Document:

EX-10.9

 Exhibit 10.9 

September 5, 2017 
 Paul Yee 

Stitch Fix, Inc. 
 One Montgomery St., Suite 1500 

San Francisco, CA 94104 
  

	Re:	Employment Terms 

 Dear Paul: 

On behalf of Stitch Fix, Inc. (the “Company”), I am pleased to offer you continued employment at the Company on the terms set forth in this
offer letter agreement (the “Agreement”). As discussed, the terms of this Agreement govern with respect to your employment, effective as of the date it is signed by you. 

1. Employment by the Company. 
 (a)
Position. You will continue to serve as the Company’s Chief Financial Officer. During the term of your employment with the Company, you will devote your best efforts and substantially all of your business time and attention to the business
of the Company, except for approved vacation periods and reasonable periods of illness or other incapacities permitted by the Company’s general employment policies. 

(b) Duties and Location. You will continue to perform those duties and responsibilities as are customary for the position of Chief
Financial Officer and as may be directed by the Company’s Chief Executive Officer, to whom you will report. Your primary office location will be the Company’s offices in San Francisco, CA. Notwithstanding the foregoing, the Company
reserves the right to reasonable require you to perform your duties at places other than your primary office location from time to time, and to require reasonable business travel. The Company may modify your job title and duties as it deems
necessary and appropriate in light of the Company’s needs and interests from time to time. 
 2. Base Salary and Employee Benefits. 

(a) Salary. You will receive for services to be rendered hereunder base salary paid at the rate of $440,000 per year, less standard
payroll deductions and tax withholdings. Your base salary will be paid on the Company’s ordinary payroll cycle. As an exempt salaried employee, you will be required to work the Company’s normal business hours, and such additional time as
appropriate for your work assignments and position, and you will not be entitled to overtime compensation. 
 (b)
Benefits. As a regular full-time employee, you will continue to be eligible to participate in the Company’s standard employee benefits offered to executive level employees, as in effect from time to time and subject to plan
terms and generally applicable Company policies. Details about these benefit plans will be provided, upon request. 

  
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 3. Expenses. The Company will reimburse you for reasonable travel, entertainment or other expenses
incurred by you in furtherance or in connection with the performance of your duties hereunder, in accordance with the Company’s expense reimbursement policy as in effect from time to time. 

4. Equity Compensation. You may have been granted certain options to purchase shares of the Company’s Common Stock or other equity awards as part
of your employment with the Company. Any such grants will continue to be governed by the applicable plan and equity grant documents, as they may be modified by the terms of this Agreement. 

5. Compliance with Confidentiality Agreement and Company Policies. Your signed At-Will Employment, Confidential Information, Invention Assignment, and
Arbitration Agreement (the “Confidentiality Agreement”) remains in full force and effect. In addition, you are required to abide by the Company’s policies and procedures, as modified from time to time within the Company’s
discretion (including without limitation, acknowledging in writing that you have read and will comply with any applicable Company Employee Handbook); provided, however, that in the event the terms of this Agreement differ from or are
in conflict with the Company’s general employment policies or practices, this Agreement shall control. 
 6. Protection of Third Party
Information. In your continued work for the Company, you will be expected not to make any unauthorized use or disclosure of any confidential or proprietary information, including trade secrets, of any former employer or other third party to whom
you have contractual obligations to protect such information. Rather, you will be expected to use only that information which is generally known and used by persons with training and experience comparable to your own, which is common knowledge in
the industry or otherwise legally in the public domain, or which is otherwise provided or developed by the Company. You represent that you are able to perform your job duties within these guidelines, and you are not in unauthorized possession of any
unpublished documents, materials, electronically-recorded information, or other property belonging to any former employer or other third party to whom you have a contractual obligation to protect such property. In addition, you represent and warrant
that your employment by the Company will not conflict with any prior employment or consulting agreement or other agreement with any third party, that you will perform your duties to the Company without violating any such agreement(s), and that you
have disclosed to the Company in writing any contract you have signed that may restrict your activities on behalf of the Company. 
 7. At-Will
Employment Relationship. Your employment relationship with the Company will continue to be at-will. Accordingly, you may terminate your employment with the Company at any time and for any reason whatsoever simply by notifying the Company; and
the Company may terminate your employment at any time, with or without Cause or advance notice. 
 8. Severance. You will be eligible for the
following severance benefits (the “Severance Benefits”), each as described and pursuant to the terms and conditions set forth below. 

(a) Termination without Cause/Resignation for Good Reason Not in Connection with a Change in Control. If the Company terminates your
employment without Cause (as defined below) (other than as a result of your death or disability) or you resign for Good Reason (as defined below) (either such termination referred to as a “Qualifying Termination”) and the Company is
not in a Change in Control Period (as defined in Section 8(b)), and provided such termination or resignation constitutes a Separation from Service (as defined under Treasury Regulation Section 1.409A-1(h), without regard to any alternative
definition thereunder, a “Separation from Service”), then subject to Sections 10 (“Conditions to Receipt of Severance Benefits”) and 11 (“Return of Property”) below and your continued compliance with the terms of
this Agreement (including without limitation Section 5 (“Compliance with Confidentiality Agreement and Company Policies”) above), the Company will provide you with the following as your sole severance benefits: 

1) Cash Severance. The Company will pay you, as cash severance, six (6) months of your base salary in effect as of your
Separation from Service date, less standard payroll deductions and tax withholdings. Subject to Section 14, the Company may pay this severance amount in either a lump sum payment 

  
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or in installments in the form of continuation of your base salary payments. The Company will notify you of its election within ten (10) business days following the Qualifying Termination.
Should the Company elect to pay you in a lump sum, such payment will be made on the Company’s first regular payroll date that is more than sixty (60) days following your Separation from Service date. Should the Company elect to pay you in
installments, such installments will be paid on the Company’s ordinary payroll dates, commencing on the Company’s first regular payroll date that is more than sixty (60) days following your Separation from Service date, and shall be
for any accrued base salary for the sixty (60)-day period plus the period from the sixtieth (60th) day until the regular payroll date, if applicable, and all salary continuation payments
thereafter, if any, shall be made on the Company’s regular payroll dates. 
 2) COBRA Severance. As an additional Severance
Benefit, the Company will continue to pay the cost of your health care coverage in effect at the time of your Separation from Service, either under the Company’s regular health plan (if permitted), or by paying your COBRA premiums (the
“COBRA Severance”), for a maximum of six (6) months. The Company’s obligation to pay the COBRA Severance on your behalf will cease if you obtain health care coverage from another source (e.g., a new employer or
spouse’s benefit plan), unless otherwise prohibited by applicable law. You must notify the Company within two (2) weeks if you obtain coverage from a new source. This payment of COBRA Severance by the Company would not expand or extend the
maximum period of COBRA coverage to which you would otherwise be entitled under applicable law. Notwithstanding the above, if the Company determines in its sole discretion that it cannot provide the foregoing COBRA Severance without potentially
violating applicable law (including, without limitation, Section 2716 of the Public Health Service Act), the Company shall in lieu thereof provide to you a taxable monthly payment in an amount equal to the monthly COBRA premium that you would
be required to pay to continue your group health coverage in effect on the date of your termination (which amount shall be based on the premium for the first month of COBRA coverage), which payments shall be made on the last day of each month
regardless of whether you elect COBRA continuation coverage and shall end on the earlier of (x) the date upon which you obtain other coverage or (y) the last day of the sixth (6th) calendar month following your Separation from Service
date. 
 (b) Termination without Cause/Resignation for Good Reason in Connection with a Change in Control. In the event of a
Qualifying Termination that occurs during the period beginning one month prior to a Change in Control and ending twelve (12) months following the closing of such Change in Control (such period, the “Change in Control Period”),
provided such Qualifying Termination constitutes a Separation from Service, then subject to Sections 10 (“Conditions to Receipt of Severance Benefits”) and 11 (“Return of Property”) below and your continued compliance with the
terms of this Agreement (including without limitation Section 5 (“Compliance with Confidentiality Agreement and Company Policies”) above), then the Company will provide you with the following as your sole severance benefits: 

1) Cash Severance. The Company will pay you, as cash severance, twelve (12) months of your base salary in effect as of your
Separation from Service date, less standard payroll deductions and tax withholdings. Subject to Section 14, the Company may pay this severance amount in either a lump sum payment or in installments in the form of continuation of your base
salary payments. The Company will notify you of its election within ten (10) business days following the Qualifying Termination. Should the Company elect to pay you in a lump sum, such payment will be made on the Company’s first regular
payroll date that is more than sixty (60) days following your Separation from Service date. Should the Company elect to pay you in installments, such installments will be paid on the Company’s ordinary payroll dates, commencing on the
Company’s first regular payroll date that is more than sixty (60) days following your Separation from Service date, and shall be for any accrued base salary for the sixty (60)-day period plus the period from the sixtieth (60th) day until the regular payroll date, if applicable, and all salary continuation payments thereafter, if any, shall be made on the Company’s regular payroll dates. 

2) COBRA Severance. As an additional Severance Benefit, the Company will provide you COBRA Severance for a maximum of twelve
(12) months. The Company’s obligation to pay the COBRA Severance on your behalf will cease if you obtain health care coverage from another source (e.g., a new employer or spouse’s benefit plan), unless otherwise prohibited by
applicable law. You must notify the Company within 

  
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two (2) weeks if you obtain coverage from a new source. This payment of COBRA Severance by the Company would not expand or extend the maximum period of COBRA coverage to which you would
otherwise be entitled under applicable law. Notwithstanding the above, if the Company determines in its sole discretion that it cannot provide the foregoing COBRA Severance without potentially violating applicable law (including, without limitation,
Section 2716 of the Public Health Service Act), the Company shall in lieu thereof provide to you a taxable monthly payment in an amount equal to the monthly COBRA premium that you would be required to pay to continue your group health coverage
in effect on the date of your termination (which amount shall be based on the premium for the first month of COBRA coverage), which payments shall be made on the last day of each month regardless of whether you elect COBRA continuation coverage and
shall end on the earlier of (x) the date upon which you obtain other coverage or (y) the last day of the twelfth (12th) calendar month following your Separation from Service date. 

3) Accelerated Vesting. As an additional Severance Benefit, the Company shall accelerate the vesting of any equity awards then held by
you such that one hundred percent (100%) of such awards shall be deemed immediately vested (and, as applicable, exercisable) as of your Separation from Service date, except to the extent that the equity award grant documentation relating to an
equity award contains an explicit provision to the contrary. 
 9. Resignation Without Good Reason; Termination for Cause; Death or Disability. If,
at any time, you resign your employment without Good Reason, or the Company terminates your employment for Cause, or if either party terminates your employment as a result of your death or disability, you will receive your base salary accrued
through your last day of employment, as well as any unused vacation (if applicable) accrued through your last day of employment. Under these circumstances, you will not be entitled to any other form of compensation from the Company, including any
Severance Benefits, other than any rights to which you are entitled under the Company’s benefit programs. In addition, under no circumstance will you receive the Severance Benefits under both Sections 8(a) and 8(b) above. 

10. Conditions to Receipt of Severance Benefits. Prior to and as a condition to your receipt of any of the Severance Benefits described above, you
shall execute and deliver to the Company an effective release of claims in favor of and in a form acceptable to the Company (the “Release”) within the timeframe set forth therein, but not later than forty-five (45) days
following your Separation from Service date, and allow the Release to become effective according to its terms (by not invoking any legal right to revoke it) within any applicable time period set forth therein (such latest permitted effective date,
the “Release Deadline”). 
 11. Return of Company Property. Upon the termination of your employment for any reason, as a
precondition to your receipt of the Severance Benefits (if applicable), within five (5) days after your Separation from Service Date (or earlier if requested by the Company), you will return to the Company all Company documents (and all copies
thereof) and other Company property within your possession, custody or control, including, but not limited to, Company files, notes, financial and operational information, customer lists and contact information, product and services information,
research and development information, drawings, records, plans, forecasts, reports, payroll information, spreadsheets, studies, analyses, compilations of data, proposals, agreements, sales and marketing information, personnel information,
specifications, code, software, databases, computer-recorded information, tangible property and equipment (including, but not limited to, computers, facsimile machines, mobile telephones, tablets, handheld devices, and servers), credit cards, entry
cards, identification badges and keys, and any materials of any kind which contain or embody any proprietary or confidential information of the Company, and all reproductions thereof in whole or in part and in any medium. You further agree that you
will make a diligent search to locate any such documents, property and information and return them to the Company within the timeframe provided above. In addition, if you have used any personally-owned computer, server, or e-mail system to receive,
store, review, prepare or transmit any confidential or proprietary data, materials or information of the Company, then within five (5) days after your Separation from Service date you must provide the Company with a computer-useable copy of
such information and permanently delete and expunge such confidential or proprietary information from those systems without retaining any reproductions (in whole or in part); and you agree to provide the Company access to your system, as requested,
to verify that the necessary copying and deletion is done. If requested, you shall deliver to the Company a signed statement certifying compliance with this section prior to the receipt of the Severance Benefits. 

  
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 12. Outside Activities. During your employment by the Company, except on behalf of the Company, you will
not directly or indirectly serve as an officer, director, stockholder, employee, partner, proprietor, investor, joint venturer, associate, representative or consultant of any other person, corporation, firm, partnership or other entity whatsoever
known by you to compete with the Company (or is planning or preparing to compete with the Company), anywhere in the world, in any line of business engaged in (or planned to be engaged in) by the Company; provided, however, that you may purchase or
otherwise acquire up to (but not more than) one percent (1%) of any class of securities of any enterprise (but without participating in the activities of such enterprise) if such securities are listed on any national or regional securities
exchange. 
 13. Definitions. For purposes of this Agreement, the following terms shall have the following meanings: 

For purposes of this Agreement, “Cause” for termination will mean your: (a) conviction (including a guilty plea or plea of nolo
contendere) of any felony; (b) commission or attempted commission of or participation in a fraud or act of dishonesty or misrepresentation against the Company; (c) willful and continued failure to follow the lawful directions of the Board
or the officers of the Company to whom you report, and failure to cure such failure within a reasonable time after receiving written notice from the Company of the claimed failure; (d) deliberate harm or injury, or attempt to deliberately harm
or injure, the Company; (e) willful misconduct that materially discredits or harms the Company or its reputation; (f) material violation or breach of any written and fully executed contract or agreement between you and the Company,
including without limitation, material breach of your Confidentiality Agreement, or of any Company policy, or of any statutory duty you owe to the Company; (g) gross negligence or willful misconduct; (h) failure to cooperate with any
investigation as requested by the Board or officers of the Company to whom you report or (i) unauthorized use of confidential information that causes material harm to the Company. The determination that a termination is for Cause shall be made
by the Company in its sole discretion. 
 For purposes of this Agreement, you shall have “Good Reason” for resigning from employment with
the Company if any of the following actions are taken by the Company without your prior written consent: (a) a material reduction in your base salary or target annual bonus (unless pursuant to a salary reduction program applicable
generally to the Company’s similarly situated employees); (b) a material reduction in your duties (including responsibilities and/or authorities), provided, however, that a change in job position (including a change in title or
change resulting from a Change in Control transaction) shall not be deemed a “material reduction” in and of itself unless your new duties are materially reduced from the prior duties; or (c) relocation of your principal place of
employment to a place that increases your one-way commute by more than thirty-five (35) miles as compared to your then-current principal place of employment immediately prior to such relocation. In order to resign for Good Reason, you must
provide written notice to the Company’s Chief Legal Officer within 90 days after the first occurrence of the event giving rise to Good Reason setting forth the basis for your resignation, allow the Company at least 30 days from receipt of such
written notice to cure such event, and if such event is not reasonably cured within such period, you must resign from all positions you then hold with the Company not later than 30 days after the expiration of the cure period. 

For purposes of this Agreement, “Change in Control” shall have the meaning ascribed to such term in the Stitch Fix, Inc. 2017 Incentive Plan,
as it may be amended from time to time. 
 14. Compliance with Section 409A. It is intended that the Severance Benefits set forth in this
Agreement satisfy, to the greatest extent possible, the exemptions from the application of Section 409A of the Internal Revenue Code of 1986, as amended, (the “Code”) (Section 409A, together with any state law of similar
effect, “Section 409A”) provided under Treasury Regulations 1.409A-1(b)(4), 1.409A-1(b)(5) and 1.409A-1(b)(9). For purposes of Section 409A (including, without limitation, for purposes of
Treasury Regulations 1.409A-2(b)(2)(iii)), your right to receive any installment payments under this Agreement (whether severance payments, reimbursements or otherwise) shall be treated as a right to receive a series of separate payments and,
accordingly, 

  
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each installment payment hereunder shall at all times be considered a separate and distinct payment. Notwithstanding any provision to the contrary in this Agreement, if the Company (or, if
applicable, the successor entity thereto) determines that any of the Severance Benefits constitute “deferred compensation” under Section 409A and you are, on the date of your Separation from Service, a “specified employee”
of the Company or any successor entity thereto, as such term is defined in Section 409A(a)(2)(B)(i) of the Code (a “Specified Employee”), then, solely to the extent necessary to avoid the incurrence of adverse personal tax
consequences under Section 409A, the timing of such Severance Benefits shall be delayed until the earliest of: (i) the date that is six (6) months and one (1) day after your Separation from Service date, (ii) the date of
your death, or (iii) such earlier date as permitted under Section 409A without the imposition of adverse taxation. Upon the first business day following the expiration of such applicable Code Section 409A(a)(2)(B)(i) period, all
payments or benefits deferred pursuant to this section shall be paid in a lump sum or provided in full by the Company (or the successor entity thereto, as applicable), and any remaining payments due shall be paid as otherwise provided herein. No
interest shall be due on any amounts so deferred. If any of the Severance Benefits are not covered by one or more exemptions from the application of Section 409A and the Release could become effective in the calendar year following the calendar
year in which you have a Separation from Service, the Release will not be deemed effective any earlier than the Release Deadline. The Severance Benefits are intended to qualify for an exemption from application of Section 409A or comply with
its requirements to the extent necessary to avoid adverse personal tax consequences under Section 409A, and any ambiguities herein shall be interpreted accordingly. Notwithstanding anything to the contrary herein, to the extent required to
comply with Section 409A, a termination of employment shall not be deemed to have occurred for purposes of any provision of this Agreement providing for the payment of amounts or benefits upon or following a termination of employment unless
such termination is also a “separation from service” within the meaning of Section 409A. With respect to reimbursements or in-kind benefits provided to you hereunder (or otherwise) that are not exempt from Section 409A, the
following rules shall apply: (i) the amount of expenses eligible for reimbursement, or in-kind benefits provided, during any one of your taxable years shall not affect the expenses eligible for reimbursement, or in-kind benefit to be provided
in any other taxable year, (ii) in the case of any reimbursements of eligible expenses, reimbursement shall be made on or before the last day of your taxable year following the taxable year in which the expense was incurred, (iii) the
right to reimbursement or in-kind benefits shall not be subject to liquidation or exchange for another benefit. If the Company’s ability to choose between a lump sum severance payment or a series of severance payments could subject you to
adverse taxation under Section 409A, then such severance payments shall be paid in installments in the case of payments under Section 8(a)(1), and in a lump sum in the case of payments under Section 8(b)(1); provided, however,
that if this difference in default treatment would subject you to adverse taxation under Section 409A, then such severance payments shall be made in a lump sum in the case of payments under Section 8(a)(1) or 8(b)(1). 

15. Section 280G; Parachute Payments. 

(a) If any payment or benefit you will or may receive from the Company or otherwise (a “280G Payment”) would
(i) constitute a “parachute payment” within the meaning of Section 280G of the Code, and (ii) but for this sentence, be subject to the excise tax imposed by Section 4999 of the Code (the “Excise Tax”),
then any such 280G Payment provided pursuant to this Agreement (a “Payment”) shall be equal to the Reduced Amount. The “Reduced Amount” shall be either (x) the largest portion of the Payment that would result in no
portion of the Payment (after reduction) being subject to the Excise Tax or (y) the largest portion, up to and including the total, of the Payment, whichever amount (i.e., the amount determined by clause (x) or by clause (y)), after taking
into account all applicable federal, state and local employment taxes, income taxes, and the Excise Tax (all computed at the highest applicable marginal rate), results in your receipt, on an after-tax basis, of the greater economic benefit
notwithstanding that all or some portion of the Payment may be subject to the Excise Tax. If a reduction in a Payment is required pursuant to the preceding sentence and the Reduced Amount is determined pursuant to clause (x) of the preceding
sentence, the reduction shall occur in the manner (the “Reduction Method”) that results in the greatest economic benefit for you. If more than one method of reduction will result in the same economic benefit, the items so reduced
will be reduced pro rata (the “Pro Rata Reduction Method”). 

  
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 (b) Notwithstanding any provision of subsection (a) above to the contrary, if the
Reduction Method or the Pro Rata Reduction Method would result in any portion of the Payment being subject to taxes pursuant to Section 409A that would not otherwise be subject to taxes pursuant to Section 409A, then the Reduction Method
and/or the Pro Rata Reduction Method, as the case may be, shall be modified so as to avoid the imposition of taxes pursuant to Section 409A as follows: (A) as a first priority, the modification shall preserve to the greatest extent
possible, the greatest economic benefit for you as determined on an after-tax basis; (B) as a second priority, Payments that are contingent on future events (e.g., being terminated without Cause), shall be reduced (or eliminated) before
Payments that are not contingent on future events; and (C) as a third priority, Payments that are “deferred compensation” within the meaning of Section 409A shall be reduced (or eliminated) before Payments that are not deferred
compensation within the meaning of Section 409A. 
 (c) Unless you and the Company agree on an alternative accounting firm or
law firm, the accounting firm engaged by the Company for general tax compliance purposes as of the day prior to the effective date of the Change in Control transaction shall perform the foregoing calculations. If the accounting firm so engaged by
the Company is serving as accountant or auditor for the individual, entity or group effecting the change in control transaction, the Company shall appoint a nationally recognized accounting or law firm to make the determinations required by this
Section 15 (“Section 280G; Parachute Payments”). The Company shall bear all expenses with respect to the determinations by such accounting or law firm required to be made hereunder. The Company shall use commercially reasonable
efforts to cause the accounting or law firm engaged to make the determinations hereunder to provide its calculations, together with detailed supporting documentation, to you and the Company within fifteen (15) calendar days after the date on
which your right to a 280G Payment becomes reasonably likely to occur (if requested at that time by you or the Company) or such other time as requested by you or the Company. 

(d) If you receive a Payment for which the Reduced Amount was determined pursuant to clause (x) of Section 15(a) and the
Internal Revenue Service determines thereafter that some portion of the Payment is subject to the Excise Tax, you agree to promptly return to the Company a sufficient amount of the Payment (after reduction pursuant to clause (x) of
Section 15(a)) so that no portion of the remaining Payment is subject to the Excise Tax. For the avoidance of doubt, if the Reduced Amount was determined pursuant to clause (y) of Section 15(a), you shall have no obligation to return
any portion of the Payment pursuant to the preceding sentence. 
 16. Dispute Resolution. To ensure the timely and economical resolution of disputes
that may arise in connection with your employment with the Company, you and the Company agree that any and all disputes, claims, or causes of action arising from or relating to the enforcement, breach, performance, negotiation, execution, or
interpretation of this Agreement, your employment, or the termination of your employment, including but not limited to statutory claims, will be resolved to the fullest extent permitted by law by final, binding and confidential arbitration, by a
single arbitrator, in San Francisco, California, conducted by JAMS, Inc. (“JAMS”) under the then-applicable JAMS rules (available upon request and also currently available at
http://www.jamsadr.com/rules-employment-arbitration/). By agreeing to this arbitration procedure, both you and the Company waive the right to resolve any such dispute through a trial by jury or judge or administrative proceeding. You
will have the right to be represented by legal counsel at any arbitration proceeding. In addition, all claims, disputes, or causes of action under this section, whether by you or the Company, must be brought in an individual capacity, and shall not
be brought as a plaintiff (or claimant) or class member in any purported class or representative proceeding, nor joined or consolidated with the claims of any other person or entity. The Arbitrator may not consolidate the claims of more than one
person or entity, and may not preside over any form of representative or class proceeding. This paragraph shall not apply to an action or claim brought in court pursuant to the California Private Attorneys General Act of 2004, as amended. The
arbitrator shall: (a) have the authority to compel adequate discovery for the resolution of the dispute and to award such relief as would otherwise be permitted by law; and (b) issue a written arbitration decision, to include the
arbitrator’s essential findings and conclusions and a statement of the award. The arbitrator shall be authorized to award any or all remedies that you or the Company would be entitled to seek in a court of law. The Company shall pay all
JAMS’ arbitration fees in excess of the amount of court fees that would be required of you if the dispute were decided in a court of law. Nothing in this letter is intended to prevent either you or the Company from obtaining injunctive relief
in court to prevent irreparable harm pending the conclusion of any such arbitration. Any awards or orders in such arbitrations may be entered and enforced as judgments in the federal and state courts of any competent jurisdiction. 

  
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 17. Miscellaneous. Your employment remains contingent upon satisfactory proof of your identity and right
to work in the United States. This Agreement, together with your Confidentiality Agreement, forms the complete and exclusive statement of your employment agreement with the Company. It supersedes any other agreements or promises made to you by
anyone, whether oral or written (including without limitation, the offer letter between you and the Company, dated April 10, 2017, which you agree is hereby superseded and you waive any rights or entitlements you may have under such agreement.
Changes in your employment terms, other than those changes expressly reserved to the Company’s or Board’s discretion in this Agreement, require a written modification approved by the Company and signed by a duly authorized officer of the
Company. This Agreement will bind the heirs, personal representatives, successors and assigns of both you and the Company, and inure to the benefit of both you and the Company, their heirs, successors and assigns. If any provision of this Agreement
is determined to be invalid or unenforceable, in whole or in part, this determination shall not affect any other provision of this Agreement and the provision in question shall be modified so as to be rendered enforceable in a manner consistent with
the intent of the parties insofar as possible under applicable law. This Agreement shall be construed and enforced in accordance with the laws of the State of California without regard to conflicts of law principles. Any ambiguity in this Agreement
shall not be construed against either party as the drafter. Any waiver of a breach of this Agreement, or rights hereunder, shall be in writing and shall not be deemed to be a waiver of any successive breach or rights hereunder. This Agreement may be
executed in counterparts which shall be deemed to be part of one original, and facsimile and electronic image copies of signatures shall be equivalent to original signatures. The Indemnity Agreement between you and the Company, dated June 12,
2017, will remain in full force and effect. 
 Please sign and date this Agreement and return it to me on or before September 12, 2017 if you wish to
accept employment at the Company under the terms described above. This offer will expire if I do not receive this signed letter by that date. I would be happy to discuss any questions that you may have about these terms. 

We are delighted to be making this offer and the Company looks forward to your favorable reply and to a productive and enjoyable work relationship. 

 

	
	Sincerely,
	
	/s/ Katrina Lake
	Katrina Lake, CEO

 Reviewed, Understood, and Accepted: 
  

					
	/s/ Paul Yee	 		 	September 7, 2017
	Paul Yee	 		 	Date

  
 8EX-10.10

 Exhibit 10.10 

February 27, 2015 
 Re.: Offer of Employment 

Dear Julie: 
 I am pleased to offer you a full
time position as Chief Operating Officer with Stitch Fix, Inc. (the “Company”). If you decide to join us, you will receive an annual base salary of $450,000. Your salary will be paid semi-monthly in accordance with the Company’s
normal payroll procedures. 
 As a full time employee, you will be eligible to receive certain employee benefits, including the eligibility
to participate in the Company’s medical, dental and vision insurance plan, subject to the terms and conditions of the applicable benefit plan or policy. The Company reserves its right to modify job titles, salaries and benefits as it deems
necessary and in its sole discretion. You will also be eligible to earn up to 10 business days of paid vacation annually, and be paid for Company holidays, in accordance with the vacation and holiday policies. If you work in San Francisco, you may
be eligible for certain benefits required by local law, including paid sick leave, health care security and commuter benefits. Please see the Company policies for employees working in San Francisco for more details. 

If you decide to join us, it will be recommended at the first meeting of the Company’s Board of Directors following your start date that
the Company grants you an incentive option to purchase 852,069 shares of the Company’s common stock (the “Option”). Subject to Company’s Board of Directors’ approval, you will be granted such stock option in accordance with
the Company’s 2011 Equity Incentive Plan (the “Plan”) and related option documents. You will be required to sign the applicable Stock Option agreement (“the Agreement”) and the options will be subject to the terms and
conditions of the Plan and the Agreement. The exercise price per share will be equal to the fair market value per share on the date the Option is granted, as determined by the Company’s Board of Directors. Twenty-five (25%) of the shares
subject to the Option shall vest upon completion of a twelve month employment at the Company and the remaining shares subject to the Option shall vest in equal monthly installments over the next thirty-six months subject to your continued service
with the Company through each vesting date, as described in the applicable option agreement. No right to any equity is earned or accrued until such time that vesting occurs, nor does the grant confer any right to continued vesting or employment.

 The Company is excited about you joining and looks forward to a beneficial and productive relationship. Nevertheless, you should be aware
that your employment with the Company is for no specified period and constitutes at-will employment. As a result, you are free to resign at any time, for any reason or for no reason. Similarly, the Company is free to conclude its employment
relationship with you at any time, with or without cause, and with or without notice. The at will employment relationship between you and the Company may not be changed, except by a specific written agreement signed by the President of the Company.
We request that, in the event of resignation, you give the Company at least two (2) weeks’ notice. 
 This offer of employment is
conditioned upon the following: 
 a. The Company reserves the right to conduct background investigations and/or reference
checks on all of its potential employees. If we do conduct a background check using an outside agency, you will be provided a disclosure and authorization form and a notice of your rights, as applicable. This job offer is contingent upon our receipt
of satisfactory results from such a background investigation and/or reference check, if any. 

 b. For purposes of federal immigration law compliance, you will be required to
provide to the Company appropriate evidence of your identity and eligibility for employment in the United States. Such documentation must be provided to us within three (3) business days of your date of hire, or our employment relationship with
you may be terminated. 
 c. You will be required to sign an acknowledgment that you have read and will comply with the
Company’s rules of conduct, which are included in the Company Employee Handbook. As a Company employee, you will be required to abide by all Company policies and directives. 

d. You are required to sign and comply with an At-Will Employment, Confidential Information, Invention Assignment and
Arbitration Agreement, a copy of which is included with this letter. Please note that we must receive your signed agreement within the first three business days of employment. 

We also ask that, if you have not already done so, you disclose to the Company any and all agreements relating to your prior employment that
may affect your eligibility to be employed by the Company or limit the manner in which you may be employed. By signing this offer letter, you represent that you are not party to any agreements that prevent you from performing the duties of the
position for which you are being hired by the Company. Moreover, you agree that, during your employment with the Company, you will not engage in any other employment, occupation, consulting or other business activity directly related to the business
in which the Company is now involved or becomes involved during the term of your employment, nor will you engage in any other activities that conflict with your obligations to the Company. Similarly, you agree that except as authorized by the owner
of the information, you will not provide any third party confidential information to the Company, including that which belongs to your former employer, and that in performing your duties for the Company you will not in any way utilize any such
information. 
 This letter, along with the At-Will Employment, Confidential Information, Invention Assignment and Arbitration Agreement and
Company’s 2011 Equity Incentive Plan and Stock Option agreement, sets forth the entire terms of your employment with the Company, and supersedes any prior representations or agreements including, any representations made during your
recruitment, interviews and pre-employment negotiations, whether written or oral. The terms of employment stated in this letter, including the at-will employment provision, may not be modified or amended except by a specific written agreement signed
by the President of the Company and you. This offer of employment will terminate if it is not accepted, signed and returned by Wednesday, March 4, 2015. 

To accept the Company’s offer, please sign and date this letter in the space provided below. If you accept our offer, your first day of
employment will be April 20, 2015. 
 We look forward to your favorable reply and to working with you at the Company. 

 

	
	Sincerely,
	
	/s/ Katrina Lake
	 Katrina Lake
 CEO

 ****************************** 

I have read the offer letter, above, in its entirety and accept employment with Stitch Fix, Inc. on the terms and conditions stated above. I agree that I am
employed by Stitch Fix, Inc. on an at will employment basis, and that my at will employment relationship may not be changed except by a specific written agreement signed by the President of Stitch Fix, Inc. and me. 

Agreed to and accepted: 
  

			
	Signature:	 	/s/ Julie Bornstein

  

			
	Name:	 	Julie Bornstein

  

			
	Date:	 	3/12/15

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