon or publish any
Proprietary Information (defined below) of the Company, unless the Company expressly authorizes such disclosure in writing or it is required
by law or in a judicial or administrative proceeding in which event you shall promptly notify the Company of the required disclosure and
assist the Company if a determination is made to resist the disclosure.  For purposes of this Paragraph 7(e), “Proprietary
Information” shall mean any and all confidential and/or proprietary knowledge, data or information of the Company or its respective
affiliated entities, including (without limitation) any information relating to financial matters, investments, budgets, business plans,
marketing plans, personnel matters, business contacts, products, processes, know-how, designs, methods, improvements, discoveries, inventions,
ideas, data, programs, and other works of authorship; provided, that it shall not include any information that is known to the Company
to be publicly available.

 

(e) Invention Assignment. 
All inventions, innovations, improvements, developments, methods, designs, analyses, reports, and all similar or related information which
relates to either the Company’s actual or anticipated business, research and development or existing or future products or services
and which were conceived, developed or made by you while you were employed by the Company (the “Work Product”) belong to the
Company and not you.  You shall promptly disclose such Work Product to the Board of Directors of the Company, and, for the period
commencing on the Execution Date and terminating on the three (3) year anniversary date of the Execution Date, perform all actions reasonably
requested by the applicable Board of Directors to establish and confirm such ownership (including, without limitation, assignments, consents,
powers of attorneys and other instruments).

 

(f)  Return of Property. 
On or before the Termination Date, you will deliver to the person designated by the Company all originals and copies of all documents
and property of the Company in your possession, under your control or to which you may have access.  You will not reproduce or appropriate
for your own use, or for the use of others, any property, Proprietary Information or Work Product.

 

8.         
Withholding: All payments under this Agreement are subject to applicable tax withholding.

 

9.         
Compliance with Section 409A of the Code. This Agreement is intended to comply with the requirements of section 409A of
the Code or an exception, and shall be administered accordingly. Notwithstanding anything in the Agreement to the contrary, distributions
may only be made under the Agreement upon an event and in a manner permitted by section 409A to the extent applicable. Payments to be
made upon termination of employment under this Agreement may only be made upon a “separation from service” under section 409A.
For purposes of section 409A, each payment shall be treated as a separate payment. In no event may you, directly or indirectly, designate
the calendar year of a payment.

 

    5

     

    

 

10.        
Governing Law. This Agreement will be governed by and construed in accordance with the laws of the State of New Jersey.

 

11.        
Entire Agreement. This Agreement constitute the entire agreement between the parties relating to the matters contained herein
and supersedes any and all prior representations, agreements, written or oral, expressed or implied.

 

12.        Severability. In the event a court, arbitrator, or other entity with jurisdiction determines that any portion of this Agreement
(other than the general release clause) is invalid or unenforceable, the remaining portions of the Agreement shall remain in full force
and effect.

 

13.        Headings; Days. Headings contained in this Agreement are for convenience of reference only and are not intended, and shall
not be construed, to modify, define, limit, or expand the intent of the parties as expressed in this Agreement, and they shall not affect
the meaning or interpretation of this Agreement. All references to a number of days throughout this Agreement refer to calendar days.

 

14.        Representations.
You agree and represent that (a) you have read carefully the terms of this Agreement, including the general release; (b) you have had
an opportunity to and have been advised by the Company to review this Agreement, including the general release, with an attorney; (c)
you understand the meaning and effect of the terms of this Agreement, including the general release; (d) you were given twenty-one (21)
days to determine whether you wished to sign this Agreement, including the general release; (e) your decision to sign this Agreement,
including the general release, is of your own free and voluntary act without compulsion of any kind; (f) no promise or inducement not
expressed in this Agreement has been made to you; and (g) you have adequate information to make a knowing and voluntary waiver.

 

15.        
Revocation Period. If you sign this Agreement, you will retain the right to revoke it for seven (7) days (“Revocation
Period”). If you revoke this Agreement, you are indicating that you have changed your mind and do not want to be legally bound
by this Agreement. This Agreement shall not be effective until after the Revocation Period has expired without your having revoked it.
To revoke this Agreement, you must send a letter to the attention of the General Counsel of the Company. The letter must be received within
seven (7) days of your execution of this Agreement. If the seventh day is a Sunday or federal holiday, then the letter must be received
by the following business day. If you revoke this Agreement on a timely basis, you shall not be eligible for the Consideration set forth
in Paragraph 3 above.

 

16.        
Expiration Date. As noted above, you have twenty-one (21) days to decide whether you wish to sign this Agreement. If you
do not sign this Agreement on or before that time, then this Agreement is withdrawn and you will not be eligible for the Consideration
set forth in Paragraph 3 above.

 

[Signature Page Follows]

 

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IN WITNESS WHEREOF, and intending
to be legally bound hereby, you and the Company hereby execute the foregoing Executive Transition and Separation Agreement as of the Execution
Date set forth below.

 

	Dr. Calvin H. Knowlton	 	Tabula Rasa Healthcare, Inc.
	/s/ Calvin H. Knowlton	 	/s/ Brian W. Adams
	Execution Date:	September 13, 2022	 	By:	Brian W. Adams
	 	 	Title:	Interim Chief Executive Officer
	 	 	Date:	September 13, 2022

 

    7

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