Document:

EX-10.10.4

 Exhibit 10.10.4 
  

 
 August 3, 2015 
 Michael
Sheridan 
 Re: Offer of Employment 
 Dear Michael: 

I am pleased to offer you a position with DocuSign, Inc. (the “Company”) as Chief Financial Officer, based in our San Francisco office,
reporting to me, commencing on or before August 1, 2015. You will receive a bi-weekly salary of $12,365.38 ($321,500 annualized) which will be paid in accordance with the Company’s normal payroll
procedures. In addition, you will be eligible for a target variable compensation equal to 40% of your salary (“Target Bonus”), based on performance against goals established by the Board of Directors of the Company, or a committee
appointed by the Board. 
 Subject to approval of the Board of Directors of the Company, or a committee appointed by the Board, you will be eligible to
receive the following equity awards: (1) a stock option to purchase up to 826,187 shares of the Company’s Common Stock with an exercise price equal to the fair market value on the date of grant (the “Option”), and (2) an
award of restricted stock units (“RSUs”) representing the right to acquire 826,187 shares of the Company’s Common Stock. Such Option and RSUs will be subject to the terms and conditions of (a) the Company’s equity
incentive program in effect at the time of grant (the “Plan”) and (b) a Stock Option Agreement and an RSU Agreement, as applicable, each in the form approved by the Board or a committee of the Board. The Option will be subject
to service-based vesting requirements set forth in the Stock Option Agreement. The RSUs will be subject to service-based requirements and a liquidity event requirement as set forth in the RSU Agreement. For a general summary of the vesting terms,
please see Attachment A hereto. The Option will be granted as an “incentive stock option” to the extent permissible under applicable law. 

You will be eligible to participate in the Successful Transaction program which is designed to drive company-wide alignment around customer adoption. Upon
achievement of our Company’s annual goal, all regular, full-time employees with be rewarded for our success. The customer adoption metric is based on the number of successfully completed transactions through DocuSign. This program provides a
stock option award covering 111 shares of the Company’s Common Stock to regular, full-time employees who join the Company before October 1, 2015. The stock options for this one-time equity program
will be granted following your date of hire and, subject to your continued service with the Company, 100% of these stock options will vest upon achievement of the company-wide metric. 

As a Company employee, you will also be eligible to receive certain employee benefits including PTO, healthcare, dental coverage, and a 401(k) plan. You
should note that the Company may modify salaries and benefits from time to time as it deems necessary. You should be aware that your employment with the Company is for no specified period and constitutes
at-will employment. As a result, you are free to resign at any time, for any reason or for no reason. 

  
 221 Main St. Suite
1000 | San Francisco, CA 94105 | toll free (877) 720-2040 | www.docusign.com 

  

	
	 /s/ Michael Sheridan

 

 
 Similarly, the Company is free to conclude its employment relationship with you at any time, with or without cause, and
with or without notice. However, in the event the Company terminates your employment without Cause (as “Cause” is defined in Attachment B), you will be eligible for severance benefits in accordance with Attachment
B hereto. In the event of a Change in Control (as defined in Attachment B), you will be eligible for enhanced Change in Control severance benefits in accordance with Attachment B. 

The Company reserves the right to conduct background investigations and/or reference checks on all of its potential employees. Your job offer, therefore, is
contingent upon a clearance of such a background investigation and/or reference check, if any. 
 For purposes of federal immigration law, you will be
required to provide to the Company documentary evidence of your identity and eligibility for employment in the United States. Such documentation must be provided to us within three (3) business days of your date of hire, or our employment
relationship with you may be terminated. 
 You agree that, during the term of your employment with the Company, you will not engage in any other
employment, occupation, consulting or other business activity directly related to the business in which the Company is now involved or becomes involved during the term of your employment, nor will you engage in any other activities that conflict
with your obligations to the Company. 
 As a Company employee, you will be expected to abide by company rules and regulations. You will be specifically
required to sign an acknowledgment that you have read and understand and will abide by the company’s Code of Conduct which you will receive on your first day of employment. You will be expected to sign and comply with an At-Will Employment, Confidential Information, Invention Assignment and Arbitration Agreement which requires, among other provisions, the assignment of patent rights to any invention made during your employment at
the Company and non-disclosure of proprietary information. The Agreement also provides that in the event of any dispute or claim relating to or arising out of our working relationship, you and the Company
agree that all such disputes shall be resolved by binding arbitration. 
 To indicate your acceptance of the Company’s offer, please sign and date
this letter in the space provided below by Monday, August 3, 2015. This letter, along with the agreement relating to proprietary rights between you and the Company, set forth the terms of your employment with the Company and supersede any
prior representations or agreements, whether written or oral. This letter may not be modified or amended except by a written agreement, signed by an officer of the Company and by you. 

We look forward to working with you at DocuSign, Inc. 
  

	
	 Sincerely,

	
	DOCUSIGN INC.
	
	 /s/ Keith Krach

	Keith Krach
	 Chairman and CEO

 ACCEPTED AND AGREED: 

  
 221 Main St. Suite
1000 | San Francisco, CA 94105 | toll free (877) 720-2040 | www.docusign.com 

  

	
	 /s/ Michael Sheridan

 

 
 ACCEPTED AND AGREED: 
  

	
	 Aug-3-2015

	
	 Date
  

Michael Sheridan

	  

	Name Signed by:
	
	 /s/ Michael Sheridan

	 Signature

  
 221 Main St. Suite
1000 | San Francisco, CA 94105 | toll free (877) 720-2040 | www.docusign.com 

  

 

 
 Attachment A 

Equity Vesting Terms 
 Stock Options

 As provided in more detail in the Option Agreement, generally, the Option shall vest and become exercisable as follows: twenty-five percent (25%) of
the shares subject to the Option shall vest on the one (1) year anniversary of the vesting commencement date, and thereafter one forty-eighth (1/48th) of the shares subject to the Option
shall vest each month thereafter on the same day of the month as the vesting commencement date (and if there is no corresponding day, on the last day of the month), subject to your continued employment or service with the Company on each such date.
In all cases, the Option will be subject to the terms and conditions of the Plan and the applicable Option Agreement. 
 RSUs 

As provided in more detail in the RSU Agreement, your RSUs will become “Vested RSUs” subject to the satisfaction of the following two
conditions: (1) the service-based requirement and (2) the occurrence of the Liquidity Event Requirement (defined below) within
six-and-one-half years after the grant date of the RSUs (the “Expiration Date”). 

Generally, 25% of the total number RSUs awarded will have the service-based requirement satisfied on the 12-month
anniversary of the vesting commencement date, and thereafter 1/16th of the total number of RSUs awarded will have the service-based requirement satisfied in a series of 12 successive equal
quarterly installments following the first anniversary of the vesting commencement date until the service-based requirement is fully satisfied on the fourth anniversary of the vesting commencement date, subject to your continued employment or
service with the Company on each such date. 
 The “Liquidity Event Requirement” will be satisfied on the first to occur of: (a) a
Change in Control (as defined in the Plan), and (b) the effective date of a registration statement of the Company filed under the Securities Act of 1933, as amended, for the sale of the Company’s Common Stock (i.e., an IPO) (each a
“Liquidity Event”). Upon the occurrence of a Liquidity Event during your employment, you will vest in and the Company will issue to you the number of shares of Common Stock that would have otherwise vested under the service-based
vesting schedule at the settlement date provided in the RSU Agreement. In the case of an IPO, the balance of the RSUs shall continue to vest thereafter in accordance with the service-based vesting schedule and Vested RSUs will settle at the
settlement dates provided in the RSU Agreement. If your employment with the Company terminates before a Liquidity Event has occurred, you will be issued shares of Common Stock for any Vested RSUs for which the service-based vesting requirement was
satisfied prior to your departure on the settlement date provided in the RSU Agreement, subject to the occurrence of the Liquidity Event prior to the Expiration Date. In all cases, the RSUs will be subject to the terms and conditions of the Plan and
the applicable RSU Agreement. 

  
 221 Main St. Suite
1000 | San Francisco, CA 94105 | toll free (877) 720-2040 | www.docusign.com 

  

	
	 /s/ Michael Sheridan

 

 
 Attachment B 

Severance Terms 
 Severance (Initial 24
Months) 
 If the Company terminates your employment without Cause (as defined below) on or before the twenty-four (24) month anniversary of your
start date and you are not entitled to Change in Control Benefits (as defined below), you will be eligible to receive the following severance benefits: 
  

	 	☐	a lump-sum cash payment equal to the sum of (a) twelve (12) months of your then-current base salary and (b) one hundred percent (100%) of your then-current annual Target
Bonus amount (the “Initial Period Severance Payment”); 

  

	 	☐	accelerated vesting of twelve forty-eighths (12/48) of your then-unvested Option shares and twelve forty-eighths (12/48) of your then-unvested RSUs; and 

 

	 	☐	subject to your timely election under COBRA, payment of your COBRA premiums until the earlier of (i) the twelve (12) month anniversary of your date of termination or (ii) the date you become eligible for
group health coverage through another employer; provided that the Company may reduce or cease these COBRA payments if it determines that it may be subject to a tax or penalty (including pursuant to Section 4980D of the Internal Revenue Code
(“Code”)) as a result of providing such payments) (the “Initial COBRA Period”). 

 Severance (After 24
Months) 
 If the Company terminates your employment without Cause at any time following the twenty-four (24) month anniversary of your start date
and you are not entitled to Change in Control Benefits (as defined below), you will be eligible to receive the following severance benefits: 
  

	 	☐	a lump-sum cash payment equal to the sum of (a) six (6) months of your then-current base salary and (b) fifty percent (50%) of your then-current annual Target Bonus
amount (the “Standard Severance Payment”); 

  

	 	☐	accelerated vesting of six forty-eighths (6/48) of your then-unvested Option shares and six forty-eighths (6/48) of your then-unvested RSUs; and 

 

	 	☐	subject to your timely election under COBRA, payment of your COBRA premiums until the earlier of (i) the six (6) month anniversary of your date of termination or (ii) the date you become eligible for
group health coverage through another employer; provided that the Company may reduce or cease these COBRA payments if it determines that it may be subject to a tax or penalty (including pursuant to Section 4980D of the Code as a result of
providing such payments (the “Standard COBRA Period”). 

 Change in Control 

In the event a Change in Control (as defined below) occurs with respect to the Company, then (a) if you remain a full-time employee of the Company for one
(1) year following such Change in Control, on the one (1) year anniversary of such Change in Control all of your then-unvested Option shares and then-unvested RSUs shall be deemed vested as of that date; (b) if your employment by the
Company is terminated by the Company without 

  
 221 Main St. Suite
1000 | San Francisco, CA 94105 | toll free (877) 720-2040 | www.docusign.com 

  

	
	 /s/ Michael Sheridan

 

 
 Cause (as defined below) in the six (6) months prior to* or twelve (12) months following such Change in Control,
you will be eligible for the Change in Control Benefits (as defined below); or (c) you choose to resign from your employment for any reason within twelve (12) months following the Change in Control, then you will be eligible to receive the
following enhanced severance benefits (the “Change in Control Benefits”): 
  

	 	☐	a lump-sum cash severance payment equal to (a) the Initial Period Severance Payment, if the qualifying termination occurs on or prior to the twenty-four (24) month
anniversary of your start date or (b) the Standard Severance Payment, if the qualifying termination occurs following the twenty-four (24) month anniversary of your start date; 

 

	 	☐	accelerated vesting of 100% of your then-unvested Option shares and 100% of your then-unvested RSUs as described in the Option Agreement and RSU Agreement, respectively; and 

 

	 	☐	subject to your timely election under COBRA, payment of your COBRA premiums for (a) the Initial COBRA Period, if the qualifying termination occurs on or prior to the twenty-four (24) month anniversary of your
start date or (b) the Standard COBRA Period, if the qualifying termination occurs following the twenty-four (24) month anniversary of your start date. 

*In order to accommodate this potential accelerated vesting, if the Company terminates your employment without Cause in the six (6) months
prior to a Change in Control, each of your outstanding Options shall have a six-month post-termination exercise period and the Options shall not terminate with respect to shares that have not vested as of your
termination date until the end of such six-month period. 
 Definitions 

For purposes of this Attachment B, “Cause” shall have the meaning set forth in the Company’s Vesting Acceleration Program
for Senior Executives (the “CIC Plan”) and “Change in Control” shall have the meaning set forth in the Plan. 

Conditions for Receipt of Severance 
 Your eligibility for
any severance payments and benefits is conditioned upon your execution of a release of claims in a form provided by the Company (the “Release”) within forty-five (45) days following your termination date and non-revocation of the Release during any applicable statutory revocation period. If you comply with these conditions, the applicable lump-sum cash severance payment will be
paid on the sixtieth (60th) day following your termination date, subject to compliance with Section 409A of the Code as set forth below. 
 No
Duplication of Benefits 
 This Attachment B contains our entire agreement about your eligibility for severance and change in
control benefits. Except as provided in this letter, you will not be entitled to severance or change in control benefits. 
 Section 409A 

All amounts paid under this letter, including this Attachment B, shall be paid less all applicable state and federal tax withholdings (if
any) and any other withholdings required by any applicable jurisdiction or authorized by you. Notwithstanding any other provision of this letter whatsoever, the Company, in its sole discretion, shall have the

  
 221 Main St. Suite
1000 | San Francisco, CA 94105 | toll free (877) 720-2040 | www.docusign.com 

  

	
	 /s/ Michael Sheridan

 

 
 right to provide for the application and effects of Section 409A of the Code (relating to deferred compensation
arrangements) and any related administrative guidance issued by the Internal Revenue Service. The Company shall have the authority to delay the payment of any amounts under this Agreement to the extent it deems necessary or appropriate to comply
with Section 409A(a)(2)(B)(i) of the Code (relating to payments made to certain “specified employees” of publicly-traded companies); in such event, any such amount to which you would otherwise be entitled during the six (6) month
period immediately following your termination of employment with the Company will be paid in a lump sum on the date six (6) months and one (1) day following the date of your termination of employment with the Company (or the next business
day if such date is not a business day), provided that you have complied with the requirements for such payment. You shall be treated as having a termination of employment under this Agreement only if such termination meets the requirements of a
“separation from service” as that term is defined in Section 409A(a)(2)(A)(i) of the Internal Revenue Code of 1986, as amended (the “Code”) and Treas. Regs. Section 1.409A-1(h),
and as amplified by any other official guidance. This letter agreement is intended to comply with the provisions of Code Section 409A; provided, however, that the Company makes no representation that the amounts payable under this letter will
comply with Code Section 409A and makes no undertaking to prevent Code Section 409A from applying to amounts payable under this letter or to mitigate its effects on any deferrals or payments made under this letter. 

  
 221 Main St. Suite
1000 | San Francisco, CA 94105 | toll free (877) 720-2040 | www.docusign.com 

  

	
	 /s/ Michael SheridanEX-10.10.5

 Exhibit 10.10.5 
  

 
 October 5, 2017 

Kirsten Wolberg 
 Re: Offer of Employment 

Dear Kirsten: 
 I am pleased to offer you a position with
DocuSign, Inc. (the “Company”) as Chief Technology and Operations Officer, based in our San Francisco office, reporting to me, commencing on November 1, 2017. 

You will receive a bi-weekly salary of $12,307.69 ($320,000.00 annualized) less applicable taxes and deductions, which
will be paid in accordance with the Company’s normal payroll procedures. In addition, you will be eligible for a target variable compensation equal to 40% of your salary, based on the terms and conditions of the FY18 Executive Incentive Plan.

 The Company will also provide a one-time signing bonus of $100,000.00, less applicable taxes and deductions. This
signing bonus will be paid within 1-month following your start date. If you elect to resign from the Company for any reason within the first 12-months of your
employment, you agree to immediately repay a pro-rata portion of this signing bonus based on the percent of time you were an employee within the first 12-months of your
start date. 
 Subject to approval of the Board of Directors of the Company, or a committee appointed by the Board, you will be eligible to receive the
following equity awards: an award of restricted stock units (“RSUs”) representing the right to acquire 200,000 shares of the Company’s Common Stock.Such RSUs will be subject to the terms and conditions of (a) the Company’s
equity incentive program in effect at the time of grant (the “Plan”) and (b) a RSU Agreement, in the form approved by the Board or a committee of the Board. The RSUs will be subject to service-based requirements and a liquidity event
requirement as set forth in the RSU Agreement. For a general summary of the vesting terms, please see Attachment A hereto. 
 Our current intention
based on applicable SEC rules, is that you will be a Named Executive Officer if, and when, DocuSign becomes a publicly traded company. It is understood and agreed that your position, compensation, responsibilities and any future designation may
change over time. 
 As a Company employee, you will also be eligible to receive certain employee benefits including PTO, healthcare, dental coverage, and a
401(k) plan. You should note that the Company may modify salaries and benefits from time to time as it deems necessary. You should be aware that your employment with the Company is for no specified period and constitutes at-will employment. As a result, you are free to resign at any time, for any reason or for no reason. Similarly, the Company is free to conclude its employment relationship with you at any time, with or without
cause, and with or without notice. The Company reserves the right to conduct background investigations and/or reference checks on all of its potential employees. Your job offer, therefore, is contingent upon a clearance of such a background
investigation and/or reference check, if any. 

 

 
  

 For purposes of federal immigration law, you will be required to provide to the Company documentary evidence
of your identity and eligibility for employment in the United States. Such documentation must be provided to us within three (3) business days of your date of hire, or our employment relationship with you may be terminated. You agree that,
during the term of your employment with the Company, you will not engage in any other employment, occupation, consulting or other business activity directly related to the business in which the Company is now involved or becomes involved during the
term of your employment, nor will you engage in any other activities that conflict with your obligations to the Company. 
 Change In Control.
Subject to approval of the Board of Directors of the Company, or a committee appointed by the Board, you will also be eligible to participate in DocuSign’s Executive Change in Control Plan (the “CIC Plan”) attached as Attachment
B hereto. 
 Section 409A. All amounts paid under this letter, including the Change in Control Benefits
provided in Attachment B, shall be paid less all applicable state and federal tax withholdings (if any) and any other withholdings required by any applicable jurisdiction or authorized by you. Notwithstanding any other provision of this letter
whatsoever, the Company, in its sole discretion, shall have the right to provide for the application and effects of Section 409A of the Code (relating to deferred compensation arrangements) and any related administrative guidance issued by the
Internal Revenue Service. The Company shall have the authority to delay the payment of any amounts under this Agreement to the extent it deems necessary or appropriate to comply with Section 409A(a)(2)(B)(i) of the Code (relating to payments
made to certain “specified employees” of publicly-traded companies); in such event, any such amount to which you would otherwise be entitled during the six (6) month period immediately following your termination of employment with the
Company will be paid in a lump sum on the date six (6) months and one (1) day following the date of your termination of employment with the Company (or the next business day if such date is not a business day), provided that you have
complied with the requirements for such payment. You shall be treated as having a termination of employment under this Agreement only if such termination meets the requirements of a “separation from service” as that term is defined in
Section 409A(a)(2)(A)(i) of the Internal Revenue Code of 1986, as amended (the “Code”) and Treas. Regs. Section 1.409A-1(h), and as amplified by any other official guidance. This letter
agreement is intended to comply with the provisions of Code Section 409A; provided, however, that the Company makes no representation that the amounts payable under this letter will comply with Code Section 409A and makes no undertaking to
prevent Code Section 409A from applying to amounts payable under this letter or to mitigate its effects on any deferrals or payments made under this letter. 

  

 

 
  

 As a Company employee, you will be expected to abide by company rules and regulations. You will be
specifically required to sign an acknowledgment that you have read and understand the company rules of conduct which are included in the employee handbook which you will receive on your first day of employment. You will be expected to sign and
comply with an Employment Confidential Information, Invention Assignment and Arbitration Agreement which requires, among other provisions, the assignment of patent rights to any invention made during your employment at the Company and non-disclosure of proprietary information. The Agreement also provides that in the event of any dispute or claim relating to or arising out of our working relationship, you and the Company agree that all such
disputes shall be resolved by binding arbitration. 
 To indicate your acceptance of the Company’s offer, please sign and date this letter in the space
provided below by October 10, 2017. This letter, along with the agreements and plans incorporated by reference herein, set forth the terms of your employment with the Company and supersede any prior representations or agreements, whether
written or oral. This letter may not be modified or amended except by a written agreement, signed by an officer of the Company and by you. 
 We look
forward to working with you at DocuSign, Inc. 
 Sincerely, 
  

			
	DocuSign Inc.	 	
		
	 /s/ Daniel Springer
	 	October 5, 2017
	Dan Springer	 	Date
		
	ACCEPTED AND AGREED:	 	
		
	October 6, 2017	 	
		
	Date	 	
		
	 Kirsten Wolberg
	 	
	Name	 	
		
	 /s/ Kirsten Wolberg
	 	
	Signature	 	

  

 

 
  

 Attachment A 

Equity Vesting Terms: Generally—RSUs 
 As
provided in more detail in the RSU Agreement, your RSUs will become “Vested RSUs” subject to the satisfaction of the following two conditions: (1) the service-based requirement and (2) the occurrence of the Liquidity Event
Requirement (defined below) within six-and-one-half years after the grant date of the RSUs (the “Expiration Date”).
Generally, 25% of the total number RSUs awarded will have the service-based requirement satisfied on the 12-month anniversary of the vesting commencement date, and thereafter 1/16 th of the total number of RSUs awarded will have the service-based requirement satisfied in a series of 12 successive equal quarterly installments following the first anniversary of the vesting
commencement date until the service- based requirement is fully satisfied on the fourth anniversary of the vesting commencement date, subject to your continued employment or service with the Company on each such date. 

The “Liquidity Event Requirement” will be satisfied on the first to occur of: (a) a Change in Control (as defined in the Plan), and
(b) the effective date of a registration statement of the Company filed under the Securities Act of 1933, as amended, for the sale of the Company’s Common Stock (i.e., an IPO) (each a “Liquidity Event”). Upon the occurrence of a
Liquidity Event during your employment, you will vest in and the Company will issue to you the number of shares of Common Stock that would have otherwise vested under the service-based vesting schedule at the settlement date provided in the RSU
Agreement. In the case of an IPO, the balance of the RSUs shall continue to vest thereafter in accordance with the service-based vesting schedule and Vested RSUs will settle at the settlement dates provided in the RSU Agreement. If your employment
with the Company terminates before a Liquidity Event has occurred, you will be issued shares of Common Stock for any Vested RSUs for which the service-based vesting requirement was satisfied prior to your departure on the settlement date provided in
the RSU Agreement, subject to the occurrence of the Liquidity Event prior to the Expiration Date. In all cases, the RSUs will be subject to the terms and conditions of the Plan and the applicable RSU Agreement. 

  

 

 
  

 Attachment B 

DOCUSIGN, INC. 

EXECUTIVE CHANGE IN CONTROL PLAN 

This Executive Change in Control Plan (the “Agreement”) by and between Kirsten Wolberg
(“Executive”) and DocuSign, Inc., a Delaware corporation (the “Company”) is effective on the Executive’s start date as an employee of the Company. 

RECITALS 
 A. The
Company’s Board of Directors (the “Board”) believes it is in the best interests of the Company and its stockholders to hire 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 

/s/ Kirsten Wolberg 

  
 1. 

 

 
  

 
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 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. For purposes of clarity, if any restricted stock unit award that Executive holds contains a condition requiring the occurrence of a liquidity event (such as an initial public offering or a change in
control) as a condition to settlement, this accelerated vesting provision will not result in a waiver of such liquidity event condition, but will apply to any separate service-based vesting requirement contained in the award. 

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) The payments and benefits provided in Section 2; and 

(b) 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. In order to accommodate this potential accelerated vesting, if Executive experiences a Qualifying Termination within 90 days 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 6 months and one day after Executive’s termination date. 

/s/ Kirsten Wolberg 

  
 2. 

 

 
  

 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. 
  

	 	5.	Limitations and Conditions on Termination Benefits 

 (a) 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. 

(b) 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. 

(c) 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). 
 (d)
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.  
 /s/ Kirsten
Wolberg 

  
 3. 

 

 
  

 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. 

(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. 
 /s/ Kirsten Wolberg 

  
 4. 

 

 
  

 (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] 

/s/ Kirsten Wolberg 

  
 5. 

 

 
  

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

	
	DOCUSIGN, INC.
	
	 /s/ Reggie Davis

	    
	Date: October 6, 2017
	    
	KIRSTEN WOLBERG
	
	 /s/ Kirsten Wolberg

	    
	Date: October 6, 2017

  
 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 90 days prior to and ending on the 24-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 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” 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. 

“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 

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. 
 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. 
 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. 
 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).

 Section 280G 
 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 

  
 A-3 

 

 
  

 
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, 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. 

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. 
 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 

  
 A-4 

 

 
  

 
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. 
 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. 

  
 A-5

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