Document:

EX-10.20

 Exhibit 10.20 

SEPARATION AGREEMENT 

This Separation Agreement (the “Agreement”) is made by and between Todd Harris (“Executive”)
and Sienna Biopharmaceuticals, Inc., a Delaware corporation (the “Company” and, together with Executive, the “Parties”) is made effective as of the date Executive signs this Agreement (the “Effective
Date”), with reference to the following facts: 
 A. Executive’s employment with the Company and status as an
officer of the Company and each of its affiliates terminated effective as of November 5, 2018 (the “Separation Date”). 

B. Executive and the Company desire to end their employment relationship amicably and to establish the obligations of the
parties including, without limitation, all amounts due and owing to Executive in connection with Executive’s employment. 

NOW, THEREFORE, in consideration of the mutual covenants and agreements hereinafter set forth, the parties agree as follows:

 1. Employment Separation. Executive acknowledges and agrees that his status as an officer and employee of the
Company terminated effective as of the Separation Date. Executive hereby agrees to execute such further document(s) as shall be determined by the Company as necessary or desirable to give effect to the termination of Executive’s status as an
officer of the Company; provided, that such documents shall not be inconsistent with any of the terms of this Agreement. 

2. Board of Directors Service. 

(a) Board Membership. Notwithstanding Executive’s separation of employment with the Company,
Executive shall continue to serve as a member of the Company’s Board of Directors (the “Board”) at the discretion of the Board and the Company’s stockholders in accordance with the Company’s bylaws. 

(b) Board Compensation. Following the Separation Date, Executive shall be eligible for compensation as a
member of the Board in accordance with the Non-Employee Director Compensation Program (the “Director Compensation Program”). Executive acknowledges that, in accordance with the Director
Compensation Program, Executive shall not be eligible for an Initial Option (as defined in the Director Compensation Program) but shall be eligible for an Annual Option (as defined in the Director Compensation Program) at the first annual meeting of
the Company’s stockholders following the Separation Date. 
 (c) Stock Options. Executive’s
options to purchase Company common stock that are outstanding as of the Separation Date shall remain outstanding and continue to vest and remain or become exercisable based on Executive’s continued Board service in accordance with their terms.
Executive acknowledges that any such options which constitute “incentive stock options” within the meaning of Section 422 of the Internal Revenue Code of 1986, as amended (the “Code”), as of the Separation Date shall
cease to constitute incentive stock options on the three-month anniversary of the Separation Date. Executive further acknowledges that to the extent Executive exercises any option that vested while Executive served the Company as an employee and
does not constitute an incentive stock option on the date of exercise, the excess of the fair market value of the Company’s common stock on the date of such exercise over the exercise price of the option shall constitute wages subject to
withholding taxes that must be satisfied prior to the completion of such exercise. 

  
 1 

 3. Final Paycheck; Expenses; Options. 

(a) Final Paycheck. Executive acknowledges that on or about the Separation Date Executive was paid all
accrued but unpaid base salary and paid time off earned through the Separation Date, less payroll deductions and withholdings. Executive is entitled to retain these payments regardless of whether Executive executes this Agreement. 

(b) Business Expenses. Executive agrees that, within five (5) business days after the Separation
Date, Executive will submit Executive’s final documented expense reimbursement statement reflecting all business expenses Executive incurred through the Separation Date, if any, for which Executive seeks reimbursement. The Company will
reimburse Executive for these expenses pursuant to its regular business practice. 
 4. Separation Payments and
Benefits. Without admission of any liability, fact or claim, the Company hereby agrees to provide the severance benefits below, subject to the execution of this Agreement and Executive’s performance of his continuing obligations pursuant to
this Agreement and his proprietary information and inventions assignment agreement with the Company (the “Confidentiality Agreement”). 

(a) Healthcare Continuation Coverage. If Executive is eligible for and timely elects to receive
continued healthcare coverage pursuant to the provisions of the Consolidated Omnibus Budget Reconciliation Act of 1985, as amended (“COBRA”), the Company shall pay the cost of monthly premiums for Executive and Executive’s
covered dependents, if any, for coverage under the Company’s group health plans during the period beginning on the Separation Date and ending on the earlier of (i) the six-month anniversary of the
Separation Date or (ii) the date Executive becomes eligible for comparable coverage under another employer’s group health plan(s), provided, however, that if (1) any plan pursuant to which such benefits are provided is not, or
ceases prior to the expiration of the continuation coverage period to be, exempt from the application of Section 409A of the Code under Treasury Regulation Section 1.409A-1(a)(5), (2) the Company is
otherwise unable to continue to cover Executive under its group health plans, or (3) the Company cannot provide the benefit without violating applicable law (including, without limitation, Section 2716 of the Public Health Service Act),
then, in any such case, an amount equal to each remaining premium shall thereafter be paid to Executive in substantially equal monthly installments over the remaining period the Company would otherwise pay the premiums. After the Company ceases to
pay premiums pursuant to the preceding sentence, Executive may, if eligible, elect to continue healthcare coverage at Executive’s expense in accordance with the provisions of COBRA. Executive acknowledges that he shall be solely responsible for
all matters relating to Executive’s continuation of coverage pursuant to COBRA, including, without limitation, Executive’s election of such coverage and his timely payment of premiums. 

(b) Sole Separation Benefit. Executive agrees that the benefits provided by this Section 4 are not
required under the Company’s normal policies and procedures and are provided as a severance solely in connection with this Agreement. Executive acknowledges and agrees that the benefits referenced in this Section 4 constitute adequate and
valuable consideration, in and of themselves, for the promises contained in this Agreement. 

  
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 5. Full Payment. Executive acknowledges that the payment and
arrangements herein shall constitute full and complete satisfaction of any and all amounts properly due and owing to Executive as a result of his employment with the Company and the termination thereof. Executive further acknowledges that, other
than the Confidentiality Agreement and the agreements evidencing Executive’s outstanding options to purchase Company common stock (collectively, the “Option Agreements”), this Agreement shall supersede each agreement entered
into between Executive and the Company regarding Executive’s employment, including, without limitation, that certain employment agreement between Executive and the Company effective as of July 26, 2017 (the “Employment
Agreement”). Each such agreement superseded hereby shall be deemed terminated and of no further effect as of the Separation Date. 

6. Executive’s Release of the Company. Executive understands that by agreeing to the release provided by this
Section 6, Executive is agreeing not to sue, or otherwise file any claim against, the Company or any of its directors, officers, employees, investors or other agents for any reason whatsoever based on anything that has occurred as of the date
Executive signs this Agreement. 
 (a) On behalf of Executive and Executive’s heirs, assigns, executors,
administrators, trusts, spouse and estate, Executive hereby releases and forever discharges the “Releasees” hereunder, consisting of the Company and each of its owners, affiliates, subsidiaries, predecessors, successors, assigns,
agents, directors, officers, partners, employees, and insurers, and all persons acting by, through, under or in concert with them, or any of them, of and from any and all manner of action or actions, cause or causes of action, in law or in equity,
suits, debts, liens, contracts, agreements, promises, liability, claims, demands, damages, loss, cost or expense, of any nature whatsoever, known or unknown, fixed or contingent (hereinafter called “Claims”), which Executive now has
or may hereafter have against the Releasees, or any of them, by reason of any matter, cause, or thing whatsoever from the beginning of time to the date hereof, including, without limiting the generality of the foregoing, any Claims arising out of,
based upon, or relating to Executive’s hire, employment, remuneration or termination by the Releasees, or any of them, Claims arising under federal, state, or local laws relating to employment, Claims of any kind that may be brought in any
court or administrative agency, including any Claims arising under the Title VII of the Civil Rights Act of 1964, as amended, 42 U.S.C. § 2000, et seq.; Americans with Disabilities Act, as amended, 42 U.S.C. § 12101 et seq.;
the Rehabilitation Act of 1973, as amended, 29 U.S.C. § 701 et seq.; Civil Rights Act of 1866, and Civil Rights Act of 1991; 42 U.S.C. § 1981, et seq.; Equal Pay Act, as amended, 29 U.S.C. § 206(d); regulations of
the Office of Federal Contract Compliance, 41 C.F.R. Section 60, et seq.; the Family and Medical Leave Act, as amended, 29 U.S.C. § 2601 et seq.; the Fair Labor Standards Act of 1938, as amended, 29 U.S.C.
§ 201 et seq.; the Employee Retirement Income Security Act, as amended, 29 U.S.C. § 1001 et seq.; the Worker Adjustment and Retraining Notification Act, as amended, 29 U.S.C. § 2101 et seq.; the Fair Credit Reporting Act and
all similar state laws regarding background checks, the California Fair Employment and Housing Act, as amended, Cal. Lab. Code § 12940 et seq.; the California Equal Pay Law, as amended, Cal. Lab. Code §§ 1197.5(a),199.5; the
Moore-Brown-Roberti Family Rights Act of 1991, as amended, Cal. Gov’t Code §§12945.2, 19702.3; California Labor Code §§ 1101, 1102; the California WARN Act, California Labor Code §§ 1400 et. seq; California Labor
Code §§ 1102.5(a),(b); claims for wages under the California Labor Code and any other federal, state or local laws of similar effect; the employment and civil rights laws of California; Claims for breach of contract; Claims arising in
tort, including, without limitation, Claims of wrongful dismissal or discharge, discrimination, harassment, retaliation, fraud, misrepresentation, defamation, libel, infliction of emotional distress, violation of public policy, and/or breach of the
implied covenant of good faith and fair dealing; and Claims for damages or other remedies of any sort, including, without limitation, compensatory damages, punitive damages, injunctive relief and attorney’s fees. 

  
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 (b) Notwithstanding the generality of the foregoing,
Executive does not release the following claims: 
 (i) Claims for unemployment compensation or any state
disability insurance benefits pursuant to the terms of applicable state law; 
 (ii) Claims for workers’
compensation insurance benefits under the terms of any worker’s compensation insurance policy or fund of the Company; 

(iii) Claims to continued participation in certain of the Company’s group benefit plans pursuant to the
terms and conditions of COBRA; 
 (iv) Claims to any benefit entitlements vested as the date of
Executive’s employment termination, pursuant to written terms of any Company employee benefit plan; 

(v) Claims for indemnification under the Company’s Bylaws, California Labor Code Section 2802 or any
other applicable law; 
 (vi) Executive’s right to bring to the attention of the Equal Employment
Opportunity Commission claims of discrimination; provided, however, that Executive does release Executive’s right to secure any damages for alleged discriminatory treatment; and 

(vii) Claims relating to Company’s obligations pursuant to this Agreement. 

(c) EXECUTIVE ACKNOWLEDGES THAT EXECUTIVE HAS BEEN ADVISED OF AND IS FAMILIAR WITH THE PROVISIONS OF CALIFORNIA
CIVIL CODE SECTION 1542, WHICH PROVIDES AS FOLLOWS: 
 “A GENERAL RELEASE DOES NOT EXTEND TO CLAIMS WHICH THE
CREDITOR DOES NOT KNOW OR SUSPECT TO EXIST IN HIS OR HER FAVOR AT THE TIME OF EXECUTING THE RELEASE, WHICH, IF KNOWN BY HIM OR HER, MUST HAVE MATERIALLY AFFECTED HIS OR HER SETTLEMENT WITH THE DEBTOR.” 

BEING AWARE OF SAID CODE SECTION, EXECUTIVE HEREBY EXPRESSLY WAIVES ANY RIGHTS EXECUTIVE MAY HAVE THEREUNDER, AS WELL AS UNDER
ANY OTHER STATUTES OR COMMON LAW PRINCIPLES OF SIMILAR EFFECT. 
 7.
Non-Disparagement and Transfer of Company Property. The Company and Executive further agree that: 

(a) Non-Disparagement. Executive agrees that he shall not
disparage, criticize or defame the Company, its affiliates and their respective affiliates, directors, officers, agents, partners, stockholders, employees, products, services, technology or business, either publicly or privately. Notwithstanding the
foregoing, nothing in this Section 7(a) shall prevent 

  
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Executive from making any truthful statement to the extent (i) necessary with respect to any litigation, arbitration or mediation involving this Agreement and the enforcement thereof; or
(ii) required by law or by any court, arbitrator, mediator or administrative or legislative body (including any committee thereof) with jurisdiction over the Company. 

(b) Transfer of Company Property. Executive warrants and represents that Executive has returned to the
Company all Personal Property (as defined below) which are the property of the Company and which he had in his possession, custody or control on the Separation Date except for any such Personal Property that is reasonably necessary for Executive to
discharge his duties as a member of the Board. Within ten days following the Separation Date, Executive shall provide a written notice to the Company detailing any Personal Property Executive deemed reasonably necessary to discharge his duties as a
member of the Board. For purposes of this Agreement, “Personal Property” includes, without limitation, all emails, books, manuals, records, reports, notes, contracts, lists, blueprints, and other documents, or materials, or copies
thereof, whether printed or electronic (including computer files and passwords), keys, building card keys, company credit cards, telephone calling cards, computer hardware and software, docking stations, cellular and portable telephone equipment,
personal digital assistant (PDA) devices and all other proprietary information relating to the business of the Company or its subsidiaries or affiliates. 

8. Executive Representations. Executive warrants and represents that (a) he has not filed or authorized the filing
of any complaints, charges or lawsuits against the Company, or any affiliate of the Company with any governmental agency or court, and that if, unbeknownst to Executive, such a complaint, charge or lawsuit has been filed on his behalf, he will
immediately cause it to be withdrawn and dismissed, (b) he has reported all hours worked as of the date of this Agreement and has been paid all compensation, wages, bonuses, commissions, and/or benefits to which he may be entitled and no other
compensation, wages, bonuses, commissions and/or benefits are due to him, except as provided in this Agreement, (c) he has no known workplace injuries or occupational diseases and has been provided and/or has not been denied any leave requested
under the Family and Medical Leave Act or any similar state law, (d) the execution, delivery and performance of this Agreement by Executive does not and will not conflict with, breach, violate or cause a default under any agreement, contract or
instrument to which Executive is a party or any judgment, order or decree to which Executive is subject, and (e) upon the execution and delivery of this Agreement by the Company and Executive, this Agreement will be a valid and binding
obligation of Executive, enforceable in accordance with its terms. 
 9. No Assignment by Executive. Executive
warrants and represents that no portion of any of the matters released herein, and no portion of any recovery or settlement to which Executive might be entitled, has been assigned or transferred to any other person, firm or corporation not a party
to this Agreement, in any manner, including by way of subrogation or operation of law or otherwise. If any claim, action, demand or suit should be made or instituted against the Company or any other Releasee because of any actual assignment,
subrogation or transfer by Executive, Executive agrees to indemnify and hold harmless the Company and all other Releasees against such claim, action, suit or demand, including necessary expenses of investigation, attorneys’ fees and costs. In
the event of Executive’s death, this Agreement shall inure to the benefit of Executive and Executive’s executors, administrators, heirs, distributees, devisees, and legatees. None of Executive’s rights or obligations may be assigned
or transferred by Executive, other than Executive’s rights to payments hereunder, which may be transferred only upon Executive’s death by will or operation of law. 

10. Governing Law. This Agreement shall be construed and enforced in accordance with, and the rights of the parties
shall be governed by, the laws of the State of California or, where applicable, United States federal law, in each case, without regard to any conflicts of laws provisions or those of any state other than California. 

  
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 11. Miscellaneous. This Agreement, collectively with the
Confidentiality Agreement, the Option Agreements, the Director Compensation Program and the Company’s bylaws, constitutes the entire agreement between the parties with regard to the subject matter hereof and supersedes, in their entirety, any
other agreements between Executive and the Company with regard to the subject matter hereof, including, without limitation, the Employment Agreement. Executive acknowledges that there are no other agreements, written, oral or implied, and that he
may not rely on any prior negotiations, discussions, representations or agreements. This Agreement may be modified only in writing, and such writing must be signed by Executive and a duly authorized officer of the Company or member of the Board and
recited that it is intended to modify this Agreement. This Agreement may be executed in separate counterparts, each of which is deemed to be an original and all of which taken together constitute one and the same agreement. 

12. Company Assignment and Successors. The Company shall assign its rights and obligations under this Agreement to any
successor to all or substantially all of the business or the assets of the Company (by merger or otherwise). This Agreement shall be binding upon and inure to the benefit of the Company and its successors, assigns, personnel and legal
representatives. 
 13. Maintaining Confidential Information. Executive reaffirms his obligations under his
Confidentiality Agreement. Executive acknowledges and agrees that the benefits provided in Section 4 shall be subject to Executive’s continued compliance with Executive’s obligations under the Confidentiality Agreement. For the
avoidance of doubt, nothing in the Confidentiality Agreement or this Agreement will be construed to prohibit Executive from filing a charge with, reporting possible violations to, or participating or cooperating with any governmental agency or
entity, including but not limited to the EEOC, the Department of Justice, the Securities and Exchange Commission, Congress, or any agency Inspector General, or making other disclosures that are protected under the whistleblower, anti-discrimination,
or anti-retaliation provisions of federal, state or local law or regulation. Executive does not need the prior authorization of the Company to make any such reports or disclosures, and Executive is not required to notify the Company that he has made
such reports or disclosures. Furthermore, in accordance with 18 U.S.C. § 1833, notwithstanding anything to the contrary in the Confidentiality Agreement or this Agreement: (i) Executive shall not be in breach of this Agreement, and shall
not be held criminally or civilly liable under any federal or state trade secret law (x) for the disclosure of a trade secret that is made in confidence to a federal, state, or local government official or to an attorney solely for the purpose
of reporting or investigating a suspected violation of law, or (y) for the disclosure of a trade secret that is made in a complaint or other document filed in a lawsuit or other proceeding, if such filing is made under seal; and (ii) if
Executive files a lawsuit for retaliation by the Company for reporting a suspected violation of law, Executive may disclose the trade secret to Executive’s attorney, and may use the trade secret information in the court proceeding, if Executive
files any document containing the trade secret under seal, and does not disclose the trade secret, except pursuant to court order. 

14. Executive’s Cooperation. After the Separation Date, Executive shall cooperate with the Company and its
affiliates, upon the Company’s reasonable request, with respect to any internal investigation or administrative, regulatory or judicial proceeding involving matters within the scope of 

  
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Executive’s duties and responsibilities to the Company or its affiliates during his employment with the Company (including, without limitation, Executive being available to the Company upon
reasonable notice for interviews and factual investigations, appearing at the Company’s reasonable request to give testimony without requiring service of a subpoena or other legal process, and turning over to the Company all relevant Company
documents which are or may have come into Executive’s possession during his employment); provided, however, that any such request by the Company shall not be unduly burdensome or interfere with Executive’s personal
schedule or ability to engage in gainful employment.
 15. Section 409A of the Code. The Company and Executive
acknowledge that the separation of the Executive’s employment with the Company is intended to constitute an involuntary separation from service for the purposes of Section 409A of Code and the related Department of Treasury regulations and
other interpretative guidance issued thereunder (“Section 409A”). This Agreement is intended, to the greatest extent permitted under law, to comply with the short-term deferral exemption and the separation pay
exemption provided in Section 409A such that no benefits or payments under this Agreement are subject to Section 409A. Notwithstanding anything herein to the contrary, the timing of any payments under this Agreement shall be made
consistent with such exemption. To the extent applicable, this Agreement shall be interpreted in accordance with Section 409A, including without limitation any such regulations or other guidance that may be issued after the Separation Date.
Notwithstanding any provision of this Agreement to the contrary, in the event that the Company determines that any amounts payable hereunder may be subject to Section 409A, the Company may, to the extent permitted under Section 409A
cooperate in good faith to adopt such amendments to this Agreement or adopt other appropriate policies and procedures, including amendments and policies with retroactive effect, that the Company determines are necessary or appropriate to avoid the
imposition of taxes under Section 409A; provided, however, that this paragraph shall not create an obligation on the part of the Company to adopt any such amendment, policy or procedure or take any such other action, nor shall the Company have
any liability for failing to do so. To the extent that any reimbursements payable pursuant to this Agreement are subject to the provisions of Section 409A, such reimbursements shall be paid to Executive no later than December 31 of the
year following the year in which the expense was incurred, the amount of expenses reimbursed in one year shall not affect the amount eligible for reimbursement in any subsequent year, and Executive’s right to reimbursement under this Agreement
will not be subject to liquidation or exchange for another benefit. 
 [Signature Page Follows] 

  
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 IN WITNESS WHEREOF, the undersigned have caused this Separation Agreement to
be duly executed and delivered as of the date indicated next to their respective signatures below, which such dates shall be on or after the Separation Date and prior to the fourteenth (14th) day following the Separation Date. 

 

							
	DATED: November 5, 2018	 		 	
			
		 		 	/s/ Todd Harris
		 		 	Todd Harris
			
		 		 	Sienna Biopharmaceuticals, Inc.
			
	DATED: November 5, 2018	 		 	
				
		 		 	By:	 	/s/ Frederick C. Beddingfield III
		 		 		 	Frederick C. Beddingfield III

 [Signature Page to Todd Harris Separation Agreement] 

  
 8EX-4.4

 Exhibit 4.4 

FORM OF DEBT SECURITY 
 [Face of
Security] 
 MARIN SOFTWARE INCORPORATED 

[If applicable, insert—FOR PURPOSES OF THE ORIGINAL ISSUE DISCOUNT PROVISIONS OF THE INTERNAL REVENUE CODE OF 1986, THE ISSUE PRICE OF
THIS SECURITY IS     % OF ITS PRINCIPAL AMOUNT AT STATED MATURITY SET FORTH BELOW (ITS “PRINCIPAL AMOUNT”), THE AMOUNT OF ORIGINAL ISSUE DISCOUNT IS     % OF ITS PRINCIPAL AMOUNT, THE YIELD TO
MATURITY IS     % AND THE ISSUE DATE IS                     ] 

[IF THE SECURITY IS A GLOBAL SECURITY, INSERT—THIS NOTE IS A GLOBAL SECURITY. IT IS EXCHANGEABLE FOR NOTES REGISTERED IN THE NAME OF
A PERSON OTHER THAN THE DEPOSITARY (AS HEREINAFTER DEFINED) OR ITS NOMINEE ONLY IN THE LIMITED CIRCUMSTANCES HEREINAFTER DESCRIBED AND MAY NOT BE TRANSFERRED EXCEPT AS A WHOLE BY THE DEPOSITARY TO A NOMINEE OF THE DEPOSITARY OR BY A NOMINEE OF
THE DEPOSITARY TO THE DEPOSITARY OR ANOTHER NOMINEE OF THE DEPOSITARY OR BY THE DEPOSITARY OR A NOMINEE OF THE DEPOSITARY TO A SUCCESSOR OF THE DEPOSITARY OR A NOMINEE OF SUCH SUCCESSOR DEPOSITARY.] 

 

			
	No.	  	$            
		  	CUSIP No.

 MARIN SOFTWARE INCORPORATED, a Delaware Corporation (herein called the “Company”, which term
includes any successor corporation under the Indenture referred to on the reverse hereof), for value received, hereby promises to pay to, or registered assigns, the principal sum of          Dollars on
                     [if Security is to bear interest prior to maturity, insert—, and to pay interest thereon from
                     or from the most recent Interest Payment Date to which interest has been paid or duly provided for, semi-annually on
                     and                      in
each year, commencing                     , at the rate of     % per annum, until the principal hereof is paid or made available
for payment [if applicable, insert—, provided that any principal and premium, and any such installment of interest, which is overdue shall bear interest at the rate of     % per annum (to the extent that the payment of such
interest shall be legally enforceable), from the dates such amounts are due until they are paid or made available for payment, and such interest shall be payable on demand]. The interest so payable, and punctually paid or duly provided for, on any
Interest Payment Date will, as provided in such Indenture, be paid to the Person in whose name this Security (or one or more Predecessor Securities) is registered at the close of business on the Record Date for such interest, which shall be the
                     or                     
(whether or not a Business Day), as the case may be, next preceding such Interest Payment Date. Any such interest not so punctually paid or duly provided for will forthwith cease to be payable to the Holder on such Record Date and may either be paid
to the Person this Security (or one or more Predecessor Securities) is registered at the close of business on a Special Record Date for the payment of such Defaulted Interest to be fixed by the Trustee, notice whereof shall be given to Holders of
Securities of this series not less than 10 days prior to such Special Record Date, or be paid at any time in any other lawful manner not inconsistent with the requirements of any securities exchange on which the Securities of this series may be
listed, and upon such notice as may be required by such exchange, all as more fully provided in said Indenture. [If the Security is not to bear interest prior to maturity, insert—The principal of this Security shall not bear interest except in
the case of a default in payment of principal upon acceleration, upon redemption or at Stated Maturity and in such case the overdue principal and any overdue premium shall bear interest at the rate of     % per annum (to the
extent that the payment of such interest shall be legally enforceable), from the dates such amounts are due until they are paid or made available for payment. Interest on any overdue principal or premium shall be payable on demand. [Any such
interest on overdue principal or premium which is not paid on demand shall bear interest at the rate of     % per annum (to the extent that the payment of such interest on interest shall be legally enforceable), from the date of
such demand until the amount so demanded is paid or made available for payment. Interest on any overdue interest shall be payable on demand.]]. 

Payment of the principal of (and premium, if any, on) and [any such] interest on this Security will be made at the office or agency of the
Company maintained for that purpose in                      in such coin or currency of [the United States of America] as at the time of payment is
legal tender for payment of public and private debts[; provided, however, that at the option of the Company payment of interest may be made by check mailed to the address of the Person entitled thereto as such address shall appear in the Register].

 Reference is hereby made to the further provisions of this Security set forth on the reverse hereof, which further provisions shall for
all purposes have the same effect as if set forth at this place. 

  
 II-1 

 Unless the certificate of authentication hereon has been manually executed by or on behalf
of the Trustee under the Indenture referred to on the reverse hereof, this Security shall not be entitled to any benefit under the Indenture or be valid or obligatory for any purpose. 

IN WITNESS WHEREOF, the Company has caused this instrument to be duly executed under its corporate seal. 

 

							
	Dated:	  		  	MARIN SOFTWARE INCORPORATED
				
		  		  	By	  	  

		  		  		  	[Title]

  

							
	Attest and Countersign	  		  		  	
			
	  
	  		  	
	Secretary	  		  	

  
 II-2 

 [Reverse of Security.] 

MARIN SOFTWARE INCORPORATED 

This Security is one of a duly authorized issue of securities of the Company (herein called the “Securities”), issued and to be
issued in one or more series under an Indenture dated as of                     , (herein called the “Indenture,” which term shall have the
meaning assigned to it in such instrument), between the Company and                             , as trustee
(herein called the “Trustee”, which term includes any successor trustee under the Indenture), to which Indenture and all indentures supplemental thereto reference is hereby made for a statement of the respective rights, limitations or
rights, duties and immunities thereunder of the Company, the Trustee and the Holders of the Securities and of the terms upon which the Securities are, and are to be, authenticated and delivered. This Security is one of the series designated on the
face hereof [, limited in aggregate principal amount to $        ]. 
 [If the Security is to be
subordinated, insert—The indebtedness evidenced by this Security is, to the extent and in the manner set forth in the Indenture, expressly subordinated and subject in right of payment to the prior payment in full of all Senior Indebtedness (as
defined in the Indenture) of the Company. This Security is issued subject to such provisions of the Indenture, and each Holder of this Security, by accepting the same, agrees to and shall be bound by such provisions and authorizes and directs the
Trustee on the Holder’s behalf to take such action as may be necessary or appropriate to acknowledge or effectuate such subordination as provided in the Indenture and appoints the Trustee such Holder’s attorney-in-fact for any and all such purposes.] 
 The Securities of this series are subject to
redemption upon not less than 30 days’, and no more than 60 days, notice provided in the manner set forth in the Indenture, [(1) on in any year commencing with the year and ending with the year at the Redemption Price equal to 100% of the
principal amount, and (2)] at any time [on or after], as a whole or in part, at the election of the principal the following Redemption Prices (expressed as percentages of the principal amount): If redeemed [on or before
                    ,     %, and if redeemed] during the 12-month period beginning of the
years indicated, 
  

							
	 Year
	  	 Redemption Price
	  	 Year
	  	 Redemption Price

and thereafter at a Redemption Price equal to     % of the principal amount together in the case of any such redemption with accrued
interest to the Redemption Date, but interest installments whose Stated Maturity is on or prior to such Redemption Date will be payable to the Holders of such Securities of record at the close of business on the relevant record dates referred to on
the face hereof, all as provided in the Indenture. 
 [If the Security is to be redeemable in part, insert—In the event of redemption
of this Security in part only, a new Security or Securities of this series for the unredeemed portion hereof will be issued in the name of the Holder hereof upon the cancellation hereof.] 

[If the Security is to be subject to repayment at the option of the Holder, insert—To be repaid at the option of the Holder, the Company
must receive this Security, with the form of “Option to Elect Repayment” hereon duly completed, at an office or agency of the Company maintained for that purpose in (or at such other place of which the Company shall from time to time
notify the Holder of this Security) not less than nor more than days prior to the Repayment Date. The exercise of the repayment option by the Holder shall be irrevocable. 

[If the Security is not to be subject to redemption at the option of the Company, insert—The Securities are not redeemable at the option
of the Company prior to Maturity.] 
 [If the Security is not to be an Original Issue Discount Security, insert—If an Event of Default
with respect to Securities of this series shall occur and be continuing, the principal of the Securities of this series may be declared due and payable in the manner and with the effect provided in the Indenture.] 

The Indenture permits, with certain exceptions as therein provided, the amendment thereof and the modification of the rights and obligations
of the Company and the rights of the Holders of the Securities of each series under the Indenture to be affected at any time by the Company with the consent of the Holders of not less than a majority in aggregate principal amount of the Securities
at the time Outstanding of each series to be affected. The Indenture also contains provisions permitting the Holders of a majority in principal amount of the Securities of each series at the time Outstanding, on behalf of the Holders of all
Securities of such series, to waive compliance by the Company with certain provisions of the Indenture and certain past defaults under the Indenture and their consequences. Any such consent or waiver by the 

 
Holder of this Security shall be conclusive and binding upon such Holder and upon all future Holders of this Security and of any Security issued upon the registration of transfer hereof or in
exchange herefor or in lieu hereof, whether or not notation of such consent of waiver is made upon this Security. 
 As provided in and
subject to the provisions of the indenture, the Holder of this Security shall not have the right to institute any proceeding with respect to the Indenture or for the appointment of a receiver or trustee or for any other remedy thereunder, unless
such Holder shall have previously given the Trustee written notice of a continuing Event of Default with respect to the Securities of this series , the Holders of not less than 25% in principal amount of the Securities of this series at the time
Outstanding shall have made written request to the trustee to institute proceedings in respect of such Event of Default as Trustee and offered the Trustee reasonable indemnity satisfactory to it, and the Trustee shall not have received from the
Holders of a majority in principal amount of Securities of this series at the time Outstanding a direction inconsistent with such request, and shall have failed to institute any such proceeding, for 60 days after receipt of such notice, request and
offer of indemnity. The foregoing shall not apply to any suit instituted by the Holder of this Security for the enforcement of any payment of principal hereof or any premium or interest hereon on or after the respective due dates expressed herein.

 No reference herein to the Indenture and no provision of this Security or of the Indenture shall alter or impair the obligation of the
Company, which is absolute and unconditional, to pay the principal of (and premium, if any, on) and interest on this Security at the times, place and rate, and in the coin or currency, herein prescribed. 

[If the Security is to be in registered form, insert—As provided in the Indenture and subject to certain limitations therein set forth,
the transfer of this Security is registrable in the Register, upon surrender of this Security for registration of transfer at the office or agency of the Company in any place where the principal of (and premium, if any, on) and interest on this
Security are payable, duly endorsed by, or accompanied by a written instrument of transfer in form satisfactory to the Company and the Registrar duly executed by, the Holder hereof or his attorney duly authorized in writing, and, thereupon one or
more new Securities of this series, of authorized denominations and for the same aggregate principal amount, will be issued to the designated transferee or transferees.] 

[The Securities of this series are issuable only in registered form in denominations of $ [and any integral multiple] [or increments of
$ in excess] thereof. As provided in the Indenture and subject to certain limitations therein set forth, Securities of this series are exchangeable for a like aggregate principal amount of Securities of this series of a different authorized
denomination, as requested by the Holder surrendering the same.] 
 [No service charge shall be made for any such registration of transfer
or exchange, but the Company may require payment of a sum sufficient to cover any tax or other governmental charge payable in connection therewith.] 

[Prior to due presentment of this Security for registration of transfer, the Company, the Trustee and any agent of the Company or the Trustee
may treat the Person in whose name this Security is registered as the owner hereof for all purposes, whether or not this Security be overdue, and neither the Company, the Trustee nor any such agent shall be affected by notice to the contrary.] 

[If the Security is a Global Security, insert—“Global Security” and “Global Securities” means a Security or
Securities evidencing all or a part of a series of Securities, issued to the Depositary (as hereinafter defined) for such Series or its nominee, and registered in the name of such Depositary or its nominee. “Depositary” means, with
respect to the Securities of any series issuable or issued in whole or in part in the form of one or more Global Securities, the person designated as the Depositary by the Company. 

No holder of any beneficial interest in this Security held on its behalf by a Depositary or a nominee of such Depositary shall have any rights
under the Indenture with respect to such Global Security, and such Depositary or nominee may be treated by the Company, the Trustee, and any agent of the Company or the Trustee as the owner of such Global Security for all purposes whatsoever.
Notwithstanding the foregoing, nothing herein shall impair, as between a Depositary and such holders of beneficial interests, the operation of customary practices governing the exercise of the rights of the Depositary as Holder of any Security. 

This Security is exchangeable, in whole but not in part, for Securities registered in the names of Persons other than the Depositary or its
nominee or in the name of a successor to the Depositary or a nominee of such successor depositary only if (i) the Depositary notifies the Company that it is unwilling or unable to continue as Depositary for this Note or if at any time such
Depositary ceases to be a clearing agency registered under the Securities Exchange Act of 1934, as amended, and, in either case, a successor depositary is not appointed by the Company within 90 days, (ii) the Company in its discretion at any
time determines not to have all of the Securities of this series represented by one or more Global Security or Securities and notifies the Trustee thereof, or (iii) an Event of Default has occurred and is continuing with respect to the
Securities of this series. If this Security is exchangeable pursuant to the preceding sentence, it shall be exchangeable for Securities issuable in authorized denominations and registered in such names as the Depositary holding this Security shall
direct. Subject to the foregoing, this Security is not exchangeable, except for a Security or Securities of the same aggregate denominations to be registered in the name of such Depositary or its nominee or in the name of a successor to the
Depositary or a nominee of such successor depositary.] 

 [The Indenture entitles Holders to receive annual reports with respect to the Trustee’s
eligibility and qualifications to serve as Trustee by filing their names and addresses with the Trustee for that purpose within two years preceding and mailing of any such annual report.] 

No recourse shall be had for the payment of the principal of (and premium, if any, on) or interest on this Security, or for any claim based
hereon, or otherwise in respect hereof, or based on or in respect of the Indenture of any indenture supplemental thereto, against any incorporator, stockholder, officer or director, as such, past, present or future, of the Company or any successor
corporation, whether by virtue of any constitution, statute or rule of law, or by the enforcement of any assessment or penalty or otherwise, all such liability being, by the acceptance hereof and as part of the consideration for the issue
hereof, expressly waived and released. 
 All terms used in this Security which are defined in the Indenture shall have the meanings
assigned to them in the Indenture. 
 This Security, including without limitation the obligation of the Company contained herein to pay the
principal of (and premium, if any, on) and interest on this Security in accordance with the terms hereof and of the Indenture, shall be construed in accordance with and governed by the laws of the State of New York. 

[Trustee’s Certificate of Authentication.] 

This is one of the Securities of the series designated herein referred to in the within-mentioned Indenture. 

                     
                                
                , as 
 [Authenticating
Agent for] the Trustee 
  

					
	 By
	  	  
	  	
		  	Authorized Officer

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