Document:

EX-10.10

 Exhibit 10.10 
  

 
 March 27, 2018 
 Daniel
Springer 
 Re: Restated Employment Terms 
 Dear Dan: 

This offer letter (the “Agreement”) amends and restates the offer letter between you and DocuSign, Inc. (the “Company”) dated
December 23, 2016 (the “Prior Agreement”). As discussed, the terms of this Agreement govern with respect to your employment, and will supersede and replace the terms and conditions set forth in the Prior Agreement. 

Position. You will continue to serve as President and Chief Executive Officer (“CEO”) of the Company and as a member of the
Company’s Board of Directors (the “Board”). During the term of your employment with the Company, you will devote your best efforts and substantially all of your business time and attention to the business of the Company, except
as otherwise provided herein and except for approved vacation periods and reasonable periods of illness or other incapacities permitted by the Company’s employment policies. You will perform those duties and responsibilities as are customary
for the position of President and CEO and as may be directed by the Board, to whom you will report. Your primary office location will be the Company’s offices in San Francisco, California. Notwithstanding the foregoing, the Company reserves the
right to reasonably require you to perform your duties at places other than your primary office location from time to time, and to require reasonable business travel. 

Salary. You will receive a base salary paid bi-weekly at the rate of $13,461.53 ($350,000 annualized) (the
“Base Salary”), less applicable payroll deductions and withholdings, in accordance with the Company’s normal payroll procedures. As an exempt salaried employee, you will be required to work the Company’s normal business
hours, and such additional time as appropriate for your work assignments and position, and you will not be entitled to overtime compensation. 
 Annual
Bonus. In addition, you will be eligible to earn an annual performance bonus, which will be targeted at one hundred percent (100%) of your Base Salary (the “Annual Bonus”). The Annual Bonus will be based upon the assessment of
the Compensation Committee of the Board (the “Compensation Committee”) of your performance and the Company’s attainment of written targeted goals as set by the Compensation Committee in its sole discretion. Bonus payments, if
any, will be subject to applicable payroll deductions and withholdings. Promptly following the close of each calendar year, the Compensation Committee will determine whether you have earned an Annual Bonus, and the amount of any such bonus, based on
the achievement of such goals. No amount of Annual Bonus is guaranteed, and you must be an employee on the Annual Bonus payment date to be eligible to receive an Annual Bonus; no partial or prorated bonuses will be provided. Your bonus eligibility
is subject to change in the discretion of the Compensation Committee. 
 Equity Awards. In connection with your commencement of employment, you
previously received certain equity awards covering shares of the Company’s Common Stock. Such equity awards will continue to be subject to the terms and conditions of the Company’s Amended and Restated 2011 Equity Incentive Plan, as
amended (the “Plan”), and the applicable award agreements; provided, however, that for all purposes in this Agreement, the term “Change in Control” shall have the 

  
 1. 

 

 
  

 meaning of Change in Control as defined in the Plan with the penultimate paragraph related to
Section 409A of such definition in the Plan disregarded in its entirety. The vested portion of any stock options you hold will be exercisable for a period of twelve (12) months following your termination of employment for any reason other
than Cause (as defined in Attachment A hereto). 
 Benefits. As a regular full-time employee of the Company, you will be eligible to
participate in the Company’s standard employee benefits (pursuant to the terms and conditions of the benefit plans and applicable policies), including but not limited to: paid time off (“PTO”), medical and dental insurance and
401(k) plan, all of which are described in summary plan descriptions and policies that will be available or provided to you by the Company. The Company may modify compensation and benefits from time to time in its discretion. 

The Company will reimburse you for reasonable travel, entertainment or other expenses incurred by you in furtherance or in connection with the performance of
your duties hereunder, in accordance with the Company’s expense reimbursement policies as in effect from time to time. 
 At-Will Employment; Severance and Change in Control Benefits. Your employment relationship with the Company is at-will. Accordingly, you may terminate your employment with
the Company at any time and for any reason whatsoever simply by notifying the Company; and the Company may terminate your employment at any time, with or without Cause (as defined in Attachment A hereto) or advance notice. However, in
the event the Company terminates your employment without Cause, or you resign your employment for Good Reason, you will be eligible for severance benefits as set forth in Attachment A. In the event of a Change in Control, you will be
eligible for Change in Control benefits as set forth in Attachment A. 
 Company Policies; Confidential Information. As a Company
employee, you are required to abide by the Company’s policies and procedures, as modified from time to time within its discretion; provided, however, that in the event the terms of this Agreement differ from or are in conflict
with the Company’s general employment policies or practices, this Agreement shall control. You have previously signed an acknowledgment that you have read and understand and will abide by the Company’s Code of Conduct. You have also
previously signed and will continue to be subject to the Company’s At-Will Employment, Confidential Information, Invention Assignment and Arbitration Agreement (the “Confidentiality
Agreement”). 
 Outside Activities. Throughout your employment with the Company, you may engage in civic and
not-for-profit activities so long as such activities do not interfere with the performance of your duties hereunder or present a conflict of interest with the Company.
Subject to the restrictions set forth herein and with the prior written consent of the Board, you may devote a reasonable amount of your time to other types of business or public activities not expressly mentioned in this paragraph. The Board may
rescind its consent to your service as a director of all other corporations, or participation in other business or public activities, if the Board, in its sole discretion, determines that such activities compromise or threaten to compromise the
Company’s business interests or conflict with your duties to the Company. In addition, pursuant to the Company’s Code of Conduct, you must obtain the prior written consent of the Company’s Legal Department in order to serve as a
director of a corporation that is a Company customer, partner or other service provider. 
 During your employment by the Company, except on behalf of the
Company, you will not directly or indirectly serve as an officer, director, stockholder, employee, partner, proprietor, investor, joint venturer, associate, representative or consultant of any other person, corporation, firm, partnership 

  
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 or other entity whatsoever known by you to compete with the Company (or is planning or preparing to compete
with the Company), anywhere in the world, in any line of business engaged in (or planned to be engaged in) by the Company; provided, however, that you may purchase or otherwise acquire up to (but not more than) one percent (1%) of any
class of securities of any such enterprise (but without participating in the activities of such enterprise) if such securities are listed on any national or regional securities exchange. 

Other Provisions. This Agreement, together with Attachment A and your Confidentiality Agreement, forms the complete and exclusive statement of your
employment agreement with the Company. It supersedes any other agreements or promises made to you by anyone, whether oral or written, including the Prior Agreement. Changes in your employment terms, other than those changes expressly reserved to the
Company’s or the Board’s discretion in this Agreement, require a written modification approved by the Company and signed by a duly authorized officer of the Company. This Agreement will bind the heirs, personal representatives, successors
and assigns of you and the Company, and inure to the benefit of you and the Company, their heirs, successors and assigns. If any provision of this Agreement is determined to be invalid or unenforceable, in whole or in part, this determination shall
not affect any other provision of this Agreement and the provision in question shall be modified so as to be rendered enforceable in a manner consistent with the intent of the parties insofar as possible under applicable law. This Agreement shall be
construed and enforced in accordance with the laws of the State of California without regard to conflicts of law principles. Any ambiguity in this Agreement shall not be construed against any party as the drafter. Any waiver of a breach of this
Agreement, or rights hereunder, shall be in writing and shall not be deemed to be a waiver of any successive breach or rights hereunder. This Agreement may be executed in counterparts which shall be deemed to be part of one original, and facsimile
and electronic image copies of signatures shall be equivalent to original signatures. 
 To indicate your acceptance of the Agreement, please sign and date
this Agreement in the space provided below.     
  

	
	 Sincerely,
  

	 DocuSign, Inc.
  

	 /s/ Rory T. O’Driscoll

	Rory T. O’Driscoll
	 On behalf of the Board of Directors

 

	 ACCEPTED AND AGREED:

 

	 Daniel Springer
  

	 /s/ Daniel Springer

	 Date

	March 27, 2018
	 Signature

  
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 Attachment A 

Severance Benefits and Change in Control Benefits 

Severance Benefits 
 If, at any time, the Company
terminates your employment without Cause (as defined below) (other than as a result of your death or disability) or you resign your employment for Good Reason (as defined below), provided such termination constitutes a Separation from Service (as
defined below) and occurs outside of the period beginning three (3) months prior to the closing of a Change in Control (as defined below) and ending twelve (12) months after the closing of a Change in Control (the “Change in
Control Period”), then subject to the Release Requirement (defined below) and Return of Company Property Obligations (defined below), your continued compliance with the terms of this Agreement and your resignation from the Board, to be
effective no later than your Separation from Service date (or such other date requested or permitted by the Board), the Company will provide you with the following severance benefits (the “Severance Benefits”): 

 

	 	•	 	Cash Severance. The Company will pay you, as cash severance, twelve (12) months of your Base Salary in effect as of your Separation from Service date, less applicable payroll deductions and withholdings (the
“Cash Severance”). The Cash Severance will be paid in a lump sum on the Company’s first regular payroll date that is at least one (1) week following the effectiveness of the Release (defined below) (subject to the
Compliance with Section 409A provision set forth below). 

  

	 	•	 	Bonus Severance. The Company will pay you the amount equal to both (i) your target Annual Bonus for the year in which your termination is effective, less applicable payroll deductions and withholdings and
(ii) your actual annual bonus that remains unpaid but earned in the year prior to the year in which your termination is effective, if any (the combined amount, the “Bonus Severance”). The Bonus Severance will be paid in a lump
sum on the Company’s first regular payroll date that is at least one (1) week following the effectiveness of the Release (subject to the Compliance with Section 409A provision set forth below). 

 

	 	•	 	COBRA Severance. If you timely elect continued coverage under COBRA, the Company will continue to pay the cost of your health care coverage in effect at the time of your Separation from Service for a maximum of
eighteen (18) months, either under the Company’s regular health plan (if permitted), or by paying your COBRA premiums (the “COBRA Severance”). The Company’s obligation to pay the COBRA Severance on your behalf will
cease if you obtain health care coverage from another source (e.g., a new employer or spouse’s benefit plan), unless otherwise prohibited by applicable law. You must notify the Company within two (2) weeks if you obtain coverage from a new
source. This payment of COBRA Severance by the Company would not expand or extend the maximum period of COBRA coverage to which you would otherwise be entitled under applicable law. Notwithstanding the above, if the Company determines in its sole
discretion that it cannot provide the foregoing COBRA Severance without potentially violating applicable law (including, without limitation, Section 2716 of the Public Health Service Act), the Company shall in lieu thereof provide to you a
taxable monthly payment in an amount equal to the monthly COBRA premium that you would be required to pay to continue your group health coverage in effect on the date of your termination (which amount shall be based on the premium for the first
month of 

  
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 COBRA coverage), which payments shall be made on the last day of each month regardless of
whether you elect COBRA continuation coverage and shall end on the earlier of (x) the date upon which you obtain other coverage or (y) the last day of the eighteenth (18th) calendar month following your Separation from Service date. 

 

	 	•	 	Accelerated Vesting. A number of shares under your then-unvested Company equity awards (excluding any performance-vested awards) shall vest in an amount equal to twelve (12) additional months of additional
vesting. 

 Change in Control Benefits 

In the event of a Change of Control, the vesting of each of your then-outstanding Company equity awards granted under any of the Company’s equity
incentive plans (excluding any performance-vested awards) will accelerate as to fifty percent (50%) of any then-unvested shares subject to each such award as of immediately prior to the Change in Control, subject to your continued employment through
the Change in Control. For clarity, any accelerated vesting that you become eligible to receive will apply to the latest vesting tranches first, so as to shorten the remaining vesting schedule. 

In addition, in the event the Company terminates your employment without Cause (other than as a result of your death or disability) or you resign for Good
Reason (as defined below) during the Change in Control Period, provided such termination or resignation constitutes a Separation from Service, then subject to the Release Requirement and Return of Company Property Obligations, your continued
compliance with the terms of this Agreement and your resignation from the Board, to be effective no later than your Separation from Service date (or such other date requested or permitted by the Board), the Company will provide you with the
following severance benefits (the “Change in Control Severance Benefits”): 
  

	 	•	 	The Cash Severance as provided above; 

  

	 	•	 	The COBRA Severance as provided above, except that the maximum duration of any such COBRA Severance shall be twelve (12) months; and 

 

	 	•	 	The vesting of each of your then-outstanding Company equity awards (excluding the PSUs) will accelerate in full. In order to accommodate this potential accelerated vesting, any then-unvested Company equity awards will
not terminate with respect to shares that have not vested as of your termination date until 3 months and one day after your termination date.     

Notwithstanding anything to the contrary in the Plan or any equity award agreements, if unvested Company equity awards are not assumed by an acquirer in a
Change in Control, your unvested equity awards (other than any performance-vested awards) shall accelerate in full prior to such Change in Control. 

Resignation Without Good Reason; Termination for Cause; Death or Disability 

If, at any time, you resign your employment with the Company without Good Reason, or the Company terminates your employment for Cause, or your employment with
the Company terminates for any reason not entitling you to the Severance Benefits or Change in Control Severance Benefits set forth above, or if your employment with the Company terminates as a result 

  
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 of your death or disability, then you will receive your Base Salary accrued through your last day of
employment, as well as any unused PTO (if applicable) accrued through your last day of employment. Under these circumstances, you will not be entitled to any other form of compensation, including any Severance Benefits or Change in Control Severance
Benefits, other than your rights to the vested portion of your Options and RSUs and any other rights to which you are entitled under the Company’s benefit programs. In addition, if you are then a member of the Board, you shall resign from the
Board, to be effective no later than the date of your employment termination (or such other date requested or permitted by the Board). 
 Conditions
to Receipt of Severance Benefits and Change in Control Severance Benefits 
 Prior to and as a condition to your receipt of the Severance Benefits or
Change in Control Severance Benefits described above, you shall execute and deliver to the Company a release of claims in favor of and in a form acceptable to the Company (the “Release”) within the timeframe set forth in the
Release, but not later than forty-five (45) days following your Separation from Service date, and allow the Release to become effective according to its terms (by not invoking any legal right to revoke it) within any applicable time period set
forth in the Release (such latest permitted effective date, the “Release Deadline”) (the “Release Requirement”). 
 In
addition, upon the termination of your employment with the Company for any reason, as a precondition to your receipt of the Severance Benefits or Change in Control Severance Benefits, within five (5) days after your termination date (or earlier
if requested by the Company), you will return to the Company all Company documents (and all copies thereof) and other Company property within your possession, custody or control, and any materials of any kind which contain or embody any proprietary
or confidential information of the Company (and all reproductions thereof in whole or in part and in any medium). You further agree that you will make a diligent search to locate any such documents, property and information and return them to the
Company within the timeframe provided above. In addition, if you have used any personally-owned computer, mobile telephone, tablet, server or e-mail system to receive, store, review, prepare or transmit any
confidential or proprietary data, materials or information of the Company, then within five (5) days after your termination date you must provide the Company with a computer-useable copy of such information and permanently delete and expunge
such confidential or proprietary information from those systems without retaining any reproductions (in whole or in part); and you agree to provide the Company access to your system, as requested, to verify that the necessary copying and deletion is
done (together with the preceding two sentences, the “Return of Company Property Obligations”). You shall deliver to the Company a signed statement certifying compliance with the Return of Company Property Obligations prior to the
receipt of the Severance Benefits or Change in Control Severance Benefits. 
 Definitions 

For purposes of this Agreement (including this Attachment A), the following terms shall have the following meanings: 

“Cause” will mean the occurrence of one or more of the following: 

(i) Your willful and continued failure to perform the duties and responsibilities of your position after there has been delivered to you a
written demand for performance from the Company which describes the basis for the Company’s belief that Executive has not substantially performed Executive’s duties and provides Executive with thirty (30) days to take corrective
action; 

  
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 (ii) Any act of personal dishonesty taken by you in connection with your responsibilities as
an employee of the Company with the intention or reasonable expectation that such action may result in substantial personal enrichment; 

(iii) Your conviction of, or plea of nolo contendere to, a felony; 

(iv) Your commission of any tortious act, unlawful act or malfeasance which causes or reasonably could cause (for example, if it became
publicly known) material harm to the 
 Company’s standing, condition or reputation; 

(v) Any material breach by you of the provisions of the At-Will Employment, Confidential Information,
Invention Assignment and Arbitration Agreement or other improper disclosure of the 
 Company’s confidential or proprietary information; provided that
you receive a written notice from the Company which describes the basis for the Company’s belief of your material breach with thirty (30) days to take corrective action (if corrective action is possible);     

(vi) A breach of any fiduciary duty owed to the Company by you that has or could reasonably be expected to have a material detrimental effect
on the Company’s reputation or business; or 
 (vii) Obstructing or impeding; endeavoring to influence, obstruct or impede, or failing
to materially cooperate with, any investigation authorized by the Board or any governmental or self-regulatory entity (an “Investigation”). However, your failure to waive attorney-client privilege relating to communications with
your own attorney in connection with an Investigation will not constitute “Cause.” 
 “Change in Control” shall have the meaning
set forth in the Plan. 
 “Code” shall mean the Internal Revenue Code of 1986, as amended, and the Treasury Regulations and other
interpretive guidance thereunder. 
 You shall have “Good Reason” for resigning from employment with the Company if any of the following
actions are taken by the Company without your prior written consent: (a) a material reduction in your Base Salary, unless such reduction is made in connection with a similar action affecting all senior executives; (b) a material reduction
in your duties or responsibilities, provided that neither a change in title, nor a change in your reporting relationships by virtue of the Company being acquired or made part of a larger entity (as, for example, where the Company becomes a
subsidiary or operating unit of the acquiring corporation following a Change in Control) will be deemed a “material reduction” in and of itself unless your new duties and responsibilities are materially reduced from your prior duties and
responsibilities; or (c) relocation of your principal place of employment to a place that increases your one-way commute by more than twenty five (25) miles as compared to your then-current principal
place of employment immediately prior to such relocation. 
 In order to resign for Good Reason, you must provide written notice to the Board within thirty
(30) days after the first occurrence of the event giving rise to Good Reason setting forth the basis for your resignation, allow the Company at least thirty (30) days from receipt of such written notice to cure such event, and if such
event is not reasonably cured within such period, you must resign from all positions you then hold with the Company not later than thirty (30) days after the expiration of the cure period. 

  
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 “Separation from Service” shall mean an involuntary separation from service within the
meaning of Section 409A of the Code. 
 No Duplication of Benefits 

Except as set forth herein, you shall not be eligible for or entitled to any additional severance benefits or change in control benefits, including but not
limited to any benefits as set forth in any separate change in control policy or plan previously adopted by the Company. 
 Compliance with
Section 409A 
 The Severance Benefits and Change in Control Severance Benefits are intended to qualify for an exemption from application of
Section 409A of the Code (“Section 409A”) or comply with its requirements to the extent necessary to avoid adverse personal tax consequences under Section 409A, and any ambiguities herein shall be
interpreted accordingly. For purposes of Section 409A (including, without limitation, for purposes of Treasury Regulations 1.409A-2(b)(2)(iii)), your right to receive any installment payments under this
Agreement (whether severance payments, reimbursements or otherwise) shall be treated as a right to receive a series of separate payments and, accordingly, each installment payment hereunder shall at all times be considered a separate and distinct
payment. Notwithstanding any provision to the contrary in this Agreement, if the Company (or, if applicable, the successor entity thereto) determines that the Severance Benefits or Change in Control Severance Benefits constitute “deferred
compensation” under Section 409A and you are, on the date of your Separation from Service, a “specified employee”, as such term is defined in Section 409A(a)(2)(B)(i) of the Code (a “Specified Employee”),
then, solely to the extent necessary to avoid the incurrence of adverse personal tax consequences under Section 409A, the timing of the Severance Benefits and Change in Control Severance Benefits shall be delayed until the earliest of:
(i) the date that is six (6) months and one (1) day after your Separation from Service date, (ii) the date of your death, or (iii) such earlier date as permitted under Section 409A without the imposition of adverse
taxation. Upon the first business day following the expiration of such applicable Code Section 409A(a)(2)(B)(i) period, all payments or benefits deferred pursuant to this paragraph shall be paid in a lump sum or provided in full, and any
remaining payments due shall be paid as otherwise provided herein. No interest shall be due on any amounts so deferred. If the Severance Benefits and Change in Control Severance Benefits are not covered by one or more exemptions from the application
of Section 409A and the Release could become effective in the calendar year following the calendar year in which you have a Separation from Service, the Release will not be deemed effective any earlier than the Release Deadline. 

Section 280G; Parachute Payments 
 Any
payments described in this letter agreement or referenced herein or otherwise which could constitute or result in your receipt of “parachute payments” within the meaning of Section 280G of the Code are referred to as
“Compensatory Payments.” 
 In the event that any portion of the Compensatory Payments will be subject to the excise tax imposed by
Section 4999 of the Code (the “Excise Tax”), then any such Compensatory Payments shall be equal to the Reduced Amount. The “Reduced Amount” shall be either (x) the largest portion of the Compensatory
Payments that would result in no portion of the Compensatory Payments (after reduction) being subject to the Excise Tax or (y) the largest portion, up to and including the total, of the Compensatory Payments, whichever amount (i.e., the amount

  
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 determined by clause (x) or by clause (y)), after taking into account all applicable federal, state and
local employment taxes, income taxes, and the Excise Tax (all computed at the highest applicable marginal rate), results in your receipt, on an after-tax basis, of the greater economic benefit notwithstanding
that all or some portion of the Compensatory Payments may be subject to the Excise Tax. If a reduction in a Compensatory Payment is required pursuant to the preceding sentence and the Reduced Amount is determined pursuant to clause (x) of the
preceding sentence, the reduction shall occur in the manner (the “Reduction Method”) that results in the greatest economic benefit for you. If more than one method of reduction will result in the same economic benefit, the items so
reduced will be reduced pro rata (the “Pro Rata Reduction Method”). 
 Unless the Company and you otherwise agree in writing, the
determination of your Excise Tax liability and the amount of any reduction, if required, shall be made in writing by an accountant chosen by the Company, which shall be from one of the six largest national accounting firms (an
“Accountant”). For purposes of its calculations and determinations, the Accountant may make reasonable assumptions and approximations concerning the application of Section 280G and Section 4999 of the Code and applicable
taxes. The Company and you shall furnish to the Accountant such information and documents as the Accountant may reasonably request in order to make its determinations. The Company shall bear all costs the Accountant may reasonably incur in
connection with any calculations contemplated hereunder. The Accountant’s determinations shall be final and binding on the Company and you. 
  

  
 9EX-10.10.9

 Exhibit 10.10.9 

DOCUSIGN, INC. 
 AMENDED
AND RESTATED RETENTION AGREEMENT 
 This Amended and Restated Retention Agreement (the “Agreement”) is effective
as of March 27, 2018, by and between Scott Olrich (“Executive”) and DocuSign, Inc., a Delaware corporation (the “Company”), and amends and restates the prior Retention Agreement and Change
in Control Plan between Executive and the Company dated April 3, 2017. 
 RECITALS 

A. The Company’s Board of Directors (the “Board”) believes it is in the best interests of the Company and its
stockholders to retain Executive and to provide Executive with certain protections in the event of Executive’s termination of employment or a Change in Control of the Company under certain circumstances. 

B. To accomplish the foregoing objectives, the Board has directed the Company, upon execution of this Agreement by Executive, to agree to the
terms provided in this Agreement. Capitalized terms not defined below shall have the meanings set forth in Exhibit A or Exhibit B, as applicable. 

AGREEMENT 
 The
parties hereto agree as follows: 
 1. At-Will Employment. Nothing in this Agreement alters
the at-will nature of Executive’s employment. Executive and the Company remain free to terminate the employment relationship at any time, for any reason, with or without notice. 

2. Benefits Upon Qualifying Termination Generally. Upon Executive’s Qualifying Termination, and subject to the conditions in
Section 5, the Company will provide Executive with the following severance benefits: 
 (a) Severance Pay. The Company will pay
Executive a lump sum cash payment, less all applicable withholdings and deductions, in an amount equal to: 
 (i) 6 months of
Executive’s then-current base salary (ignoring any decrease in base salary that forms the basis for Good Reason); and 
 (ii) 50% of
Executive’s target annual bonus for the performance year in which the Qualifying Termination occurs. 
 (b) Continued Health
Insurance Coverage. Provided Executive timely elects COBRA continuation coverage, the Company will pay the COBRA premiums to continue and maintain health care coverage for Executive and any dependents who are covered at the time of the
Executive’s termination of employment under the Company’s group health plans. The Company will make such payments until the earliest of: (i) 6 months following the Qualifying Termination date; (ii) the date when Executive becomes
eligible for substantially equivalent health insurance coverage in connection with new employment or self-employment; or (iii) the 

  
 1. 

 date Executive ceases to be eligible for COBRA continuation coverage for any reason. Notwithstanding the
foregoing, if the Company determines in its sole discretion that it cannot pay the COBRA premiums without potentially incurring financial costs or penalties under applicable law, the Company may pay Executive a taxable cash payment equal to the
amount that the Company would have otherwise paid for COBRA premiums (based on the premium for the first month of coverage), which payment will be made regardless of whether Executive or Executive’s eligible dependents elect COBRA continuation
coverage and will be paid in monthly installments on the same schedule and over the same time period that the COBRA premiums would otherwise have been paid on behalf of Executive. 

(c) Equity Vesting Acceleration. The vesting of each of Executive’s then-outstanding equity compensation awards granted under any
of the Company’s equity incentive plans will accelerate as to the number of shares subject to each such award that would have become vested, in the ordinary course, within the first 6 months following Executive’s termination date,
effective on Executive’s date of termination and subject to Section 5(a). 
 Subject to the payment timing rules contained in Exhibit
B, any severance payments and benefits under this Section 2 will be paid on the later of (x) 10 business days after the effective date of the Release and (y) the date of Executive’s Qualifying Termination. 

3. Qualifying Termination During the Change in Control Period. Upon Executive’s Qualifying Termination during the Change in Control
Period, and subject to the conditions in Section 5, the Company will provide Executive with the following severance benefits: 
 (a)
Severance Pay. The Company will pay Executive a lump sum cash payment, less all applicable withholdings and deductions, in an amount equal to 12 months of Executive’s then-current base salary (ignoring any decrease in base salary that
forms the basis for Good Reason). 
 (b) Continued Health Insurance Coverage. Provided Executive timely elects COBRA continuation
coverage, the Company will pay the COBRA premiums to continue and maintain health care coverage for Executive and any dependents who are covered at the time of the Executive’s termination of employment under the Company’s group health
plans. The Company will make such payments until the earliest of: (i) 12 months following the Qualifying Termination date; (ii) the date when Executive becomes eligible for substantially equivalent health insurance coverage in connection with
new employment or self-employment; or (iii) the date Executive ceases to be eligible for COBRA continuation coverage for any reason. Notwithstanding the foregoing, if the Company determines in its sole discretion that it cannot pay the COBRA
premiums without potentially incurring financial costs or penalties under applicable law, the Company may pay Executive a taxable cash payment equal to the amount that the Company would have otherwise paid for COBRA premiums (based on the premium
for the first month of coverage), which payment will be made regardless of whether Executive or Executive’s eligible dependents elect COBRA continuation coverage and will be paid in monthly installments on the same schedule and over the same
time period that the COBRA premiums would otherwise have been paid on behalf of Executive. 

  
 2. 

 (c) Equity Vesting Acceleration. The vesting of each of Executive’s then-outstanding
compensatory equity awards granted under any of the Company’s equity incentive plans will accelerate in full, subject to Section 5(a). In order to accommodate this potential accelerated vesting, if Executive experiences a Qualifying
Termination within three months prior to a Change in Control, any then-unvested compensatory equity awards will not terminate with respect to shares that have not vested as of Executive’s termination date until three months and one day after
Executive’s termination date. 
 Subject to the payment timing rules contained in Exhibit B, any severance payments and benefits under
this Section 3 will be paid on the latest of (x) 10 business days after the effective date of the Release, (y) the date of Executive’s Qualifying Termination, and (z) the date of the Change in Control. 

4. Change in Control Acceleration. In the event of a Change of Control, the vesting of each of Executive’s then-outstanding equity
compensation awards granted under any of the Company’s equity incentive plans will accelerate as to 25% of any then-unvested shares subject to each such award as of immediately prior to the Change in Control subject to 

Executive’s continued employment through the Change in Control and subject to Section 5(a). 

5. Limitations and Conditions on Termination Benefits 

(a) Treatment of Performance-Based Awards. Notwithstanding the foregoing, the accelerated vesting provisions contained in this Agreement
will only apply to service-based vesting provisions, and will not result in a waiver of any performance or milestone-based vesting conditions (a “Performance Condition”) contained in any such equity compensation award. The
terms and conditions of the applicable award agreement will control the treatment of any vesting provision conditioned on the satisfaction of a Performance Condition in connection with Executive’s termination. 

(b) Release Prior to Payment of Benefits. In order to be eligible to receive any benefits under Sections 2 or 3, Executive must
(i) execute and return a general waiver and release, in a form provided by the Company and reasonably acceptable to Executive, of all employment related obligations of and claims and causes of action against the Company (a
“Release”), to the Company within the applicable time period set forth therein and (ii) not revoke the Release within the revocation period (if any) set forth therein; provided, however, that in no event may the
applicable time period or revocation period extend beyond sixty (60) days following Executive’s termination date. 
 (c) Income
and Employment Taxes. Executives agrees that Executive will be responsible for any applicable taxes of any nature (including any penalties or interest that may apply to such taxes) that the Company reasonably determines apply to any payment made
hereunder, that Executive’s receipt of any benefit hereunder is conditioned on Executive’s satisfaction of any applicable withholding or similar obligations that apply to such benefit, and that any cash payment owed hereunder will be
reduced to satisfy any such withholding or similar obligations that may apply. 

  
 3. 

 (d) Related Matters. Executive further acknowledges and agrees that as a condition to
receipt of any severance benefits, Executive must (i) comply with Executive’s obligations under Executive’s At-Will Employment, Confidential Information, Invention Assignment and Arbitration
Agreement; and (ii) resign from all officer and director positions with the Company and/or any affiliate (unless otherwise requested by the Company). 

(e) Section 409A and Section 280G. Executive and the Company understand that payments under this
Agreement may be subject to Sections 409A and 280G of the Code, and the parties agree to abide by the Section 409A and Section 280G provisions contained in Exhibit B to this Agreement. 

6. Miscellaneous Provisions.  

(a) Interaction with Other Benefits. In the event that Executive would be entitled to a greater level of payments or benefits under the
terms and conditions of an individual equity compensation award, offer letter or other employment-related agreement, or a severance plan or policy provided by the Company or its successor, but for the existence of this Agreement, Executive shall be
entitled to receive the greater of the payments and benefits provided for hereunder or the benefits under such other agreement, plan or policy subject to the applicable terms and conditions thereof. 

(b) Complete Agreement. This Agreement supersedes any agreement (or portion thereof) concerning similar subject matter dated prior to
the date of this Agreement, and by execution of this Agreement both parties agree that any such predecessor agreement (or portion thereof) shall be deemed null and void; provided that, for clarification purposes, this Agreement shall not
affect any agreement between the Company and Executive regarding intellectual property matters, non-solicitation or non-competition restrictions or confidential
information. The parties further agree that this Agreement does not supersede the provisions of Executive’s offer letter or employment agreement with the Company which do not address termination or severance benefits or Executive’s At-Will Employment, Confidential Information, 
 Invention Assignment and Arbitration Agreement. 

(c) Waiver. No provision of this Agreement may be waived unless the waiver is agreed to in writing and signed by Executive and by an
authorized officer of the Company. No waiver by either party of any breach of, or of compliance with, any condition or provision of this Agreement shall be considered a waiver at another time. 

(d) Successors and Assigns. This Agreement is personal to Executive and will not be assignable by Executive otherwise than by will or
the laws of descent and distribution. This Agreement will inure to the benefit of and be binding upon the Company and its successors and assigns. From and after a Change in Control, the term “Company” when used in this Agreement will also
be read to include any entity that actually employs Executive, if different from the Company. 
 (e) Choice of Law. The validity,
interpretation, construction and performance of this Agreement shall be governed by the laws of the State of California without reference to conflict of laws provisions, and the parties hereto submit to the exclusive jurisdiction of the state and
federal courts of the State of California. 

  
 4. 

 (f) Severability. The invalidity or unenforceability of any provision or provisions of
this Agreement shall not affect the validity or enforceability of any other provision hereof, which shall remain in full force and effect. 

(g) Notice. Notices and all other communications contemplated by this Agreement will be in writing and will be deemed to have been duly
given when personally delivered or when mailed by U.S. registered or certified mail, return receipt requested and postage prepaid. Mailed notices to Executive shall be addressed to Executive at the home address which Executive most recently
communicated to the Company in writing. In the case of the Company, mailed notices shall be addressed to its corporate headquarters, and all notices shall be directed to the attention of the Board. 

(h) Counterparts. This Agreement may be executed in counterparts, each of which shall be deemed an original, but all of which together
will constitute one and the same instrument, and facsimile and electronic signatures shall be equivalent to original signatures. 

[SIGNATURE PAGE FOLLOWS] 

  
 5. 

 IN WITNESS WHEREOF, the
parties have executed this Agreement as of the date written below. 
  

			
	 DOCUSIGN, INC.

 

	By:	 	 /s/ Daniel Springer

		 	Daniel Springer
		 	Name: Dan Springer
		 	 Title: CEO
  

	 SCOTT OLRICH

 

		 	 /s/ Scott Olrich

		 	Date: March 27, 2018

  
 6. 

 EXHIBIT A 

DEFINITIONS 

“Cause” will mean the occurrence of one or more of the following: 

(i) Executive’s willful and continued failure to perform the duties and responsibilities of Executive’s position after there has been
delivered to Executive a written demand for performance from the Company which describes the basis for the Company’s belief that Executive has not substantially performed Executive’s duties and provides Executive with thirty (30) days
to take corrective action; 
 (ii) any act of personal dishonesty taken by Executive in connection with 

Executive’s responsibilities as an employee of the Company with the intention or reasonable expectation that such action may result in substantial
personal enrichment of Executive; 
 (iii) Executive’s conviction of, or plea of nolo contendere to, a felony; 

(iv) Executive’s commission of any tortious act, unlawful act or malfeasance which causes or reasonably could cause (for example, if it
became publicly known) material harm to the Company’s standing, condition or reputation; 
 (v) any material breach by Executive of the
provisions of the At-Will Employment, Confidential Information, Invention Assignment and Arbitration Agreement or other improper disclosure of the Company’s confidential or proprietary information; 

(vi) a breach of any fiduciary duty owed to the Company by Executive that has or could reasonably be expected to have a material detrimental
effect on the Company’s reputation or business; or 
 (vii) Executive (A) obstructing or impeding; (B) endeavoring to
influence, obstruct or impede, or (C) failing to materially cooperate with, any investigation authorized by the Board or any governmental or self-regulatory entity (an “Investigation”). However, Executive’s failure
to waive attorney-client privilege relating to communications with Executive’s own attorney in connection with an Investigation will not constitute “Cause.” 

“Change in Control” will have the meaning set forth in the Company’s Amended and Restated 2011 Equity Incentive
Plan. 
 “Change in Control Period” means the period beginning three months prior to and ending on the 12-month anniversary of the effective date of a Change in Control. 
 “COBRA”
means the Consolidated Omnibus Budget Reconciliation Act of 1985, as amended together with any analogous provisions of applicable state law. 

  
 A-1 

 “Code” means Internal Revenue Code of 1986, as amended, and the Treasury
regulations and formal guidance promulgated thereunder, each as may be amended or modified from time to time. 
 “Good
Reason” for Executive’s resignation of employment will exist following the occurrence of any of the following without Executive’s express written consent: 

(i) a material reduction or material change in Executive’s duties or responsibilities without Executive’s consent, provided that
neither a change in title, nor a change in Executive’s reporting relationships by virtue of the Company being acquired or made part of a larger entity (as, for example, where the Company becomes a subsidiary or operating unit of the acquiring
corporation following a Change in Control) will be deemed a “material reduction” or “material change” in and of itself unless Executive’s new duties and responsibilities are materially reduced from the prior duties and
responsibilities; 
 (ii) a material reduction in Executive’s base compensation, unless such reduction is made in connection with a
similar action affecting all senior executives; or 
 (iii) a relocation of Executive’s principal place of employment to a place that
increases Executive’s one-way commute by more than fifty (50) miles as compared to Executive’s then-current principal place of employment immediately prior to such relocation. 

In order to resign for Good Reason, Executive must provide written notice to Board within 90 days after the first occurrence of the event
giving rise to Good Reason setting forth the basis for Executive’s resignation, allow the Company at least 30 days from receipt of such written notice to cure such event, and if such event is not reasonably cured within such period, Executive
must resign from all positions Executive then holds with the Company not later than 30 days after the expiration of the cure period.     

The effective date for such a resignation for Good Reason (in the absence of cure) will be the earlier of the following dates: (i) the
date of expiration of the Company’s cure period or (ii) the date that the Company advises Executive in writing that it does not intend to cure. For the purposes of delivery of notice under subsection (i) above, a material change or
material reduction that occurs incrementally over a period of time (not to exceed twelve (12) months) shall be deemed to have occurred when such change or reduction, in the aggregate, becomes material. 

“Qualifying Termination” shall mean the termination of Executive’s employment by the Company without Cause
or by Executive with Good Reason. 

  
 A-2 

 EXHIBIT B 

SECTION 409A AND SECTION 280G MATTERS 

1. Section 409A  
 (a)
It is intended that the Agreement shall comply with the requirements of Section 409A of the Code, and any payments hereunder are intended to be exempt from, or if not so exempt, to comply with the requirements of Section 409A of the Code,
and this Agreement shall be interpreted, operated and administered accordingly. To the extent that any provision of the Agreement is ambiguous, but a reasonable interpretation of the provision would cause any payment or benefit to comply with or be
exempt from the requirements of Section 409A of the Code, Executive and the Company intend the term to be interpreted as such in order to avoid adverse personal tax consequences under Section 409A. 

(b) No severance or other payments or benefits otherwise payable to Executive upon a termination of employment under the Agreement or otherwise
will be payable until Executive has a “separation from service” as defined under Treasury Regulation Section 1.409A-1(h), without regard to any alternative definition thereunder. 

(c) If the period during which Executive may sign the Release begins in one calendar year and ends in the following calendar year, then no
severance payments or benefits that that would constitute deferred compensation within the meaning of Section 409A of the Code will be paid or provided until the later calendar year. 

(d) The severance payments and benefits under the Agreement are intended to satisfy the exemptions from application of Section 409A of the
Code provided under Treasury Regulations Sections 1.409A-1(b)(4), 1.409A-1(b)(5) and 1.409A-1(b)(9). However, if such exemptions
are not available and Executive is a “specified employee” within the meaning of Section 409A of the Code at the time of Executive’s separation from service, then, solely to the extent necessary to avoid adverse personal tax
consequences under Section 409A of the Code, any payments payable under the Agreement on account of a separation from service that would constitute deferred compensation within the meaning of Section 409A of the Code and that would (but
for this provision) be payable within 6 months following the date of termination, shall instead be paid on the next business day following the expiration of such six month period or, if earlier, upon Executive’s death. Each installment payment
under the Agreement is a “separate payment” for purposes of Treasury Regulations Section 1.409A-2(b)(2)(i). 

2. Section 280G  
 (a)
If any payment or benefit (including payments and benefits pursuant to the Agreement) that Executive would receive in connection with a Change in Control from the Company or otherwise (a “Transaction Payment”) would
(i) constitute a “parachute payment” within the meaning of Section 280G of the Code, and (ii) but for this sentence, be subject to the excise tax imposed by Section 4999 of the Code (the “Excise
Tax”), then the Company shall cause to be determined, before any amounts of the Transaction Payment are paid to Executive, which of the following two alternative forms of payment would result in Executive’s receipt, on an after-tax basis, 

  
 B-1 

 of the greater amount of Transaction Payments notwithstanding that all or some portion of the Transaction Payment
may be subject to the Excise Tax: (1) payment in full of the entire amount of the Transaction Payments (a “Full Payment”), or (2) payment of only a portion of the Transaction Payments so that Executive receives the
largest payment possible without the imposition of the 
 Excise Tax (a “Reduced Payment”). For purposes of determining whether to
make a Full Payment or a Reduced Payment, the Company shall cause to be taken into account all applicable federal, state, local and foreign income and employment taxes and the Excise Tax (all computed at the highest applicable marginal rate, net of
the maximum reduction in federal income taxes which could be obtained from a deduction of such state and local taxes). If a Reduced Payment is made, (x) Executive shall have no rights to any additional payments and/or benefits constituting the
forfeited portion of the Full Payment, and (y) reduction in payments and/or benefits will occur in the manner that results in the greatest economic benefit for Executive. If more than one method of reduction will result in the same economic
benefit, the items so reduced will be reduced pro rata. Notwithstanding the foregoing, if such reduction would result in any portion of the Transaction Payments being subject to penalties pursuant to Section 409A that would not otherwise be
subject to such penalties, then the reduction method shall be modified so as to avoid the imposition of penalties pursuant to Section 409A as follows: (A) Transaction Payments that are contingent on future events (e.g., being terminated
without Cause), shall be reduced (or eliminated) before Transaction Payments that are not contingent on future events; and (B) Transaction Payments that are “deferred compensation” within the meaning of Section 409A shall be
reduced (or eliminated) before Transaction Payments that are not deferred compensation within the meaning of Section 409A. In the event that acceleration of vesting of any equity compensation awards is to be reduced, such acceleration of
vesting will be cancelled in the reverse order of the date of grant of Executive’s equity awards. In no event will the Company or any stockholder be liable to Executive for any amounts not paid as a result of the operation of this provision.

 (b) The professional firm engaged by the Company for general tax purposes as of the day prior to the effective date of the Change in
Control shall make all determinations required to be made under this Exhibit B. If the professional firm so engaged by the Company is serving as accountant or auditor for the individual, entity or group effecting the Change in Control,
the Company shall appoint a nationally recognized independent registered public accounting firm to make the determinations required hereunder. The Company shall bear all expenses with respect to the determinations by such professional firm required
to be made hereunder. 
 (c) The professional firm engaged to make the determinations hereunder shall provide its calculations, together with
detailed supporting documentation, to the Company and Executive within a reasonable period after the date on which Executive’s right to a Transaction Payment is triggered or such other time as reasonably requested by the Company or Executive.
If the professional firm determines that no Excise Tax is payable with respect to the Transaction Payment, either before or after the application of the Reduced Amount, it shall furnish the Company and Executive with detailed supporting calculations
of its determinations that no Excise Tax will be imposed with respect to such Transaction Payment. Any good faith determinations of the professional firm made hereunder shall be final, binding and conclusive upon the Company and Executive. 

  
 B-2 

 (d) Notwithstanding the foregoing, if the Company is privately held as of immediately prior to a
Change in Control and it is deemed necessary by the Company to avoid any potential imposition of the adverse tax results provided for by Sections 280G and 4999 of the Code, then as a further condition to any payment or benefit provided for in the
Agreement or otherwise, the Company may require Executive to submit any payment or benefit provided for in the Agreement or from any other source that the Company reasonably determines may constitute an “excess parachute payment” (as
defined in Section 280G(b)(1) of the Code) for approval by the Company’s stockholders prior to the Closing of the Change in Control in the manner required by the terms of Section 280G(b)(5)(B) of the Code, so that no payments or
benefits will be deemed to constitute a “parachute payment” subject to the excise taxes under Sections 280G and 4999 of the Code. 
  

  
 B-3

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