Document:

Incentive Stock Option Agreement

 Exhibit 10.9 
 Incentive Stock Option Agreement 
 under the Demandware, Inc.

 2004 Stock Option and Grant Plan 
  

			
	 Name of Optionee:
	  	Thomas Ebling (the “Optionee”)
		
	 No. of Option Shares:
	  	930,232 Shares of Common Stock
		
	 Grant Date:
	  	February 11, 2010 (the “Grant Date”)
		
	 Expiration Date:
	  	February 10, 2020 (the “Expiration Date”)
		
	 Vesting Reference Date:
	  	December 31, 2009 (the “Vesting Reference Date”)
		
	 Option Exercise Price/Share:
	  	$0.43 per share (the “Option Exercise Price”)

 Pursuant to the Demandware, Inc. 2004 Stock Option and Grant Plan (the “Plan”), Demandware,
Inc., a Delaware corporation (together with all successors thereto, the “Company”), hereby grants to the Optionee, who is an officer, employee, director, consultant or other key person of the Company or any of its Subsidiaries, an option
(the “Stock Option”) to purchase on or prior to the Expiration Date, or such earlier date as is specified herein, all or any part of the number of shares of Common Stock, par value $0.001 per share (“Common Stock”), of the
Company indicated above (the “Option Shares,” and such shares once issued shall be referred to as the “Issued Shares”), at the Option Exercise Price per share, subject to the terms and conditions set forth in this Incentive Stock
Option Agreement (this “Agreement”) and in the Plan. This Stock Option is intended to qualify as an “incentive stock option” as defined in Section 422(b) of the Internal Revenue Code of 1986, as amended from time to time
(the “Code”). If the Optionee disposes of Issued Shares within two years from the Grant Date or one year after such Issued Shares were acquired pursuant to exercise of this option, the Participant shall notify the Company in writing of
such disposition. The Optionee acknowledges receipt of a copy of the Plan and represents that he or she is familiar with the terms and provisions thereof, and accepts this Stock Option subject to all of the terms and provisions thereof. 

1. Definitions. For the purposes of this Agreement, the following terms shall have the following respective meanings. All
capitalized terms used herein and not otherwise defined shall have the respective meanings set forth in the Plan. 
 An
“Affiliate” of any Person means a Person that directly or indirectly, through one or more intermediaries, controls, is controlled by or is under common control with the first mentioned Person. A Person shall be deemed to control
another Person if such first Person possesses directly or indirectly the power to direct, or cause the direction of, the management and policies of the second Person, whether through the ownership of voting securities, by contract or otherwise.

 “Bankruptcy” shall mean (i) the filing of a voluntary petition under
any bankruptcy or insolvency law, or a petition for the appointment of a receiver or the making of an assignment for the benefit of creditors, with respect to the Optionee or any Permitted Transferee, or (ii) the Optionee or any Permitted
Transferee being subjected involuntarily to such a petition or assignment or to an attachment or other legal or equitable interest with respect to the Optionee’s or such Permitted Transferee’s assets, which involuntary petition or
assignment or attachment is not discharged within 60 days after its date, and (iii) the Optionee or any Permitted Transferee being subject to a transfer of the Stock Option or the Issued Shares by operation of law (including by divorce, even if
not insolvent), except by reason of death. 
 “Cause” for termination shall be deemed to exist upon (a) a
good faith finding by the Board of Directors of the Company of (i) the Optionee’s deliberate and continual failure to satisfactorily perform his 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) the Optionee’s dishonesty, gross negligence or gross misconduct in
connection with the business of the Company which has a substantial adverse effect on the Company; (b) the Optionee’s indictment or conviction, or the entry of a pleading of guilty or nolo contendere by the Optionee, to any crime involving
moral turpitude or any felony, but excluding any conviction arising as a result of the Optionee’s title or position with the Company and that is not based on the Optionee’s personal conduct; or (c) the Optionee’s violation of any
of the terms of his invention/non-disclosure or non-competition agreement with the Company. The Optionee shall be entitled to at least ten (10) days’ prior written notice of the Company’s intention to terminate his 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 of Directors his position regarding any dispute relating to the existence of such Cause. 

“Good Reason” shall mean, without the Optionee’s consent, (a) the relocation of the Optionee’s principal
place of employment with the Company to a place more than fifty (50) miles from his initial principal place of employment with the Company (other than in a direction that reduces his daily commuting distance); (b) a reduction in the level
of the Optionee’s (then) base salary of more than 20%; or (c) the hiring or presence of a Company Executive or employee with greater authority than the Optionee in any matters relating to the Company. 

“Permitted Transferees” shall mean any of the following to whom the Optionee may transfer Issued Shares hereunder (as
set forth in Section 8): the Optionee’s spouse, children (natural or adopted), stepchildren or a trust for their sole benefit of which the Optionee is the settlor; provided, however, that any such trust does not require or
permit distribution of any Issued Shares during the term of this Agreement unless subject to its terms. Upon the death of the Optionee (or a Permitted Transferee to whom shares have been transferred hereunder), the term Permitted Transferees shall
also include such deceased Optionee’s (or such deceased Permitted Transferee’s) estate, executions, administrations, personal representations, heirs, legatees and distributees, as the case may be. 

  
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 “Person” shall mean any individual, corporation, partnership (limited or
general), limited liability company, limited liability partnership, association, trust, joint venture, unincorporated organization or any similar entity. 
 “Sale Event” shall mean, regardless of form thereof, consummation of (i) the sale of all or substantially all of the assets of the Company on a consolidated basis to an unrelated
person or entity, (ii) a merger, reorganization or consolidation in which the outstanding shares of Stock are converted into or exchanged for securities of the successor entity and the holders of the Company’s outstanding voting power
immediately prior to such transaction do not own a majority of the outstanding voting power of the successor entity immediately upon completion of such transaction, (iii) the sale of all or a majority of the outstanding capital stock of the
Company to an unrelated person or entity or (iv) any other transaction in which the owners of the Company’s outstanding voting power immediately prior to such transaction do not own at least a majority of the outstanding voting power of
the successor entity immediately upon completion of the transaction; provided, however, that “Sale Event” shall not include any financing transaction of the Company (whether public or private) that would otherwise be and/or trigger a
“Sale Event” under (iii) and/or (iv) above. 
 “Subsidiary” shall mean any corporation
(other than the Company) in any unbroken chain of corporations or other entities beginning with the Company if each of the corporations (other than the last corporation in the unbroken chain) owns stock or other interests possessing 50 percent or
more of the total combined voting power of all classes of stock or in one of the other corporations in the chain. 
 2.
Vesting, Exercisability and Termination. 
 (a) No portion of this Stock Option may be exercised until such portion
shall have vested. 
 (b) Except as set forth below and in Section 6, and subject to the determination
of the Committee in its sole discretion to accelerate the vesting schedule hereunder, this Stock Option shall be vested and exercisable with respect to: (i) twenty-five percent (25%) of the Option Shares on the one (1) year
anniversary of the Vesting Reference Date; and (ii) one forty-eighth (1/48th) of the Option Shares at the end of each month starting with the thirteenth (13th) month following the Vesting Reference Date. 

Notwithstanding anything herein to the contrary, but without limitation of Section 6, (a) upon the consummation of a Sale
Event, 50% of the Option Shares that are not then vested will be accelerated and become vested and exercisable and (b) in the event that the Optionee’s employment with the Company and its Subsidiaries or a successor entity is terminated
within twelve (12) months following a Sale Event (i) by the Company or its successor without Cause or (ii) by the Optionee for Good Reason, then all remaining unvested Option Shares (whether under this Stock Option or a substitute
award as provided in Section 6) shall be accelerated and become vested and exercisable upon the effective date of such termination. 

  
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 (c) Termination. Except as may otherwise be provided by the Committee, if the
Optionee’s employment with the Company or a Subsidiary is terminated, the period within which to exercise this Stock Option may be subject to earlier termination as set forth below: 

(i) Termination Due to Death, Disability or Retirement. If the Optionee’s employment terminates by reason of
such Optionee’s death, disability (as defined in Section 422(c) of the Code) or retirement (after attainment of age 60), this Stock Option may be exercised, to the extent exercisable on the date of such termination, by the Optionee, the
Optionee’s legal representative or legatee for a period of twelve (12) months from the date of death, disability or retirement or until the Expiration Date, if earlier, subject in any event to Section 6. 

(ii) Other Termination. If the Optionee’s employment terminates for any reason other than death, disability or
retirement (after attainment of age 60), and unless otherwise determined by the Committee, this Stock Option may be exercised, to the extent exercisable on the date of termination, for a period of 90 days from the date of termination or until the
Expiration Date, if earlier, provided, however, if the Optionee’s employment is terminated for Cause, this Stock Option shall terminate immediately upon the date of such termination. 

For purposes hereof, the Committee’s determination of the reason for termination of the Optionee’s employment shall be
conclusive and binding on the Optionee and his or her representatives or legatees or Permitted Transferees. Any portion of the Stock Option that is not exercisable on the date of termination of the employment shall terminate immediately and be null
and void. 
 3. Exercise of Stock Option. 

(a) The Optionee may exercise this Stock Option only in the following manner: Prior to the Expiration Date (subject to Section 2(c)
and Section 6), the Optionee may deliver a Stock Option exercise notice (an “Exercise Notice”) in the form of Appendix A hereto indicating his or her election to purchase some or all of the Option Shares with respect to
which this Stock Option is exercisable at the time of such notice. Such notice shall specify the number of Option Shares to be purchased. Payment of the purchase price may be made by one or more of the methods described below. Payment instruments
will be received subject to collection. 
 (i) in cash, by certified or bank check, or other instrument
acceptable to the Committee in U.S. funds payable to the order of the Company in an amount equal to the purchase price of such Option Shares; 
 (ii) by the Optionee delivering to the Company a promissory note if the Board has expressly authorized the loan of funds to the Optionee for the purpose of enabling or assisting the Optionee to effect the
exercise of his or her Stock Option; provided that at least so much of the exercise price as represents the par value of the Stock shall be paid other than with a promissory note if otherwise required by state law; or 

  
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 (iii) if the Company’s Initial Public Offering has occurred, then
(A) through the delivery (or attestation to ownership) of shares of Common Stock that have been purchased by the Optionee on the open market or that have been held by the Optionee for at least six months and are not subject to restrictions
under any plan of the Company and in any event with an aggregate Fair Market Value (as of the date of such exercise) equal to the option purchase price, (B) by the Optionee delivering to the Company a properly executed Exercise Notice together
with irrevocable instructions to a broker to promptly deliver to the Company cash or a check payable and acceptable to the Company to pay the option purchase price, provided that in the event the Optionee chooses to pay the option purchase price as
so provided, the Optionee and the broker shall comply with such procedures and enter into such agreements of indemnity and other agreements as the Committee shall prescribe as a condition of such payment procedure, or (C) a combination of (i),
(ii), (iii)(A) and (iii)(B) above. 
 (b) Certificates for the Option Shares so purchased will be issued and delivered to the
Optionee upon compliance to the satisfaction of the Committee with all requirements under applicable laws or regulations in connection with such issuance. Until the Optionee shall have complied with the requirements hereof and of the Plan, the
Company shall be under no obligation to issue the Option Shares subject to this Stock Option, and the determination of the Committee as to such compliance shall be final and binding on the Optionee. The Optionee shall not be deemed to be the holder
of, or to have any of the rights of a holder with respect to, any shares of Common Stock subject to this Stock Option unless and until this Stock Option shall have been exercised pursuant to the terms hereof, the Company shall have issued and
delivered the Issued Shares to the Optionee, and the Optionee’s name shall have been entered as a stockholder of record on the books of the Company. Thereupon, the Optionee shall have full dividend and other ownership rights with respect to
such Issued Shares, subject to the terms of this Agreement. 
 (c) Notwithstanding any other provision hereof or of the Plan, no
portion of this Stock Option shall be exercisable after the Expiration Date. 
 4. Incorporation of Plan.
Notwithstanding anything herein to the contrary, this Stock Option shall be subject to and governed by all the terms and conditions of the Plan. 
 5. Transferability of Stock Option. This Agreement is personal to the Optionee and is not transferable by the Optionee in any manner other than by will or by the laws of descent and
distribution. The Stock Option may be exercised during the Optionee’s lifetime only by the Optionee (or by the Optionee’s guardian or personal representative in the event of the Optionee’s incapacity). The Optionee may elect to
designate a beneficiary by providing written notice of the name of such beneficiary to the Company, and may revoke or change such designation at any time by filing written notice of revocation or change with the Company; such beneficiary may
exercise the Optionee’s Stock Option in the event of the Optionee’s death to the extent provided herein. If the Optionee does not designate a beneficiary, or if the designated beneficiary predeceases the Optionee, the legal representative
of the Optionee may exercise this Stock Option to the extent provided herein in the event of the Optionee’s death. 

  
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 6. Effect of Certain Transactions. In the case of a Sale Event, this Stock
Option shall terminate upon the effective time of any such Sale Event unless provision is made in connection with such transaction in the sole discretion of the parties thereto for the continuation or assumption of this Stock Option heretofore
granted, or the substitution of this Stock Option with a new Stock Option of the successor entity or a parent thereof, with such adjustment as to the number and kind of shares and the per share exercise prices as such parties shall agree. In the
event of such termination, the Optionee shall be permitted, for a specified period of time prior to the consummation of the Sale Event as determined by the Committee, to exercise all portions of the Stock Option which are then exercisable.

 7. Withholding Taxes. The Optionee shall, not later than the date as of which the exercise of this Stock Option
becomes a taxable event for federal income tax purposes, pay to the Company or make arrangements satisfactory to the Committee for payment of any federal, state and local taxes required by law to be withheld on account of such taxable event. Subject
to approval by the Committee, the Optionee may elect to have the minimum tax withholding obligation satisfied, in whole or in part, by authorizing the Company to withhold from shares of Common Stock to be issued or transferring to the Company, a
number of shares of Common Stock with an aggregate Fair Market Value that would satisfy the minimum withholding amount due. The Optionee acknowledges and agrees that the Company or any Subsidiary of the Company has the right to deduct from payments
of any kind otherwise due to the Optionee, or from the Option Shares to be issued in respect of an exercise of this Stock Option, any federal, state or local taxes of any kind required by law to be withheld with respect to the issuance of Option
Shares to the Optionee. 
 8. Restrictions on Transfer of Issued Shares. None of the Issued Shares acquired upon
exercise of the Stock Option shall be sold, assigned, transferred, pledged, hypothecated, given away or in any other manner disposed of or encumbered, whether voluntarily or by operation of law, unless such transfer is in compliance with all
applicable securities laws (including, without limitation, the Securities Act of 1933, as amended, and the rules and regulations thereunder (the “Act”)), and such disposition is in accordance with the terms and conditions of this
Section 8 such disposition does not cause the Company to become subject to the reporting requirements of the Securities Exchange Act of 1934, as amended. In connection with any transfer of Issued Shares, the Company may require the transferor
to provide at the Optionee’s own expense an opinion of counsel to the transferor, satisfactory to the Company, that such transfer is in compliance with all foreign, federal and state securities laws (including, without limitation, the Act). Any
attempted disposition of Issued Shares not in accordance with the terms and conditions of this Section 8 shall be null and void, and the Company shall not reflect on its records any change in record ownership of any Issued Shares as a result of
any such disposition, shall otherwise refuse to recognize any such disposition and shall not in any way give effect to any such disposition of any Issued Shares. Subject to the foregoing general provisions, Issued Shares may be transferred pursuant
to the following specific terms and conditions: 
 (a) Transfers to Permitted Transferees. The Optionee may sell, assign,
transfer or give away any or all of the Issued Shares to Permitted Transferees; provided, however, that such Permitted Transferee(s) shall, as a condition to any such transfer, agree to be subject to the provisions of this Agreement to
the same extent as the Optionee (including, 

  
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without limitation, the provisions of Sections 8, 10 and 11) and shall have delivered a written acknowledgment to that effect to the Company. 

(b) Transfers Upon Death. Upon the death of the Optionee, any Issued Shares then held by the Optionee at the time of such death
and any Issued Shares acquired thereafter by the Optionee’s legal representative pursuant to this Agreement shall be subject to the provisions of Sections 8, 10 and 11, if applicable, and the Optionee’s estate, executors, administrators,
personal representatives, heirs, legatees and distributees shall be obligated to convey such Issued Shares to the Company or its assigns under the terms contemplated hereby. 
 (c) Company’s Right of First Refusal. In the event that the Optionee (or any Permitted Transferee holding Issued Shares subject to this Section 8(c)) desires to sell or otherwise transfer
all or any part of the Issued Shares, the Optionee (or Permitted Transferee) first shall give written notice to the Company of the Optionee’s (or Permitted Transferee’s) intention to make such transfer. Such notice shall state the number
of Issued Shares which the Optionee (or Permitted Transferee) proposes to sell (the “Offered Shares”), the price and the terms at which the proposed sale is to be made and the name and address of the proposed transferee. At any time within
30 days after the receipt of such notice by the Company, the Company or its assigns may elect to purchase all or any portion of the Offered Shares at the price and on the terms offered by the proposed transferee and specified in the notice. The
Company or its assigns shall exercise this right by mailing or delivering written notice to the Optionee (or Permitted Transferee) within the foregoing 30-day period. If the Company or its assigns elect to exercise its purchase rights under this
Section 8(c), the closing for such purchase shall, in any event, take place within 45 days after the receipt by the Company of the initial notice from the Optionee (or Permitted Transferee). In the event that the Company or its assigns do not
elect to exercise such purchase right, or in the event that the Company or its assigns do not pay the full purchase price within such 45-day period, the Optionee (or Permitted Transferee) may, within 60 days thereafter, sell the Offered Shares to
the proposed transferee and at the same price and on the same terms as specified in the Optionee’s (or Permitted Transferee’s) notice. Any Shares purchased by such proposed transferee shall no longer be subject to the terms of this
Agreement. Any Shares not sold to the proposed transferee shall remain subject to this Agreement. Notwithstanding the foregoing, the restrictions under this Section 8(c) shall terminate in accordance with Section 12(a). 

9. Escrow Arrangement. 
 (a) Escrow. In order to carry out the provisions of Sections 8 and 10 of this Agreement more effectively, the Company shall hold any Issued Shares in escrow together with separate stock powers
executed by the Optionee in blank for transfer, and any Permitted Transferee shall, as an additional condition to any transfer of Issued Shares, execute a like stock power as to such Issued Shares. The Company shall not dispose of the Issued Shares
except as otherwise provided in this Agreement. In the event of any repurchase by the Company (or any of its assigns), the Company is hereby authorized by the Optionee and any Permitted Transferee, as the Optionee’s and each such Permitted
Transferee’s attorney-in-fact, to date and complete the stock powers necessary for the transfer of the Issued Shares being purchased and to transfer such Issued Shares in accordance with the terms hereof. At such time as any Issued Shares are
no longer subject to the Company’s repurchase, first refusal and drag along rights, the Company 

  
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shall, at the written request of the Optionee, deliver to the Optionee (or the relevant Permitted Transferee) a certificate representing such Issued Shares with the balance of the Issued Shares
to be held in escrow pursuant to this Section 9. 
 (b) Remedy. Without limitation of any other provision of this
Agreement or other rights, in the event that the Optionee, any Permitted Transferees or any other person or entity is required to sell the Optionee’s Issued Shares pursuant to the provisions of Sections 8 and 10 of this Agreement and in
the further event that he or she refuses or for any reason fails to deliver to the Company or its designated purchaser of such Issued Shares the certificate or certificates evidencing such Issued Shares together with a related stock power, the
Company or such designated purchaser may deposit the applicable purchase price for such Issued Shares with a bank designated by the Company, or with the Company’s independent public accounting firm, as agent or trustee, or in escrow, for the
Optionee, any Permitted Transferees or other person or entity, to be held by such bank or accounting firm for the benefit of and for delivery to him, her, them or it, and/or, in its discretion, pay such purchase price by offsetting any indebtedness
then owed by the Optionee as provided above. Upon any such deposit and/or offset by the Company or its designated purchaser of such amount and upon notice to the person or entity who was required to sell the Issued Shares to be sold pursuant to the
provisions of Sections 8 and 10, such Issued Shares shall at such time be deemed to have been sold, assigned, transferred and conveyed to such purchaser, the holder thereof shall have no further rights thereto (other than the right to withdraw the
payment thereof held in escrow, if applicable), and the Company shall record such transfer in its stock transfer book or in any appropriate manner. 
 10. Drag Along Right. In the event the holders of a majority of the Company’s equity securities then outstanding (the “Majority Shareholders”) determine to sell or otherwise
dispose of all or substantially all of the assets of the Company or all or fifty percent (50%) or more of the capital stock of the Company in each case in a transaction constituting a change in control of the Company, to any non-Affiliate(s) of
the Company or any of the Majority Shareholders, or to cause the Company to merge with or into or consolidate with any non-Affiliate(s) of the Company or any of the Majority Shareholders (in each case, the “Buyer”) in a bona fide
negotiated transaction (a “Sale”), the Optionee, including any Permitted Transferees, shall be obligated to and shall upon the written request of the Majority Shareholders (subject to Section 6): (a) sell, transfer and deliver,
or cause to be sold, transferred and delivered, to the Buyer, his or her Issued Shares (including for this purpose all of such Optionee’s or his or her Permitted Transferee’s Issued Shares that presently or as a result of any such
transaction may be acquired upon the exercise of options (following the payment of the exercise price therefor)) on substantially the same terms applicable to the Majority Shareholders (with appropriate adjustments to reflect the conversion of
convertible securities, the redemption of redeemable securities and the exercise of exercisable securities as well as the relative preferences and priorities of preferred stock); and (b) execute and deliver such instruments of conveyance and
transfer and take such other action, including voting such Issued Shares in favor of any Sale proposed by the Majority Shareholders and executing any purchase agreements, merger agreements, indemnity agreements, escrow agreements or related
documents, as the Majority Shareholders or the Buyer may reasonably require in order to carry out the terms and provisions of this Section 10. The obligations under this Section 10 shall terminate in accordance with Section 12(a).

  
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 11. Lockup Provision. The Optionee agrees, in connection with the initial
underwritten public offering of the Common Stock pursuant to a registration statement under the Securities Act, (i) not to (a) offer, pledge, announce the intention to sell, sell, contract to sell, sell any option or contract to purchase,
purchase any option or contract to sell, grant any option, right or warrant to purchase, or otherwise transfer or dispose of, directly or indirectly, any shares of Common Stock or any other securities of the Company or (b) enter into any swap
or other agreement that transfers, in whole or in part, any of the economic consequences of ownership of shares of Common Stock or other securities of the Company, whether any transaction described in clause (a) or (b) is to be settled by
delivery of securities, in cash or otherwise, during the period beginning on the date of the filing of such registration statement with the Securities and Exchange Commission and ending 180 days after the date of the final prospectus relating to the
offering (plus up to an additional 34 days to the extent requested by the managing underwriters for such offering in order to address Rule 2711(f) of the National Association of Securities Dealers, Inc. or any similar successor provision), and
(ii) to execute any agreement reflecting clause (i) above as may be requested by the Company or the managing underwriters at the time of such offering. The Company may impose stop-transfer instructions with respect to the shares of Common
Stock or other securities subject to the foregoing restriction until the end of the “lock-up” period. 
 12.
Miscellaneous Provisions. 
 (a) Termination. The restrictions on transfer of Issued Shares under
Section 8(c) and the Drag Along obligations under Section 10 shall terminate upon the closing of the Company’s Initial Public Offering or upon consummation of any Sale Event, in either case as a result of which shares of the Company
(or successor entity) of the same class as the Issued Shares are registered under Section 12 of the Exchange Act and publicly traded on NASDAQ/NMS or any national security exchange. 

(b) Equitable Relief. The parties hereto agree and declare that legal remedies may be inadequate to enforce the provisions of this
Agreement and that equitable relief, including specific performance and injunctive relief, may be used to enforce the provisions of this Agreement. 
 (c) Adjustments for Changes in Capital Structure. If, as a result of any reorganization, recapitalization, reclassification, stock dividend, stock split, reverse stock split or other similar change
in the Common Stock, the outstanding shares of Common Stock are increased or decreased or are exchanged for a different number or kind of shares of the Company’s stock, the provisions contained in this Agreement shall apply with equal force to
additional and/or substitute securities, if any, received by the Optionee in exchange for, or by virtue of his or her ownership of, Issued Shares. 
 (d) Change and Modifications. This Agreement may not be orally changed, modified or terminated, nor shall any oral waiver of any of its terms be effective. This Agreement may be changed, modified
or terminated only by an agreement in writing signed by the Company and the Optionee. 

  
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 (e) Governing Law. This Agreement shall be governed by and construed in accordance
with the laws of Delaware without regard to conflict of law principles. 
 (f) Headings. The headings are intended only
for convenience in finding the subject matter and do not constitute part of the text of this Agreement and shall not be considered in the interpretation of this Agreement. 
 (g) Saving Clause. If any provision(s) of this Agreement shall be determined to be illegal or unenforceable, such determination shall in no manner affect the legality or enforceability of any other
provision hereof. 
 (h) Notices. All notices, requests, consents and other communications shall be in writing and be
deemed given when delivered personally, by telex or facsimile transmission or when received if mailed by first class registered or certified mail, postage prepaid. Notices to the Company or the Optionee shall be addressed as set forth underneath
their signatures below, or to such other address or addresses as may have been furnished by such party in writing to the other. 

(i) Benefit and Binding Effect. This Agreement shall be binding upon and shall inure to the benefit of the parties hereto, their
respective successors, permitted assigns, and legal representatives. The Company has the right to assign this Agreement, and such assignee shall become entitled to all the rights of the Company hereunder to the extent of such assignment. 

(j) Counterparts. For the convenience of the parties and to facilitate execution, this Agreement may be executed in two or more
counterparts, each of which shall be deemed an original, but all of which shall constitute one and the same document. 

[SIGNATURE PAGE FOLLOWS] 

  
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 The foregoing Agreement is hereby accepted and the terms and conditions thereof hereby
agreed to by the undersigned as of the date first above written. 
  

			
	DEMANDWARE, INC.
		
	By:	 	 /s/ Scott Dussault

		 	  Name: Scott Dussault
		 	  Title: Chief Financial Officer
	
	Address:
	
	10 Presidential Way
	Woburn, MA
	01810

 The foregoing Agreement is hereby accepted and the terms and conditions thereof hereby agreed to by
the undersigned as of the date first above written. 
  

			
		 	OPTIONEE:
		
		 	 /s/ Thomas D. Ebling

		 	Name: THOMAS D. EBLING
		
		 	Address:
		
		 	 144 NEHOIDEN ROAD

		
		 	 WABAN, MA 02468

		
		 	  

		
	[SPOUSE’S CONSENT1	 	
	I acknowledge that I have read the foregoing Incentive Stock Option Agreement and understand the contents thereof.	 	
		
	                             
                                         
          ]	 	

  

	1 	 A spouse’s consent is required only if the Optionee’s state of residence is one of the following community property states: Arizona,
California, Idaho, Louisiana, New Mexico, Nevada, Texas, Washington and Wisconsin. 

  
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	DESIGNATED BENEFICIARY:
	
	 GAYANE Z. EBLING

	
	Beneficiary’s Address:
	
	 144 NEHOIDEN ROAD

	
	 WABAN, MA 02468

	
	  

  
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 Appendix A 
 STOCK OPTION EXERCISE NOTICE 
  

							
	Demandware, Inc.	  		  		  	
	Attention: CFO	  		  		  	
	  
	  		  		  	
	  
	  		  		  	

 Pursuant to the terms of my stock option agreement dated
             (the “Agreement”) under the Demandware, Inc. 2004 Stock Option and Grant Plan, I, [Insert Name]
                            , hereby [Circle One] partially/fully exercise such option by including
herein payment in the amount of $             representing the purchase price for [Fill in number of Option Shares]
             option shares. I have chosen the following form(s) of payment: 
  

	 	[    ]	1.        Cash 

  

	 	[    ]	2.        Certified or bank check payable to Demandware, Inc. 

 

	 	[    ]	3.        Other (as described in the Agreement (please describe))
                                         
                       . 

 In connection with my exercise of the option as set forth above, I hereby represent and warrant to Enigma Holdings, Inc. as follows: 

(i) I am purchasing the option shares for my own account for investment only, and not for resale or with a view to the
distribution thereof. 
 (ii) I have had such an opportunity as I have deemed adequate to obtain from Demandware,
Inc. such information as is necessary to permit me to evaluate the merits and risks of my investment in Demandware, Inc. and have consulted with my own advisers with respect to my investment in Demandware, Inc. 

(iii) I have sufficient experience in business, financial and investment matters to be able to evaluate the risks involved
in the purchase of the option shares and to make an informed investment decision with respect to such purchase. 

(iv) I can afford a complete loss of the value of the option shares and am able to bear the economic risk of holding such
option shares for an indefinite period of time. 
 (v) I understand that the option shares may not be registered
under the Securities Act of 1933, as amended (it being understood that the option shares are being issued and sold in reliance on the exemption provided in Rule 701 thereunder) or any applicable state securities or “blue sky” laws and may
not be sold or otherwise transferred or disposed of in the absence of an effective registration statement under the Securities Act of 1933, as amended and under any applicable state securities or “blue sky” laws (or exemptions from the
registration requirement thereof). I further acknowledge that certificates representing option shares will bear restrictive legends reflecting the foregoing. 

  
 13 

 
	
	Sincerely yours,
	
	  

	Name:
	
	Address:
	
	  

	
	  

	
	  

  
 14Letter Agreement with Scott J. Dussault

 Exhibit 10.10 
 

 
  
 10 Presidential Way 

Woburn, MA 01801 USA 

September 19, 2008 
 Mr. Scott Dussault 
 23 Leland Hill Road 
 Sutton, MA 01590 
 Dear Scott: 

On behalf of Demandware, Inc. (the “Company”). I am pleased to confirm our employment offer to you for the position of Chief
Financial Officer. This offer is contingent upon your acknowledgement that you have no prior contractual agreements with a former employer that would exclude you from doing business with our clients, partners, or our technology. In this position you
will report to me and you will be an integral member of Demandware’s Executive team. Your responsibilities will include but are not limited to, providing financial leadership, administrative discipline and structure for the company for the
prospect of an IPO, and contributing to the strategic leadership of the business. As the Chief Financial officer you will need to provide leadership for financial statement preparation, financial analysis, and the Treasury function. You will act as
a business partner to the Senior Executive Team and play a lead role in driving the budgeting and forecasting processes, capital improvements and investments, and manage the negotiations of lines of credit and any potential acquisitions. 

Your starting salary will be $7916.66 payable semi monthly ($190,000.00 annualized) and your employment will commence as early as
convenient for you but no later than October 20, 2008. In addition to the annual salary specified above, you are eligible to earn annual incentive bonuses totaling $40,000.00. These bonuses will be based on the achievement of mutually agreed upon
milestones or objectives. Subject to Board approval, you will be granted 400,000 options to purchase shares of Demandware, Inc. common stock pursuant to our Employee Stock Option Plan. These options will be subject to acceleration in full on the
event of change of control of the organization if you are terminated without cause within 12 months of a change of control This will be incorporated into the Stock Option Grant document. Otherwise, the exercise price of the options will be set at
the fair market value as of the date of grant. As more fully spelled out in the Employee Stock Option Agreement, your options shall vest as follows: twenty-five percent (25%) of the options on the one (1) year anniversary of your employment; and one
forty-eighth (1/48th) of the options at the end of each month starting with the thirteenth (13th) month following the start date of your employment. 
 You will be eligible to participate in all other employee welfare benefit plans generally made available by the Company to similarly-situated employees. Your participation will be in accordance with the
plan rules and regulations as to eligibility, waiting periods etc. While these plans are subject to change without notice, they generally include medical, dental, short term and long term disability insurance as well as life insurance in the amount
of 1x’s your annual salary. In addition you may elect to 

 
participate in the Demandware 401K plan as well as a flexible spending plan (Section 125 Plan). Initially you will be entitled to up to three weeks of vacation time and an additional 5 personal
days. 
 This offer is contingent on your execution and delivery to us of (i) this agreement, (ii) the Company’s Non-Disclosure and
Developments Agreement attached hereto, and (iii) the Employee Non-Solicitation and Non-Competition Agreement attached hereto by, Monday, September 22, 2008, after which time this offer will terminate if not accepted. The execution of each of the
above referenced documents is a condition of your employment. Please note that your written acceptance of this offer also confirms your understanding and agreement that your employment with the Company is “at-will,” meaning that either you
or the Company may terminate your employment at any time and for any reason. You further acknowledge that this letter does not constitute an employment contract. 
 If you are not a US Citizen it may be necessary for you to obtain a work permit or Visa from the U.S. Department of Homeland Security. If this is the case, the company will engage Immigration Attorneys
and will make every reasonable effort to obtain the necessary authorizations for you to work in the U.S. If such a Work Permit, or Visa, is required, then it will become a condition of your employment and your employment will terminate if you are
denied permission to work in the U.S. 
 We are tremendously excited about the opportunity for you to join our team. Please feel free to contact
me if you need any further information prior to the deadline indicated above. 
  

			
		 	Yours turly,          
		 	

		 	John Pearce          
		 	President & CEO 
		 	Demandware, Inc

  
 

 
 Accepted this 19 day of September, 2008 

			
	From:    	  	Tom Ebling
	To:	  	Scott Dussault

 Date: February 26, 2010 
 Subject: 2010 Performance Bonus 
 Your bonus opportunity for 2010 is $40,000. This is
funded based upon company financial performance as follows: 
 The funding of this bonus does not guarantee that you will receive a bonus. In
order to achieve any of this potential bonus, you must meet your individual objectives and be an employee at the time the bonus is paid. Your individual objectives and the portion of the bonus earned upon achievement are as follows: 

Individual Objectives for 1H 2010 
  

							
	 	 	 	  	Portion	 
	 1.    
	 	IPO compliance plan	  	 	    20%    	  
	 2.
	 	Metrics and reporting (including customer profitability) on timely basis	  	 	    20%    	  
		 		  	 	 	 
	 3.
	 	HR, Legal, Facilities	  	 	    15%    	  
		 		  	 	 	 
	 4.
	 	Effective forecasting of GMV, Capital, Proforma Services, Expenses	  	 	    25%    	  
		 		  	 	 	 
	 5.
	 	Securing line of debt suffcient to fund 2010 major capital purchases, particularly PODs.	  	 	    20%    	  
		 		  	 	 	 

 In each case, we will assess the achievement of the objective as Excellent, Good, Satisfactory or Unsatisfactory. You
will earn full value for Excellent, 90% for Good, 75% for Satisfactory or 0% for Unsatisfactory. 
 Bonuses will be distributed in February
2011. 
 Sincerely, 
 Thomas Ebling

 CEO 

			
	From:    	  	Tom Ebling
	To:	  	Scott Dussault

 Date: July 9, 2010 
 Subject: 2010 Performance Bonus 
 Your bonus opportunity for 2010 is $40,000. This is
funded based upon company financial performance as follows: 
 The funding of this bonus does not guarantee that you will receive a bonus. In
order to achieve any of this potential bonus, you must meet your individual objectives and be an employee at the time the bonus is paid. Your individual objectives and the portion of the bonus earned upon achievement are as follows: 

Individual Objectives for 2H 2010 
  

							
	 	 	 	  	Portion	 
	 1.    
	 	Publish IPO compliance timeline early in 2H and adherence to it	  	 	    15%    	  
	 2.
	 	Metrics and reporting (including customer profitability) on timely basis	  	 	    15%    	  
		 		  	 	 	 
	 3.
	 	HR, Legal, Facilities	  	 	    15%    	  
		 		  	 	 	 
	 4.
	 	Effective forecasting of GMV, Capital, Proforma Services, Expenses	  	 	    20%    	  
		 		  	 	 	 
	 5.
	 	I-banker wording to be supplied as draft by Scott	  	 	    15%    	  
		 		  	 	 	 
	 6.
	 	2011 budgeting and 2011-2013 planning support to enable rapid decision making and analysis of various options	  	 	    20%    	  
		 		  	 	 	 

 In each case, we will assess the achievement of the objective as Excellent, Good, Satisfactory or Unsatisfactory. You
will earn full value for Excellent, 90% for Good, 75% for Satisfactory or 0% for Unsatisfactory. 
 Bonuses will be distributed in February
2011. 
 Sincerely, 
 /s/ Thomas
Ebling 
 Thomas Ebling 
 CEO

 DEMANDWARE, INC. 

5 Wall Street 
 Burlington, MA 
 April 4, 2011 

Scott J. Dussault 
 23 Leland Hill Rd.

 Sutton, MA 01590 
 Re: Acceleration
of Vesting 
 Dear Scott: 
 Demandware, Inc. (the “Company”) recognizes that the possibility of a change in control of the Company exists and that such possibility, and the uncertainty and questions which it may raise, may
cause you to terminate your employment with the Company. As a result, in order to induce you to remain in the employment of the Company, the Company agrees with you as follows with respect to your options to purchase 800,000 shares of Common Stock
of the Company you have pursuant to the Non-Qualified Stock Option Agreements, dated as of November 11, 2008, September 29, 2009 and June 3, 2010, respectively, between you and the Company (the “NQO”): 

1. In the event of a Sale (as defined in the NQO), the vesting schedule of the option shall be accelerated in part so that the option
shall become exercisable for an additional number of shares equal to 50% of the Shares subject to the option. The remaining Shares (as defined in the NQO) shall continue to become vested in accordance with the original vesting schedule set forth in
the NQO; provided, however, that the option shall become immediately exercisable in full if, following the Sale, the Participant's employment with the Company or the acquiring or succeeding corporation is terminated for Good Reason (as defined
below) by the Participant or is terminated without Cause (as defined below) by the Company or the acquiring or succeeding corporation. 
 2. For purposes of this letter, (i) “Cause” means (a) commission of, or indictment or conviction of, any felony or any crime involving dishonesty; (b) participation in any fraud
against the Company; (c) your breach of any material provision of any invention and non-disclosure agreement or non-competition and non-solicitation agreement with the Company; and (ii) “Good Reason” means the occurrence, without
your consent, of either of the following events or circumstances: (a) the relocation of the Company's offices such that your daily commute is increased by at least 35 miles; or (b) to the substantial diminution of your duties,
responsibilities, or authority. 
 3. The Company's obligations under this letter shall terminate upon the termination of your
employment with the Company prior to a Sale; provided such termination is month than six months prior to the consummation of such Sale. 

 4. The NQO, as supplemented and modified by this letter, together with the other writings
referred to in such NQO or delivered pursuant thereto which form a part thereof, contain the entire agreement between the parties with respect to the subject matter thereof and hereof and amend, restate and supersede all prior and contemporaneous
arrangements or understandings with respect thereto. 
 5. On and after the date hereof, each reference in the NQO to
“hereunder,” “hereof,” “herein” or words of like import, and each reference in the other documents entered into in connection with such NQO, shall mean and be a reference to such NQO, as supplemented and modified
hereby. The NQO shall remain in full force and effect and is hereby ratified and confirmed. 
 Please indicate your agreement
with the foregoing by signing in the space provided Below. 
  

			
	Very truly yours,
	
	DEMANDWARE, INC.
		
	By:	 	 /s/ Sheila M. Flaherty

		 	Name: Sheila M Flaherty
		 	Title: VP & GENERAL COUNSEL

 Agreed and acknowledged 
 as of the date set forth below: 
  

	
	 /s/ Scott J. Dussault

	Scott J. Dussault
	
	Date: April 4, 2010

  
 - 6 -

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