Document:

Warrant to purchase Series C convertible preferred stock

 Exhibit 10.7 
 THIS WARRANT AND THE SHARES ISSUABLE HEREUNDER HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “ACT”), OR THE SECURITIES LAWS OF ANY STATE AND, EXCEPT AND PURSUANT TO
THE PROVISIONS OF ARTICLE 5 BELOW, MAY NOT BE OFFERED, SOLD OR OTHERWISE TRANSFERRED, PLEDGED OR HYPOTHECATED UNLESS AND UNTIL REGISTERED UNDER SAID ACT AND APPLICABLE STATE SECURITIES LAW OR, IN THE OPINION OF LEGAL COUNSEL IN FORM AND SUBSTANCE
SATISFACTORY TO THE ISSUER OF THESE SECURITIES, SUCH OFFER, SALE OR TRANSFER, PLEDGE OR HYPOTHECATION IS EXEMPT FROM REGISTRATION. 
 WARRANT TO PURCHASE STOCK 
  

			
	Company: Demandware, Inc., a Delaware corporation
	
	Number of Shares: 69,278, subject to adjustment
	
	Class of Stock: Series C Convertible Preferred Stock, $0.01 par value per share
	
	Warrant Price: $1.299106, subject to adjustment
	
	Issue Date: July 18, 2008
	
	Expiration Date: July 17,2018
		
	 Credit Facility:
	 	This Warrant is issued in connection with that certain Loan and Security Agreement of even date herewith between Silicon Valley Bank and the Company.

THIS WARRANT CERTIFIES THAT, for good and valuable consideration, SILICON VALLEY BANK (Silicon Valley Bank, together with any successor
or permitted assignee or transferee of this Warrant or of any shares issued upon exercise hereof, is referred to hereinafter as “Holder”) is entitled to purchase the number of fully paid and nonassessable shares (the “Shares”) of
the class of securities (the “Class”) of the above-named company (the “Company” ) at the above-stated Warrant Price, all as set forth above and as adjusted pursuant to Article 2 of this Warrant, subject to the provisions and upon
the terms and conditions set forth in this Warrant. 
 ARTICLE 1. EXERCISE. 

1.1 Method of Exercise. Holder may exercise this Warrant by delivering the original of this Warrant together with a
duly executed Notice of Exercise in substantially the form attached as Appendix 1 to the principal office of the Company. Unless Holder is exercising the conversion right set forth in Article 1.2, Holder shall also deliver to the Company a check,
wire transfer (to an account designated by the Company), or other form of payment acceptable to the Company for the aggregate Warrant Price for the Shares being purchased. 

1.2 Conversion Right. In lieu of exercising this Warrant as specified in Article 1.1, Holder may from time to time
convert this Warrant, in whole or in part, into a number of Shares determined by dividing (a) the aggregate fair market value of the Shares or other securities otherwise issuable upon exercise of this Warrant minus the aggregate Warrant Price
of such Shares by (b) the fair market value of one Share. The fair market value of the Shares shall be determined pursuant to Article 1.3. 

 1.3 Fair Market Value. If the Company’s common stock is traded
in a public market and the Shares are common stock, the fair market value of a Share shall be the closing price of a share of common stock reported for the business day immediately before Holder delivers this Warrant together with its Notice of
Exercise to the Company (or in the instance where the Warrant is exercised immediately prior to the effectiveness of the Company’s initial public offering (“IPO”), the “price to public” per share price specified in the final
prospectus relating to such offering). If the Company’s common stock is traded in a public market and the Shares are preferred stock, the fair market value of a Share shall be the closing price of a share of the Company’s common stock
reported for the business day immediately before Holder delivers this Warrant together with its Notice of Exercise to the Company (or, in the instance where the Warrant is exercised immediately prior to the effectiveness of the IPO, the initial
“price to public” per share price specified in the final prospectus relating to such offering), in both cases, multiplied by the number of shares of the Company’s common stock into which a Share is convertible. If the Company’s
common stock is not traded in a public market, the Board of Directors of the Company shall determine fair market value in its reasonable good faith judgment. 
 1.4 Delivery of Certificate and New Warrant. Promptly after Holder exercises or converts this Warrant and, if applicable, the Company receives payment of the aggregate Warrant Price, the Company
shall deliver to Holder certificates for the Shares acquired and, if this Warrant has not been fully exercised or converted and has not expired, a new Warrant representing the Shares not so acquired. 

1.5 Replacement of Warrants. On 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 amount to the Company or, in the case of mutilation, on surrender and cancellation of
this Warrant, the Company shall execute and deliver, in lieu of this Warrant, a new warrant of like tenor. 
 1.6
Treatment of Warrant Upon Acquisition of Company. 
 1.6.1 “Acquisition”. For the purpose
of this Warrant, “Acquisition” means any sale, license, or other disposition of all or substantially all of the assets of the Company, or any reorganization, consolidation, merger or sale of outstanding capital stock of the Company where
the holders of the Company’s securities before the transaction beneficially own less than a majority of the outstanding voting securities of the surviving entity after the transaction. 

1.6.2 Treatment of Warrant at Acquisition. 
 A) Upon the written request of the Company, Holder agrees that, in the event of an Acquisition in which the sole consideration is cash, either (a) Holder shall exercise its conversion or purchase
right under this Warrant and such exercise will be deemed effective immediately prior to the consummation of such Acquisition or (b) if Holder elects not to exercise the Warrant, this Warrant will expire upon the consummation of such
Acquisition. The Company shall provide the Holder with written notice of its request relating to the foregoing (together with such reasonable information as the Holder may request in connection with such contemplated Acquisition giving rise to such
notice), 

  
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which is to be delivered to Holder not less than ten (10) days prior to the closing of the proposed Acquisition. 
 B) Upon the written request of the Company, Holder agrees that, in the event of an Acquisition that is an “arms length” sale of all or substantially all of the Company’s assets (and only
its assets) to a third party that is not an Affiliate (as defined below) of the Company (a “True Asset Sale”), either (a) Holder shall exercise its conversion or purchase right under this Warrant and such exercise will be deemed
effective immediately prior to the consummation of such Acquisition or (b) if Holder elects not to exercise the Warrant, this Warrant will continue until the Expiration Date if the Company continues as a going concern following the closing of
any such True Asset Sale. The Company shall provide the Holder with written notice of its request relating to the foregoing (together with such reasonable information as the Holder may request in connection with such contemplated Acquisition giving
rise to such notice), which is to be delivered to Holder not less than ten (10) days prior to the closing of the proposed Acquisition. 

C) Upon the closing of any Acquisition other than those particularly described in subsections (A) and (B) above, the successor entity shall
assume the obligations of this Warrant, and this Warrant shall be exercisable for the same securities, cash, and property as would be payable for the Shares issuable upon exercise of the unexercised portion of this Warrant as if such Shares were
outstanding on the record date for the Acquisition and subsequent closing. The Warrant Price and/or number of Shares shall be adjusted accordingly. 
 As used in this Section 1.6, “Affiliate” shall mean any person or entity that owns or controls directly or indirectly ten percent (10%) or more of the stock of Company, any
person or entity that controls or is controlled by or is under common control with such persons or entities, and each of such person’s or entity’s officers, directors, joint venturers or partners, as applicable. 

D) Notwithstanding the foregoing provisions of Section 1.6.2(C), in the event of an Acquisition in which all of the following requirements are met,
this Warrant, to the extent not exercised or converted on or prior to the closing of such Acquisition, shall terminate and be of no further force or effect as of immediately following such closing: (i) the acquiror is subject to the reporting
requirements of Section 13 or Section 15(d) of the Securities Exchange Act of 1934, as amended, (ii) the class and series of shares or other security of the acquiror that would be received by Holder in connection with such Acquisition
were Holder to exercise or convert this Warrant on or prior to the closing thereof is listed for trading on a national securities exchange or approved for quotation on an automated inter-dealer quotation system, and (iii) Holder would not be
contractually restricted from publicly re-selling within three (3) months following the closing of such Acquisition, nor restricted under applicable securities laws from publicly re-selling within six (6) months following the closing of
such Acquisition, all of the acquiror shares and/or other securities that would be received by Holder in such Acquisition were Holder to exercise or convert this Warrant in full on or prior to the closing thereof. 

ARTICLE 2. ADJUSTMENTS TO THE SHARES. 

	

  
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 2.1 Stock Dividends, Splits, Etc. If the Company declares or pays a
dividend on the outstanding shares of the Class payable in common stock or other securities, then upon exercise of this Warrant, for each Share acquired, Holder shall receive, without cost to Holder, the total number and kind of securities to which
Holder would have been entitled had Holder owned the Shares of record as of the date the dividend occurred. If the Company subdivides the outstanding shares of the Class by reclassification or otherwise into a greater number of shares or takes any
other action which increase the amount of common stock into which the one share of the Class is convertible, the number of Shares purchasable hereunder shall be proportionately increased and the Warrant Price shall be proportionately decreased. If
the outstanding shares of the Class are combined or consolidated, by reclassification or otherwise, into a lesser number of shares, the Warrant Price shall be proportionately increased and the number of Shares shall be proportionately decreased.

 2.2 Reclassification, Exchange, Combinations or Substitution. Upon any reclassification, exchange,
substitution, or other event that results in a change of the number and/or class of the securities issuable upon exercise or conversion of this Warrant, Holder shall be entitled to receive, upon exercise or conversion of this Warrant, the number and
kind of securities and property that Holder would have received for the Shares if this Warrant had been exercised immediately before such reclassification, exchange, substitution, or other event. Such an event shall include, without limitation, any
automatic conversion of the outstanding or issuable securities of the Company of the same class or series as the Shares to common stock pursuant to the terms of the Company’s Certificate of Incorporation. The Company or its successor shall
promptly issue to Holder an amendment to this Warrant setting forth the number and kind of such new securities or other property issuable upon exercise or conversion of this Warrant as a result of such reclassification, exchange, substitution or
other event that results in a change of the number and/or class of securities issuable upon exercise or conversion of this Warrant. The amendment to this Warrant shall provide for adjustments which shall be as nearly equivalent as may be practicable
to the adjustments provided for in this Article 2 including, without limitation, adjustments to the Warrant Price and to the number of securities or property issuable upon exercise of the new Warrant. The provisions of this Article 2.2 shall
similarly apply to successive reclassifications, exchanges, substitutions, or other events. 
 2.3 Adjustments
for Diluting Issuances. The number of shares of common stock issuable upon conversion of the Shares shall be subject to adjustment, from time to time in the manner set forth in the Company’s Certificate of Incorporation as if the Shares
were issued and outstanding on and as of the date of any such required adjustment. The provisions set forth for the Class in the Company’s Certificate of Incorporation relating to the above in effect as of the Issue Date may not be amended,
modified or waived, without the prior written consent of Holder unless such amendment, modification or waiver affects the rights associated with the Shares in the same manner as such amendment, modification or waiver affects the rights associated
with all other shares of the Class. 
 2.4 No Impairment. The Company shall not, by amendment of its
Certificate of Incorporation or through a reorganization, transfer of assets, consolidation, merger, dissolution, issue, or sale of securities or any other voluntary action, avoid or seek to avoid the observance or performance of any of the terms to
be observed or performed under this Warrant by the Company, but shall at all times in good faith assist 

  
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in carrying out of all the provisions of this Article 2 and in taking all such action as may be necessary or appropriate to protect Holder’s rights under this Article against impairment.

 2.5 Fractional Shares. No fractional Shares shall be issuable upon exercise or conversion of the
Warrant and the number of Shares to be issued shall be rounded down to the nearest whole Share. If a fractional share interest arises upon any exercise or conversion of the Warrant, the Company shall eliminate such fractional share interest by
paying Holder the amount computed by multiplying the fractional interest by the fair market value of a full Share. 
 2.6 Certificate as to Adjustments. Upon each adjustment of the Warrant Price, Class and/or number of Shares, the Company shall promptly notify Holder in writing, and, at the Company’s expense,
promptly compute such adjustment, and furnish Holder with a certificate of its Chief Financial Officer setting forth such adjustment and the facts upon which such adjustment is based. The Company shall, upon written request, furnish Holder a
certificate setting forth the Warrant Price, Class and number of Shares in effect upon the date thereof and the series of adjustments leading to such Warrant Price, Class and number of Shares. 

ARTICLE 3. REPRESENTATIONS AND COVENANTS OF THE COMPANY. 
 3.1 Representations and Warranties. The Company represents and warrants to, and agrees with, the Holder as follows: 

(a) The initial Warrant Price referenced on the first page of this Warrant is not greater than the price per share at
which shares of the same class and series as the Shares were last issued in an arms-length transaction in which at least $500,000 of such shares were sold. 
 (b) All Shares which may be issued upon the exercise of the purchase right represented by this Warrant, and all securities, if any, issuable upon conversion of the Shares, shall, upon issuance, be duly
authorized, validly issued, fully paid and nonassessable, and free of any liens and encumbrances except for restrictions on transfer provided for herein or under applicable federal and state securities laws. 

(c) The Company’s capitalization table attached hereto as Schedule 1 is true and complete as of the Issue
Date. 
 3.2 Notice of Certain Events. If the Company proposes at any time (a) to declare any
dividend or distribution upon the outstanding shares of the same class and series as the Shares, whether in cash, property, stock, or other securities and whether or not a regular cash dividend; (b) to offer for subscription or sale pro rata to
the holders of the outstanding shares of the same class and series as the Shares any additional shares of any class or series of the Company’s stock (other than pursuant to contractual pre-emptive rights); (c) to effect any
reclassification, reorganization or recapitalization of any of its stock; or (d) to effect an Acquisition or to liquidate, dissolve or wind up; then, in connection with each such event, the Company shall give Holder: (1) at least 10 days
prior written notice of the date on which a record will be taken for such dividend, distribution, or subscription rights (and specifying the date on which the holders of shares of the same class and series as the Shares will be entitled thereto) or
for 

  
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determining rights to vote, if any, in respect of the matters referred to in (c) and (d) above; and (2) in the case of the matters referred to in (c) and (d) above at
least 10 days prior written notice of the date when the same will take place (and specifying the date on which the holders of shares of the same class and series as the Shares will be entitled to exchange their shares for the securities or other
property deliverable upon the occurrence of such event). 
 3.3 Registration Under Securities Act of 1933, as
amended. The Company agrees that the Shares or, if the Shares are convertible into common stock of the Company, such common stock, shall have certain incidental, or “Piggyback,” and S-3 registration rights pursuant to and as set forth
in the Company’s Second Amended and Restated Investor Rights Agreement, as amended by that certain Amendment No. 1 thereto of even date herewith among the Company, Silicon Valley Bank and the other parties named therein, as further amended
and in effect from time to time. 
 3.4 No Shareholder Rights. Except as provided in this Warrant, Holder
will not have any rights as a shareholder of the Company until the exercise of this Warrant. 
 3.5 Certain
Information. The Company agrees to provide Holder at any time and from time to time with such information as Holder may reasonably request for purposes of Holder’s compliance with regulatory, accounting and reporting requirements applicable
to Holder. 
 ARTICLE 4. REPRESENTATIONS, WARRANTIES AND COVENANTS OF THE HOLDER. The Holder represents and warrants to, and agrees with,
the Company as follows: 
 4.1 Purchase for Own Account. This Warrant and the securities to be acquired
upon exercise of this Warrant by Holder will be acquired for investment for Holder’s account, not as a nominee or agent, and not with a view to the public resale or distribution within the meaning of the Act. Holder also represents that it has
not been formed for the specific purpose of acquiring this Warrant or the Shares. 
 4.2 Disclosure of
Information. Holder has received or has had full access to all the information it considers necessary or appropriate to make an informed investment decision with respect to the acquisition of this Warrant and its underlying securities. Holder
further has had an opportunity to ask questions and receive answers from the Company regarding the terms and conditions of the offering of this Warrant and its underlying securities and to obtain additional information (to the extent the Company
possessed such information or could acquire it without unreasonable effort or expense) necessary to verify any information furnished to Holder or to which Holder has access. 

4.3 Investment Experience. Holder understands that the purchase of this Warrant and its underlying securities
involves substantial risk. Holder has experience as an investor in securities of companies in the development stage and acknowledges that Holder can bear the economic risk of such Holder’s investment in this Warrant and its underlying
securities and has such knowledge and experience in financial or business matters that Holder is capable of evaluating the merits and risks of its investment in this Warrant and its underlying securities and/or has a preexisting personal or business
relationship with the Company and certain of its officers, directors 

  
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or controlling persons of a nature and duration that enables Holder to be aware of the character, business acumen and financial circumstances of such persons. 

4.4 Accredited Investor Status. Holder is an “accredited investor” within the meaning of Regulation D
promulgated under the Act. 
 4.5 The Act. Holder understands that this Warrant and the Shares issuable
upon exercise or conversion hereof have not been registered under the Act in reliance upon a specific exemption therefrom, which exemption depends upon, among other things, the bona fide nature of the Holder’s investment intent as expressed
herein. Holder understands that this Warrant and the Shares issued upon any exercise or conversion hereof must be held indefinitely unless subsequently registered under the Act and qualified under applicable state securities laws, or unless
exemption from such registration and qualification are otherwise available. 
 4.6 Lock-Up Agreement. The
Holder, if requested by the Company and the managing underwriter of the Company’s IPO, agrees not to sell or otherwise transfer or dispose of any securities of the Company held by the Holder for a period specified by the managing underwriter
not to exceed 180 days following the effective date of the registration statement for such IPO; and the Holder agrees to execute a “lock-up” agreement with the Company and the managing underwriter of such IPO confirming such agreement if
requested by the Company; provided that: (i) such lock-up and agreements set forth in this Section 4.6 shall only apply to the initial public offering of common stock of the Company to be sold by or on behalf of the Company in an
underwritten offering, and (ii) all stockholders of the Company then holding at least 5% of the outstanding common stock (on an as converted basis) of the Company and all officers and directors of the Company enter into similar agreements and
are not released, in whole or part, from such lock-up obligations in connection with such IPO. 
 ARTICLE 5. MISCELLANEOUS. 

5.1 Term: This Warrant is exercisable in whole or in part at any time and from time to time on or before the
Expiration Date. 
 5.2 Legends. This Warrant and the Shares (and the securities issuable, directly or
indirectly, upon conversion of the Shares, if any) shall be imprinted with a legend in substantially the following form: 
 THIS
WARRANT AND THE SHARES ISSUABLE HEREUNDER HAVE NOT BEEN REGISTERED UNDER THE ACT, OR THE SECURITIES LAWS OF ANY STATE AND, EXCEPT AND PURSUANT TO THE PROVISIONS OF ARTICLE 5 OF THAT CERTAIN WARRANT TO PURCHASE STOCK ISSUED BY THE COMPANY TO SILICON
VALLEY BANK DATED AS OF JULY 18, 2008, MAY NOT BE OFFERED, SOLD OR OTHERWISE TRANSFERRED, PLEDGED OR HYPOTHECATED UNLESS AND UNTIL REGISTERED UNDER SAID ACT AND APPLICABLE STATE SECURITIES LAW OR, IN THE OPINION OF LEGAL COUNSEL IN FORM AND
SUBSTANCE SATISFACTORY TO THE ISSUER OF THESE SECURITIES, SUCH OFFER, SALE OR TRANSFER, PLEDGE OR 

  
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HYPOTHECATION IS EXEMPT FROM REGISTRATION. 
 5.3
Compliance with Securities Laws on Transfer. This Warrant and the Shares issuable upon exercise of this Warrant (and the securities issuable, directly or indirectly, upon conversion of the Shares, if any) may not be transferred or assigned in
whole or in part without compliance with applicable federal and state securities laws by the transferor and the transferee (including, without limitation, the delivery of investment representation letters and legal opinions reasonably satisfactory
to the Company, as reasonably requested by the Company). The Company shall not require Holder to provide an opinion of counsel if the transfer is to SVB Financial Group (Silicon Valley Bank’s parent company) or any other affiliate of Holder,
provided that any such transferee is an “accredited investor” as defined in Regulation D promulgated under the Act. 
 5.4 Transfer Procedure. After receipt by Silicon Valley Bank (“Bank”) of the executed Warrant, Bank will transfer all of this Warrant to SVB Financial Group, Holder’s parent company.
Subject to the provisions of Article 5.3 and upon providing the Company with written notice, SVB Financial Group and any subsequent Holder may transfer all or part of this Warrant or the Shares issuable upon exercise of this Warrant (or the
securities issuable directly or indirectly, upon conversion of the Shares, if any) to any transferee, provided, however, in connection with any such transfer, SVB Financial Group or any subsequent Holder will give the Company notice of the portion
of the Warrant being transferred with the name, address and taxpayer identification number of the transferee and Holder will surrender this Warrant to the Company for reissuance to the transferee(s) (and Holder if applicable). The Company may refuse
to transfer this Warrant or the Shares to any person who directly competes with the Company, unless, in either case, the stock of the Company is publicly traded. 

5.5 Notices. All notices and other communications from the Company to the Holder, or vice versa, shall be deemed
delivered and effective when given personally or mailed by first-class registered or certified mail, postage prepaid, at such address as may have been furnished to the Company or Holder, as the case may (or on the first business day after
transmission by facsimile) be, in writing by the Company or such holder from time to time. All notices to Holder shall be addressed as follows until the Company receives notice of a change of address in connection with a transfer or otherwise:

 SVB Financial Group 
 Attn: Treasury Department 
 3003 Tasman Drive, HA 200 

Santa Clara, CA 95054 
 Telephone: 408-654-7400 
 Facsimile: 408-496-2405 

Notice to the Company shall be addressed as follows until Holder receives notice of a change in address: 

Demandware, Inc. 
 Attn:
                                        

 10 Presidential Way, Floor 2 

Woburn, MA 01801 

  
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 Telephone:
                                        

 Facsimile:
                                        

 5.6 Waiver. This Warrant and any term hereof may be changed, waived, discharged or terminated only by
an instrument in writing signed by the party against which enforcement of such change, waiver, discharge or termination is sought. 
 5.7 Attorney’s Fees. In the event of any dispute between the parties concerning the terms and provisions of this Warrant, the party prevailing in such dispute shall be entitled to collect from
the other party all costs incurred in such dispute, including reasonable attorneys’ fees. 
 5.8
Automatic Conversion upon Expiration. In the event that, upon the Expiration Date, the fair market value of one Share (or other security issuable upon the exercise hereof) as determined in accordance with Section 1.3 above is greater
than the Warrant Price in effect on such date, then this Warrant shall automatically be deemed on and as of such date to be converted pursuant to Section 1.2 above as to all Shares (or such other securities) for which it shall not previously
have been exercised or converted, and the Company shall promptly deliver a certificate representing the Shares (or such other securities) issued upon such conversion to Holder. 

5.9 Counterparts. This Warrant may be executed in counterparts, all of which together shall constitute one and the
same agreement. 
 [Remainder of page left blank intentionally] 

  
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 5.10 Governing Law. This Warrant shall be governed by and construed
in accordance with the laws of the State of California, without giving effect to its principles regarding conflicts of law. 
  

			
	“COMPANY”
	
	DEMANDWARE, INC.
		
	By:	 	/s/ John Pearce
	Name:	 	John Pearce
		 	(Print)
	Title:	 	CEO
	
	“HOLDER”
	
	SILICON VALLEY BANK
		
	By:	 	/s/ Mark Gallagher
	Name:	 	Mark Gallagher
		 	(Print)
	Title:	 	SVP

  
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 APPENDIX 1  
 NOTICE OF EXERCISE 
 1. Holder elects to purchase
                         shares of the Common/Series
                 Preferred [strike one] Stock of
                                 pursuant to the terms of the attached Warrant,
and tenders payment of the purchase price of the shares in full. 
 [or] 

1. Holder elects to convert the attached Warrant into Shares/cash [strike one] in the manner specified in the Warrant. This conversion is
exercised for
                                         
    of the Shares covered by the Warrant. 
 [Strike paragraph that does not apply.] 

2. Please issue a certificate or certificates representing the Shares in the name specified below: 

 
  

Holders Name 
  

 
  

 

(Address) 
 3. By its execution below and for the benefit of the Company, Holder hereby restates each of the representations and warranties in Article 4 of the Warrant as of the date hereof. 

 

			
	HOLDER:
	
	 
		
	By:	 	 
		
	Name:	 	 
		
	Title:	 	 
		
	(Date):	 	 

  
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 SCHEDULE 1 
 Company Capitalization Table 
 See attached 

  
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 Demandware, Inc. Capitalization Table Post Series C Add-on Round 

May 31, 2008 
  

																																																													
	 	 	Series A
Preferred 	 	 	Series B
Preferred	 	 	Orig.
Series C
Preferred	 	 	Orig.
Series C
T-Y
Allocation	 	 	Series 
C
Add-on
Preferred	 	 	Series C
Total 	 	 	Total Pref
Stock O/S	 	 	%	 	 	Common
Stock -
Founder	 	 	Common
Stock
Exercised	 	 	Unvested
Restricted
Stock 	 	 	Stock
Options 	 	 	Warrants	 	 	Fully
Diluted
Stock O/S	 	 	%	 
	 Craig Dynes
	 				 				 				 				 				 				 				 				 				 	 	79,167	  	 				 				 				 	 	79,167	  	 	 	0.15	% 
	 Wayne Whitcomb (Restricted Stock Grant)
	 				 				 				 				 				 				 				 				 				 	 	287,500	  	 	 	12,500	  	 				 				 	 	300,000	  	 	 	0.58	% 
																
	 NBVP – A
	 	 	2,633,981	  	 	 	2,619,490	  	 	 	2,582,228	  	 	 	199,621	  	 	 	1,711,906	  	 	 	4,493,755	  	 	 	9,747,226	  	 	 	26.46	% 	 				 				 				 				 				 	 	9,747,226	  	 	 	18.86	% 
	 NBVP – B
	 	 	1,291,019	  	 	 	1,283,916	  	 	 	1,265,652	  	 	 	97,842	  	 	 	839,074	  	 	 	2,202,568	  	 	 	4,777,503	  	 	 	12.97	% 	 				 				 				 				 				 	 	4,777,503	  	 	 	9.24	% 
	 General Catalyst Group III
	 	 	3,787,948	  	 	 	3,767,109	  	 	 	3,713,521	  	 	 	287,076	  	 	 	2,461,906	  	 	 	6,462,503	  	 	 	14,017,560	  	 	 	38.05	% 	 				 				 				 				 				 	 	14,017,560	  	 	 	27.12	% 
	 General Catalyst Group Entrepreneurs Fund III
	 	 	137,052	  	 	 	136,297	  	 	 	134,359	  	 	 	10,387	  	 	 	89,074	  	 	 	233,820	  	 	 	507,169	  	 	 	1.38	% 	 				 				 				 				 				 	 	507,169	  	 	 	0.98	% 
	 Tom Meusel
	 	 	50,000	  	 	 	—  	  	 	 	—  	  	 	 	—  	  	 	 	—  	  	 	 	—  	  	 	 	50,000	  	 	 	0.14	% 	 				 	 	175,000	  	 				 				 				 	 	225,000	  	 	 	0.44	% 
	 Dan O’Connor
	 	 	70,000	  	 	 	—  	  	 	 	—  	  	 	 	—  	  	 	 	—  	  	 	 	—  	  	 	 	70,000	  	 	 	0.19	% 	 				 				 				 				 				 	 	70,000	  	 	 	0.14	% 
	 Stephan Schambach
	 	 	1,343,162	  	 	 	1,543,207	  	 	 	1,418,731	  	 	 	297,462	  	 	 	1,056,119	  	 	 	2,772,312	  	 	 	5,658,681	  	 	 	15.36	% 	 	 	4,800,000	  	 				 				 				 				 	 	10,458,681	  	 	 	20.23	% 
	 Ulrike Mueller
	 	 	150,000	  	 	 	—  	  	 	 	—  	  	 	 	—  	  	 	 	—  	  	 	 	—  	  	 	 	150,000	  	 	 	0.41	% 	 				 				 				 				 				 	 	150,000	  	 	 	0.29	% 
	 Udo Timpe
	 	 	50,000	  	 	 	—  	  	 	 	—  	  	 	 	—  	  	 	 	—  	  	 	 	—  	  	 	 	50,000	  	 	 	0.14	% 	 				 				 				 				 				 	 	50,000	  	 	 	0.10	% 
	 T Ventures
	 	 	—  	  	 	 	1,815,538	  	 	 	—  	  	 	 	—  	  	 	 	—  	  	 	 	—  	  	 	 	1,815,538	  	 	 	4.93	% 	 				 				 				 				 				 	 	1,815,538	  	 	 	3.51	% 
																
	 Stock Options Outstanding/ Reserved
	 				 				 				 				 				 				 				 				 				 				 				 	 	7,206,553	  	 				 	 	7,206,553	  	 	 	13.94	% 
	 Stock Options Avail. for Issuance
	 				 				 				 				 				 				 				 				 				 				 				 	 	2,159,094	  	 				 	 	2,159,094	  	 	 	4.18	% 
	 Stock Options exercised – former EEs
	 				 				 				 				 				 				 				 				 				 	 	130,186	  	 				 				 				 	 	130,186	  	 	 	0.25	% 
		 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	 TOTALS
	 	 	9,513,162	  	 	 	11,165,557	  	 	 	9,114,491	  	 	 	892,388	  	 	 	6,158,079	  	 	 	16,164,958	  	 	 	36,843,677	  	 	 	100.00	% 	 				 	 	671,853	  	 	 	12,500	  	 	 	9,365,647	  	 				 	 	51,693,677	  	 	 	100.00	% 
		 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
		 				 				 	 	1.299106	  	 	 	1.299106	  	 	 	1.299106	  	 				 				 				 				 				 				 				 				 				 			
		 				 				 	$	11,840,689.95	  	 	$	1,159,306.61	  	 	$	7,999,997.38Letter Agreement with Thomas D. Ebling

 Exhibit 10.8 
 

 
 February 11, 2010 
 Tom Ebling 
 144 Nehoiden Road 
 Waban, MA 02468 
 Dear Tom: 

On behalf of Demandware, Inc. (the “Company”). I am pleased to set forth the terms of your employment with the Company:

 1. You will be employed to serve on a full-time basis as President and Chief Executive Officer (“CEO”), effective
February 11, 2010. As CEO, you will report directly to the Board of Directors of the Company (the “Board”) and have such duties and responsibilities as are customary for such position and as are otherwise assigned to you by the Board
from time to time. 
 2. Your salary will be $22,916.67 per month ($275,000 on an annualized basis), subject to tax and other
withholdings as required by law. Such salary may be adjusted from time to time in accordance with normal business practice and in the sole discretion of the Company. 
 3. You will be eligible for an annual bonus of up to $150,000, as determined by the Board in its sole discretion. You may participate in any and all other bonus and benefit programs that the Company
establishes and makes available to its employees from time to time, provided you are eligible under (and subject to all provisions of) the plan documents governing those programs. 

4. You may be eligible for a maximum of 160 hours of “paid time off” per calendar year. The number of PTO hours for which you
are eligible shall accrue at the rate of 6.66 hours per semi-monthly pay period that you are employed during such calendar year. 
 5. Subject to the approval of the Board, the Company will grant you an equity award under the Company’s 2004 Stock Option and Grant Plan (the “Plan”) such that, following such award, you
will be the beneficial owner of 6.0% of the outstanding shares of the Company on a fully-diluted basis immediately following such grant (the “Initial Award”). We anticipate that there will be an equity financing in the near term (the
“Series E Financing”), and, upon the completion of such financing, the Company will grant to you an additional equity award under the Plan such that, following such award, when combined with the Initial Award, you will be the beneficial
owner of that percentage of the outstanding shares of the Company on a fully-diluted basis immediately following the initial closing of the Series E Financing as is equal to the percentage beneficially owned by you immediately prior to such
financing. Such awards will be made in the form of (i) incentive stock options (within the meaning of Section 422 of the Internal Revenue Code) to purchase 930,000 shares of the Company’s common stock and (ii) the remaining
portion of the award will consist of a mix of nonqualified stock options and restricted common stock (“Restricted Stock”), as agreed upon by you and the Company. The purchase price for the incentive stock 

 Tom Ebling 
 February 11, 2010 
 Page 2 
 options and nonqualified stock options (the “Options”) and the Restricted Stock will be equal the fair market value of the Company’s common stock at the time of Board approval of each
award, as applicable. The Options and any Restricted Stock will be subject to four-year vesting, commencing as of your employment start date, and will be subject to a 12-month cliff. In the event of a Change of Control (as defined below), the
vesting schedule for your options will be accelerated as follows: (a) 50% of the options or restricted shares that are not then vested will be accelerated and become vested and exercisable (or free from the Company’s repurchase option, as
applicable) upon the consummation of the Change of Control: and (b) if, during the twelve months following the Change of Control, your employment with the Company is terminated by the Company (or the acquiring company) without Cause (as defined
below), or by you for Good Reason (as defined below), then all remaining unvested options or restricted shares shall vest and become exercisable (or free from the Company’s repurchase option, as applicable) upon such termination. The Options
and the Restricted Stock shall be subject to all other terms and provisions set forth in the Plan and in such Incentive Stock Option Agreement, Nonqualified Stock Option Agreement and Restricted Stock Agreement as is acceptable to the Company.

 6. If the Company terminates your employment without Cause or you resign for Good Reason, you shall be eligible to receive an
amount equal to the remaining salary you would have received if you had been employed through the date that is six months following the termination date, less applicable taxes and withholdings, payable in accordance with the Company’s regular
payroll procedures over the remainder of the six-month period, provided that you execute and allow to become binding a release of claims prepared by the Company within 10 days following the termination of your employment. The distribution of any
severance payments shall be subject to the provisions of Exhibit A attached hereto. 
 7. For purposes of this offer
letter, “Cause” for termination shall be deemed to exist upon (a) a good faith finding by the Board of (i) your deliberate and continual failure to satisfactorily perform your assigned duties for the Company, after ten
(10) days’ written notice by certified mail of such failure to perform, specifying that the failure constitutes Cause (other than as a result of authorized vacation or sickness, illness or injury), or (ii) your dishonesty, gross
negligence or gross misconduct in connection with the business of the Company which has a substantial adverse effect on the Company; (b) your indictment or conviction, or the entry of a pleading of guilty or nolo contendere by you, to any crime
involving moral turpitude or any felony, but excluding any conviction arising as a result of your title or position with the Company and that is not based on your personal conduct; or (c) your violation of any of the terms of your
invention/non-disclosure or non-competition agreement with the Company, signed in connection with your execution of this letter. You shall be entitled to at least ten (10) days’ prior written notice of the Company’s intention to
terminate your employment for “Cause” (as defined herein) (except for conviction of a felony) specifying the grounds for such termination, and a reasonable opportunity to cure any conduct or act, if curable, alleged as grounds for such
termination, and a reasonable opportunity to present to the Board your position regarding any dispute relating to the existence of such Cause. For purposes of this offer letter, “Good Reason” shall mean, without your consent, (a) the
relocation of your principal place of employment with the Company to a place more than fifty (50) miles from your 

  
 - 2 -

 Tom Ebling 
 February 11, 2010 
 Page 3 
 initial principal place of employment with the Company (other than in a direction that reduces your daily commuting distance); (b) a reduction in the level of your (then) base salary of more than
20%; or (c) the hiring or presence of a Company Executive or employee with greater authority than you in any matters relating to the Company. 
 8. You will be required to execute an Invention and Non-Disclosure Agreement and a Non-Competition and Non-Solicitation Agreement in the forms attached as Exhibit B and Exhibit C, as a
condition of employment. 
 9. You represent that you are not bound by any employment contract, restrictive covenant or other
restriction preventing you from entering into employment with or carrying out your responsibilities for the Company, or which is in any way inconsistent with the terms of this letter. 

10. You agree to provide to the Company, within three days of your hire date, documentation of your eligibility to work in the United
States, as required by the Immigration Reform and Control Act of 1986. You may need to obtain a work visa in order to be eligible to work in the United States. If that is the case, your employment with the Company will be conditioned upon your
obtaining a work visa in a timely manner as determined by the Company. 
 11. This letter shall not be construed as an
agreement, either expressed or implied, to employ you for any stated term, and shall in no way alter the Company’s policy of employment at will, under which both you and the Company remain free to terminate the employment relationship, with or
without cause, at any time, with or without notice, subject to the terms specific above. 
 [REMAINDER OF THIS PAGE INTENTIONALLY
LEFT BLANK] 

  
 - 3 -

 Tom Ebling 
 February 11, 2010 
 Page 4 

If you agree with the employment provisions of this letter, please sign the enclosed duplicate of this letter in the space provided below
and return it to me, by February 11, 2010. If you do not accept this offer by February 12, 2010, this offer will be revoked. 
  

									
		 		 	Very Truly Yours,
					
		 		 		 	By:	 	/s/ Larry Bohn
		 		 		 	Name:	 	Larry Bohn
		 		 		 	Title:	 	Director
			
		 		 	
					
		 		 		 	By:	 	/s/ Michael Skok
		 		 		 	Name:	 	Michael Skok
		 		 		 	Title:	 	Director

  

					
	The foregoing correctly sets forth the terms of my employment by Demandware, Inc.	 		 	
			
	/s/ Tom Ebling	 	Date:	 	Feb 11, 2010
	Name: Tom Ebling	 		 	

  
 - 4 -

 Tom Ebling 
 February 11, 2010 
 Page 5 

Exhibit A 
 Payments Subject to Section 409A 
 1. Subject to this Exhibit A, payments
or benefits under Section 6 of the offer letter shall begin only upon the date of your “separation from service” (determined as set forth below) which occurs on or after the termination of your employment. The following rules shall
apply with respect to distribution of the payments and benefits, if any, to be provided to you under the offer letter, as applicable: 
 (a) It is intended that each installment of the payments and benefits provided in the offer letter shall be treated as a separate “payment” for purposes of Section 409A of the Code and the
guidance issued thereunder (“Section 409A”). Neither the Company nor you shall have the right to accelerate or defer the delivery of any such payments or benefits except to the extent specifically permitted or required by
Section 409A. 
 (b) If, as of the date of your “separation from service” from the Company, you
are not a “specified employee” (within the meaning of Section 409A), then each installment of the payments and benefits shall be made on the dates and terms set forth in Section 6 of the offer letter. 

(c) If, as of the date of your “separation from service” from the Company, you are a “specified
employee” (within the meaning of Section 409A), then: 
 (i) Each installment of
the payments and benefits due under Section 6 of the offer letter that, in accordance with the dates and terms set forth herein, will in all circumstances, regardless of when your separation from service occurs, be paid within the Short-Term
Deferral Period (as hereinafter defined) shall be treated as a short-term deferral within the meaning of Treasury Regulation Section 1.409A-1(b)(4) to the maximum extent permissible under Section 409A. For purposes of this offer letter, the
“Short-Term Deferral Period” means the period ending on the later of the 15th day of the
third month following the end of your tax year in which the separation from service occurs and the 15th day of the third month following the end of the Company’s tax year in which the separation from service occurs; and 

(ii) Each installment of the payments and benefits due under Section 6 of the offer letter that is not described in
this Exhibit A, Section 1(c)(i) and that would, absent this subsection, be paid within the six-month period following your “separation from service” from the Company shall not be paid until the date that is six months and one day after
such separation from service (or, if earlier, your death), with any such installments that are required to be delayed being accumulated during the six-month period and paid in a lump sum on the date that is six months and one day following your
separation from service and any subsequent installments, if any, being paid in accordance with the dates and terms set forth herein; provided, however, that the preceding provisions of this sentence shall not apply to any installment of payments and
benefits if and to the maximum extent that that such installment is deemed to be paid under a separation pay plan that does not provide for a deferral of compensation by reason of the application of Treasury 

  
 - 5 -

 Tom Ebling 
 February 11, 2010 
 Page 6 
 Regulation 1.409A-1(b)(9)(iii) (relating to separation pay upon an involuntary separation from service). Any installments that qualify for the exception under Treasury Regulation
Section 1.409A-1(b)(9)(iii) must be paid no later than the last day of your second taxable year following the taxable year in which the separation from service occurs. 
 2. The determination of whether and when your separation from service from the Company has occurred shall be made and in a manner consistent with, and based on the presumptions set forth in, Treasury
Regulation Section 1.409A-1(h). Solely for purposes of this Exhibit A, Section 2, “Company” shall include all persons with whom the Company would be considered a single employer under Section 414(b) and 414(c) of the Code.

 3. All reimbursements and in-kind benefits provided under the offer letter shall be made or provided in accordance with the
requirements of Section 409A to the extent that such reimbursements or in-kind benefits are subject to Section 409A. 

4. The Company makes no representation or warranty and shall have no liability to you or to any other person if any of the provisions of
the offer letter (including this Exhibit) are determined to constitute deferred compensation subject to Section 409A but that do not satisfy an exemption from, or the conditions of, that section. 

  
 - 6 -

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