0001261333FALSE00012613332023-03-072023-03-07

UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
WASHINGTON, D.C. 20549
______________________________________
FORM 8-K
______________________________________

CURRENT REPORT

Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934

Date of Report (Date of earliest event reported): March 7, 2023
Commission File Number: 001-38465
______________________________________
DOCUSIGN, INC.
(Exact name of registrant as specified in its charter)
______________________________________
Delaware91-2183967
(State or Other Jurisdiction of Incorporation)(I.R.S. Employer Identification Number)
221 Main St.Suite 1550San FranciscoCalifornia94105
(Address of Principal Executive Offices)(Zip Code)

(415) 489-4940
(Registrant's Telephone Number, Including Area Code)

Check the appropriate box below if the Form 8-K filing is intended to simultaneously satisfy the filing obligation of the registrant under any of the following provisions (see General Instructions A.2. below):
¨Written communications pursuant to Rule 425 under the Securities Act (17 CFR 230.425)
¨Soliciting material pursuant to Rule 14a-12 under the Exchange Act (17 CFR 240.14a-12)
¨Pre-commencement communications pursuant to Rule 14d-2(b) under the Exchange Act (17 CFR 240.14d-2(b))
¨Pre-commencement communications pursuant to Rule 13e-4(c) under the Exchange Act (17 CFR 240.13e-4(c))

Securities registered pursuant to Section 12(b) of the Act:
Title of each classTrading SymbolName of each exchange on which registered
Common Stock, par value $0.0001 per shareDOCUThe Nasdaq Global Select Market
Indicate by check mark whether the registrant is an emerging growth company as defined in Rule 405 of the Securities Act of 1933 (§230.405 of this chapter) or Rule 12b-2 of the Securities Exchange Act of 1934 (§240.12b-2 of this chapter).

Emerging growth company ¨

If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act. ¨




Item 5.02     Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers.

(b)    Transition and Separation of Cynthia Gaylor, Chief Financial Officer

On March 8, 2023, Cynthia Gaylor, the Company’s Chief Financial Officer and principal accounting and financial officer, notified the Company of her intention to resign. Ms. Gaylor’s planned departure is not a result of any disagreement regarding the Company’s financial statements or disclosures. The effective date of Ms. Gaylor’s resignation will be June 15, 2023, or such earlier date as determined by the Company or Ms. Gaylor (the “Separation Date”). Ms. Gaylor will continue to provide services to the Company in her current capacities to provide for the orderly transition of her duties through the Separation Date (the “Transition Period”). If mutually agreed, the Company may retain Ms. Gaylor for additional transition services after June 15, 2023.

On March 9, 2023, the Company entered into a transition services and separation agreement with Ms. Gaylor (the “Transition Agreement”), which provides for, among other things, the severance and vesting benefits contemplated in the Executive Severance and Change in Control Agreement, dated as of March 12, 2021, between the Company and Ms. Gaylor (the “Gaylor Severance Agreement”), as amended by that certain severance and acceleration enhancement letter with the Company, dated as of June 21, 2022, between the Company and Ms. Gaylor (the “First Amendment Letter”), as further amended by the Expanded Severance Letter as described and defined below (together with the First Amendment Letter, the “Amended Letters”). The Gaylor Severance Agreement was filed as Exhibit 10.29 to the Company’s Annual Report on Form 10-K, as filed with the Securities and Exchange Commission (the “SEC”) on March 31, 2021, and is incorporated by reference herein. The First Amendment Letter was filed as Exhibit 10.2 to the Company’s Current Report on Form 8-K as filed with the SEC on June 22, 2022, and is incorporated by reference herein. The Form of the Expanded Severance Letter is filed herewith as Exhibit 10.3, and is incorporated by reference herein.

The Transition Agreement provides for the following benefits in consideration of her continued services during the Transition Period: (i) payment of Ms. Gaylor’s current base salary during the Transition Period, at the rate of $500,000 per year (the “Transition Salary”); (ii) continuation of health benefits; (iii) a restricted stock unit award, valued at $3.0 million as of the date of grant, with 100% of the shares underlying such award to vest on June 15, 2023 (the “Retention Grant”); (iv) a cash bonus of $1.0 million to become earned on June 15, 2023 (the “Retention Bonus”); and (v) continued vesting of Ms. Gaylor’s outstanding equity awards during the Transition Period, pursuant to the Transition Agreement, which includes a general release of claims in favor of the Company.

The Transition Agreement also provides that, following the termination of the Transition Period, and in exchange for Ms. Gaylor’s second general release of claims in favor of the Company, the Company will provide Ms. Gaylor the following benefits, in satisfaction of the Gaylor Severance Agreement and the Amendment Letters (collectively, the “Severance Benefits”): (i) a payment of $500,000 as cash severance, which amount represents 12 months of Ms. Gaylor’s base salary at the time of her resignation; (ii) a payment of $500,000 as bonus severance, which represents 100% of Ms. Gaylor’s target annual bonus amount for fiscal 2024; (iii) an additional bonus payment of up to approximately $150,000, which represents Ms. Gaylor’s target bonus for the performance period of February 1st through July 31st under the Company’s incentive plan for fiscal 2024, prorated for Ms. Gaylor’s days of service during that period (the “Prorated Bonus”); (iv) up to 12 months of COBRA coverage; and (v) vesting acceleration of Ms. Gaylor’s time-based equity awards as if she had remained employed through June 15, 2024.

The Transition Agreement further provides that, in the event that Ms. Gaylor is terminated without “Cause” or resigns for “Good Reason” (as such terms are defined in the Transition Agreement) on or prior to June 15, 2023, in addition to the Severance Benefits, the Company shall provide Ms. Gaylor with the following benefits subject to Ms. Gaylor’s execution of a second general release of claims in favor of the Company: (i) payment of the remainder of the Transition Salary, payment of the Prorated Bonus and payment of the Retention Bonus, in each case as if Ms. Gaylor had remained employed through June 15, 2023; (ii) acceleration of vesting of Ms. Gaylor’s time-based equity awards as if she had remained employed through June 15, 2024; and (iii) full acceleration of vesting of the Retention Grant.

As required by the Gaylor PSUs (as defined below), Ms. Gaylor also remains eligible to vest in a portion of her outstanding performance-based restricted stock units (the “Gaylor PSUs”), to the extent that the Company achieves the applicable performance goals at the end of the applicable performance period, with the portion of shares achieved prorated based on the length of her employment, as though she remained employed through June 15, 2023, during the performance period. The Company’s Forms of PSU Agreement (the “PSU Agreements”), pursuant to which the Gaylor PSUs were granted, were filed as Exhibit 10.1 to the Company’s Quarterly Report on Form 10-Q, as filed with the SEC on September 6, 2019 and Exhibit 10.5 to the Company’s Quarterly Report on Form 10-Q, as filed with the SEC on June 9, 2022, and are each incorporated by reference herein.




Additionally, as agreed in the Gaylor Severance Agreement and further reflected in the Transition Agreement, in the event that the Company is subject to a “Change in Control” (as such term is defined in the Gaylor Severance Agreement) on or prior to September 15, 2023, the Company shall provide Ms. Gaylor with the following benefits subject to Ms. Gaylor executing a general release of claims in favor of the Company: (i) 100% acceleration of vesting of Ms. Gaylor’s remaining unvested time-based equity awards and (ii) the Gaylor PSUs shall vest in accordance with the PSU Agreements, as though she remained employed through June 15, 2023.

The foregoing description of the Transition Agreement is not complete and is qualified in its entirety by reference to the full text of the Transition Agreement, which is filed as Exhibit 10.1 hereto.


(c)     Robert Chatwani, President and General Manager, Growth

On March 7, 2023, the board of directors (the “Board”) of the Company designated Robert Chatwani, the Company’s President and General Manager, Growth, as an “officer” within the meaning of Section 16 of, and Rule 16a-1(f) of the rules promulgated under, the Securities Exchange Act of 1934, as amended (the "Exchange Act"), effective immediately.

Mr. Chatwani, age 47, has served as our President and General Manager, Growth since February 22, 2023. From March 2017 to February 2023, he served as Chief Marketing Officer at Atlassian, Inc., a SaaS company. Prior to Atlassian, he served as Chief Revenue & Marketing Officer for social e-commerce platform Spring. He also previously served in various roles of increasing responsibility at eBay Inc., including most recently as Chief Marketing Officer of North America. Mr. Chatwani holds a B.S. in marketing from DePaul University and an MBA from UC Berkeley Haas School of Business.

Mr. Chatwani does not have any family relationships with any of the Company’s directors or executive officers and, since the beginning of the Company’s last fiscal year, there have been no transactions between the Company and Mr. Chatwani or any member of his immediate family that would require disclosure pursuant to Item 404(a) of Regulation S-K of the Securities Act of 1933, as amended (the "Securities Act"), except for the arrangements described in this Current Report on Form 8-K.

Pursuant to his offer letter (the “Chatwani Offer Letter”), Mr. Chatwani will (i) receive an annual base salary of $510,000; (ii) be eligible to receive a cash bonus of up to 100% of his annual base salary, subject to the achievement of certain performance criteria; (iii) receive a one-time signing bonus of $1,000,000, subject to his continued employment or service with the Company on the one-year anniversary of his start date; (iv) be eligible to receive an initial award of restricted stock units with a target value of $20,000,000 (the “Chatwani New Hire RSUs”), and which shall vest over four years, subject to his continued employment or service with the Company on each vesting date; and (v) be eligible to receive an additional award of restricted stock units with a target value of $5,000,000 (the “Chatwani Additional RSUs”), which shall vest in equal quarterly installments over two years, subject to his continued employment or service with the Company on such date. The foregoing description of the Chatwani Offer Letter is not complete and is qualified in its entirety by reference to the full text of the Chatwani Offer Letter, which is filed as Exhibit 10.2 hereto.

Additionally, the Company has entered into an executive severance and change in control agreement (the “Chatwani Severance Agreement”) with Mr. Chatwani, substantially in the form of executive severance and change in control agreements entered into with the Company’s other executive officers.

If Mr. Chatwani experiences a Qualifying Termination (as defined in the Chatwani Severance Agreement), subject to certain conditions, including Mr. Chatwani delivering a release of all employment related obligations of and claims and causes of action against the Company, and depending on whether the Qualifying Termination occurs during a Control Period (as defined in the Chatwani Severance Agreement), the Company shall provide Mr. Chatwani with certain severance benefits, including: (i) severance pay consisting of Mr. Chatwani’s salary and up to 50% of Mr. Chatwani’s target annual bonus, (ii) payment of Mr. Chatwani’s COBRA premiums of up to six months, and (iii) partial vesting acceleration of outstanding non-performance equity compensation awards.

The foregoing description of the Chatwani Severance Agreement is not complete and is qualified in its entirety by reference to the full text of the Chatwani Severance Agreement, which is filed as Exhibit 10.3 hereto.

The Company has entered into its standard form of Indemnification Agreement with Mr. Chatwani. The form of the indemnification agreement was previously filed by the Company as Exhibit 10.1 on Form 8-K filed with the SEC on December 3, 2020 and incorporated by reference herein.





(e)     Enhanced Severance Benefits

Previously, the Company entered into amendments (each, a "Severance Agreement Amendment") to the existing Executive Severance and Change in Control Agreements with each of Cynthia Gaylor, the Company’s Chief Financial Officer; Stephen Shute, the Company’s President, Worldwide Field Operations; Inhi Cho Suh, the Company’s President of Product and Technology; and James Shaughnessy, the Company’s Chief Legal Officer (the "Covered Officers"), pursuant to which the Company will provide certain enhanced benefits (the "Enhanced Severance Benefits") to each of the Covered Officers in the event of their termination without “Cause” (as defined in their existing Executive Severance and Change in Control Agreements).

The Enhanced Severance Benefits for Ms. Gaylor, Mr. Shaughnessy and Mr. Shute are described in the Company’s Form 8-K filed with the SEC on June 22, 2022, and are qualified in their entirety by reference to the full text of the applicable Severance Agreement Amendment, which were filed as Exhibits 10.2, 10.3, and 10.4 thereto, respectively. The Enhanced Severance Benefits for Ms. Suh are described in the Company’s Form 8-K filed with the SEC on September 8, 2022, and are qualified in its entirety by reference to the full text of the applicable Severance Agreement Amendment, which was filed as Exhibit 10.3.

On March 7, 2023, the Board approved amendments to the Severance Agreement Amendments with each of the Covered Officers (each, an "Expanded Severance Letter") to extend the period of time during which the Company will provide the Enhanced Severance Benefits to December 31, 2023 (instead of June 21, 2023). All other terms and conditions of the existing Executive Severance and Change in Control Agreements and Severance Agreement Amendments remain unchanged.

The Board also approved amendments to Mr. Chatwani’s Severance Agreement (the “Chatwani Severance Agreement Amendment”) to provide substantially the same enhanced benefits in the event of his termination without “Cause” (as defined in the Chatwani Severance Agreement) until December 31, 2023, such that he would receive (i) 12 months of base salary severance, (ii) a payment equal to 100% of his target bonus, (iii) 12 months of COBRA coverage and (iv) 12 months of vesting acceleration under the time-based restricted stock unit awards granted under the Chatwani Offer Letter. All other terms and conditions of the Chatwani’s Severance Agreement remain unchanged.

The foregoing descriptions of the Expanded Severance Letters are not complete and are qualified in their entirety by reference to the full text of the form of Expanded Severance Letter, which is filed as Exhibit 10.4 hereto.


Item 9.01     Financial Statements and Exhibits.

(d) Exhibits:
Exhibit No.Description
10.1
10.2
10.3
10.4
104Cover Page Interactive Data File (embedded within the Inline XBRL document)




SIGNATURES

Pursuant to the requirements of the Securities Exchange Act of 1934, the registrant has duly caused this report to be signed on its behalf by the undersigned thereunto duly authorized.

Date: March 10, 2023
DOCUSIGN, INC.
By:/s/ James P. Shaughnessy
James P. Shaughnessy
Chief Legal Officer


EXHIBIT 10.1
TRANSITION SERVICES & SEPARATION AGREEMENT
This Transition Services & Separation Agreement (“Agreement”) is entered into by and between Cynthia Gaylor (“Executive” or “You”) and DocuSign, Inc., a Delaware corporation (“DocuSign” or the “Company”), each individually referred to as a “Party” and collectively referred to as the “Parties”). This Agreement will become effective on the date that it is signed by both Parties (the “Agreement Date”).
RECITALS
WHEREAS, Executive is currently the Chief Financial Officer of the Company;
WHEREAS, Executive is a party to that certain (a) offer letter with the Company dated August 28, 2020 (the “Offer Letter”), (b) Amended and Restated Executive Severance and Change in Control Agreement with the Company effective as of March 31, 2021 (the “Severance and CIC Agreement”), (c) severance and acceleration enhancement letter with the Company dated June 21, 2022 (the “First Amendment Letter”) and (d) severance and acceleration enhancement letter with the Company entered into concurrently with this Agreement (the “Second Amendment Letter” and, together with the Severance and CIC Agreement and the First Amendment Letter, the “Severance and CIC Documentation”), which provide for certain benefits in the event of a qualifying termination;
WHEREAS, Executive and the Company wish to provide for the orderly transition of Executive’s responsibilities throughout the Transition Period (as defined below);
WHEREAS, the Company is willing to extend to Executive, and Executive is willing to accept, certain benefits in exchange for a release of claims, covenant not to sue and certain other undertakings, all on the terms and subject to the conditions set forth herein;
NOW, THEREFORE, in consideration of the promises and covenants set forth in this Agreement, and for good and valuable consideration, the sufficiency of which is hereby acknowledged by both Parties, the Parties agree as follows:
1.Continued Employment; Transition Services; Separation Date. Beginning on the Agreement Date and through and including June 15, 2023 (the “Transition Period”), Executive agrees to provide the following transition services (the “Transition Services”): (1) continue to serve as the Company’s Chief Financial Officer and (2) provide reasonable transition services to the Company, or such other reasonable services as the Company may request, including, but not limited to, the transitioning of Executive’s responsibilities in good faith and assistance in the hiring of a new chief financial officer of the Company and the execution of the Company’s financial documents required to be filed with the Securities Exchange Commission consistent with her role as Chief Financial Officer and subject to customary standards. Executive’s employment with the Company will terminate on the day immediately following the final day of the Transition Period, or such earlier date determined by the Company (the “Separation Date”).
2.Consideration for Transition Services. In consideration for the Transition Services, Executive executing this Agreement and the undertakings described herein, including the release of claims set forth in Section 7 and Section 10 of this Agreement (together, the “Release”), DocuSign shall provide the following benefits:
A.Cash Compensation. DocuSign will continue to pay Executive 100% of Executive’s current base salary during the Transition Period according to the Company’s standard bi-monthly payroll calendar.
B.Benefits. As a full-time employee, Executive will remain eligible for health and welfare benefits during the Transition Period. Following the Separation Date, Executive will be eligible for
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health continuation benefits under COBRA; provided that it is Executive’s responsibility to timely enroll in COBRA continuation and to timely pay COBRA premium(s) should Executive elect such coverage.
C.Retention RSUs. Promptly following the date of this agreement (as applicable, the “Grant Date”), the Company will grant Executive time-vesting restricted stock units under the Company’s 2018 Equity Incentive Plan for a number of shares to be determined by dividing $3,000,000 by the average closing market price of the Company’s common stock over the sixty (60) consecutive trading days ending on the Grant Date, rounded down to the nearest whole share (the “Retention RSUs”). The Retention RSUs shall vest in full on the final day of the Transition Period, subject to Executive’s Continuous Service (as defined below) on such vesting date. The Retention RSUs will be subject to the Company’s standard form of award agreement (as issued to reflect the Retention RSUs, the “Retention RSU Agreement”). Other than the Retention RSUs, Executive will not be entitled to receive any new equity awards during the Transition Period.
D.Cash Retention Award. Subject to Executive’s Continuous Service through the final day of the Transition Period, the Company will pay Executive $1,000,000 (the “Cash Retention Award”) within 10 business days following the Separation Date.
E.Continued Equity Vesting. Executive currently holds the following outstanding equity awards: (a) restricted stock units granted on July 25, 2022, June 9, 2022, April 10, 2022, June 10, 2021 and October 10, 2020 (collectively, the “RSUs”) governed by award agreements (the “RSU Award Agreements”) and (b) performance restricted stock units granted on June 10, 2021 and June 10, 2022 (collectively, the “PSUs”) governed by award agreements (the “PSU Award Agreements”). Executive’s service during the Transition Period will constitute “Continuous Service” for purposes of Executive’s Retention RSUs, Cash Retention Award, RSUs and PSUs. Executive will continue to vest in the RSUs and PSUs during the Transition Period according to the existing vesting schedules applicable to such awards as of the date of this Agreement.
3.Separation Consideration. Upon Executive’s Qualifying Transitional Termination (defined below), subject to Executive’s execution and non-revocation of the general release and waiver of claims set forth on Exhibit A (the “Second Release”) by the Second Release Deadline (as defined in the Second Release), and Executive’s continued compliance with the terms of this Agreement, Executive will be entitled to the severance and benefits pursuant to the Severance and CIC Documentation as follows, in all cases less applicable payroll deductions and tax withholdings (except the COBRA Benefit):
A.Cash Severance. DocuSign will pay Executive the gross amount of the following:
(i)Salary. $500,000 (the “Cash Severance”), which represents twelve (12) months of Executive’s base salary.
(ii)Target Bonus. $500,000 (the “Bonus Severance”), which represents 100% of Executive’s target annual bonus for the current performance year.
(iii)Prorated Bonus. An amount equal to Executive’s target bonus for the performance period of February 1st through July 31st (the “First Period”) under the FY24 Company Incentive Plan, prorated for Executive’s days of service during the First Period as if Executive had remained employed through June 15, 2023 (the “Prorated Bonus Severance”).
DocuSign will pay the Cash Severance, the Bonus Severance and the Prorated Bonus Severance to Executive in a lump sum, within 10 business days following the Second Release Effective Date (as defined in the Second Release).


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B.COBRA. For purposes of this Agreement, “COBRA” means the Consolidated Omnibus Budget Reconciliation Act of 1985, as amended. If Executive timely elects continued coverage under COBRA, DocuSign 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 Separation Date under the Company’s group health plan (the “COBRA Benefit”), until the earliest of (a) twelve (12) months following the Separation Date; or (b) the date Executive ceases to be eligible for COBRA continuation coverage for any reason. Notwithstanding the foregoing, if DocuSign determines in its sole discretion that it cannot provide the foregoing COBRA Benefit without potentially incurring financial costs or violating applicable law (including, without limitation, Section 2716 of the Public Health Service Act), DocuSign shall in lieu thereof provide Executive a taxable cash payment in an amount equal to the monthly COBRA premium that the Company would be required to pay to continue Executive’s group health coverage in effect on the Separation Date (which amount shall be based on the premium for the first month of COBRA coverage), which payments will be paid in monthly installments on the same schedule and over the same time period that the COBRA Benefit would otherwise have been paid on behalf of Executive regardless of whether Executive elects COBRA continuation coverage and shall end on the last day of the twelfth (12th) calendar month following the Separation Date. Executive shall have no right to an additional gross‑up payment to account for the fact that such COBRA premium amounts are paid on an after‑tax basis.
C.RSU Acceleration. On the Second Release Effective Date, Executive’s RSUs will vest as to that number of shares subject thereto that would have been vested had Executive remained in Continuous Service (as defined in the RSU Award Agreements) through the date twelve (12) months following June 15, 2023, provided that in the event that the Company is subject to a Change in Control (as defined in the Severance and CIC Agreement) that closes on or before Executive’s Qualifying Transitional Termination, then the RSUs shall accelerate and vest in full. The number of shares subject to Executive’s RSUs and the number of shares eligible to accelerate and vest pursuant to the preceding sentence for each outstanding RSU have been communicated to Executive. The shares that vest pursuant to this paragraph shall be issued and delivered to Executive promptly, and in any event no later than thirty (30) business days, following the Second Release Effective Date.
D.Retention RSU Acceleration. On the Second Release Effective Date, Executive’s Retention RSUs will accelerate and vest in full. The shares that vest pursuant to this paragraph shall be issued and delivered to Executive promptly, and in any event no later than thirty (30) business days, following the Second Release Effective Date.
E.PSU Vesting. Executive’s PSUs shall vest according to the applicable PSU Award Agreements such that Executive will be entitled to receive the number of shares that would have vested under the PSUs assuming Executive had remained employed and been subject to a Qualifying Termination (as defined in the PSU Award Agreements) on June 15, 2023in accordance with the applicable PSU Award Agreement. In the event that the Company is subject to a Change in Control (as defined in the Severance and CIC Agreement) that closes on or before Executive’s Qualifying Transitional Termination, then Executive’s PSUs shall vest according to the applicable PSU Award Agreements. The number of shares subject to Executive’s PSUs, the maximum number of shares issuable under each PSU and Executive’s pro rata portion of each applicable Performance Period have been communicated to Executive.
F.Change in Control Following Qualifying Transitional Termination and On or Prior to September 15, 2023. Notwithstanding anything to the contrary in Section 3.A through Section 3.E above, in the event that the Company is subject to a Change in Control (as defined in the Severance and CIC Agreement) that closes following Executive’s Qualifying Transitional Termination and on or prior to September 15, 2023, then DocuSign shall provide Executive the following benefits, subject to Executive’s continued compliance with the terms of this Agreement:
(i)RSU Vesting. Any remaining unvested time-based RSUs shall accelerate and vest, and shall be issued and delivered to Executive promptly (and in any event no later than ten (10) business days) following the Second Release Effective Date.
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(ii)PSU Vesting. Executive’s PSUs shall vest in accordance with the applicable PSU Award Agreements, assuming Executive had remained employed and been subject to a Qualifying Termination (as defined in the PSU Award Agreements) on June 15, 2023.
G.Change in Control After September 15, 2023. Notwithstanding anything to the contrary in Sections 3.A through 3.F above, in the event that the Company is subject to a Change in Control (as defined in the Severance and CIC Agreement) that closes after September 15, 2023 and before the expiration of the Performance Period of one or more PSUs (as applicable, PSUs with an unexpired Performance Period, the “Ongoing PSUs”), such Ongoing PSUs shall vest in accordance with the applicable PSU Award Agreements, assuming Executive had remained employed and been subject to a Qualifying Termination (as defined in the PSU Award Agreements) on June 15, 2023.
In order to accommodate potential vesting acceleration pursuant to Sections 3.C through 3.G:
(i)Executive’s outstanding and unvested time-based RSUs shall remain outstanding until December 31, 2024, on which date any shares subject to the RSUs that do not accelerate and vest pursuant to Section 3.C or Section 3.F above shall be cancelled for no consideration; and
(ii)Executive’s outstanding and unvested PSUs shall remain outstanding until the applicable Determination Date (as defined in the PSU Award Agreements), or if earlier, immediately prior to a Change in Control, in accordance with the terms of the applicable PSU Award Agreements, on which date any shares subject to the PSUs that do not vest pursuant to Section 3.E, Section 3.F or Section 3.G above shall be cancelled for no consideration.
H.If Executive’s Qualifying Transitional Termination occurs prior to the end of the Transition Period, then Executive, in addition to the amounts set forth above in this Section 3, will be entitled to (i) a lump sum payment of all unpaid base salary compensation to which the Executive would otherwise be entitled under Section 2.A of this Agreement from the Qualifying Transitional Termination through the end of the Transition Period assuming Executive had remained employed through June 15, 2023 and (ii) full acceleration and payment of the Cash Retention Award.
For purposes of this Agreement:
Qualifying Transitional Termination” means termination of Executive’s employment upon completion of the Transition Period or, if earlier, due to (a) termination by the Company other than for Cause (as defined below, provided Executive (together with counsel of her choosing) has had an opportunity to be heard by the Board of Directors of the Company with respect to any alleged action or conduct constituting Cause and a majority of the Board of Directors of the Company has determined that a termination for Cause is warranted) or (b) Executive’s resignation for Good Reason (as defined in the Severance and CIC Agreement).
Cause” means 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;
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iv.Executive’s commission of any unlawful act 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;
vii.Executive materially (A) obstructing or impeding; (B) endeavoring to influence, obstruct or impede, or (C) failing to materially cooperate with, any material 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”; or
viii.a material breach by Executive of any written Company policy as in effect as of the date of this Agreement or the Company’s code of conduct that has been made available to Executive prior to such breach;
provided, however, that the action or conduct described in the clauses above (excluding (iii)) will constitute “Cause” only if such action or conduct continues after the Company has provided Executive with written notice thereof and thirty (30) days to cure the same if such action or conduct is curable.
The employment, severance and vesting benefits outlined above are not otherwise owed to Executive, and are provided solely as consideration for the Release and the Second Release, as applicable, and the promises and covenants made by Executive herein. Executive acknowledges that, without limiting Section 11, DocuSign does not owe Executive, or anyone on Executive’s behalf, nor shall Executive become eligible for, any other compensation or benefits from DocuSign, other than the foregoing.
4.At-Will Employment. Subject to Section 3 above, you will remain an at-will employee of the Company during the Transition Period, such that you or the Company may terminate your employment relationship at any time, for any reason, with or without notice.
5.Tax Responsibility. Executive acknowledges and agrees that DocuSign has not made any representations to Executive regarding the tax consequences of any amounts received pursuant to this Agreement. The Parties agree that in the event any taxing authority determines that any settlement monies tendered as part of this Agreement are taxable: (a) Executive shall be solely responsible for the payment of all such taxes and penalties assessed against Executive; and (b) DocuSign has no duty to defend Executive against any such tax claim, penalty or assessment.
6.Non-Admission of Liability. Executive acknowledges and agrees in good faith that this Agreement is the result of a compromise and shall not be considered an admission of liability or responsibility by DocuSign.







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7.General Release and Waiver of Claims. In consideration of the covenants, payments and other benefits set forth herein, Executive unconditionally, irrevocably and absolutely releases and discharges DocuSign and all of its current, former, and future parent corporations, subsidiary corporations, affiliate corporations, and its and their directors, officers, agents, and employees, and each of their successors and assigns (hereinafter referred to collectively as the “Released Parties”) from any and all known and unknown losses, liabilities, claims, demands, causes of action or suits of any type, whether in law or in equity, related directly or indirectly, or in any way connected with any transaction, affairs, or occurrences between them (collectively, the “Released Claims”), including, without limitation, Executive’s employment with DocuSign, Executive’s application for employment with DocuSign and any associated background check process, any rights or benefits that would otherwise apply under the Severance and CIC Documentation, the Offer Letter or otherwise, and/or Executive’s termination from said employment, in each case through the date hereof.
The Released Claims specifically include, without limitation, any and all contract or tort claims, claims for wrongful termination, retaliation, employment discrimination, emotional distress, fraud, misrepresentation, defamation, invasion of privacy, interference with prospective economic advantage, breach of contract, misrepresentation, promissory estoppel or reliance, exemption misclassification, failure to pay wages due or other monies owed, including, without limitation, severance, overtime compensation, accrued and unused vacation; claims for penalties, interest, attorneys’ fees and costs, including but not limited to penalties recoverable under the Private Attorneys General Act; and claims arising under Title VII of the Civil Rights Act of 1964, the Americans with Disabilities Act, the Equal Pay Act, the Fair Labor Standards Act, the Family and Medical Leave Act,; the Older Workers’ Benefit Protection Act of 1990, as amended, the California Family Rights Act, the California Fair Employment and Housing Act, the Occupational Safety and Health Act, the California Labor Code, including but not limited to the Private Attorneys General Act, any applicable California Industrial Wage Orders, all as amended, and any other local, state or federal law, rule, or regulation relating to or affecting Executive’s employment by DocuSign.
Executive and the Company do not intend to release claims that Executive may not release as a matter of law, including but not limited to claims for indemnity under California Labor Code Section 2802, under the indemnification agreement between Executive and the Company, indemnification under any organizational document of the Company, directors’ and officers’ insurance coverage, any worker’s compensation claims that Executive may possess or claim that cannot be released as a matter of law, although Executive represents that Executive she is not currently aware of any such claim, or any claims for enforcement of this Agreement. To the fullest extent permitted by law, any dispute regarding the scope of this general release shall be determined by an arbitrator under the procedures set forth in the arbitration clause contained in the At-Will Employment, Confidential Information, Invention Assignment, and Arbitration Agreement. The release contained herein shall not be construed to waive any right to apply for unemployment insurance benefits.
8.Covenant Not to Sue. To the fullest extent permitted by law, at no time subsequent to the execution of this Agreement will Executive pursue, or cause or knowingly permit the prosecution of, in any state, federal or foreign court, or before any local, state, federal or foreign administrative agency, or any other tribunal, of any charge, claim or action of any kind, nature and character whatsoever, known or unknown, which Executive may now have, have ever had, or may in the future have against the Released Parties, which is based in whole or in part on any Released Claim. Nothing in this section shall prohibit or impair Executive or the Company from complying with all applicable laws, nor shall this Agreement be construed to obligate either Party to commit (or aid or abet in the commission of) any unlawful act.






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9.Protected Rights. You understand that nothing in this Agreement, including the General Release and Waiver of Claims, Covenant Not to Sue, and Non-disparagement sections contained herein, limits, impedes or restricts your ability to file a charge or complaint with the Equal Employment Opportunity Commission, the National Labor Relations Board (the “NLRB”), the Occupational Safety and Health Administration, the Securities and Exchange Commission or any other federal, state or local government agency or commission (“Government Agencies”). You further understand that this Agreement does not limit your ability to communicate with any Government Agencies or otherwise participate and/or assist in any investigation or proceeding that may be conducted by any Government Agency, including providing documents (including this Agreement) or other information, without notice to the Company. This Agreement does not limit your right to receive an award for information provided to any Government Agencies.
10.Unknown Claims. Executive understands and agrees that this Agreement extends to all claims of every nature, known or unknown, suspected or unsuspected, past or present, and that any and all rights Executive may have under Section 1542 of the California Civil Code or any analogous state or federal law or regulation are hereby expressly waived. Section 1542 provides:
“A GENERAL RELEASE DOES NOT EXTEND TO CLAIMS THAT THE CREDITOR OR RELEASING PARTY DOES NOT KNOW OR SUSPECT TO EXIST IN HIS OR HER FAVOR AT THE TIME OF EXECUTING THE RELEASE AND THAT, IF KNOWN BY HIM OR HER, WOULD HAVE MATERIALLY AFFECTED HIS OR HER SETTLEMENT WITH THE DEBTOR OR RELEASED PARTY.”
Executive certifies that Executive has read all of this Agreement, including the release provisions contained herein and the provision of Section 1542 quoted above, and Executive fully understands all of the same.
11.Representation Regarding No Pending Claims. Executive represents Executive has not filed any lawsuit, claim, or complaint against DocuSign in any state or federal court, or with any administrative agency or tribunal.
12.Non-disparagement. Subject to the Protected Rights section above, and otherwise to the fullest extent permitted by applicable law, you agree that you will not, directly or indirectly, disparage or make negative remarks regarding Releasees or their products, services, agents, representatives, directors, officers, shareholders, attorneys, employees, vendors, affiliates, successors or assigns, or any person acting by, through, under or in concert with any of them, with any written or oral statement, including, but not limited to, any statement posted on social media (including online company review sites) or otherwise on the Internet, whether or not made anonymously or with attribution. In turn, the Company agrees to instruct its current executive officers and the current members of its Board of Directors not to, directly or indirectly, disparage or make negative remarks regarding Executive. Nothing in this section shall prohibit you or the Company’s executive officers or members of the Board of Directors from providing truthful information in response to a subpoena or other legal process. Further, nothing in this Agreement prevents you from discussing or disclosing information about unlawful acts in the workplace, such as harassment or discrimination or any other conduct that you have reason to believe is unlawful.
13.Return of DocuSign Property. Executive hereby warrants to DocuSign that, no later than the Separation Date, Executive will return to DocuSign all property of DocuSign of any type whatsoever that has been in Executive’s possession or control. Executive may retain her Company-issued laptop; provided, however, that all Company data and/or other proprietary and/or confidential information on these devices is permanently deleted/wiped by a Company IT professional no later than five (5) business days following the Separation Date.


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14.At-Will Employment, Confidential Information, Invention Assignment, and Arbitration Agreement. Executive hereby acknowledges that Executive remains subject to Executive’s obligations under the At-Will Employment, Confidential Information, Invention Assignment, and Arbitration Agreement previously executed by the Executive 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. Executive further confirms that Executive will deliver to the Company, no later than the Separation Date, all documents and data of any nature containing or pertaining to such proprietary information and that Executive will not take any such documents or data or any reproduction thereof. For the avoidance of doubt, Executive is not subject to non-competition or non-solicitation covenants, other than as provided under Executive’s At-Will Employment, Confidential Information, Invention Assignment, and Arbitration Agreement.
15.Balances Owed. Executive acknowledges and represents that as of the date Executive signs this agreement, Executive will have been paid all wages, commissions, compensation, benefits, and other amounts and has been provided all leaves of absence and/or other accommodations that DocuSign has ever owed to Executive prior to the date Executive signed this Agreement. Between the date Executive signs this Agreement and Executive’s Separation Date, DocuSign agrees to pay all wages and benefits owed to Executive at that time.
16.Indemnification. For the avoidance of doubt, Executive will continue to be covered by any indemnification under organizational documents and bylaws of the Company, the Indemnity Agreement, dated December 19, 2020, between Executive and the Company and any other indemnification agreement between Executive and the Company, and remain named as an insured on the director and officer liability insurance policy currently maintained by the Company, or as may be maintained by the Company from time to time and as otherwise required by applicable laws, and in any event, for no less than six (6) years following the Separation Date.
17.No Assignment or Transfer of Claims. Executive represents and warrants that Executive has not assigned or transferred to any other person or entity any rights, claims or causes of action constituting a Released Claim, and no other person or entity has any interest in any such claim, except as disclosed by the terms of this Agreement.
18.Expenses. The Company will reimburse, promptly upon presentation of invoices within thirty (30) days from the date on which the parties agree upon the final form of Transition Agreement, Executive’s expenses for legal or other advisors incurred in the review and finalization of this Agreement (and any related documents), up to an aggregate of $50,000.
19.Entire Agreement. This Agreement (together with the Second Release; the At-Will Employment, Confidential Information, Invention Assignment, and Arbitration Agreement; the Retention RSU Agreement, the RSU Award Agreements; and the PSU Award Agreements) constitute the full and entire agreement between the Parties regarding the subject matter of this Agreement, and supersede and replace the Severance and CIC Documentation in all respects.
20.Applicable Law; Severability. The validity, interpretation, and performance of this Agreement shall be construed and interpreted according to the laws of the State of California. If any provision of this Agreement, or part, is held invalid, void or voidable as against public policy or otherwise, the invalidity shall not affect other provisions, or parts, which may be given effect without the invalid provision or part. To this extent, the provisions, and parts thereof, of this Agreement are declared to be severable.
21.Successors and Assigns; Counterparts. This Agreement shall be binding upon and inure to the benefit of the Parties hereto and their respective heirs, legal representatives, successors and assigns. This Agreement may be signed in counterparts. An electronic or facsimile signature shall have the same force and effect as an original signature, and trigger the obligations under this Agreement.


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22.Taxes. All payments made under this Agreement, including settlement of RSUs and PSUs, will be subject to reduction to reflect taxes or other charges required to be withheld by law. To the extent (i) any payments to which Executive becomes entitled under this Agreement, or any agreement or plan referenced herein, in connection with Executive’s termination of employment with the Company constitute deferred compensation subject to Section 409A of the Internal Revenue Code of 1986, as amended (the “Code”) and (ii) Executive is deemed at the time of such termination of employment to be a “specified” employee under Section 409A of the Code, then such payment or payments shall not be made or commence until the earlier of (i) the expiration of the six (6)‑month period measured from the date of Executive’s “separation from service” (as such term is at the time defined in regulations under Section 409A of the Code) with the Company; or (ii) the date of Executive’s death following such separation from service; provided, however, that such deferral shall only be effected to the extent required to avoid adverse tax treatment to Executive, including (without limitation) the additional twenty percent (20%) tax for which Executive would otherwise be liable under Section 409A(a)(1)(B) of the Code in the absence of such deferral. Upon the expiration of the applicable deferral period, any payments which would have otherwise been made during that period (whether in a single sum or in installments) in the absence of this paragraph shall be paid to Executive or Executive’s beneficiary in one lump sum (without interest). Except as otherwise expressly provided herein, to the extent any expense reimbursement or the provision of any in‑kind benefit under this Agreement (or otherwise referenced herein) is determined to be subject to (and not exempt from) Section 409A of the Code, the amount of any such expenses eligible for reimbursement, or the provision of any in‑kind benefit, in one calendar year shall not affect the expenses eligible for reimbursement or in kind benefits to be provided in any other calendar year, in no event shall any expenses be reimbursed after the last day of the calendar year following the calendar year in which Executive incurred such expenses, and in no event shall any right to reimbursement or the provision of any in‑kind benefit be subject to liquidation or exchange for another benefit. To the extent that any provision of this Agreement is ambiguous as to its exemption or compliance with Section 409A, the provision will be read in such a manner so that all payments hereunder are exempt from Section 409A to the maximum permissible extent, and for any payments where such construction is not tenable, that those payments comply with Section 409A to the maximum permissible extent. To the extent any payment under this Agreement may be classified as a “short‑term deferral” within the meaning of Section 409A, such payment shall be deemed a short‑term deferral, even if it may also qualify for an exemption from Section 409A under another provision of Section 409A. Payments pursuant to this Agreement (or referenced in this Agreement), and each installment thereof, are intended to constitute separate payments for purposes of Section 1.409A‑2(b)(2) of the regulations under Section 409A. Any termination of Executive’s employment is intended to constitute a separation from service and will be determined consistent with the rules relating to a “separation from service” as such term is defined in Treasury Regulation Section 1.409A‑1.
23.Arbitration; Attorneys’ Fees. Any and all disputes or claims arising out of or related to the validity, enforceability, interpretation, performance or breach of this Agreement shall be resolved through arbitration pursuant to the At-Will Employment, Confidential Information, Invention Assignment, and Arbitration Agreement.
THE PARTIES CERTIFY THAT THEY HAVE READ THIS AGREEMENT, KNOW ITS CONTENTS, FULLY UNDERSTAND IT, AND ENTER INTO IT VOLUNTARILY AND FREE OF COERCION. NO PARTY IS BEING INFLUENCED BY ANY STATEMENT MADE BY OR ON BEHALF OF ANY OTHER PARTY TO THIS AGREEMENT, EXCEPT AS EXPRESSED HEREIN.
[Signature Page Follows]

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IN WITNESS WHEREOF, the undersigned have executed this Agreement on the dates shown below.

EXECUTIVE

SIGNED: /s/ Cynthia Gaylor                    DATE: March 9, 2023
     Cynthia Gaylor


DOCUSIGN, INC.

SIGNED: /s/ Jim Shaughnessy                    DATE: March 9, 2023
BY:     Jim Shaughnessy
TITLE:     Chief Legal Officer


[Signature Page to Transition Services Agreement]





EXHIBIT A

SECOND RELEASE

To be executed following the final day of employment

This General Release of Claims and Covenant Not to Sue (the “Second Release”) is entered into between Cynthia Gaylor (“Executive” or “You”) and DocuSign, Inc., a Delaware corporation (“DocuSign” or the “Company”), collectively referred to as the “Parties”.
WHEREAS, on March [___], 2023, Executive and the Company entered into an agreement regarding Executive’s transition and separation from service with the Company (the “Separation Agreement,” to which this Second Release is attached as Exhibit A);
WHEREAS, on [_______________], 2023, Executive’s service with the Company terminated (the “Separation Date”);
WHEREAS, Executive and the Company desire to mutually, amicably and finally resolve and compromise all issues and claims surrounding Executive’s service and separation from service with the Company;
NOW THEREFORE, in consideration for the mutual promises and undertakings of the parties as set forth below, Executive and the Company hereby enter into this Second Release.
1.Acknowledgment of Payment of Wages. By Executive’s signature below, Executive acknowledges that, on the Separation Date, the Company paid Executive for all wages, fees, salary, reimbursable expenses previously submitted by Executive. By signing below, Executive acknowledges that the Company does not owe Executive any other amounts, except as specified under the Separation Agreement. Executive agrees to promptly submit for reimbursement all final outstanding expenses, if any.
2.Consideration. In exchange for Executive’s agreement to this Second Release and Executive’s other promises in the Separation Agreement and herein, the Company agrees to provide Executive with the consideration set forth in Section 3 of the Separation Agreement. By signing below, Executive acknowledges that Executive is receiving the consideration in exchange for waiving Executive’s rights to claims referred to in this Second Release and Executive would not otherwise be entitled to the consideration.
3.Return of Company Property: Executive hereby warrants to the Company that Executive has returned to the Company all property or data of the Company of any type whatsoever that has been in Executive’s possession, custody or control.









4.General Release and Waiver of Claims. In consideration of the covenants, payments and other benefits set forth herein, Executive unconditionally, irrevocably and absolutely releases and discharges DocuSign and all of its current, former, and future parent corporations, subsidiary corporations, affiliate corporations, and its and their directors, officers, agents, and employees, and each of their successors and assigns (hereinafter referred to collectively as the “Released Parties”) from any and all known and unknown losses, liabilities, claims, demands, causes of action or suits of any type, whether in law or in equity, related directly or indirectly, or in any way connected with any transaction, affairs, or occurrences between them (collectively, the “Released Claims”), including, without limitation, Executive’s employment with DocuSign, Executive’s application for employment with DocuSign and any associated background check process, any rights or benefits that would otherwise apply under the Severance and CIC Documentation, the Offer Letter or otherwise, and/or Executive’s resignation from said employment, in each case through the date hereof.
The Released Claims specifically include, without limitation, any and all contract or tort claims, claims for wrongful termination, retaliation, employment discrimination, emotional distress, fraud, misrepresentation, defamation, invasion of privacy, interference with prospective economic advantage, breach of contract, misrepresentation, promissory estoppel or reliance, exemption misclassification, failure to pay wages due or other monies owed, including, without limitation, severance, overtime compensation, accrued and unused vacation; claims for penalties, interest, attorneys’ fees and costs, including but not limited to penalties recoverable under the Private Attorneys General Act; and claims arising under Title VII of the Civil Rights Act of 1964, the Americans with Disabilities Act, the Equal Pay Act, the Fair Labor Standards Act, the Family and Medical Leave Act, the Age Discrimination in Employment Act of 1967, as amended (“ADEA”); the Older Workers’ Benefit Protection Act of 1990, as amended, the California Family Rights Act, the California Fair Employment and Housing Act, the Occupational Safety and Health Act, the California Labor Code, including but not limited to the Private Attorneys General Act, any applicable California Industrial Wage Orders, all as amended, and any other local, state or federal law, rule, or regulation relating to or affecting Executive’s employment by DocuSign.
Executive and the Company do not intend to release claims that Executive may not release as a matter of law, including but not limited to claims for indemnity under California Labor Code Section 2802, under the indemnification agreement between Executive and the Company, indemnification under any organizational document of the Company, directors’ and officers’ insurance coverage, any worker’s compensation claims that Executive may possess or claim that cannot be released as a matter of law, although Executive represents that Executive she is not currently aware of any such claim, or any claims for enforcement of this Second Release or payments under Section 3 of the Separation Agreement. To the fullest extent permitted by law, any dispute regarding the scope of this general release shall be determined by an arbitrator under the procedures set forth in the arbitration clause contained in the At-Will Employment, Confidential Information, Invention Assignment, and Arbitration Agreement. The release contained herein shall not be construed to waive any right to apply for unemployment insurance benefits.



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5.Covenant Not to Sue. To the fullest extent permitted by law, at no time subsequent to the execution of this Second Release will Executive pursue, or cause or knowingly permit the prosecution of, in any state, federal or foreign court, or before any local, state, federal or foreign administrative agency, or any other tribunal, of any charge, claim or action of any kind, nature and character whatsoever, known or unknown, which Executive may now have, have ever had, or may in the future have against the Released Parties, which is based in whole or in part on any Released Claim. Nothing in this section shall prohibit or impair Executive or the Company from complying with all applicable laws, nor shall this Second Release be construed to obligate either Party to commit (or aid or abet in the commission of) any unlawful act.
6.Protected Rights. You understand that nothing in this Second Release or the Agreement, including the General Release and Waiver of Claims, Covenant Not to Sue, and Non-disparagement sections contained therein or herein, limits, impedes or restricts your ability to file a charge or complaint with the Equal Employment Opportunity Commission, the National Labor Relations Board (the “NLRB”), the Occupational Safety and Health Administration, the Securities and Exchange Commission or any other federal, state or local government agency or commission (“Government Agencies”). You further understand that this Second Release does not limit your ability to communicate with any Government Agencies or otherwise participate and/or assist in any investigation or proceeding that may be conducted by any Government Agency, including providing documents (including this Second Release) or other information, without notice to the Company. This Second Release does not limit your right to receive an award for information provided to any Government Agencies.
7.Unknown Claims. Executive understands and agrees that this Second Release extends to all claims of every nature, known or unknown, suspected or unsuspected, past or present, and that any and all rights Executive may have under Section 1542 of the California Civil Code or any analogous state or federal law or regulation are hereby expressly waived. Section 1542 provides:
“A GENERAL RELEASE DOES NOT EXTEND TO CLAIMS THAT THE CREDITOR OR RELEASING PARTY DOES NOT KNOW OR SUSPECT TO EXIST IN HIS OR HER FAVOR AT THE TIME OF EXECUTING THE RELEASE AND THAT, IF KNOWN BY HIM OR HER, WOULD HAVE MATERIALLY AFFECTED HIS OR HER SETTLEMENT WITH THE DEBTOR OR RELEASED PARTY.”
Executive certifies that Executive has read all of this Second Release, including the release provisions contained herein and the provision of Section 1542 quoted above, and Executive fully understands all of the same.










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8.Review of Separation Agreement; Expiration of Offer. You understand that you may take up to twenty-one (21) days to consider this Agreement (the “Consideration Period”). The offer set forth in this Second Release, if not accepted by you before the end of the Consideration Period, will automatically expire. By signing below, you affirm that you were advised to consult with an attorney prior to signing this Second Release. You also understand you may revoke this Second Release within seven (7) days of signing this document and that the separation compensation to be provided to you pursuant to Section 3 of the Separation Agreement will be provided only after the expiration of that seven (7) day revocation period. If you intend to revoke this Second Release, such timely revocation must be provided in writing and sent via hand delivery or signed via DocuSign to the attention of the Company’s Chief Legal Officer at jim.shaughnessy@docusign.com.
9.Second Release Effective Date. This Second Release is effective on the eighth (8th) day after you sign it and without revocation by you (the “Second Release Effective Date”).
10.Other Terms of Separation Agreement Incorporated Herein. All other terms of the Separation Agreement to the extent not inconsistent with the terms of this Second Release are hereby incorporated in this Second Release as though fully stated herein and apply with equal force to this Second Release.
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IN WITNESS WHEREOF, the undersigned have executed this Second Release on the dates shown below.
EXECUTIVE

SIGNED: _______________________________        DATE:________________________
     Cynthia Gaylor


DOCUSIGN, INC.

SIGNED: _______________________________        DATE: _______________________
BY:     Jim Shaughnessy
TITLE:    Chief Legal Officer



[To be executed no earlier than the final day of employment]
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EXHIBIT 10.2


DOCUSIGN

January 3, 2023

Robert Chatwani


Re: Offer of Employment
Dear Robert:
I am pleased to offer you a position with DocuSign, lnc. (the "Company") as President and General Manager, Growth, based in our San Francisco office, reporting to me, with an expected commencement date of February 20, 2023 or sooner ("Start Date"). In the event that your job requires you to be in a DocuSign office or attend a business event that requires you to be vaccinated against COVID 19 then you must be vaccinated. You will receive an initial annual salary of $510,000, less applicable taxes and deductions, which will be paid biweekly in accordance with the Company's normal payroll procedures. In addition, you will be eligible for a target bonus equal to 100% of your then-current annual salary, subject to the terms and conditions of the Company Incentive Plan ("CIP") in effect for each applicable fiscal year. The CIP document contains important information including eligibility, pro-ration for employees on a leave of absence or hired mid-year, and the measures used to track Company's achievement of targets for the plan year as established by management.

Sign-On Bonus. The Company will pay you a one-time signing bonus of $1,000,000 (the "Sign-On Bonus"), to be paid out in your first payroll following your Start Date. The Sign-On Bonus will be subject to withholding requirements and authorized deductions. The payment of the Sign-On Bonus is an advance and will not be fully earned unless you remain employed by DocuSign for one full year from your Start Date. lf you resign without Good Reason or are terminated by DocuSign for Cause before the one-year anniversary of your Start Date you agree to repay the full amount of the Sign-On Bonus Advance at the time of your departure (less 8.33% for each full month of work completed after your Start Date). In the event of a Qualifying Termination prior to the one-year anniversary of your Start Date, DocuSign will waive any right to recoup any portion of the Sign-On Bonus. As a condition of receiving the Sign-On Bonus payment, you agree and authorize the Company to deduct any unearned portion of the advance from your final wages, to the extent permitted by applicable laws. lf you fail to repay the Sign-On Bonus advance within fourteen days of your departure, interest will accrue on the amount owed at the rate of 1.5% per month. In addition to paying interest, should any dispute arise concerning your obligation to repay the Sign-On Bonus and an arbitration or other legal proceeding results, the prevailing party in any such dispute shall be entitled to recover its or his reasonable attorneys' fees and costs incurred to the extent they concern the Sign-On Bonus, its repayment, and/or your obligation to repay it.

For purposes of the foregoing paragraph, "Cause," "Good Reason" and "Qualifying Termination" have the same meanings as those terms are used in the Company's Executive Severance and Change in Control Agreement, attached hereto.

Equity Awards. Subject to approval of the Board of Directors of the Company, or a committee appointed by the Board, you shall receive the following awards of restricted stock units ("RSUs") representing the right to acquire shares of Common Stock of DocuSign, lnc.:

a new hire grant of time-vesting RSUs with a target value of $20 million (the "New Hire Grant"); and




An additional grant of time-vesting RSUs with a target value of $5 million (the "Additional Grant").

The number of RSUs you receive will generally be determined by dividing the applicable target value by the average closing stock price over a period of 1O trading days immediately prior to the Vesting Commencement Date. The Vesting Commencement Date will typically be the 10th day of the first month following your Start Date. 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"), (b) an RSU Agreement, as applicable, in the form approved by the Board or a committee of the Board, and (c) applicable law. The RSUs will be subject to service-based requirements as set forth in the RSU Agreement. For a general summary of the vesting terms, please see Attachment A hereto.

Additional Benefits. 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. Please note your Start Date is subject to change if your background check has not been completed 13 days prior to your Start Date. Should your employment begin prior to the completion of the Company's background investigation, and you subsequently fail or do not satisfy the background investigation, your employment may be terminated.

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. lf you require work authorization to lawfully work in the U.S., this must be obtained prior to your State Date and your Start Date is subject to change if proof of such authorization is not obtained by the Company by Monday of the week prior to your Start Date.

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 acknowledgement 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 At-Will Employment, Confidential lnformation, lnvention 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.

Expenses. The Company will, in accordance with applicable Company policies and guidelines, reimburse you for all reasonable and necessary expenses you incur in connection with the performance of services on behalf of the Company during your employment with the Company, on terms no less favorable than for any other U.S. based executive officer of the Company. In addition, subject to and promptly following the Start Date the Company will reimburse your fair, reasonable and documented expenses for legal or other advisors incurred in the review and finalization of this Agreement and related documentation (not to exceed $4,000). Subject to the preceding, the reimbursement for all such expenses shall be paid pursuant to the Company's policies and practices, following your submission of proper documentation for such expenses.




lndemnification. In the event the Company's Board of Directors (or a committee thereof) determines that you are an "officer" of the Company within the meaning of Section 16 of the Securities Exchange Act of 1934, as amended, then you and the Company will enter into an indemnification agreement on substantially the same terms applicable to the Company's other officers and directors.

To indicate your acceptance of the Company's offer, please sign and date this letter in the space provided be ow by January 4, 2023. This letter (including any documents referenced herein), 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, lnc.


Sincerely,
DocuSign, lnc.
/s/ Jennifer Christie
Jennifer Christie, Chief People Officer



ACCEPTED AND AGREED

/s/ Robert Chatwani

Robert Chatwani







Attachment A

RSU Vesting Terms

As provided in more detail in the RSU Agreement, your RSUs will become "Vested RSUs" subject to the satisfaction of the following service-based requirements:

New Hire Grant, $20m target value: 25% of the total number of RSUs awarded will vest on the 12-month anniversary of the Vesting Commencement Date, and thereafter 1116th of the total number of RSUs awarded will vest in a series of 12 successive equal quarterly installments following the first anniversary of the Vesting Commencement Date until the grant is fully vested on the fourth anniversary of the Vesting Commencement Date, subject to your continued employment or service with the Company on each such date.
Additional Grant, $5m target value: 12.5% of the total number of RSUs awarded will vest one quarter after the Vesting Commencement Date and each quarter thereafter until the grant is fully vested on the second anniversary of the Vesting Commencement Date, subject to your continued employment or service with the Company on each such date.

Vested RSUs will generally be delivered to you ("settled") on a quarterly basis (March, June, September and December).

The RSUs will be subject to the terms and conditions of the Plan and the applicable RSU Agreement.


EXHIBIT 10.3

DOCUSIGN


DOCUSIGN, INC.
EXECUTIVE SEVERANCE AND CHANGE IN CONTROL AGREEMENT

This Executive Severance and Change in Control Agreement (the "Agreement") by and between Robert Chatwani ("Executive") and DocuSign, Inc., a Delaware corporation (the "Company ") is effective on February 23, 2023.
RECITALS

A.The Company's Board of Directors (the "Board'') or the Compensation Committee of the Board (the "Committee") 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 Committee 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:

l.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 Outside the Change in Control Period. Upon Executive's Qualifying Termination outside a 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:

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 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 ("Company Equity Awards") (other than Performance Awards (as defined below)) 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. With respect to awards that would otherwise vest only upon satisfaction of performance criteria ("Performance Awards"), the vesting of such awards will accelerate as set forth in the terms of the applicable performance-based equity award agreement.

d.Additional Benefits During Enhanced Severance Period. Notwithstanding anything to the contrary in this Section 2, the following shall apply during the period beginning on your commencement of employment and ending on August 21, 2023 or such later date as may be approved by the Company's Board of Directors or a committee thereof (such period, the "Enhanced Severance Period''). Solely upon your termination without Cause occurring during the Enhanced Severance Period and outside of a Change in Control Period:

i.the amount of cash severance payable under Section 2(a)(i) shall be twelve (12) months of your then-current base salary;

ii.the amount of cash severance payable under Section 2(a)(ii) shall be 100% of your target annual bonus for the performance year in which such termination occurs;

iii.    the number of months of COBRA premiums payable under Section 2(b) shall be twelve (12) months;

iv.the vesting of your New Hire Grant and your Additional Grant (as referenced in your offer letter with the Company) 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 twelve (12) months following your termination date; and

v.(e) the vesting of any other Company Equity Awards (other than (x) the New Hire Grant and the Additional Grant and (y) any performance RSUs issued to you, which will accelerate as set forth in the terms of the applicable performance-based equity award agreement) 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 six (6) months following your termination date.

vi.The payments and benefits, including vesting acceleration, set forth in this Section 2(d) shall be in place of, and shall not duplicate, the payments and benefits, including vesting acceleration, provided upon your termination without Cause under Section 2(a)-(c) For the avoidance of doubt, you remain eligible for applicable payments and benefits, including vesting acceleration, upon your resignation for Good Reason under Section 2. This Section 2(d) shall automatically terminate upon the expiration of the Enhanced Severance Period, after which you shall no longer be eligible to receive the payments and benefits set forth in this Section 2(d), but will remain eligible to receive the payments and benefits set forth elsewhere in this Agreement subject to its terms and conditions.




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:

i.12 months of Executive's then-current base salary (ignoring any decrease in base salary that forms the basis for Good Reason); and

ii.No target annual bonus for the performance year in which the Qualifying Termination occurs (this means no pro rata or partial annual bonus payment will be owed).

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.

c.The vesting of each of Executive's Company Equity Awards (other than Performance Awards) will accelerate in full. The vesting of Performance Awards will accelerate as set forth in the terms of the applicable performance-based equity award agreement. 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. 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.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 ali 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.

e.Clawback/Recoupment. Ali amounts payable to Executive hereunder shall be subject to recoupment pursuant to the Company's current compensation clawback or recoupment policy, and any additional compensation clawback or recoupment policy or amendments to the current policy adopted by the Board or as required by law during the term of Executive's employment with the Company that is applicable generally to executive officers of the Company. No recovery of compensation under such a clawback or recoupment policy will be an event g1vmg rise to a right to resign for "Good Reason" or constitute a "constructive" termination without "Cause" under this Agreement.

5.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. Notwithstanding anything to the contrary herein, this Agreement supersedes any agreement (or portion thereof) concerning similar subject matter dated prior to the Agreement Date, 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 prov1s1011 or prov1s1ons 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]



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

DOCUSIGN, INC.

By: /s/ Allan Thygesen

Allan Thygesen, Chief Executive Officer

January 3, 2023


EXECUTIVE:

By: /s/ Robert Chatwani

Robert Chatwani

January 3, 2023








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 actor 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 prov1s1ons 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;

vii.Executive (A) obstructing or impeding; (B) endeavoring to influence, obstructor 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"; or

viii.    a material breach by Executive of any written Company policy or the Company's code of conduct that has been made available to Executive prior to such breach;

provided, however, that the action or conduct described in the clauses above (excluding (iii)) will constitute "Cause" only if such action or conduct continues after the Company has provided Executive with written notice thereof and thirty (30) days to cure the same if such action or conduct is curable.

"Change in Control" will have the meaning set forth in the Company's Amended and Restated 201 Equity Incentive Plan.

"Change in Control Period'' means the period beginning 90 days 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.

"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;

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 thirty (30) 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.




EXHIBIT B

SECTION 409A AND SECTION 280G MATTERS


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-l(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- l(b)(4), 1.409A-l(b)(5) and 1.409A-l(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 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 foil 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.7

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.

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)(l) 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.

EXHIBIT 10.4
DocuSign, Inc.
[__________] [___], 2023
[First Name Last Name]
Delivered via e-mail
Dear [First Name]:
Reference is made to the letter agreement by and between you DocuSign, Inc. (the “Company”) dated [_______] [__], 2022 (the “First Amendment Letter”). Defined terms used in this amendment letter (this “Second Amendment Letter”), but not defined in this Second Amendment Letter, shall have the meanings ascribed thereto in the First Amendment Letter.
On behalf of the Company’s Board of Directors (the “Board”), I am pleased to extend the Enhanced Severance Period under the First Amendment Letter to December 31, 2023 (instead of June 21, 2023).
For the avoidance of doubt, you remain eligible for the payments and benefits, including vesting acceleration, upon your termination for Good Reason under Section 2 of your Executive Severance and Change in Control Agreement (the “Severance Agreement”).
All other terms and conditions of the Severance Agreement, including but not limited to the payment and other conditions set forth in Section 4 thereof, will continue in full force and effect. Your employment status is and continues to be “at will”. The First Amendment Letter, as amended by this Second Amendment Letter, and this Second Amendment Letter shall automatically terminate on December 31, 2023, after which you shall no longer be eligible to receive the payments and benefits set forth herein and thereunder, but will remain eligible to receive the payments and benefits set forth in the Severance Agreement subject to its terms and conditions.
This Second Amendment Letter may be executed in counterparts, each of which when so executed and delivered will be deemed an original, and all of which together shall constitute one and the same instrument.
[Signature Page to Second Amendment Letter Follows]

    


Please sign this Second Amendment Letter below to indicate your acceptance of these terms and return it to me.
Sincerely,
DocuSign, Inc.
________________________________
_______________________________
Date
I have read and understand this Second Amendment Letter and hereby acknowledge, accept and agree to the terms as set forth above and further acknowledge that no other commitments were made to me as part of this Second Amendment Letter except as specifically set forth herein.
Executive
________________________________
[First Name Last Name]
_______________________________
Date

[Signature Page to Second Amendment Letter]
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