EX-4.2



 Exhibit 4.2 

THIS WARRANT AND THE UNDERLYING SECURITIES HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “ACT”), OR UNDER
THE SECURITIES LAWS OF ANY STATE. THESE SECURITIES MAY NOT BE OFFERED, SOLD OR OTHERWISE TRANSFERRED, PLEDGED OR HYPOTHECATED EXCEPT AS PERMITTED UNDER THE ACT AND APPLICABLE STATE SECURITIES LAWS IN ACCORDANCE WITH APPLICABLE REGISTRATION
REQUIREMENTS OR AN EXEMPTION THEREFROM. THE ISSUER OF THESE SECURITIES MAY REQUIRE AN OPINION OF COUNSEL REASONABLY SATISFACTORY TO THE ISSUER THAT SUCH OFFER, SALE, TRANSFER, PLEDGE OR HYPOTHECATION OTHERWISE COMPLIES WITH THE ACT AND ANY
APPLICABLE STATE SECURITIES LAWS. THIS WARRANT MUST BE SURRENDERED TO THE COMPANY OR ITS TRANSFER AGENT AS A CONDITION PRECEDENT TO THE SALE, TRANSFER, PLEDGE OR HYPOTHECATION OF ANY INTEREST IN ANY OF THE SECURITIES REPRESENTED HEREBY. 

WARRANT TO PURCHASE SHARES OF COMMON STOCK 

of 
 DOCUSIGN, INC.

 Dated as of January 23, 2011 

Void after the date specified in Section 7 

THIS CERTIFIES THAT, for value received, Kranz & Associates, LLC, or its registered assigns (the “Holder”),
is entitled, subject to the provisions and upon the terms and conditions set forth herein, to purchase from DocuSign, Inc., a Washington corporation (the “Company”), shares of the Company’s
Common Stock (the “Shares”), in the amounts, at such times and at the price per share set forth in Section 1. The term “Warrant” as used herein shall include this Warrant and any warrants
delivered in substitution or exchange therefor as provided herein. 
 The following is a statement of the rights of the Holder and the
conditions to which this Warrant is subject, and to which Holder, by acceptance of this Warrant, agrees: 
 1. Number and Price of Shares;
Exercise Period. 
 (a) Number of Shares. Subject to any previous exercise of the Warrant, the Holder shall have the right
to purchase up to 18,061 Shares, as may be adjusted pursuant hereto prior to (or in connection with) the expiration of this Warrant as provided in Section 7. 

(b) Exercise Price. The exercise price per Share shall be equal to $0.15, subject to adjustment pursuant hereto (the
“Exercise Price”). 
 (c) Exercise Period. This Warrant shall be exercisable, in whole or
in part, at the election by the Holder and prior to the expiration of this Warrant as set forth in Section 7. 
 2. Exercise of the
Warrant. 
 (a) Exercise. The purchase rights represented by this Warrant may be exercised at the election of the Holder,
in whole or in part, by: (i) the tender to the Company at its principal office (or such other office or agency as the Company may designate) of a notice of exercise in the form of Exhibit A (the “Notice of
Exercise”), duly completed and executed by or on behalf of the Holder, together with the surrender of this Warrant; and (ii) the payment to the Company of an amount equal to (x) the Exercise Price multiplied by
(y) the number of Shares being purchased, by wire transfer or certified, cashier’s or other check acceptable to the Company and payable to the order of the Company. 







 (b) Stock Certificates. The rights under this Warrant shall be deemed to
have been exercised and the Shares issuable upon such exercise shall be deemed to have been issued immediately prior to the close of business on the date this Warrant is exercised in accordance with its terms, and the person entitled to receive the
Shares issuable upon such exercise shall be treated for all purposes as the holder of record of such Shares as of the close of business on such date. As promptly as reasonably practicable on or after such date, the Company shall issue and deliver to
the person or persons entitled to receive the same a certificate or certificates for that number of shares issuable upon such exercise. In the event that the rights under this Warrant are exercised in part and have not expired, the Company shall
execute and deliver a new Warrant reflecting the number of Shares that remain subject to this Warrant. 
 (c) No Fractional Shares or
Scrip. No fractional shares or scrip representing fractional shares shall be issued upon the exercise of the rights under this Warrant. In lieu of such fractional share to which the Holder would otherwise be entitled, the Company
shall make a cash payment equal to the Exercise Price multiplied by such fraction. 
 3. Replacement of the Warrant. Subject to
the receipt of evidence reasonably satisfactory to the Company of the loss, theft, destruction or mutilation of this Warrant and, in the case of loss, theft or destruction, on delivery of an indemnity agreement reasonably satisfactory in form and
substance to the Company or, in the case of mutilation, on surrender and cancellation of this Warrant, the Company at the expense of the Holder shall execute and deliver, in lieu of this Warrant, a new warrant of like tenor and amount. 

4. Transfer of the Warrant. 

(a) Warrant Register. The Company shall maintain a register (the “Warrant Register”)
containing the name and address of the Holder or Holders. Until this Warrant is transferred on the Warrant Register in accordance herewith, the Company may treat the Holder as shown on the Warrant Register as the absolute owner of this Warrant
for all purposes, notwithstanding any notice to the contrary. Any Holder of this Warrant (or of any portion of this Warrant) may change its address as shown on the Warrant Register by written notice to the Company requesting a change. 

(b) Warrant Agent. The Company may appoint an agent for the purpose of maintaining the Warrant Register referred to in
Section 4(a), issuing the Shares or other securities then issuable upon the exercise of the rights under this Warrant, exchanging this Warrant, replacing this Warrant or conducting related activities. 

(c) Transferability of the Warrant. Subject to the provisions of this Warrant with respect to compliance with the
Securities Act of 1933, as amended (the “Securities Act”) and limitations on assignments and transfers, including without limitation compliance with the restrictions on transfer set forth in
Section 5, title to this Warrant may be transferred by endorsement (by the transferor and the transferee executing the assignment form attached as Exhibit B (the “Assignment Form”))
and delivery in the same manner as a negotiable instrument transferable by endorsement and delivery. 
 (d) Exchange of the Warrant
upon a Transfer. On surrender of this Warrant (and a properly endorsed Assignment Form) for exchange, subject to the provisions of this Warrant with respect to compliance with the Securities Act and limitations on assignments and
transfers, the Company shall issue to 

  
 2 








 
or on the order of the Holder a new warrant or warrants of like tenor, in the name of the Holder or as the Holder (on payment by the Holder of any applicable transfer taxes) may direct, for the
number of shares issuable upon exercise hereof, and the Company shall register any such transfer upon the Warrant Register. This Warrant (and the securities issuable upon exercise of the rights under this Warrant) must be surrendered to the Company
or its warrant or transfer agent, as applicable, as a condition precedent to the sale, pledge, hypothecation or other transfer of any interest in any of the securities represented hereby. 

(e) Taxes. In no event shall the Company be required to pay any tax which may be payable in respect of any transfer involved in
the issue and delivery of any certificate in a name other than that of the Holder, and the Company shall not be required to issue or deliver any such certificate unless and until the person or persons requesting the issue thereof shall have paid to
the Company the amount of such tax or shall have established to the satisfaction of the Company that such tax has been paid or is not payable. 

5. Restrictions on Transfer of the Warrant and Shares; Compliance with Securities Laws. By acceptance of this Warrant, the Holder agrees
to comply with the following: 
 (a) Restrictions on Transfers. Subject to Section 5(b), this Warrant may not be
transferred or assigned in whole or in part without the Company’s prior written consent, and any attempt by Holder to transfer or assign any rights, duties or obligations that arise under this Warrant without such permission shall be void. Any
transfer of this Warrant or the Shares (the “Securities”) must be in compliance with all applicable federal and state securities laws. The Holder agrees not to make any sale, assignment, transfer, pledge or other disposition
of all or any portion of the Securities, or any beneficial interest therein, unless and until the transferee thereof has agreed in writing for the benefit of the Company to take and hold such Securities subject to, and to be bound by, the terms and
conditions set forth in this Warrant to the same extent as if the transferee were the original Holder hereunder, and 
 (i) there is then in
effect a registration statement under the Securities Act covering such proposed disposition and such disposition is made in accordance with such registration statement, or 

(ii) (A) such Holder shall have given prior written notice to the Company of such Holder’s intention to make such disposition and
shall have furnished the Company with a detailed description of the manner and circumstances of the proposed disposition, (B) the transferee shall have confirmed to the satisfaction of the Company in writing, substantially in the form of
Exhibit A-1, that the Securities are being acquired (i) solely for the transferee’s own account and not as a nominee for any other party, (ii) for investment and (iii) not with a view
toward distribution or resale, and shall have confirmed such other matters related thereto as may be reasonably requested by the Company, and (C) if requested by the Company, such Holder shall have furnished the Company, at the Holder’s
expense, with (i) an opinion of counsel, reasonably satisfactory to the Company, to the effect that such disposition will not require registration of such Securities under the Securities Act or (ii) a “no action” letter from the
Securities and Exchange Commission to the effect that the transfer of such Securities without registration will not result in a recommendation by the staff of the Securities and Exchange Commission that action be taken with respect thereto,
whereupon such Holder shall be entitled to transfer such Securities in accordance with the terms of the notice delivered by the Holder to the Company. 

(b) Permitted Transfers. Permitted transfers include (i) a transfer not involving a change in beneficial ownership, or
(ii) transactions involving the distribution without consideration of Securities by any Holder to (x) a parent, subsidiary or other affiliate of a Holder that is a corporation, (y) any of the Holder’s partners, members or other
equity owners, or retired partners or members, or to the estate of any of 

  
 3 








 
its partners, members or other equity owners or retired partners or members, or (z) a venture capital fund that is controlled by or under common control with one or more general partners or
managing members of, or shares the same management company with, the Holder; provided, in each case, that the Holder shall give written notice to the Company of the Holder’s intention to effect such disposition and shall have furnished
the Company with a detailed description of the manner and circumstances of the proposed disposition. 
 (c) Investment Representation
Statement. Unless the rights under this Warrant are exercised pursuant to an effective registration statement under the Securities Act that includes the Shares with respect to which the Warrant was exercised, it shall be a condition
to any exercise of the rights under this Warrant that the Holder shall have confirmed to the satisfaction of the Company in writing, substantially in the form of Exhibit A-1, that the
Shares so purchased are being acquired solely for the Holder’s own account and not as a nominee for any other party, for investment and not with a view toward distribution or resale and that the Holder shall have confirmed such other matters
related thereto as may be reasonably requested by the Company. 
 (d) Securities Law Legend. The Securities shall
(unless otherwise permitted by the provisions of this Warrant) be stamped or imprinted with a legend substantially similar to the following (in addition to any legend required by state securities laws): 

THE SECURITIES REPRESENTED HEREBY HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “ACT”), OR UNDER THE
SECURITIES LAWS OF CERTAIN STATES. THESE SECURITIES MAY NOT BE OFFERED, SOLD OR OTHERWISE TRANSFERRED, PLEDGED OR HYPOTHECATED EXCEPT AS PERMITTED UNDER THE ACT AND APPLICABLE STATE SECURITIES LAWS IN ACCORDANCE WITH APPLICABLE REGISTRATION
REQUIREMENTS OR AN EXEMPTION THEREFROM. THE ISSUER OF THESE SECURITIES MAY REQUIRE AN OPINION OF COUNSEL REASONABLY SATISFACTORY TO THE ISSUER THAT SUCH OFFER, SALE OR TRANSFER, PLEDGE OR HYPOTHECATION OTHERWISE COMPLIES WITH THE ACT AND ANY
APPLICABLE STATE SECURITIES LAWS. THIS CERTIFICATE MUST BE SURRENDERED TO THE COMPANY OR ITS TRANSFER AGENT AS A CONDITION PRECEDENT TO THE SALE, TRANSFER, PLEDGE OR HYPOTHECATION OF ANY INTEREST IN ANY OF THE SECURITIES REPRESENTED HEREBY. 

(e) Market Stand-off Legend. The Shares issued upon exercise hereof shall also be
stamped or imprinted with a legend in substantially the following form: 
 THE SHARES REPRESENTED BY THIS CERTIFICATE ARE SUBJECT TO
RESTRICTIONS ON TRANSFERABILITY AND RESALE, INCLUDING A LOCK-UP PERIOD IN THE EVENT OF A PUBLIC OFFERING, AS SET FORTH IN THE WARRANT PURSUANT TO WHICH THESE SHARES WERE ISSUED, A COPY OF WHICH MAY BE OBTAINED
AT THE PRINCIPAL OFFICE OF THE COMPANY. 
 (f) Instructions Regarding Transfer Restrictions. The Holder consents to the
Company making a notation on its records and giving instructions to any transfer agent in order to implement the restrictions on transfer established in this Section 5. 

(g) Removal of Legend. The legend referring to federal and state securities laws identified in Section 5(d) stamped
on a certificate evidencing the Shares and the stock transfer instructions and record notations with respect to such securities shall be removed and the Company shall issue a 

  
 4 








 
certificate without such legend to the holder of such securities if (i) such securities are registered under the Securities Act, or (ii) such holder provides the Company with an opinion
of counsel reasonably acceptable to the Company to the effect that a sale or transfer of such securities may be made without registration or qualification. 

6. Adjustments. Subject to the expiration of this Warrant pursuant to Section 7, the number and kind of shares purchasable
hereunder and the Exercise Price therefor are subject to adjustment from time to time, as follows: 
 (a) Merger or
Reorganization. If at any time there shall be any reorganization, recapitalization, merger or consolidation (a “Reorganization”) involving the Company (other than as otherwise
provided for herein or as would cause the expiration of this Warrant under Section 7 in which shares of the Company’s stock are converted into or exchanged for securities, cash or other property, then, as a part of such Reorganization,
lawful provision shall be made so that the Holder shall thereafter be entitled to receive upon exercise of this Warrant, the kind and amount of securities, cash or other property of the successor corporation resulting from such Reorganization,
equivalent in value to that which a holder of the Shares deliverable upon exercise of this Warrant would have been entitled in such Reorganization if the right to purchase the Shares hereunder had been exercised immediately prior to such
Reorganization. In any such case, appropriate adjustment (as determined in good faith by the Board of Directors of the successor corporation) shall be made in the application of the provisions of this Warrant with respect to the rights and interests
of the Holder after such Reorganization to the end that the provisions of this Warrant shall be applicable after the event, as near as reasonably may be, in relation to any shares or other securities deliverable after that event upon the exercise of
this Warrant. 
 (b) Reclassification of Shares. If the securities issuable upon exercise of this Warrant are changed
into the same or a different number of securities of any other class or classes by reclassification, capital reorganization, conversion of all outstanding shares of the relevant class or series (other than as would cause the expiration of this
Warrant pursuant to Section 7) or otherwise (other than as otherwise provided for herein) (a “Reclassification”), then, in any such event, in lieu of the number of Shares which the Holder would otherwise have been
entitled to receive, the Holder shall have the right thereafter to exercise this Warrant for a number of shares of such other class or classes of stock that a holder of the number of securities deliverable upon exercise of this Warrant immediately
before that change would have been entitled to receive in such Reclassification, all subject to further adjustment as provided herein with respect to such other shares. 

(c) Subdivisions and Combinations. In the event that the outstanding shares of common stock are subdivided (by stock
split, by payment of a stock dividend or otherwise) into a greater number of shares of such securities, the number of Shares issuable upon exercise of the rights under this Warrant immediately prior to such subdivision shall, concurrently with the
effectiveness of such subdivision, be proportionately increased, and the Exercise Price shall be proportionately decreased, and in the event that the outstanding shares of common stock are combined (by reclassification or otherwise) into a lesser
number of shares of such securities, the number of Shares issuable upon exercise of the rights under this Warrant immediately prior to such combination shall, concurrently with the effectiveness of such combination, be proportionately decreased, and
the Exercise Price shall be proportionately increased. 
 (d) Notice of Adjustments. Upon any adjustment in accordance
with this Section 6, the Company shall give notice thereof to the Holder, which notice shall state the event giving rise to the adjustment, the Exercise Price as adjusted and the number of securities or other property purchasable upon the
exercise of the rights under this Warrant, setting forth in reasonable detail the method of calculation of 

  
 5 








 
each. The Company shall, upon the written request of any Holder, furnish or cause to be furnished to such Holder a certificate setting forth (i) such adjustments, (ii) the Exercise
Price at the time in effect and (iii) the number of securities and the amount, if any, of other property that at the time would be received upon exercise of this Warrant. 

7. Expiration of the Warrant. This Warrant shall expire and shall no longer be exercisable as of the earliest of: 

(a) 5:00 p.m., Pacific time, on October 30, 2020; 

(b) Immediately prior to the closing of (i) the acquisition of the Company by another entity by means of any transaction or series of
related transactions to which the Company is a party (including, without limitation, any stock acquisition, reorganization, merger or consolidation, but excluding any sale of stock for capital raising purposes and any transaction effected primarily
for purposes of changing the Company’s jurisdiction of incorporation) other than a transaction or series of related transactions in which the holders of the voting securities of the Company outstanding immediately prior to such transaction or
series of related transactions retain, immediately after such transaction or series of transactions, as a result of shares in the Company held by such holders prior to such transaction or series of transactions, at least a majority of the total
voting power represented by the outstanding voting securities of the Company or such other surviving or resulting entity (or if the Company or such other surviving or resulting entity is a wholly-owned subsidiary immediately following such
acquisition, its parent), or (ii) a sale, lease or other disposition of all or substantially all of the, assets of the Company and its subsidiaries taken as a whole by means of any transaction or series of related transactions, except where
such sale, lease, or other disposition is to a wholly owned subsidiary of the Company; and 
 (c) Immediately prior to the closing of an
underwritten public offering pursuant to an effective registration statement filed with the Securities and Exchange Commission under the Securities Act of 1933, as amended (the “Act”), covering the offering and sale of the Company’s
common stock. 
 8. No Rights as a Stockholder. Nothing contained herein shall entitle the Holder to any rights as a stockholder of
the Company or to be deemed the holder of any securities that may at any time be issuable on the exercise of the rights hereunder for any purpose nor shall anything contained herein be construed to confer upon the Holder, as such, any right to vote
for the election of directors or upon any matter submitted to stockholders at any meeting thereof, or to give or withhold consent to any corporate action (whether upon any recapitalization, issuance of stock, reclassification of stock, change of par
value or change of stock to no par value, consolidation, merger, conveyance or otherwise) or to receive notice of meetings, or to receive dividends or subscription rights or any other rights of a stockholder of the Company until the rights under the
Warrant shall have been exercised and the Shares purchasable upon exercise of the rights hereunder shall have become deliverable as provided herein. 

9. Market Stand-off. The Holder of this Warrant hereby agrees, in connection with a firm
commitment underwritten public offering by Company of shares of its Common Stock pursuant to a registration statement under the Securities Act of 1933, as amended (an “IPO”), and upon request of Company or the underwriters managing such
IPO, not to sell, make any short sale of, loan, grant any option for the purchase of, or otherwise dispose of any securities of Company, however or whenever acquired (other than those included in the registration) without the prior written consent
of Company or such underwriters, as the case may be, for such period of time (not to exceed 180 days (and for such additional period, not to exceed 18 days, after the expiration of the 180-day period, as the
underwriters shall request in order to facilitate compliance with FINRA Rule 2711)) from the effective date of such registration as may be 

  
 6 








 
requested by Company or such managing underwriters and to execute an agreement reflecting the foregoing as may be requested by the underwriters at the time of the IPO. Holder agrees that Company
may instruct its transfer agent to place stop-transfer notations in its records to enforce the provisions of this Section 9. 
 10.
Representations and Warranties of the Holder. By acceptance of this Warrant, the Holder represents and warrants to the Company as follows: 

(a) No Registration. The Holder understands that the Securities have not been, and will not be, registered under the
Securities Act by reason of a specific exemption from the registration provisions of the Securities Act, the availability of which depends upon, among other things, the bona fide nature of the investment intent and the accuracy of the
Holder’s representations as expressed herein or otherwise made pursuant hereto. 
 (b) Investment Intent. The
Holder is acquiring the Securities for investment for its own account, not as a nominee or agent, and not with a view to, or for resale in connection with, any distribution thereof. The Holder has no present intention of selling, granting any
participation in, or otherwise distributing the Securities, nor does it have any contract, undertaking, agreement or arrangement for the same. 

(c) Investment Experience. The Holder has substantial experience in evaluating and investing in private placement
transactions of securities in companies similar to the Company, and has such knowledge and experience in financial or business matters so that it is capable of evaluating the merits and risks of its investment in the Company and protecting its own
interests. 
 (d) Speculative Nature of Investment. The Holder understands and acknowledges that the Company has a
limited financial and operating history and that its investment in the Company is highly speculative and involves substantial risks. The Holder can bear the economic risk of its investment and is able, without impairing its financial condition, to
hold the Securities for an indefinite period of time and to suffer a complete loss of its investment. 
 (e) Access to Data.
The Holder has had an opportunity to ask questions of officers of the Company, which questions were answered to its satisfaction. The Holder believes that it has received all the information that it considers necessary or appropriate for
deciding whether to acquire the Securities. The Holder understands that any such discussions, as well as any information issued by the Company, were intended to describe certain aspects of the Company’s business and prospects, but were not
necessarily a thorough or exhaustive description. The Holder acknowledges that any business plans prepared by the Company have been, and continue to be, subject to change and that any projections included in such business plans or otherwise are
necessarily speculative in nature, and it can be expected that some or all of the assumptions underlying the projections will not materialize or will vary significantly from actual results. 

(f) Accredited Investor. The Holder is an “accredited investor” within the meaning of Regulation D, Rule 501(a),
promulgated by the Securities and Exchange Commission and agrees to submit to the Company such further assurances of such status as may be reasonably requested by the Company. 

(g) Residency. The residency of the Holder (or, in the case of a partnership or corporation, such entity’s principal
place of business) is correctly set forth on the signature page hereto. 
 (h) Restrictions on Resales. The Holder
acknowledges that the Securities must be held indefinitely unless subsequently registered under the Securities Act or an exemption from such registration is available. The Holder is aware of the provisions of Rule 144 promulgated under the
Securities Act, which 

  
 7 








 
permit resale of shares purchased in a private placement subject to the satisfaction of certain conditions, which may include, among other things, the availability of certain current public
information about the Company; the resale occurring not less than a specified period after a party has purchased and paid for the security to be sold; the number of shares being sold during any three-month period not exceeding specified limitations;
the sale being effected through a “broker’s transaction,” a transaction directly with a “market maker” or a “riskless principal transaction” (as those terms are defined in the Securities Act or the Securities
Exchange Act of 1934, as amended, and the rules and regulations promulgated thereunder); and the filing of a Form 144 notice, if applicable. The Holder acknowledges and understands that the Company may not be satisfying the current public
information requirement of Rule 144 at the time the Holder wishes to sell the Securities and that, in such event, the Holder may be precluded from selling the Securities under Rule 144 even if the other applicable requirements of Rule 144 have been
satisfied. The Holder acknowledges that, in the event the applicable requirements of Rule 144 are not met, registration under the Securities Act or an exemption from registration will be required for any disposition of the Securities. The Holder
understands that, although Rule 144 is not exclusive, the Securities and Exchange Commission has expressed its opinion that persons proposing to sell restricted securities received in a private offering other than in a registered offering or
pursuant to Rule 144 will have a substantial burden of proof in establishing that an exemption from registration is available for such offers or sales and that such persons and the brokers who participate in the transactions do so at their own risk.

 (i) No Public Market. The Holder understands and acknowledges that no public market now exists for any of the
securities issued by the Company and that the Company has made no assurances that a public market will ever exist for the Company’s securities. 

(j) Brokers and Finders. The Holder has not engaged any brokers, finders or agents in connection with the Securities, and
the Company has not incurred nor will incur, directly or indirectly, as a result of any action taken by the Holder, any liability for brokerage or finders’ fees or agents’ commissions or any similar charges in connection with the
Securities. 
 (k) Tax Advisors. The Holder has reviewed with its own tax advisors the U.S. federal, state and local and
non-U.S. tax consequences of this investment and the transactions contemplated by this Warrant. With respect to such matters, the Holder relies solely on any such advisors and not on any statements or
representations of the Company or any of its agents, written or oral. The Holder understands that it (and not the Company) shall be responsible for its own tax liability that may arise as a result of this investment and the transactions contemplated
by this Warrant. 
 11. Miscellaneous. 

(a) Amendments. Except as expressly provided herein, neither this Warrant nor any term hereof may be amended, waived,
discharged or terminated other than by a written instrument referencing this Warrant and signed by the Company and the Holder. 
 (b)
Waivers. No waiver of any single breach or default shall be deemed a waiver of any other breach or default theretofore or thereafter occurring. 

(c) Notices. All notices and other communications required or permitted hereunder shall be in writing and shall be mailed
by registered or certified mail, postage prepaid, sent by facsimile or electronic mail (if to the Holder) or otherwise delivered by hand, messenger or courier service addressed: 

  
 8 








 (i) if to the Holder, to the Holder at the Holder’s address, facsimile number or electronic
mail address as shown in the Company’s records, as may be updated in accordance with the provisions hereof, or until any such Holder so furnishes an address, facsimile number or electronic mail address to the Company, then to and at the
address, facsimile number or electronic mail address of the last holder of this Warrant for which the Company has contact information in its records; or 

(ii) if to the Company, to the attention of the President or Chief Financial Officer of the Company at the Company’s address as shown on
the signature page hereto, or at such other address as the Company shall have furnished to the Holder. 
 Each such notice or other
communication shall for all purposes of this Warrant be treated as effective or having been given (i) if delivered by hand, messenger or courier service, when delivered, or (ii) if sent by mail, at the earlier of its receipt or 72 hours
after the same has been deposited in a regularly maintained receptacle for the deposit of the United States mail, addressed and mailed as aforesaid, or (iii) if sent by facsimile, upon confirmation of facsimile transfer or, if sent by
electronic mail, upon confirmation of delivery when directed to the relevant electronic mail address. In the event of any conflict between the Company’s books and records and this Warrant or any notice delivered hereunder, the Company’s
books and records will control absent fraud or error. 
 (d) Governing Law. This Warrant and all actions arising out of or in
connection with this Warrant shall be governed by and construed in accordance with the laws of the State of Washington, without regard to the conflicts of law provisions of the State of Washington, or of any other state. 

(e) Jurisdiction and Venue. Each of the Holder and the Company irrevocably consents to the exclusive jurisdiction and venue of
any court within King County, State of Washington, in connection with any matter based upon or arising out of this Warrant or the matters contemplated herein, and agrees that process may be served upon them in any manner authorized by the laws of
the State of Washington for such persons. 
 (f) Titles and Subtitles. The titles and subtitles used in this Warrant are used
for convenience only and are not to be considered in construing or interpreting this Warrant. All references in this Warrant to sections, paragraphs and exhibits shall, unless otherwise provided, refer to sections and paragraphs hereof and exhibits
attached hereto. 
 (g) Severability. If any provision of this Warrant becomes or is declared by a court of competent
jurisdiction to be illegal, unenforceable or void, portions of such provision, or such provision in its entirety, to the extent necessary, shall be severed from this Warrant, and such illegal, unenforceable or void provision shall be replaced with a
valid and enforceable provision that will achieve, to the extent possible, the same economic, business and other purposes of the illegal, unenforceable or void provision. The balance of this Warrant shall be enforceable in accordance with its terms.

 (h) Waiver of Jury Trial. EACH OF THE HOLDER AND THE COMPANY WAIVES, TO THE FULLEST EXTENT PERMITTED BY LAW, ANY
AND ALL RIGHT TO TRIAL BY JURY IN ANY LEGAL PROCEEDING (WHETHER BASED ON CONTRACT, TORT OR OTHERWISE) ARISING OUT OF OR RELATED TO THIS WARRANT. 

  
 9 








 (i) Saturdays, Sundays and Holidays. If the last or appointed day for the taking of
any action or the expiration of any right required or granted herein shall be a Saturday, Sunday or U.S. federal holiday, then such action may be taken or such right may be exercised on the next succeeding day that is not a Saturday, Sunday or U.S.
federal holiday. 
 (j) Rights and Obligations Survive Exercise of the Warrant. Except as otherwise provided herein, the rights
and obligations of the Company and the Holder under this Warrant shall survive exercise of this Warrant. 
 (k) Entire
Agreement. Except as expressly set forth herein, this Warrant (including the exhibits attached hereto) constitutes the entire agreement and understanding of the Company and the Holder with respect to the subject matter hereof and supersede
all prior agreements and understandings relating to the subject matter hereof. 
 (signature page follows)


  
 10 








 The Company and the Holder sign this Warrant as of the date stated on the first page. 

 

			
	DOCUSIGN, INC.
		
	By:	 	 /s/ Steve King

	Name:	 	Steve King
	Title:	 	President and Chief Executive Officer
		
	Address:	 	 DocuSign, Inc.
 1301 2ND Avenue, Ste 2000
 Seattle, Washington 98101



  

			
	 AGREED AND ACKNOWLEDGED,
  

KRANZ & ASSOCIATES, LLC


		
	By:	 	 /s/ Deborah L. Kranz

	Name:	 	Deborah L. Kranz
		
	Address:	 	 830 Menlo Ave, Ste 105
 Menlo Park, CA
94025

	Fax number: 650-321-4666
	Email address: dkranz@kranzassoc.com

 (Signature Page to Warrant to Purchase Share of Common Stock) 







 EXHIBIT A 

NOTICE OF EXERCISE 
  

					
	TO:	  		  	DocuSign, Inc. (the “Company”)
		
	Attention:	  	President
		
	(1)	  	Exercise. The undersigned elects to purchase the following pursuant to the terms of the attached warrant:
			
		  		  	Number of
shares:                                        
                                         
                                         
                          
			
		  		  	Type of
security:                                       
                                         
                                         
                             
		
	(2)	  	Method of Exercise. The undersigned elects to exercise the attached warrant pursuant to:
			
		  		  	 ☐       A cash payment, and tenders herewith payment of
the purchase price for such shares in full, together with all applicable transfer taxes, if any.

		
	(3)	  	Stock Certificate. Please issue a certificate or certificates representing the shares in the name of:
			
		  	☐	  	The undersigned
			
		  	☐	  	Other—Name:                                   
                                         
                                         
                                       
			
		  		  	Address:                                     
                                         
                                         
                                         
    
			
		  		  	                                      
                                         
                                         
                                         
                 
			
		  		  	                                      
                                         
                                         
                                         
                 
		
	(4)	  	Unexercised Portion of the Warrant. Please issue a new warrant for the unexercised portion of the attached warrant in the name of:
			
		  	☐	  	The undersigned
			
		  	☐	  	Other—Name:                                   
                                         
                                         
                                     
			
		  		  	
    Address:                 
                                         
                                         
                                         
          

			
		  		  	
                      
                                         
                                         
                                         
                       

			
		  	☐	  	Not applicable
		
	(5)	  	Investment Intent. The undersigned represents and warrants that the aforesaid shares are being acquired for investment for its own account, not as a nominee or agent, and not with a view to, or for resale in
connection with, the distribution thereof, and that the undersigned has no present intention of selling, granting any participation in, or otherwise distributing the shares, nor does it have any contract, undertaking, agreement or arrangement for
the same, and all representations and warranties of the undersigned set forth in Section 10 of the attached warrant are true and correct as of the date hereof.


  
 A-1 









	(6)	Investment Representation Statement and Market Stand-Off Agreement. The undersigned has executed, and delivers herewith, an Investment Representation Statement and Market Stand-Off Agreement in a form substantially similar to the form attached to the warrant as Exhibit A-1. 


 
  

	
	  
 (Print name of the
warrant holder)
  

	  

	 (Signature)
  

	  

	 (Name and title of signatory, if applicable)

 

	  

	 (Date)
  

	  

	 (Fax number)
  

	  

	(Email address)



  
 A-2 








 EXHIBIT A-1 

INVESTMENT REPRESENTATION STATEMENT 

AND 
 MARKET STAND-OFF AGREEMENT 
  

			
	INVESTOR:	  	                                      
                                         
                                         
                                         
       
		
	COMPANY:	  	DOCUSIGN, INC.
		
	SECURITIES:	  	THE WARRANT ISSUED ON JANUARY 23, 2011 (THE “WARRANT”) AND THE SECURITIES ISSUED OR ISSUABLE UPON EXERCISE THEREOF
		
	DATE:	  	                                      
                                         
     

 In connection with the purchase or acquisition of the above-listed Securities, the undersigned Investor
represents and warrants to, and agrees with, the Company as follows: 
 1. No Registration. The Investor understands that the
Securities have not been, and will not be, registered under the Securities Act of 1933, as amended (the “Securities Act”), by reason of a specific exemption from the registration provisions of the
Securities Act, the availability of which depends upon, among other things, the bona fide nature of the investment intent and the accuracy of the Investor’s representations as expressed herein or otherwise made pursuant hereto.

 2. Investment Intent. The Investor is acquiring the Securities for investment for its own account, not as a nominee or agent, and
not with a view to, or for resale in connection with, any distribution thereof. The Investor has no present intention of selling, granting any participation in, or otherwise distributing the Securities, nor does it have any contract, undertaking,
agreement or arrangement for the same. 
 3. Investment Experience. The Investor has substantial experience in evaluating and
investing in private placement transactions of securities in companies similar to the Company, and has such knowledge and experience in financial or business matters so that it is capable of evaluating the merits and risks of its investment in the
Company and protecting its own interests. 
 4. Speculative Nature of Investment. The Investor understands and acknowledges that the
Company has a limited financial and operating history and that its investment in the Company is highly speculative and involves substantial risks. The Investor can bear the economic risk of its investment and is able, without impairing its financial
condition, to hold the Securities for an indefinite period of time and to suffer a complete loss of its investment. 
 5. Access to Data.
The Investor has had an opportunity to ask questions of officers of the Company, which questions were answered to its satisfaction. The Investor believes that it has received all the information that it considers necessary or appropriate for
deciding whether to acquire the Securities. The Investor understands that any such discussions, as well as any information issued by the Company, were intended to describe certain aspects of the Company’s business and prospects, but were not
necessarily a thorough or exhaustive description. The Investor acknowledges that any business plans prepared by the 

  
 A-1-1 








 
Company have been, and continue to be, subject to change and that any projections included in such business plans or otherwise are necessarily speculative in nature, and it can be expected that
some or all of the assumptions underlying the projections will not materialize or will vary significantly from actual results. 
 6.
Accredited Investor. The Investor is an “accredited investor” within the meaning of Regulation D, Rule 501(a), promulgated by the Securities and Exchange Commission and agrees to submit to the Company such further assurances of such
status as may be reasonably requested by the Company. 
 7. Residency. The residency of the Investor (or, in the case of a partnership
or corporation, such entity’s principal place of business) is correctly set forth on the signature page hereto. 
 8. Restrictions on
Resales. The Investor acknowledges that the Securities must be held indefinitely unless subsequently registered under the Securities Act or an exemption from such registration is available. The Investor is aware of the provisions of Rule 144
promulgated under the Securities Act, which permit resale of shares purchased in a private placement subject to the satisfaction of certain conditions, which may include, among other things, the availability of certain current public information
about the Company; the resale occurring not less than a specified period after a party has purchased and paid for the security to be sold; the number of shares being sold during any three-month period not exceeding specified limitations; the sale
being effected through a “broker’s transaction,” a transaction directly with a “market maker” or a “riskless principal transaction” (as those terms are defined in the Securities Act or the Securities Exchange Act
of 1934, as amended, and the rules and regulations promulgated thereunder); and the filing of a Form 144 notice, if applicable. The Investor acknowledges and understands that the Company may not be satisfying the current public information
requirement of Rule 144 at the time the Investor wishes to sell the Securities and that, in such event, the Investor may be precluded from selling the Securities under Rule 144 even if the other applicable requirements of Rule 144 have been
satisfied. The Investor understands and acknowledges that, in the event the applicable requirements of Rule 144 are not met, registration under the Securities Act or an exemption from registration will be required for any disposition of the
Securities. The Investor understands that, although Rule 144 is not exclusive, the Securities and Exchange Commission has expressed its opinion that persons proposing to sell restricted securities received in a private offering other than in a
registered offering or pursuant to Rule 144 will have a substantial burden of proof in establishing that an exemption from registration is available for those offers or sales and that those persons and the brokers who participate in the transactions
do so at their own risk. 
 9. No Public Market. The Holder understands and acknowledges that no public market now exists for any of
the securities issued by the Company and that the Company has made no assurances that a public market will ever exist for the Company’s securities. 

10. Brokers and Finders. The Investor has not engaged any brokers, finders or agents in connection with the Securities, and the Company
has not incurred nor will incur, directly or indirectly, as a result of any action taken by the Investor, any liability for brokerage or finders’ fees or agents’ commissions or any similar charges in connection with the Securities. 

11. Legal Counsel. The Investor has had the opportunity to review the Warrant, the exhibits and schedules attached thereto and the
transactions contemplated by the Warrant with its own legal counsel. The Investor is not relying on any statements or representations of the Company or its agents for legal advice with respect to this investment or the transactions contemplated by
the Warrant. 

  
 A-2 








 12. Tax Advisors. The Investor has reviewed with its own tax advisors the U.S. federal,
state and local and non-U.S. tax consequences of this investment and the transactions contemplated by the Warrant. With respect to such matters, the Investor relies solely on such advisors and not on any
statements or representations of the Company or any of its agents, written or oral. The Investor understands that it (and not the Company) shall be responsible for its own tax liability that may arise as a result of this investment or the
transactions contemplated by the Warrant. 
 13. Market Stand-off. The Investor hereby agrees,
in connection with a firm commitment underwritten public offering by Company of shares of its Common Stock pursuant to a registration statement under the Securities Act of 1933, as amended (an “IPO”), and upon request of Company or the
underwriters managing such IPO, not to sell, make any short sale of, loan, grant any option for the purchase of, or otherwise dispose of any securities of Company, however or whenever acquired (other than those included in the registration) without
the prior written consent of Company or such underwriters, as the case may be, for such period of time (not to exceed 180 days (and for such additional period, not to exceed 18 days, after the expiration of the
180-day period, as the underwriters shall request in order to facilitate compliance with FINRA Rule 2711)) from the effective date of such registration as may be requested by Company or such managing
underwriters and to execute an agreement reflecting the foregoing as may be requested by the underwriters at the time of the IPO. Investor agrees that Company may instruct its transfer agent to place stop-transfer notations in its records to enforce
the provisions of this Section 13. 
 (signature page follows) 

  
 A-3 








 The Investor is signing this Investment Representation Statement and Market Stand-Off Agreement on the date first written above. 
  

	
	 INVESTOR
  

	  

	 (Print name of the investor)

 

	  

	 (Signature)
  

	  

	 (Name and title of signatory, if applicable)

 

	  

	 (Street address)
  

	  

	(City, state and ZIP)



  
 A-4 








 EXHIBIT B 

ASSIGNMENT FORM 
  

			
	ASSIGNOR:	  	  

		
	COMPANY:	  	DOCUSIGN, INC.
		
	WARRANT:	  	THE WARRANT TO PURCHASE SHARES OF COMMON STOCK ISSUED ON JANUARY 23, 2011 (THE “WARRANT”)
		
	DATE:	  	________________________________

  

	(1)	Assignment. The undersigned registered holder of the Warrant (“Assignor”) assigns and transfers to the assignee named below
(“Assignee”) all of the rights of Assignor under the Warrant, with respect to the number of shares set forth below: 


 

			
	 Name of Assignee:
	  	  

		
	 Address of Assignee:
	  	  

		
		  	  

		
	 Number of Shares Assigned:
	  	  


 and does irrevocably constitute and appoint
             as attorney to make such transfer on the books of DocuSign, Inc., maintained for the purpose, with full power of substitution in the premises. 

 

	(2)	Obligations of Assignee. Assignee agrees to take and hold the Warrant and any shares of stock to be issued upon exercise of the rights thereunder (the “Securities”) subject to, and to be
bound by, the terms and conditions set forth in the Warrant to the same extent as if Assignee were the original holder thereof. 

  

	(3)	Investment Intent. Assignee represents and warrants that the Securities are being acquired for investment for its own account, not as a nominee or agent, and not with a view to, or for resale in connection with,
the distribution thereof, and that Assignee has no present intention of selling, granting any participation in, or otherwise distributing the shares, nor does it have any contract, undertaking, agreement or arrangement for the same, and all
representations and warranties set forth in Section 10 of the Warrant are true and correct as to Assignee as of the date hereof. 

  

	(4)	Investment Representation Statement and Market Stand-Off Agreement. Assignee has executed, and delivers herewith, an Investment Representation Statement and Market Stand-Off Agreement in a form substantially similar to the form attached to the Warrant as Exhibit A-1. 


  
 C-1 








 Assignor and Assignee are signing this Assignment Form on the date first set forth above. 

 

			
	ASSIGNOR	  	ASSIGNEE
		
	  
	  	  

	 (Print name of Assignor)
  
	  	(Print name of Assignee)
	  
	  	  

	 (Signature of Assignor)
  
	  	(Signature of Assignee)
	  
	  	  

	 (Print name of signatory, if applicable)

 
	  	(Print name of signatory, if applicable)
	  
	  	  

	(Print title of signatory, if applicable)	  	(Print title of signatory, if applicable)
		
	 Address:
  
	  	Address:
		
	  
  
	  	  

		
	  
	  	  



  
 C-2