Document:

EX-10.9

 Exhibit 10.9 

Execution Copy 
 AMENDED
AND RESTATED EMPLOYMENT AGREEMENT 
 This Amended and Restated Employment Agreement (this “Agreement”), entered
into as of March 30, 2015 (the “Signing Date”), between JJill Topco Holdings, LP (the “Parent”), and PAULA BENNETT (“Executive” and, together with Parent, the
“Parties”), amends and restates in its entirety, effective as of the Effective Date (defined below), that certain employment agreement dated March 30, 2012, by and among Jill Intermediate LLC (“Jill
Intermediate”), Jill Acquisition LLC (the “Company”), and Executive (the “Prior Agreement”). In addition, JJ Holdings GP, LLC (“Parent GP”), and JJill Holdings, Inc.
(“Buyer”), each join this Agreement, and Parent shall cause Jill Intermediate to join this Agreement as soon as practicable following the Effective Date (as defined below), and shall be Parties hereto, for the limited purposes
set forth in paragraph 22. As soon as practicable following the Effective Date, Parent shall cause the Company to join this Agreement and become a Party hereto. 

RECITALS 
 WHEREAS,
pursuant to the Membership Interest Purchase Agreement entered into on the Signing Date, by and among Buyer, Jill Intermediate, the members of Jill Intermediate and JJ Holding Company Limited (the “Purchase Agreement”), the parties
to the Purchase Agreement have agreed to consummate the transactions set forth therein, upon the terms and subject to the conditions of the Purchase Agreement (the “Transaction”); 

WHEREAS, in connection with the execution and delivery of the Purchase Agreement, the Parties wish to enter into this Agreement to
amend and restate the Prior Agreement to, among other things, set forth the terms and conditions of Executive’s continued employment with the Company commencing on the date on which the Transaction closes (the “Effective
Date”), including, without limitation, the terms and conditions of Executive’s retirement from the Company, which the Parties anticipate will occur at some time during the period of Parent’s indirect ownership of the Company; 

WHEREAS, to secure Executive’s skills and services, for the benefit of Parent GP, Parent, the Company, and their respective direct
or indirect subsidiaries, whether existing on the Effective Date or thereafter acquired or formed (collectively, the “J.Jill Companies”), the Company desires to continue to employ Executive and Executive desires to accept such
continued employment with the Company and to provide such skills and services to the J.Jill Companies, on the terms and conditions set forth herein; and 

WHEREAS, the Prior Agreement shall continue to govern the terms of Executive’s employment with the Company and Jill Intermediate
through the date immediately preceding the Effective Date. 
 NOW, THEREFORE, in consideration of the mutual promises, terms,
covenants, and conditions set forth in this Agreement, and the performance of each, the 

 
Parties, and for the limited purposes set forth herein, Parent, Parent GP, and Jill Intermediate, intending to be legally bound, agree as follows: 

AGREEMENTS 

1.    Term. The term of this Agreement shall begin on the Effective Date and shall continue until
Executive’s employment with the Company ends in accordance with paragraph 6 below (such period, the “Term”). In the event that the Transaction does not close, this Agreement shall automatically terminate, and cease to have
any further force or effect, on the date on which the Purchase Agreement terminates in accordance with its terms, and in such event, notwithstanding anything contained herein, no party hereto shall have any liability or obligation hereunder. 

2.    Position and Duties. 

(a)    Position and Duties at the Company. During the Term, Executive shall be employed as Chief Executive Officer
(“CEO”) of the Company and, until such time as the Company hires a new President (the “New President”), Executive shall also be employed as President of the Company. During the Term, Executive shall be the
senior-most executive officer of the Company. 
 (b)    Position and Duties at the Parent and Intermediary
Entities. During the Term until such time as either (x) the Parent is no longer the ultimate parent of the Company (or the successor to the Company’s business) as the result of an Approved Partnership Sale (as such term is defined in
that certain Amended and Restated Agreement of Limited Partnership of Parent to be executed by the parties thereto in the form attached hereto, as such may be further amended from time to time in accordance therewith (the “Parent
LPA”)) or (y) as a result of a Public Offering (as such term is defined in the Parent LPA), the equity securities of the Buyer or any of its subsidiaries or successors become listed on an established securities market (such entity
whose securities become listed, the “IPO Entity”) (either of (x) and (y), a “Parent Separation”), Executive shall serve as the CEO and the senior-most executive officer of Parent and, prior to a Parent
Separation, any intermediary entities between the Company and the Parent, and until a New President is hired by Parent, Executive shall serve as President of Parent and any intermediary entities between the Company and the Parent, including, without
limitation, the Buyer. In all events, during the Term and on or following a Public Offering, Executive shall be the CEO and the senior-most executive of the IPO Entity. 

(c)    Reporting and Board Duties. During the Term, Executive shall serve as a member of, and shall report
directly to, the Board of Directors of Parent GP (the “GP Board”) and, to the extent designated by the GP Board, Executive shall report to the board of directors of Buyer; provided, that following a Parent Separation, Executive
shall cease to be a member of the GP Board and shall report solely to the board of directors of the Company and, if applicable, its ultimate parent company; provided, further that following a Public Offering during the Term, Executive shall also be
nominated for election as a member of, and shall report directly to, the board of directors of the IPO Entity. As used herein, the term “Board” shall be deemed to refer to the GP 

  
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 Board prior to a Parent Separation and after a Parent Separation, the Company and, if applicable, the ultimate
parent of the Company, including on or after a Public Offering, the board of directors of the IPO Entity. During the Term, the GP Board may also require Executive to serve as a member of the board of directors of Buyer and/or any other subsidiary of
Parent, in each case without additional compensation. 
 (d)    Scope of Duties. During the Term, Executive
shall have such responsibilities, duties, and authorities as are commensurate with the position of CEO and, if applicable, President of a company the size and nature of the Company and as may be assigned by the Board consistent with such positions.
During the Term, all executive officers of the Company and, prior to a Parent Separation, of Parent (including any New President) and any intermediary entities, including, without limitation, the Buyer, and on and after a Parent Separation, the
ultimate parent of the Company (including, if applicable, the IPO Entity), shall report directly to Executive or her designee; provided, however, that Parent, Buyer, and the Company shall each be permitted to hire (i) a Non-Executive Chairman and (ii) a chief legal/compliance officer, each of whom may report directly to the Board or its designee. Executive shall fulfill her duties and responsibilities in a reasonable and
appropriate manner and in compliance with the Company’s policies and practices and applicable law. 

(e)    Standard of Performance. During the Term, Executive shall devote her full business time and attention to
the business and affairs of the J.Jill Companies and shall not be engaged in or employed by or provide services to any other business enterprise without the written approval of the Board; provided, however, that Executive may manage her personal
affairs, finances, and investments, may participate in charitable and not-for-profit activities, and may serve on those industry boards and advisory groups (and retain
any compensation from same) set forth on Annex A attached hereto as of the Signing Date, all without the necessity of obtaining Board approval, and may serve on industry boards and advisory groups not listed on Annex A (and retain any compensation
from same) subject to the Board’s consent (which consent shall not be unreasonably withheld), so long as such service does not create an actual or potential conflict of interest with, or interfere with the performance of, Executive’s
duties hereunder or conflict with Executive’s covenants under paragraph 7, 8 or 10 of this Agreement, in each case as determined in the sole judgment of the Board. 

3.    Compensation. For all services rendered by Executive (including her agreement to the covenants
contained in paragraphs 7(b)-(d) through 10 of this Agreement), the Company shall compensate Executive as follows: 

(a)    Base Salary. As of the Effective Date, the gross annual salary payable to Executive shall be Seven Hundred
Thousand Dollars ($700,000.00) per year, which shall be paid in substantially equal installments on a regular basis in accordance with the Company’s standard payroll procedures, but not less than monthly (the “Base Salary”).
During the Term, the Base Salary shall be reviewed by the Board (or the appropriate committee of the Board) annually at the same time as other executive reviews and shall be subject to increase (but not decrease) by the Board (or the appropriate
committee of the Board) in its discretion. After any such increase, “Base Salary” for purposes of this Agreement shall mean such increased amount. 

  
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 (b)    Annual Bonus. For all of 2015 (without proration) and
subsequent fiscal years ending during the Term, Executive shall be eligible for an annual bonus as set forth herein (the “Annual Bonus”). The Annual Bonus shall be determined by the Board based upon the Company’s achievement of
financial and other goals to be determined annually by the Board, in consultation with Executive, which goals shall, except as otherwise agreed by the Board and Executive, apply for all senior executives of the Company who are participants in the
Annual Bonus plan. For 2015, the Annual Bonus shall be determined based on the EBITDA goals already approved by the board of directors of Jill Intermediate and/or the Company prior to the Signing Date, including the amount of the Annual Bonus
achievable based on actual results in comparison to the targets. Executive’s target Annual Bonus shall be equal to one hundred percent (100%) of Executive’s Base Salary (the “Target Bonus”), and if all performance
objectives for the applicable performance year are obtained or exceeded, the Executive shall receive no less than the Target Bonus. In addition, Executive shall have an opportunity under the terms of the Annual Bonus to receive an Annual Bonus in
excess of the Target Bonus as set forth in the applicable Annual Bonus plan. Executive’s target bonus opportunity as a percentage of Base Salary shall be reviewed by the Board (or the appropriate committee of the Board) annually at the same
time as the review of Executive’s Base Salary and shall be subject to increase (but not decrease) by the Board (or the appropriate committee of the Board) in its discretion. After any such increase, “Target Bonus” for
purposes of this Agreement shall mean such increased amount. The Annual Bonus awarded for a fiscal year shall be determined by the Board after the end of such fiscal year and shall be paid in cash and in accordance with the Company’s customary
practices for payment of annual bonuses to senior executive employees in the calendar year following, and not within, the fiscal year for which the Annual Bonus is earned, but in all events no later than the earlier of (i) seventy-five
(75) days after the later of (x) the close of the fiscal year for which the Annual Bonus was earned and (y) the completion of such fiscal year’s financial audit or (ii) April 15 of such calendar year; provided, however,
that except as otherwise provided in this Agreement, Executive must be employed through the end of the applicable fiscal year to be entitled to receive the Annual Bonus. 

(c)    Benefits and Perquisites. During the Term, Executive shall be entitled to participate in the employee
benefit plans and programs of the Company in accordance with the terms of such plans and programs and shall be entitled to the same perquisites as are made available to other senior executive employees of the Company. 

(d)    Vacation. During the Term, Executive shall be entitled to not less than four (4) weeks of paid
vacation during each calendar year (pro-rated for any partial calendar year of employment) in accordance with the Company’s policies and practices for senior executive employees of the Company. 

(e)    Class A Common Units. As of the Effective Date, Executive shall be entitled to receive an
allocation of Class A Common Units of Parent pursuant to a Grant Agreement in the form attached hereto and the Parent agrees to execute such Grant Agreement as of the Effective Date (the “Grant Agreement”). 

  
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 4.    Expense Reimbursement. During the Term, the
Company shall reimburse Executive for (or, at the Company’s option, pay) all business travel and other out-of-pocket expenses reasonably incurred by Executive in
the performance of her duties under this Agreement. All reimbursable expenses shall be appropriately documented by Executive upon submission of any request for reimbursement in a manner consistent with the Company’s expense reporting policies
and applicable federal and state tax recordkeeping requirements. The amount of expenses eligible for reimbursement during any taxable year of Executive under this Agreement will not affect the expenses eligible for reimbursement in any other taxable
year of Executive, and Executive’s right to reimbursement of expenses is not subject to liquidation or exchange for another benefit. The Company shall also pay directly to the Executive’s counsel the legal fees incurred in connection with
the review of this Agreement, its Exhibits and related documentation, subject to a cap of $25,000. 
 5.    Place
of Performance. During the Term, Executive shall carry out her duties and responsibilities under this Agreement principally in and from the Company’s offices in the Quincy, Massachusetts, area. Executive understands that her
position will involve substantial travel and agrees to undertake such travel as may be necessary or desirable in the performance of her duties and responsibilities under this Agreement. 

6.    Termination; Rights on Termination. Executive’s employment and the Term may be ended in
any one of the ways set forth in sub-paragraphs 6(a)-6(e). Except as otherwise may be agreed between the applicable J.Jill Companies and Executive at the time such
employment ends, upon Executive’s separation from employment with the Company she shall be deemed to have resigned from any and all offices and directorships she then holds relating to any J.Jill Company and, if requested by the Company,
Executive shall deliver written instruments of resignation evidencing such resignations. 
 (a)    Termination by
the Company for Cause. The Board may terminate the Term and Executive’s employment hereunder for Cause (as defined below) effective immediately upon provision of notice to Executive that her employment has been terminated for Cause, subject
to any applicable cure periods described below; provided that any termination for Cause after the consummation a Public Offering shall require a majority vote of the Board. For purposes of this Agreement, “Cause” shall mean any of
the following: (i) Executive’s willful breach of any provision of paragraph 7(b)-(d), 8 or 10 of this Agreement; (ii) Executive’s willful failure to follow a lawful directive of the Board; (iii) Executive’s willful or
gross neglect in the performance or nonperformance of any of her duties or responsibilities hereunder; (iv) Executive’s dishonesty with respect to any material matter arising in the performance of her duties for any J.Jill Company that
results in material injury to the financial condition or business reputation of any J.Jill Company, or Executive’s fraud or willful misconduct in connection with her duties for any J.Jill Company; (v) Executive’s use of alcohol or

  
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 drugs in a manner that materially interferes with the performance of her duties for any J.Jill Company; or
(vi) Executive’s conviction of or plea of no contest to any misdemeanor involving theft, fraud, dishonesty, or act of moral turpitude or to any felony. In the event of a breach or failure described in clauses (i), (ii), (iii), (iv), or
(v) the Board shall provide Executive with notice of the facts and circumstances which constitute such breach or failure and, if curable, shall provide Executive a ten (10) day period in which to cure such breach or failure and shall not
terminate Executive for Cause if Executive cures such breach or failure within such ten (10) day period. In the event that the Term and Executive’s employment hereunder are terminated by the Board for Cause, no compensation or benefits
shall be payable to Executive after the date of such termination, except as provided for in paragraph 6(f)(i). 

(b)    Termination for Executive’s Death or Disability. The Term and Executive’s employment hereunder
shall terminate automatically upon Executive’s death during the Term. If the Disability (as defined herein) of Executive has occurred during the Term, the Company may provide Executive with written notice of the termination of the Term and
Executive’s employment hereunder. In such event, the Term and Executive’s employment hereunder shall terminate effective on the thirtieth (30th) day following receipt of such notice by
Executive. In the event that the Term and Executive’s employment hereunder are terminated due to Executive’s death or Disability, no compensation or benefits shall be payable to Executive or her estate after the date of such termination,
except as provided for in paragraph 6(f)(i). For purposes of this Agreement, “Disability” shall mean either (i) Executive’s inability to perform the essential duties and responsibilities of her position (even with
reasonable accommodation taken into account) by reason of Executive’s mental or physical disability, illness, or impairment that has already lasted for a period of ninety (90) or more days during any twelve (12) month period, or
(ii) Executive’s inability to perform the essential duties and responsibilities of her position (even with reasonable accommodation taken into account) by reason of Executive’s mental or physical disability, illness, or impairment
that can be expected to result in death or that can be expected to last for a period of ninety (90) or more days during any twelve (12) month period, as determined by a physician selected by the Company and reasonably agreeable to
Executive. 
 (c)    Termination due to Mandatory Retirement. At any time during the Term, the Company may,
without Cause and for any reason whatsoever, require Executive to mandatorily retire from her employment with the Company and to terminate the Term hereunder, effective upon the expiration of a notice period of no less than thirty (30) days set
forth in a written notice delivered to Executive by the Company (such termination, a “Mandatory Retirement”); provided, that the notice period stated above may, upon consultation with the Board, be waived by Executive, in which
case such Mandatory Retirement shall be effective immediately upon the Board’s acceptance of Executive’s waiver of the notice period. In the event that the Term and Executive’s employment hereunder are terminated as a result of a
Mandatory Retirement, no compensation or benefits shall be payable to Executive except as provided for in paragraph 6(f)(iii). 

  
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 (d)    Termination by Executive For Good Reason.
Executive may terminate the Term and her employment hereunder for Good Reason (as defined below). “Good Reason” shall mean, without Executive’s prior written consent (i) a material reduction in Executive’s duties
and responsibilities; provided, that Executive hereby acknowledges that the hiring of (x) a President who reports to Executive or her designees and is granted customary duties and responsibilities commensurate with the title of President and/or
(y) a chief legal/compliance officer reporting to the Board shall not constitute Good Reason pursuant to this clause (i); (ii) removal of Executive as CEO or President of the Company or Parent or failure to elect or reelect (or removal of)
Executive as a member of the Board; provided, that neither (x) the hiring by the Company and/or Parent of a New President pursuant to paragraph 2 of this Agreement who reports to Executive, nor (y) the removal of Executive from the GP
Board or, as CEO or the senior-most executive officer of Parent, in each case following a Parent Separation shall constitute Good Reason pursuant to this clause (ii); (iii) a reduction of Base Salary or Target Bonus opportunity;
(iv) Executive’s no longer serving as the senior most executive officer in Parent, or the Company; (v) a change in reporting structure such that Executive no longer reports to the Board; (vi) the failure of any executive officer
of the Company or Parent, other than the chief legal/compliance officer, to report directly to Executive or her designee; (vii) a material breach of the Grant Agreement by Parent, (viii) the relocation of Executive’s principal work
location outside of the Quincy, Massachusetts, area; (ix) following a Parent Separation, Executive is not the senior-most executive of the entity that directly or indirectly owns 100% of the Company’s securities and/or assets; provided,
however, Executive shall not be entitled to resign for Good Reason unless (A) Executive gives the Board a written statement of the basis for Executive’s belief that Good Reason exists, (B) such written statement is provided not later
than ninety (90) days after the later of Executive’s knowledge of the existence of the condition that Executive believes forms the basis for resignation for Good Reason or the occurrence of such condition (which for any event that has a
materiality standard shall be measured from the last event giving rise to the event(s) being material), (C) Executive gives the Board at least thirty (30) days after receipt of such written statement to cure the basis for such belief (the
“Cure Period”), and (D) the Board does not cure the basis for such belief within the Cure Period. In the event that the Term and Executive’s employment hereunder are terminated by Executive for Good Reason, no compensation
or benefits shall be payable to Executive except as provided for in paragraph 6(f)(iii). For the avoidance of doubt, Executive hereby acknowledges and agrees that the consummation of the Transaction shall not constitute “Good Reason”
pursuant to the Prior Agreement or this Agreement. 
 (e)    Termination by Executive Without Good Reason or due to
Voluntary Retirement. Executive may resign or terminate her employment hereunder without Good Reason on at least either (i) thirty (30) days’ prior written notice to the Board for any resignation or termination without Good Reason
(other than a Voluntary Retirement) or (ii) six (6) months’ prior written notice to the Board of a Voluntary Retirement; provided, that the notice period stated above may be waived by the Board in its absolute discretion, in which
case, such resignation or termination shall be effective immediately upon the Board’s receipt of notice thereof from Executive. In the event that the Term and Executive’s employment hereunder are terminated by Executive without

  
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 Good Reason (other than a Voluntary Retirement), no compensation or benefits shall be payable to Executive after
the date of such termination, except as provided for in paragraph 6(f)(i). In the event of Executive’s Voluntary Retirement during the Term, no compensation or benefits shall be payable to Executive after the date of such termination, except as
provided for in paragraph 6(f)(ii). For purposes of this Agreement, Executive’s “Voluntary Retirement” shall mean (i) Executive’s voluntary resignation of her employment, other than for Good Reason, on no less than
six (6) months’ prior written notice, to be effective on or after the 30-month anniversary of the Effective Date (or such other earlier date determined by the Board to be Executive’s retirement
date if the Board waives the six (6) month prior notice requirement). 
 (f)    Payments Due Upon
Termination. 
 (i)    Upon a termination of the Term and Executive’s employment hereunder (A) by reason
of Executive’s death, (B) due to Executive’s Disability, (C) by the Company for Cause, or (D) by Executive without Good Reason (and not due to a Voluntary Retirement), Executive (or her estate, if applicable) shall be
entitled to receive (1) any Base Salary payable to Executive pursuant to paragraph 3(a) of this Agreement, accrued up to and including the date on which Executive’s employment is terminated, less required statutory deductions, paid in
accordance with the Company’s standard payroll procedures; (2) any payments, benefits and rights under any employee benefit and equity plans, programs or agreements of any J.Jill Company to which Executive is entitled upon termination of
her employment with the Company (including, without limitation, under this Agreement, but excluding any benefit plans or programs providing for cash severance benefits, or the Grant Agreement), in accordance with the terms and conditions of the
applicable employee benefit or equity plans, programs or agreements of any J.Jill Company; (3) reimbursement for any unreimbursed business expenses under paragraph 4 of this Agreement incurred by Executive prior to her date of termination, paid
in accordance with the Company’s reimbursement policies and procedures; (4) except in the case of Executive’s termination for Cause, payment of any unpaid Annual Bonus earned for any fiscal year which has been completed prior to
Executive’s date of termination, paid in accordance with paragraph 3(b) of this Agreement; and (5) continuation of any rights Executive may have under paragraph 18 of this Agreement in accordance with such paragraph (collectively, the
“Accrued Obligations”). For the avoidance of doubt, upon termination of Executive’s employment for any reason, Executive’s rights with respect to her equity interests in the Parent (or any successor thereto) shall be
governed by the terms of the Grant Agreement and Parent LPA, as applicable. 
 (ii)    Upon a termination of the Term
and Executive’s employment hereunder due to Executive’s Voluntary Retirement, and provided that Executive satisfies the requirements set forth in paragraph 6(g) of this Agreement, Executive shall be entitled to receive (1) the Accrued
Obligations, and (2) payment of any Annual Bonus for the fiscal year of such termination, prorated based on the number of days Executive was actively employed by the Company during such fiscal year and determined as if Executive had remained
actively employed through the payment date (with any personal non-financial performance goals deemed to be achieved at 100%), payable at the time any such Annual Bonus would otherwise be paid in accordance
with paragraph 3(b) of this Agreement. 

  
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 (iii)    In the event that the Term and Executive’s employment
hereunder are terminated due to Mandatory Retirement or by Executive for Good Reason, and provided that Executive satisfies the requirements set forth in paragraph 6(g) of this Agreement, then Executive shall be paid or be entitled to receive the
Accrued Obligations, and (1) an Annual Bonus for the year of termination based on the actual bonus Executive would have received had she remained employed for the full performance period and through the date of payment (with any personal non-financial performance goals deemed achieved at 100%), payable in accordance with paragraph 3(b) of this Agreement, and (2) to the extent that such termination occurs prior to the 30-month anniversary of the Effective Date, (A) continued payment of Executive’s Base Salary during the eighteen (18) month period after the effective date of such termination (such period, the
“Continuation Period”), and (B) during the Continuation Period, or, if shorter, until coverage is obtained from another employer (which coverage Executive shall promptly disclose to the Company), to the extent permitted by
applicable law, Executive shall also receive a continuation of the medical and dental coverage to which Executive was entitled under paragraph 3(c) immediately prior to such termination (including dependent coverage), at the same premium cost to
Executive as determined immediately prior to such termination; provided, that any right Executive has to COBRA under Employer’s group health plan will run concurrently with the continuation of coverage provided herein, and, provided further,
that any Company-paid premiums shall be reported as taxable income to Executive. Notwithstanding the foregoing, Executive shall not be entitled to the amounts and benefits set forth in clauses (1) and (2) above following a Mandatory Retirement
or termination by Executive for Good Reason if in connection with such retirement or termination of employment, Parent GP and Executive enter into a written agreement memorializing the terms of Executive’s continued GP Board service,
except as may expressly be provided in such agreement. 
 (g)    Post-Employment Covenants; Release.
Notwithstanding any provision of this Agreement to the contrary, the payment of any amount or provision of any benefit pursuant to paragraph 6(f)(ii) or 6(f)(iii) of this Agreement (other than items (1), (2), (3), and (5) set forth in the
definition of Accrued Obligations) (collectively, the “Severance Benefits”) shall be conditioned upon (i) Executive’s not violating any of her obligations under paragraph 7(b)-(d), 8(d) or 10 of this Agreement,
(ii) Executive’s not materially violating any of her obligations under paragraph 8(c) or 9 of this Agreement, (iii) Executive’s execution, delivery to the Board, and non-revocation of a
general release of the J.Jill Companies and their respective affiliates and their respective employees, officers, directors, owners and members from any and all claims, obligations and liabilities of any kind whatsoever, including, without
limitation, those arising from or in connection with Executive’s employment or termination of employment with the Company, Executive’s service as a director or officer of any J.Jill Company or removal therefrom, or this Agreement
(including, without limitation, civil rights claims), in the form attached hereto (modified as necessary to conform to then-existing legal requirements) (the “Release”), and (iv) the expiration of any revocation period
contained in such Release; provided, that Executive shall not be treated as incurring a violation 

  
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 described in clause (i) or (ii) above unless the Company provides Executive with written notice of the facts
and circumstances that constitute such violation and, if curable, provides Executive a ten (10) day period in which to cure such violation and such violation is not cured within such ten (10) day period. If Executive fails to execute the
Release in a timely manner so as to permit any revocation period to expire prior to the end of the sixty (60) day period immediately following Executive’s termination of employment, or timely revokes her acceptance of such Release
following its execution, Executive shall not be entitled to any of the Severance Benefits. Further, to the extent that any of the Severance Benefits constitutes “nonqualified deferred compensation” for purposes of Section 409A of the
Internal Revenue Code of 1986, as amended (the “Code”), any payment of any amount or provision of any benefit otherwise scheduled to occur prior to the sixtieth (60th) day following the date of Executive’s termination of
employment hereunder, but for the condition on executing the Release as set forth herein, shall not be made until the first regularly scheduled payroll date following such sixtieth (60th) day, after which any remaining Severance Benefits shall
thereafter be provided to Executive according to the applicable schedule set forth herein. 
 (h)    Provisions that
Survive Termination or Expiration of Agreement. All rights and obligations of the Parties under this Agreement shall cease as of the effective date of termination of Executive’s employment under this Agreement, except that (i) the
Company’s obligations under paragraphs 6, 17 and 18 of this Agreement, (ii) Buyer’s, Parent’s, and Parent GP’s obligations under paragraphs 6(k) and 18 of this Agreement and the Parent’s obligations under the Grant
Agreement, and (iii) Executive’s obligations under paragraphs 7(b)-(d), 8, 9, 10, 16 and 17 of this Agreement shall, in each of clauses (i), (ii), and (iii) above, survive such termination in accordance with their terms. 

(i)    No Mitigation; Right to Offset. In the event of any termination of Executive’s employment under this
Agreement for any reason, Executive shall not be under any duty to mitigate damages by seeking subsequent employment, and the Company’s obligation to make any payments hereunder shall not be subject to offset for any reason other than for any
debts or expenses that Executive owes to the Company. All payments and benefits payable under this Agreement are gross payments subject to applicable taxes and withholdings. 

(j)    Compliance with Code Section 409A. 

(i)    To the extent this Agreement is subject to Section 409A of the Code
(“Section 409A”), the Parties intend all payments under this Agreement to comply with the requirements of Section 409A, and this Agreement shall, to the extent practical, be operated and administered to effectuate
such intent. In furtherance thereof, if payment or provision of any amount or benefit hereunder at the time specified in this Agreement would subject such amount or benefit to any additional tax under Section 409A, the payment or provision of such
amount or benefit shall be postponed to the earliest commencement date on which the payment or the provision of such amount or benefit could be made without incurring such additional tax (including paying any severance that is delayed in a lump sum
upon the earliest possible payment 

  
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 date which is consistent with Section 409A). In addition, to the extent that any regulations or guidance issued
under Section 409A (after application of the previous provision of this paragraph) would subject Executive to the payment of interest or any additional tax under Section 409A, the Parties agree, to the extent reasonably possible, to amend this
Agreement in order to avoid the imposition of any such interest or additional tax under Section 409A, which amendment shall have the minimum economic effect necessary on Executive and be reasonably determined in good faith by the Parties; provided
however, that the Parties shall not be required to substitute a cash payment for any non-cash benefit herein. 

(ii)    A termination of Executive’s employment shall not be deemed to have occurred for purposes of any provision
of this Agreement providing for the payment of any amounts or benefits that are considered nonqualified deferred compensation under Section 409A upon or following a termination of Executive’s employment, unless such termination is also a
“separation from service” within the meaning of Section 409A and the payment thereof prior to a “separation from service” would violate Section 409A. For purposes of any such provision of this Agreement relating to any such
payments or benefits, references to a “termination,” “termination of employment” or like terms shall mean “separation from service.” 

(iii)    For purposes of Section 409A, Executive’s right to receive any installment payments pursuant to this
Agreement shall be treated as a right to receive a series of separate and distinct payments. Whenever a payment under this Agreement specifies a payment period with reference to a number of days (e.g., “payment shall be made within
thirty (30) days following the date of termination”), the actual date of payment within the specified period shall be within the sole discretion of the Company; provided that if the payment date can fall in one of two calendar years it
shall be paid in the second calendar year. 
 (iv)    With respect to any payment under this Agreement constituting
nonqualified deferred compensation subject to Section 409A, (A) all expenses or other reimbursements provided herein shall be payable in accordance with the Company’s policies in effect from time to time, but in any event shall be made on
or prior to the last day of the taxable year following the taxable year in which such expenses were incurred by Executive; (B) no such reimbursement or expenses eligible for reimbursement in any taxable year shall in any way affect the expenses
eligible for reimbursement in any other taxable year; and (C) the right to reimbursement or in-kind benefits shall not be subject to liquidation or exchange for another benefit. 

(v)    If Executive is deemed on the date of termination to be a “specified employee” within the meaning of
that term under Section 409A, then with regard to any payment or the provision of any benefit under this Agreement that is considered nonqualified deferred compensation under Section 409A payable on account of a “separation from service,”
such payment or benefit shall be made or provided on the first business day following the earlier of (A) the expiration of the six (6)-month period measured from the date of such “separation from service” of Executive, and
(B) the date of Executive’s death (the “Delay Period”). Upon the expiration of the Delay Period, all 

  
 11 

 payments and benefits delayed pursuant to this paragraph 6(j) (whether they would have otherwise been payable in
a single sum or in installments in the absence of such delay) shall be paid or reimbursed to Executive in a lump sum on the first business day following the Delay Period, and any remaining payments and benefits due under this Agreement shall be paid
or provided in accordance with the normal payment dates specified for them herein. 
 (k)    Compliance with Code
Section 280G. If a change in control of Parent, Buyer, or the Company occurs prior to the date on which either Parent’s, Buyer’s, or the Company’s stock becomes publicly traded and if any payments, benefits or entitlements
provided to Executive under this Agreement, its Exhibits or otherwise would constitute a “parachute payment” for purposes of Section 280G of the Code and such payments would be eligible for exemption under Section 280G(b)(5) of the Code,
Parent, Buyer, or the Company, as applicable, agrees to use commercially reasonable efforts to seek the requisite stockholder vote of the payments pursuant to Section 280G of the Code and Executive agrees to cooperate therein. Notwithstanding any
provision of this Agreement to the contrary, if any amounts or benefits to be paid or provided under this Agreement or otherwise would cause payments or benefits (or other compensation) to not be fully deductible by Parent, Buyer, or the Company or
their respective affiliates for federal income tax purposes because of Section 280G of the Code, or any successor provision thereto (or that would subject Executive to the excise tax imposed by Section 4999 of the Code, or any successor
provision thereto), such payments and benefits (and other compensation) will be reduced to the extent necessary such that no portion of such payments or benefits (or other compensation) will be subject to the excise tax imposed by Section 4999
of the Code, or any successor provision thereto; provided, that such a reduction will be made only if, by reason of such reduction, Executive’s net after-tax benefit exceeds the net after-tax benefit she would realize if such reduction were not made. The determination of whether any such payments or benefits to be provided under this Agreement or otherwise would not be so deductible (or whether
Executive would be subject to such excise tax) shall be made at the expense of Parent, Buyer, or the Company, as applicable, if requested by either Executive or Parent, Buyer, or the Company, as applicable, by a firm of independent accountants or a
law firm selected by the Board and reasonably acceptable to Executive. Any such reduction of such payments and benefits (and other compensation) shall be made by reducing the payments and benefits due to Executive under this Agreement or otherwise
in the following order: (i) payments under paragraph 6(f)(iii)(2)(A) of this Agreement, as applicable, in inverse order from the last date of payment, (ii) the payment under paragraph 6(f)(ii)(2) or (f)(iii)(1) as applicable, (iv) all
other payments and benefits under paragraph 6(f)(iii) of this Agreement, as applicable, in inverse order from the last date the payment or benefit is to be paid or provided, (v) payments and benefits under paragraph 6(f)(i)(4) of this
Agreement, and (vi) any other payments and benefits due to Executive that constitute a “parachute payment” for purposes of Section 280G of the Code, with any cash payments being reduced first before any
non-cash payments in inverse order from the last date of payment. 

  
 12 

 7.    Executive Covenants. 

(a)    The Parties acknowledge and agree that during her employment with the J.Jill Companies, she will perform each of
the following duties except as otherwise set forth herein: (1) have the primary duty of managing the day-to-day operations of the J.Jill Companies;
(2) customarily and regularly direct the work of all executives of the J.Jill Companies (including the New President); and (3) have the authority to hire or fire other employees of the Company or have particular weight given to her
suggestions and recommendations as to the hiring, firing, advancement, promotion, or any other change of status of other employees of the Company. Executive further acknowledges and agrees that by reason of the J.Jill Companies’ investment of
time, training, money, trust, exposure to the public, or exposure to customers, vendors, or other business relationships, she will gain (1) a high level of notoriety, fame, reputation, or public persona as the J.Jill Companies’
representative or spokesperson, or (2) a high level of influence or credibility with the J.Jill Companies’ respective customers, vendors, or other business relationships. Executive further acknowledges and agrees that she will be
intimately involved in the planning for or direction of the business of the J.Jill Companies, and that she has or will obtain selective or specialized skills, knowledge, abilities, or customer contacts or information by reason of working for the
J.Jill Companies. 
 (b)    During Executive’s employment with the J.Jill Companies and for a period of eighteen
(18) months thereafter (the “Noncompetition Restricted Period”), Executive shall not, either directly or indirectly, for herself or on behalf of or in conjunction with any other person, company, partnership, corporation,
business, group, or other entity (each, a “Person”) engage, within the Territory (as described below), as an officer, director, owner, partner, member, joint venturer, or in a managerial capacity (whether as an employee, independent
contractor, agent, representative, or consultant), in any business engaged in the Business of the J.Jill Companies (as defined below). 

(c)    During Executive’s employment with the J.Jill Companies and for a period of twenty-four (24) months
thereafter (the “Nonsolicitation Restricted Period”), Executive shall not, either directly or indirectly, for herself or on behalf of or in conjunction with any Person, cause any Person to solicit or attempt to solicit, recruit or
attempt to recruit, any employee or contract worker of the Company or any employee of the Associated Companies (as defined below) with whom Executive had material business contact during the course of her employment with the J.Jill Companies to end
his or her relationship with the J.Jill Companies. 
 (d)    In addition, in furtherance of the Company’s
reasonable efforts to safeguard Confidential Information (defined below), Executive agrees that, during Executive’s employment with the J.Jill Companies and during the Noncompetition Restricted Period, Executive shall not serve as a council
member or participate in any similar capacity for Gerson Lehrman Group, Inc., Coleman Research, GuidePoint Global, or any other firm the primary purpose of which is to connect its clients with executives or industry specialists (whether through in-person meetings, telephone conversations, on-line forums or other mediums) as a means for its clients to conduct primary research on a particular company, industry or
business sector. 

  
 13 

 (e)    For purposes of paragraphs 7 through 10: 

(i)    The “Territory” shall be defined as the United States of America and any other territory where
Executive is working at the time of Executive’s termination of employment with the J.Jill Companies; which Executive acknowledges and agrees is the territory in which she is providing services to the J.Jill Companies pursuant to this Agreement.

 (ii)    The “Associated Companies” shall mean the J.Jill Companies and any company in which any
J.Jill Company has a twenty percent or greater ownership interest. 
 (iii)    The “Business of the J.Jill
Companies” shall be defined as a women’s retail, catalog, phone and/or internet apparel business (regardless of its form of organization, and including a division of a general retailer, such as a department store, if the division is
engaged in a specialty retail or specialty catalog business for women, including, for purposes of illustration, but not limited to, ANN INC. and its subsidiaries, Chico’s FAS, Inc. and its subsidiaries, Coldwater Creek Inc., Eddie Bauer LLC,
Inc., Eileen Fisher Inc. and its subsidiaries, Nordstrom Inc., Sundance Catalog, L.L. Bean, Inc., Lands’ End, The Talbots, Inc., and The Gap, Inc.). Notwithstanding the foregoing, “Business of the J.Jill Companies” shall not
include any affiliate, subsidiary or division of any Person engaged in women’s retail, catalog, phone and/or internet apparel business if (A) such affiliate, subsidiary or division is not itself engaged in a women’s retail, catalog,
phone and/or internet apparel business, and (B) Executive does not provide services to any entity engaged in a women’s retail, catalog, phone and/or internet apparel business. 

(f)    The covenants in this paragraph 7 are severable and separate, and the unenforceability of any specific covenant
shall not affect the provisions of any other covenant. If any provision of this paragraph 7 relating to the time period, scope, or geographic area of the restrictive covenants shall be declared by a court of competent jurisdiction or arbitrator to
exceed the maximum time period, scope, or geographic area, as applicable, that such court or arbitrator deems reasonable and enforceable, then this Agreement shall automatically be considered to have been amended and revised to reflect such
determination. 
 (g)    All of the covenants in this paragraph 7 shall be construed as an agreement independent of any
other provisions in this Agreement, and the existence of any claim or cause of action Executive may have against any J.Jill Company, whether predicated on this Agreement or otherwise, shall not constitute a defense to the enforcement by such J.Jill
Company of such covenants. 
 (h)    Executive has carefully read and considered the provisions of this paragraph 7
and, having done so, agrees that the restrictive covenants in this paragraph 7 impose a fair and reasonable restraint on Executive and are reasonably required to protect the interests of the J.Jill Companies and their respective officers, directors,
employees, and equityholders. 

  
 14 

 (i)    Executive agrees to disclose in advance the existence and terms of
the restrictions and covenants contained in this paragraph 7 to any employer or other service recipient by whom Executive may be employed or retained during the Noncompetition Restricted Period and/or the Nonsolicitation Restricted Period, as
applicable. 
 8.    Trade Secrets and Confidential Information. 

(a)    For purposes of this paragraph, “Confidential Information” means any data or information (other
than Trade Secrets) that is valuable to the Company or the Associated Companies (or, if owned by someone else, is valuable to that third party) and not generally known to the public or to competitors in the industry, including, but not limited to,
any nonpublic information (regardless of whether in writing or retained as personal knowledge) pertaining to research and development; product costs, designs and processes; equityholder information; pricing, cost, or profit factors; quality
programs; annual budget and long-range business plans; marketing plans and methods; contracts and bids; business ideas and methods, store concepts, inventions, innovations, developments, graphic designs, web site designs, patterns, specifications,
procedures, databases and personnel. “Trade Secret” means trade secret as defined by applicable state law. In the absence of such a definition, Trade Secret means information including, but not limited to, any technical or
nontechnical data, formula, pattern, compilation, program, device, method, technique, drawing, process, financial data, financial plan, product plan, list of actual or potential customers or suppliers or other information similar to any of the
foregoing, which (i) derives economic value, actual or potential, from not being generally known to, and not being readily ascertainable by proper means by, other persons who can derive economic value from its disclosure or use and (ii) is
the subject of efforts that are reasonable under the circumstances to maintain its secrecy. 
 (b)    Executive
acknowledges that in the course of her employment with the J.Jill Companies, she has received or will receive and has had or will have access to Confidential Information and Trade Secrets of the Company and the Associated Companies, and that
unauthorized or improper use or disclosure by Executive of such Confidential Information or Trade Secrets will cause serious and irreparable harm to the J.Jill Companies. Accordingly, Executive is willing to enter into the covenants contained in
paragraphs 7, 8, 9 and 10 of this Agreement in order to provide the J.Jill Companies with what Executive considers to be reasonable protection for their respective interests. 

(c)    Executive hereby agrees to hold in confidence all Confidential Information of the Company and the Associated
Companies that came into her knowledge during her employment by the J.Jill Companies and will not disclose, publish or make use of such Confidential Information without the prior written consent of the Board for as long as the information remains
Confidential Information. 
 (d)    Executive hereby agrees to hold in confidence all Trade Secrets of the Company and
the Associated Companies that came into her knowledge during her employment by the Company and shall not disclose, publish, or make use of at any time after the date hereof such Trade Secrets without the prior written consent of the Board for as
long as the information remains a Trade Secret. 

  
 15 

 (e)    Notwithstanding the foregoing, the provisions of this paragraph 8
will not apply to (i) information required to be disclosed by Executive in the ordinary course of her duties hereunder, or required to be disclosed by law, judicial (including arbitration or mediation) or governmental proceedings, (ii) any
litigation, arbitration or mediation involving this Agreement, its Annex, any of its Exhibits or any other agreement to which the Company or any of its affiliates and Executive are parties, or (iii) Confidential Information or Trade Secrets
that otherwise becomes generally known in the industry or to the public through no act of Executive or any person or entity acting by or on Executive’s behalf. 

(f)    The Parties agree that the restrictions stated in this paragraph 8 are in addition to and not in lieu of
protections afforded to trade secrets and confidential information under applicable state and federal law. Nothing in this Agreement is intended to or shall be interpreted as diminishing or otherwise limiting any J.Jill Company’s rights under
applicable state or federal law to protect their respective trade secrets and confidential information. 

9.    Return of Company Property. All records, designs, patents, business plans, financial statements, manuals,
memoranda, customer lists, computer data, customer information, and other property or information delivered to or compiled by Executive by or on behalf of the Company, the Associated Companies, of their respective representatives, vendors or
customers shall be and remain the property of the Company, and be subject at all times to its discretion and control. Upon the reasonable request of the Company and, in any event, upon the termination of Executive’s employment with the J.Jill
Companies, Executive shall deliver all such materials to the Company. Notwithstanding the foregoing, Executive shall be entitled to retain her personal non-business related papers and any information relating
to her compensation hereunder or status as an equityholder in Parent. 
 10.    Work Product and
Inventions. 
 (a)    Works. Executive acknowledges that Executive’s work on and contributions to
documents, programs, methodologies, protocols, and other expressions in any tangible medium (including, without limitation, all business ideas and methods, store concepts, inventions, innovations, developments, graphic designs (such as catalog
designs, in-store signage and posters), web site designs, patterns, specifications, procedures or processes, market research, databases, works of authorship, products, and other works of creative authorship)
which have been or will be prepared by Executive, or to which Executive has contributed or will contribute, in connection with Executive’s services to any J.Jill Company (collectively, “Works”), are and will be within the scope
of Executive’s employment and part of Executive’s duties and responsibilities. Executive’s work on and contributions to the Works will be rendered and made by Executive for, at the instigation of, and under the overall direction of
any J.Jill Company, and are and at all times shall be regarded, together with the Works, as “work made for 

  
 16 

 hire” as that term is used in the United States Copyright Laws. However, to the extent that any court or
agency should conclude that the Works (or any of them) do not constitute or qualify as a “work made for hire”, Executive hereby assigns, grants, and delivers exclusively and throughout the world to the Company all rights, titles, and
interests in and to any such Works, and all copies and versions, including all copyrights and renewals. Executive agrees to cooperate with the Company and to execute and deliver to the Company and its successors and assigns, any assignments and
documents the Company requests for the purpose of establishing, evidencing, and enforcing or defending its complete, exclusive, perpetual, and worldwide ownership of all rights, titles, and interests of every kind and nature, including all
copyrights, in and to the Works, and Executive constitutes and appoints the Board as its agent to execute and deliver any assignments or documents Executive fails or refuses to execute and deliver, this power and agency being coupled with an
interest and being irrevocable; provided that after the termination of Executive’s employment hereunder, the Company shall reimburse Executive for all reasonable out of pocket expenses incurred by Executive in rendering such services as are
approved by the Board. Without limiting the preceding provisions of this paragraph 10(a), Executive agrees that the Company may edit and otherwise modify, and use, publish and otherwise exploit, the Works in all media and in such manner as the
Company, in its sole discretion, may determine. 
 (b)    Inventions and Ideas. Executive shall disclose
promptly to the Board (which shall receive it in confidence), and only to the Board, any invention or idea of Executive in any way connected with Executive’s services or related to the Business of the J.Jill Companies, any J.Jill Company’s
research or development, or demonstrably anticipated research or development (developed alone or with others), conceived or made during the Term or within three (3) months thereafter and hereby assigns to the Company any such invention or idea.
Executive agrees to cooperate with the Company and sign all papers deemed necessary by the Company to enable it to obtain, maintain, protect and defend patents covering such inventions and ideas and to confirm the Company’s exclusive ownership
of all rights in such inventions, ideas and patents, and irrevocably appoints the Board as its agent to execute and deliver any assignments or documents Executive fails or refuses to execute and deliver promptly, this power and agency being coupled
with an interest and being irrevocable; provided that after the termination of Executive’s employment hereunder, the Company shall reimburse Executive for all reasonable out of pocket expenses incurred by Executive in rendering such services as
are approved by the Board. This constitutes the Company’s written notification that this assignment does not apply to an invention for which no equipment, supplies, facility or trade secret information of any J.Jill Company was used and which
was developed entirely on Executive’s own time, unless (a) the invention relates (i) directly to the Business of the J.Jill Companies, or (ii) any J.Jill Company’s actual or demonstrably anticipated research or development,
or (b) the invention results from any work performed by Executive for any J.Jill Company. 
 11.    No Prior
Agreements. Executive hereby represents and warrants to the Company that the execution of this Agreement by Executive and her employment by the J.Jill Companies and the performance of her duties hereunder will not violate or be a
breach of any agreement with any former employer, client, or any other person or entity. 

  
 17 

 12.    Assignment; Binding Effect. Executive understands
that she has been selected for employment by the J.Jill Companies on the basis of her personal qualifications, experience, and skills. Executive agrees, therefore, that she cannot assign all or any portion of her performance under this Agreement.
The Company and Parent may each assign this Agreement to the purchaser of substantially all of the assets of the Company, or to any other J.Jill Company, provided that any such assignment does not adversely affect Executive’s financial rights
and duties under this Agreement or the Grant Agreement, expand any restrictive covenant hereunder or impair her rights to resign for Good Reason. Subject to the preceding two sentences, as of the Signing Date, this Agreement shall be binding upon,
inure to the benefit of, and be enforceable by the Parties (including, for the avoidance of doubt, by Executive against Parent GP and the Buyer with respect to Section 22) and their respective heirs, legal representatives, successors, and
assigns. In the event of Executive’s death while any payment, benefit or entitlement is due to her hereunder or otherwise, such payment, benefit or entitlement shall be paid to her spouse (or if such spouse is not alive, to her estate). 

13.    Complete Agreement; Waiver; Amendment. This Agreement shall be binding on the Parties as of
the Signing Date, but shall not amend or supersede the Prior Agreement until the Effective Date. Except as otherwise provided in this Agreement, as of the Effective Date, Executive has no oral representations, understandings, or agreements with any
of the J.Jill Companies or any of its officers, directors, or representatives covering the same subject matter as this Agreement (including, without limitation, the restrictive covenants contained in paragraphs 7(b)-(d) through 10 of this
Agreement); other than the provisions of the Purchase Agreement for which Executive is a third-party beneficiary, the Parent LPA, the Amended and Restated Limited Liability Company Agreement of Parent GP to be executed by the parties thereto in the
form attached hereto, as such may be further amended from time to time in accordance therewith, and the Subscription and Rollover Agreement by and among the Parent, the Buyer, JJIP, LLC, and Executive dated as of March 30, 2015. Except as
otherwise provided in this Agreement, including the preceding sentence, as of the Effective Date, this Agreement, the Release and the Grant Agreement are the final, complete, and exclusive statement of expression of the agreement between Parent GP,
Parent, Buyer, Jill Intermediate, the Company, and Executive with respect to the subject matter hereof (including, without limitation, the restrictive covenants contained in paragraphs 7(b)-(d) through 10 of this Agreement), and cannot be varied,
contradicted, or supplemented by evidence of any prior or contemporaneous oral or written agreements (including without limitation the Prior Agreement). This written Agreement may not be later modified except by a further writing signed by
(i) a duly authorized officer of the Company or a member of the Board (in each case other than Executive) and (ii) Executive, and no term of this Agreement may be waived except by a writing signed by the party waiving the benefit of such
term. 

  
 18 

 14.    Notice. Whenever any notice is required
hereunder, it shall be given in writing addressed as follows: 
  

			
	To the Parent:	  	JJill Topco Holdings, LP
		  	c/o TowerBrook Capital Partners L.P.
		  	Park Avenue Tower
		  	65 East 55th Street, 27th Floor
		  	New York, NY 10022
		  	Attn: General Counsel | North America
		
	To any other J.Jill Company:	  	c/o Jill Acquisition LLC
		  	4 Batterymarch Park
		  	Quincy, MA 02169
		  	Attn: General Counsel

 To Executive, to the most recent address the Company has on file for Executive. 

15.    Severability: Headings. If any portion of this Agreement is held invalid or inoperative, the
other portions of this Agreement shall be deemed valid and operative and, so far as is reasonable and possible, effect shall be given to the intent manifested by the portion held invalid or inoperative. This severability provision shall be in
addition to, and not in place of, the provisions of paragraph 7(f) of this Agreement. The paragraph and section headings are for reference purposes only and are not intended in any way to describe, interpret, define or limit the extent of the
Agreement or of any part hereof. 
 16.    Equitable Remedy. Because of the difficulty of measuring
economic losses to the J.Jill Companies as a result of a breach of the covenants set forth in paragraphs 7(b)-(d) through 10 of this Agreement, and because of the immediate and irreparable damage that would be caused to the J.Jill Companies for
which monetary damages would not be a sufficient remedy, it is hereby agreed that in addition to all other remedies that may be available to the J.Jill Companies, at law or in equity, each J.Jill Company shall be entitled to seek specific
performance and any injunctive or other equitable relief as a remedy for any breach or threatened breach by Executive of any provision of paragraphs 7(b)-(d) through 10 of this Agreement. Each J.Jill Company may seek temporary and/or permanent
injunctive relief for an alleged violation of paragraphs 7(b)-(d), 8, 9 and/or 10 of this Agreement without the necessity of first arbitrating the matter pursuant to paragraph 17 of this Agreement and without the necessity of posting a bond. 

17.    Arbitration. Except for an action by any J.Jill Company for injunctive relief as described in
paragraph 16 of this Agreement, any disputes or controversies arising under or related to this Agreement or Executive’s employment with the Company will be settled by binding arbitration in Wilmington, Delaware through the use of and in
accordance with the applicable rules of the American Arbitration Association relating to arbitration of commercial disputes (“AAA”) and pursuant to the Federal Arbitration Act. One neutral arbitrator shall hear the dispute. The
determination and findings of such arbitrator will be binding on all parties and may be enforced, if necessary, in any court of competent jurisdiction. The arbitrator shall be mutually 

  
 19 

 
acceptable to the parties and need not be selected from the AAA’s roster of arbitrators if the parties can agree otherwise. If the parties are unable to agree on an arbitrator, then the
arbitrator shall be selected pursuant to the AAA’s rules. Except as prohibited by applicable law, each party shall be liable for its or her own legal fees and expenses, and shall split equally all arbitration and administration fees, as well as
all fees and expenses of the arbitrator. Notwithstanding the foregoing, disputes or controversies relating to Executive’s status as, or rights arising as, an equityholder of Parent shall be governed by the terms of the Grant Agreement, the
Parent LPA, and related documents. 
 18.    Indemnification/D&O Liability Insurance. In
addition to any rights to be indemnified and covered under directors’ and officers’ liability insurance policies pursuant to the Purchase Agreement, Parent GP, Parent, Buyer, and the Company shall indemnify Executive (and her legal
representatives, heirs or other successors) to the fullest extent permitted by applicable law or, if greater, pursuant to Parent GP’s, Parent’s, Buyer’s, or the Company’s corporate documents in effect as of the Effective Date (or
pursuant to any amendments thereafter which are favorable to Executive), as applicable, against all reasonable costs, charges and expenses incurred or sustained by Executive (or her legal representatives, heirs or other successors), including the
reimbursement of reasonable costs and expenses of legal counsel, in connection with any action, suit or proceeding to which Executive (or her legal representatives, heir or other successors) may be made a party by reason of Executive’s being or
having been an officer, director or employee of any J.Jill Company or her serving or having served as a director, officer or employee of another enterprise at the request of Parent GP, Parent, Buyer, or the Company; provided that neither Parent GP,
Parent, Buyer, nor the Company shall indemnify Executive for any costs, charges or expenses incurred or sustained by Executive as a result of any act or omission described in paragraph 6(a)(i)-(vi) of this Agreement. In addition, during the Term and
for six (6) years thereafter, Executive shall be covered, at the Company’s expense, by officer and director liability insurance in amounts and on terms no less favorable to her in any respect than the coverage afforded to other executives
and/or directors of Parent GP, Parent, Buyer, or the Company. 
 19.    Parent, Parent GP, Jill Intermediate,
Buyer, and Company Representations. Parent, Parent GP, Jill Intermediate, Buyer, and the Company represent to Executive that (i) the execution and delivery of this Agreement has been fully and validly authorized by all
necessary corporate actions, (ii) the officer signing this Agreement is duly authorized to do so, and (iii) upon execution and delivery of this Agreement by the aforementioned parties, it shall be a valid and binding obligation of such
party enforceable against it in accordance with their terms, extent to the extent that enforceability may be limited by applicable bankruptcy, insolvency or similar laws affecting the enforcement of creditors’ rights generally. 

20.    Jointly Drafted. The Parties and their respective counsel have participated jointly in the
negotiation and drafting of this Agreement. In the event that an ambiguity or question of intent or interpretation arises, this Agreement shall be construed as if drafted jointly by the Parties, and no presumption or burden of proof shall arise
favoring or disfavoring any party by virtue of the authorship of any of the provisions of this Agreement. 

  
 20 

 21.    Governing Law. This Agreement shall in all
respects be governed by and construed in accordance with the laws of the State of Delaware, not including the choice-of-law rules thereof. All Parties hereby consent to
the exclusive and sole jurisdiction and venue of the state and federal courts located in Delaware for the litigation of disputes not subject to arbitration and waive any claims of improper venue, lack of personal jurisdiction, or lack of subject
matter jurisdiction as to any such disputes. 
 22.    Joinder of Parent GP, Jill Intermediate, and
Buyer. 
 (a)    Parent GP joins this Agreement for the limited purposes of acknowledging
(i) Executive’s right to be appointed to the GP Board and (ii) the provisions in paragraphs 6(f)(iii), 6(h), 12, 13, 18, and 19 of this Agreement. 

(b)    Buyer joins this Agreement for the limited purposes of acknowledging the provisions in paragraphs 6(h), 12,
13, 18, and 19 of this Agreement 
 (c)    Jill Intermediate joins this Agreement for the limited purposes of
acknowledging (i) the Agreement as an amendment and restatement of the Prior Agreement and (ii) the provisions in paragraphs 12, 13 and 19 of this Agreement. 

For the avoidance of doubt, following any Parent Separation, Parent and Parent GP shall each be released from the provisions of this Agreement (other than
with respect to Section 18 with respect to acts or omissions prior to the Parent Separation and with respect to the Grant Agreement), and, except as otherwise provided with respect to Section 18 and with respect to the Grant Agreement,
shall no longer have any obligations or liability hereunder to Executive or any other party to this Agreement. 
 [REMAINDER OF PAGE
INTENTIONALLY LEFT BLANK]     

  
 21 

 IN WITNESS WHEREOF, each of the Company, Jill Intermediate, Parent GP, Parent and
Executive has caused this Agreement to be duly executed as of the date first written above. 
  

			
		 	Jill Acquisition LLC
		
		 	 /s/ David Biese

		
	By:	 	 David Biese

	Title:	 	 CFO

  
 [Signature Page to
Employment Agreement for Paula Bennett – Jill Acquisition LLC] 

 
			
	JJill Topco Holdings, LP
		
	By:	 	JJ Holdings GP, LLC
		 	its general partner
		
		 	 /s/ Glenn Miller

		
	By:	 	Glenn Miller
	Title:	 	Vice President and Secretary

  
 [Signature Page to
Employment Agreement for Paula Bennett – JJill Topco Holdings, LP] 

 
			
	 For the limited purposes set forth in

paragraph 22:

		
		 	Jill Intermediate LLC
		
		 	 /s/ David Biese

		
	By:	 	 David Biese

	Title:	 	 CFO

  
 [Signature Page to
Employment Agreement for Paula Bennett – Jill Intermediate LLC] 

 
			
	 For the limited purposes set forth in

paragraph 22:

		
		 	 JJ Holdings GP, LLC

		
		 	 /s/ Glenn Miller

		
	 By:
	 	 Glenn Miller

	 Title:
	 	 Vice President and Secretary

  
 [Signature Page to
Employment Agreement for Paula Bennett – JJ Holdings GP, LLC] 

 
			
	 For the limited purposes set forth in

paragraph 22:

		
		 	 JJill Holdings, Inc.

		
		 	 /s/ Glenn Miller

		
	 By:
	 	 Glenn Miller

	 Title:
	 	 Vice President and Secretary

  
 [Signature Page to
Employment Agreement for Paula Bennett – JJill Holdings, Inc.] 

 
	
	 /s/ Paula Bennett

	PAULA BENNETT

  
 [Signature Page to
Employment Agreement for Paula Bennett – Paula Bennett] 

 Annex A 

Advisory and Industry Board Memberships 

None.EX-10.10

 Exhibit 10.10 

EXECUTION VERSION 

AMENDED AND RESTATED EMPLOYMENT AGREEMENT

 This Amended and Restated Employment Agreement (this “Agreement”) is made and entered into as of May 22, 2015
by and between Jill Acquisition LLC (the “Company”) and DAVID BIESE (“Executive” and, together with the Company, the “Parties”), and amends and restates in its entirety, effective as of the
Effective Date (defined below), that certain employment agreement dated March 30, 2012, by and between the Company and Executive, as amended on March 13, 2015 (the “Prior Agreement”). JJill Topco Holdings, LP
(“Parent”), also joins this Agreement for the limited purpose of acknowledging the provisions in paragraph 3(e) below. 

R E C I T A L S 

WHEREAS, pursuant to the Membership Interest Purchase Agreement entered into as of March 30, 2015, by and among JJill Holdings,
Inc., Jill Intermediate LLC (“Jill Intermediate”), the members of Jill Intermediate and JJ Holding Company Limited (the “Purchase Agreement”), the parties to the Purchase Agreement have agreed to consummate the
transactions set forth therein, upon the terms and subject to the conditions of the Purchase Agreement (the “Transaction”); 

WHEREAS, in connection with the consummation of the Transaction, the Parties wish to enter into this Agreement to amend and restate the
Prior Agreement to, among other things, set forth the terms and conditions of Executive’s continued employment with the Company commencing on the date on which the Transaction closes (the “Effective Date”); 

WHEREAS, to secure Executive’s skills and services, for the benefit of the Company and its direct and indirect subsidiaries and
parent companies, and any company in which the Parent has a twenty percent or greater ownership interest, whether existing on the Effective Date or thereafter acquired or formed (collectively, the “J.Jill Companies”), the Company
desires to continue to employ Executive and Executive desires to accept such continued employment with the Company and to provide such skills and services to the J.Jill Companies, on the terms and conditions set forth herein; and 

WHEREAS, the Prior Agreement shall continue to govern the terms of Executive’s employment with the Company through the date
immediately preceding the Effective Date. 
 NOW, THEREFORE, in consideration of the mutual promises, terms, covenants, and
conditions set forth in this Agreement, and the performance of each of, the Parties, intending to be legally bound, agree as follows: 

 AGREEMENTS 

1.    Term. Subject to earlier termination pursuant to paragraph 6 of this Agreement, the term of this
Agreement shall begin on the Effective Date and continue for a period of five (5) years following the Effective Date (the “Initial Term”), unless extended or earlier terminated in accordance with the terms of this Agreement. If
not earlier terminated, this Agreement shall be automatically extended for an additional one (1) year period at the end of the Initial Term and on each subsequent anniversary thereof unless, at least ninety (90) days before the expiration
of the Initial Term or subsequent anniversary, the Company or Executive provides written notice of its or his intention not to extend the Term (a “Notice of Non-Renewal”), in which case the
Term and Executive’s employment shall automatically terminate at the end of the Initial Term or the applicable anniversary thereof (the Initial Term and any renewal or earlier termination is referred to as the “Term”). 

2.    Position and Duties. The Company hereby employs Executive as the Senior Vice President - Chief
Financial Officer of the Company, reporting to the Company’s Chief Executive Officer (the “CEO”). Executive shall have such responsibilities, duties, and authorities as are commensurate with the position of Senior Vice
President - Chief Financial Officer or as are assigned to him by the CEO. Executive shall fulfill his duties and responsibilities in a reasonable and appropriate manner and in compliance with the Company’s policies and practices and applicable
law. During the Term, Executive shall devote his full business time and attention to the business and affairs of the J.Jill Companies and shall not be engaged in or employed by or provide services to any other business enterprise without the written
approval of the CEO; provided, however, that Executive may manage his personal affairs, finances, and investments, and may participate in charitable and not-for-profit
activities, all without the necessity of obtaining the CEO’s approval, so long as such service does not create an actual or potential conflict of interest with, or interfere with the performance of, Executive’s duties hereunder or conflict
with Executive’s covenants under paragraphs 7 through 11 of this Agreement, in each case as determined in the sole judgment of the CEO. 

3.    Compensation. For all services rendered by Executive (including his compliance with the covenants in
paragraphs 7 through 11 of this Agreement), the Company shall compensate Executive as follows: 
 (a)    Base
Salary. As of the Effective Date, the gross annual salary payable to Executive shall be Four Hundred Twenty-Three Thousand Two Hundred Twenty-Five Dollars ($423,225.00) per year, which shall be paid in substantially equal installments on a
regular basis in accordance with the Company’s standard payroll procedures, but not less than monthly (the “Base Salary”). The Base Salary shall be reviewed by the Board of Directors of JJ Holdings GP, LLC or JJ Holdings, Inc.
(or the appropriate committee of the Board, as applicable, either such board or any such committee, the “Board”) periodically and shall be subject to increase (but not decrease) by the Board (or the appropriate committee of the
Board) in its discretion. 

  
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 (b)    Annual Bonus. For all of 2015 (without proration) and
subsequent fiscal years, Executive shall be eligible for an annual bonus (the “Annual Bonus”). The Annual Bonus shall be determined by the Board based upon the Company’s achievement of financial and other goals to be proposed
annually by Executive and approved by the Board. If all performance objectives are fully met, the target amount of the Annual Bonus shall be equal to forty-five percent (45%) of Executive’s Base Salary
(pro-rated for partial years), but a higher bonus shall be possible for exceptional performance. The Annual Bonus shall be paid in accordance with the Company’s customary practices for payment of annual
bonuses to senior executive employees within seventy-five (75) days after the later of (i) the close of the fiscal year for which the Annual Bonus was earned and (ii) the completion of the applicable fiscal year financial audit, but
in no event later than April 15 of the following calendar year; provided, however, that Executive must be employed through the end of the applicable fiscal year to be entitled to receive the Annual Bonus. 

(c)    Benefits and Perquisites. Executive shall be entitled to participate in the employee benefit plans
and programs of the Company in accordance with the terms of such plans and programs and shall be entitled to the same perquisites as are made available to other senior executive employees of the Company. 

(d)    Vacation. Executive shall be entitled to not less than four (4) weeks of paid vacation during
each calendar year (pro-rated for any partial calendar year of employment) in accordance with the Company’s policies and practices for senior executive employees of the Company. 

(e)    Class A Common Interests. Subject to Executive executing the Subscription and Rollover
Agreement attached hereto (the “Rollover Agreement”) Executive shall be entitled to receive an allocation of Class A Common Interests of Parent pursuant to a Grant Agreement substantially in the form attached hereto (the
“Grant Agreement”). 
 4.    Expense Reimbursement. The Company shall reimburse Executive
for (or, at the Company’s option, pay) all business travel and other out-of-pocket expenses reasonably incurred by Executive in the performance of his duties under
this Agreement. All reimbursable expenses shall be appropriately documented by Executive upon submission of any request for reimbursement in a manner consistent with the Company’s expense reporting policies and applicable federal and state tax
recordkeeping requirements. The amount of expenses eligible for reimbursement during any taxable year of Executive under this Agreement will not affect the expenses eligible for reimbursement in any other taxable year of Executive, and
Executive’s right to reimbursement of expenses is not subject to liquidation or exchange for another benefit. 

5.    Place of Performance. Executive shall carry out his duties and responsibilities under this Agreement
principally in and from the Company’s offices in the Quincy, Massachusetts, area. Executive understands that his position will involve substantial travel and agrees to undertake such travel as may be necessary or desirable in the performance of
his duties and responsibilities under this Agreement. 

  
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 6.    Termination; Rights on Termination. Executive’s
employment and the Term may be terminated in any one of the following ways: 
 (a)    Termination by the
Company for Cause. The Company may terminate the Term and Executive’s employment for Cause (as defined below), and such termination for Cause shall be effective immediately upon provision of notice to Executive that his employment has been
terminated for Cause. For purposes of this Agreement, “Cause” shall mean: (i) Executive’s breach of any material provision of this Agreement; (ii) Executive’s failure to follow a lawful directive of the CEO;
(iii) Executive’s negligence in the performance or nonperformance of any of his duties or responsibilities; (iv) Executive’s dishonesty, fraud, or willful misconduct with respect to the business or affairs of any J.Jill Company;
(v) Executive’s conviction of or plea of no contest to any misdemeanor involving theft, fraud, dishonesty, or act of moral turpitude or to any felony; or (vi) Executive’s use of alcohol or drugs in a manner that materially
interferes with the performance of his duties for the Company. In the event of termination of Executive’s employment for Cause, no compensation or benefits shall be payable to Executive after the date of such termination, except as provided for
in paragraph 6(f) of this Agreement; provided, however, that in the event of a breach or failure described in clauses (i), (ii), (iii), or (vi) which can be cured by Executive, the Company shall provide Executive with notice of the facts and
circumstances which constitute such breach or failure and shall provide Executive a ten (10) day period in which to cure such breach or failure and shall not terminate Executive for Cause if Executive cures such breach or failure within such
ten (10) day period. 
 (b)    Termination for Executive’s Death or Disability. In the event
that Executive dies or becomes Disabled, no compensation or benefits shall be payable to Executive or his estate after the date of termination, except as provided for in paragraph 6(f) of this Agreement. For purposes of this Agreement,
“Disabled” shall mean either (i) Executive’s inability to perform the essential duties and responsibilities of his position (even with reasonable accommodation taken into account) by reason of Executive’s mental or
physical disability, illness, or impairment that has already lasted for a period of ninety (90) or more days during any twelve (12) month period, or (ii) Executive’s inability to perform the essential duties and responsibilities
of his position (even with reasonable accommodation taken into account) by reason of Executive’s mental or physical disability, illness, or impairment that can be expected to result in death or that can be expected to last for a period of
ninety (90) or more days during any twelve (12) month period, as determined by a physician selected by the Company and reasonably agreeable to Executive. 

(c)    Termination by the Company Without Cause. At any time during the Term, the Company may, without
Cause and for any reason whatsoever, terminate the Term and Executive’s employment, effective immediately upon provision of notice to Executive or at such later date specified by the Company. In the event Executive’s employment is
terminated during the Term without Cause, and not by reason of Executive’s death or disability, and provided that Executive fully complies with his obligations under paragraphs 7 through 11 of this Agreement and executes the Release (as defined
in paragraph 6(g) of this Agreement) such that it becomes irrevocable within sixty (60) days after his termination, then Executive shall be paid compensation pursuant to paragraph 6(g) of this Agreement. 

  
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 (d)    Termination by Executive For Good Reason. Executive may
terminate the Term and Executive’s employment for Good Reason (as defined below) effective on the first day after the end of the Cure Period (defined herein). “Good Reason” shall mean: (i) a reduction in Executive’s
level below the level of Senior Vice President; (ii) a material reduction in Executive’s Base Salary; or (iii) the relocation of Executive’s principal work location outside of the Quincy, Massachusetts, area without the
Executive’s consent; provided, however, Good Reason shall not exist unless (A) Executive gives the Board a written statement of the basis for Executive’s belief that Good Reason exists, (B) such written statement is provided not
later than sixty (60) days after the initial existence of the condition which Executive believes forms the basis for resignation for Good Reason, (C) Executive gives the Board at least thirty (30) days after receipt of such written
statement to cure the basis for such belief (the “Cure Period”), and (D) the Board does not cure the basis for such belief within the Cure Period. In the event Executive terminates his employment for Good Reason, and provided
that Executive fully complies with his obligations under paragraphs 7 through 11 of this Agreement and executes the Release such that it becomes irrevocable within sixty (60) days after his termination, then Executive shall be paid compensation
and severance pursuant to paragraph 6(g) of this Agreement. For the avoidance of doubt, Executive hereby acknowledges and agrees that the consummation of the Transaction shall not constitute “Good Reason” pursuant to the Prior Agreement or
this Agreement. 
 (e)    Termination by Executive Without Good Reason. Executive may
resign or terminate his employment hereunder without Good Reason (including, without limitation, Executive’s retirement); provided, that if (i) Executive has provided ninety (90) days’ prior written notice of his intention to
resign or terminate his employment hereunder, (ii) Executive continues to provide services through such 90-day period or any shorter period as determined in the Board’s absolute discretion, and
(iii) Executive fully complies with his obligations under paragraphs 7 through 11 of this Agreement and executes the Release such that it becomes irrevocable within sixty (60) days after his termination, Executive shall be entitled to a
Prorated Bonus (defined in paragraph 6(g)), which bonus shall be paid on the date that bonuses for such calendar year are paid to executives of the Company, generally, but in no event later than April 15 of the calendar year following the
calendar year in which Executive’s employment was terminated. Except as set forth in this paragraph 6(e) and paragraph 6(f), no compensation or benefits shall be payable to Executive after the date of termination. For the avoidance of doubt, no
Prorated Bonus shall be payable to Executive if Executive provides a Notice of Non-Renewal in accordance with paragraph 1 of this Agreement. 

(f)    Payment Through Termination. Upon termination of Executive’s employment and of
this Agreement for any reason except a termination without Cause or for Good Reason, Executive shall be entitled to receive his Base Salary and all benefits and reimbursements due through the effective date of termination. Such Base Salary shall be
paid in accordance with the Company’s standard payroll procedures. No other compensation or benefits will be due or payable to Executive after such 

  
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termination, except as provided by paragraph 6(e), if applicable, this paragraph 6(f), the Rollover Agreement, the Grant Agreement, the Incentive Equity Plan of JJill Topco Holdings, LP or as
otherwise required under the terms of the Company’s employee benefit plans and programs or applicable law. 

(g)    Payment for Termination Without Cause or For Good Reason. In the event
Executive’s employment is terminated without Cause or for Good Reason, and provided that Executive fully complies with his obligations under paragraphs 7 through 11 of this Agreement and executes (and does not revoke), within sixty
(60) days after his termination, a full and complete release of all claims against the J.Jill Companies and their respective affiliates, substantially in the form attached hereto (the “Release”), then Executive shall be paid:
(i) all compensation earned and all benefits and reimbursements due through the effective date of termination; (ii) an amount equal to one times Executive’s then-current annual Base Salary, paid in substantially equal bi-monthly installments on regularly scheduled payroll dates for the 12-month period that begins on the first regular payroll date that is sixty (60) days after Executive
experiences a “separation from service” within the meaning of Section 409A(a)(2)(A)(i) of the Internal Revenue Code of 1986, as amended (the “Code”); provided, that such first payment shall be a lump sum payment equal to
the amount of all payments due from the date of such termination through the date of such first payment; and (iii) a Prorated Bonus (defined below), which bonus shall be paid on the date that bonuses for such calendar year are paid to
executives of the Company, generally, but in no event later than April 15 of the calendar year following the calendar year in which Executive’s employment was terminated. In all applicable circumstances, the Company will provide the
completed Release to Executive within seven (7) days following the date of termination. During the 12-month period immediately after the effective date of Executive’s termination, or, if earlier,
until coverage is obtained by Executive from another employer (which coverage Executive shall promptly disclose to the Company), to the extent permitted by applicable law, Executive shall also receive a continuation of the medical and dental
coverage to which Executive was entitled under paragraph 3(c) of this Agreement immediately prior to such termination (including dependent coverage), at the same premium cost to Executive as determined immediately prior to such termination;
provided, that any right Executive has to COBRA under Employer’s group health plan will run concurrently with the continuation of coverage provided herein, and, provided further, that any Company-paid premiums shall be reported as taxable
income to Executive. Executive’s rights under any employee benefit plan or program of the Company shall be governed by the terms of such plan or program. Notwithstanding the foregoing, if the Release fails to become irrevocable on or before the
last day of the 60-day period that starts on the date of Executive’s separation from service (within the meaning of Section 409A(a)(2)(A)(i) of the Code), Executive shall forfeit any right to any
compensation and severance under this paragraph 6(g). The term “Prorated Bonus” means an amount equal to the product of X multiplied by Y, where 

“X” equals a fraction, the numerator of which is the number of full weeks through the date of Executive’s termination of
employment in the fiscal year of Executive’s termination and the denominator of which is 52, and 

  
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 “Y” equals the Annual Bonus that would have been payable to Executive under paragraph
3(b) had Executive been a participant in such bonus plan for the fiscal year and been employed on the date bonuses under such plan were paid to participants. 

(h)    Expiration of Agreement. If the Company or Executive gives written notice pursuant to paragraph 1 of
its or Executive’s intent not to extend this Agreement beyond the Initial Term or any subsequent anniversary thereof, and as a result of such written notice Executive’s employment terminates in accordance with paragraph 1, no compensation
or benefits shall be payable to Executive after the date of termination except as provided for in paragraph 6(f). 

(i)    Provisions that Survive Termination or Expiration of Agreement. All rights and obligations of the
Company and Executive under this Agreement shall cease as of the effective date of termination or expiration of this Agreement, except that (i) the Company’s payment and other obligations under paragraph 6 of this Agreement, if any, and
its rights and/or obligations under paragraphs 17 and 18 of this Agreement shall survive such termination or expiration in accordance with their terms, and (ii) Executive’s obligations under paragraphs 7 through 11, 17, and 18 of this
Agreement shall survive such termination or expiration in accordance with their terms. 
 (j)    Right to
Offset. In the event of any termination of Executive’s employment under this Agreement for any reason, the Company’s obligation to make any payments hereunder shall be subject to offset for any outstanding amounts that Executive owes
to any J.Jill Company. All payments and benefits payable under this Agreement are gross payments subject to applicable taxes and withholdings. 

(k)    Compliance with Code Section 409A. 

(i)    To the extent this Agreement is subject to Section 409A of the Code
(“Section 409A”), the Parties intend all payments under this Agreement to comply with the requirements of Section 409A, and this Agreement shall, to the extent practical, be operated and administered to
effectuate such intent. In furtherance thereof, if payment or provision of any amount or benefit hereunder at the time specified in this Agreement would subject such amount or benefit to any additional tax under Section 409A, the payment or
provision of such amount or benefit shall be postponed to the earliest commencement date on which the payment or the provision of such amount or benefit could be made without incurring such additional tax (including paying any severance that
is delayed in a lump sum upon the earliest possible payment date which is consistent with Section 409A). In addition, to the extent that any regulations or guidance issued under Section 409A (after application of the previous provision of this
paragraph) would subject Executive to the payment of interest or any additional tax under Section 409A, the Parties agree, to the extent reasonably possible, to amend this Agreement in order to avoid the imposition of any such interest or additional
tax under Section 409A, which amendment shall have the minimum economic effect necessary on Executive and be reasonably determined in good faith by the Parties; provided however, that the Parties shall not be required to substitute a cash payment
for any non-cash benefit herein. 

  
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 (ii)    A termination of Executive’s employment shall not be deemed to
have occurred for purposes of any provision of this Agreement providing for the payment of any amounts or benefits that are considered nonqualified deferred compensation under Section 409A upon or following a termination of Executive’s
employment, unless such termination is also a “separation from service” within the meaning of Section 409A and the payment thereof prior to a “separation from service” would violate Section 409A. For purposes of any such
provision of this Agreement relating to any such payments or benefits, references to a “termination,” “termination of employment” or like terms shall mean “separation from service.” 

(iii)    With respect to any payment under this Agreement constituting nonqualified deferred compensation subject to
Section 409A, (A) all expenses or other reimbursements provided herein shall be payable in accordance with the Company’s policies in effect from time to time, but in any event shall be made on or prior to the last day of the taxable year
following the taxable year in which such expenses were incurred by Executive; (B) no such reimbursement or expenses eligible for reimbursement in any taxable year shall in any way affect the expenses eligible for reimbursement in any other
taxable year; and (C) the right to reimbursement or in-kind benefits shall not be subject to liquidation or exchange for another benefit. 

(iv)    If Executive is deemed on the date of termination to be a “specified employee” within the meaning of
that term under Section 409A, then with regard to any payment or the provision of any benefit under this Agreement that is considered nonqualified deferred compensation under Section 409A payable on account of a “separation from service,”
such payment or benefit shall be made or provided on the first business day following the earlier of (A) the expiration of the six (6)-month period measured from the date of such “separation from service” of Executive, and
(B) the date of Executive’s death (the “Delay Period”). Upon the expiration of the Delay Period, all payments and benefits delayed pursuant to this paragraph 6(k) (whether they would have otherwise been payable in a single
sum or in installments in the absence of such delay) shall be paid or reimbursed to Executive in a lump sum on the first business day following the Delay Period, and any remaining payments and benefits due under this Agreement shall be paid or
provided in accordance with the normal payment dates specified for them herein. 
 (l)    Compliance with
Code Section 280G. If a change in control of any J.Jill Company occurs and any payment or benefit made under this Agreement or any other agreements providing Executive rights to compensation or equity would constitute a “parachute
payment” within the meaning of Section 280G of the Code, each payment or benefit will be reduced as a result of such change in control, to the extent necessary to avoid the imposition of any excise tax under Section 4999 of the Code;
provided, however, such payment or benefit will be restored to the extent the exception under Section 280G(b)(5)(ii) is satisfied with respect to such payment or benefit. 

  
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 7.    Executive Covenants. 

(a)    Executive acknowledges and agrees that during his employment with the Company, he will perform each of the
following duties: (1) have the primary duty of managing the Company or a customarily recognized department of subdivision thereof; (2) customarily and regularly direct the work of two or more employees; and (3) have the authority to
hire or fire other employees or have particular weight given to his suggestions and recommendations as to the hiring, firing, advancement, promotion, or any other change of status of other employees. Executive further acknowledges and agrees that by
reason of the Company’s investment of time, training, money, trust, exposure to the public, or exposure to customers, vendors, or other business relationships, he will gain (1) a high level of notoriety, fame, reputation, or public persona
as the Company’s representative or spokesperson, or (2) a high level of influence or credibility with the customers, vendors, or other business relationships of the J.Jill Companies. Executive further acknowledges and agrees that he will
be intimately involved in the planning for or direction of the business of the J.Jill Companies or a defined unit of the business of the J.Jill Companies, and that he has or will obtain selective or specialized skills, knowledge, abilities, or
customer contacts or information by reason of working for the Company. 
 (b)    During Executive’s
employment with the Company and for a period of twelve (12) months thereafter (such period, the “Restricted Period”), Executive shall not, either directly or indirectly, for himself or on behalf of or in conjunction with any
other person, company, partnership, corporation, business, group, or other entity (each, a “Person”): 

(i)    solicit or attempt to solicit, recruit or attempt to recruit, any employee, agent, or contract worker of the
J.Jill Companies with whom Executive had material business contact during the course of his employment with the Company to end her or his relationship with any J.Jill Company; 

(ii)    solicit or attempt to solicit any business related to the Business of the J.Jill Companies (as described below)
from any Person who, as of the date of the solicitation or attempted solicitation or within twelve (12) months prior to that date, is or was a customer of any J.Jill Company or an actively sought prospective customer with whom Executive had
material business contact (through sales calls, presentations, or other business dealings) during the course of his employment with the Company; or 

(c)    During Executive’s employment with the Company and for a period of six (6) months after a
termination of Executive’s employment for any reason, Executive shall not, either directly or indirectly, for himself or on behalf of or in conjunction with any other Person, engage, within the Territory (as described below), as an officer,
director, owner, partner, member, joint venturer, or in a managerial capacity (whether as an employee, independent contractor, agent, representative, or consultant), in any businesses: Sycamore Partners or any of its affiliates or portfolio
companies or Golden Gate Capital or any of its affiliates or portfolio companies. 

  
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 (d)    In addition, in furtherance of the Company’s reasonable
efforts to safeguard Confidential Information (defined below), Executive agrees that, during Executive’s employment with the Company and during the Restricted Period, Executive shall not serve as a council member or participate in any similar
capacity for Gerson Lehrman Group, Inc., Coleman Research, GuidePoint Global, or any other firm the primary purpose of which is to connect its clients with executives or industry specialists (whether through
in-person meetings, telephone conversations, on-line forums or other mediums) as a means for its clients to conduct primary research on a particular company, industry or
business sector. 
 (e)    For purposes of paragraphs 7 through 11 of this Agreement: 

(i)    The “Territory” shall be defined as the United States of America and any other territory where
employee is working at the time of termination of employment with Company; which Executive acknowledges and agrees is the territory in which he is providing services to the Company pursuant to this Agreement. 

(ii)    The “Business of the J.Jill Companies” shall be defined as a women’s retail, catalog, phone
and/or internet apparel business (regardless of its form of organization, and including a division of a general retailer, such as a department store, if the division is engaged in a specialty retail or specialty catalog business, including, for
purposes of illustration, but not limited to, ANN INC. and its subsidiaries, Chico’s FAS, Inc. and its subsidiaries, Coldwater Creek Direct, Eddie Bauer LLC, Eileen Fisher Inc. and its subsidiaries, Nordstrom Inc., J. Crew and its subsidiaries,
L.L. Bean, Inc., Lands End, The Talbots, Inc. and The Gap Inc.). 
 (f)    The covenants in this paragraph 7 are
severable and separate, and the unenforceability of any specific covenant shall not affect the provisions of any other covenant. If any provision of this paragraph 7 relating to the time period, scope, or geographic area of the restrictive covenants
shall be declared by a court of competent jurisdiction or arbitrator to exceed the maximum time period, scope, or geographic area, as applicable, that such court or arbitrator deems reasonable and enforceable, then this Agreement shall automatically
be considered to have been amended and revised to reflect such determination. 
 (g)    All of the covenants in
this paragraph 7 shall be construed as an agreement independent of any other provisions in this Agreement, and the existence of any claim or cause of action Executive may have against any J.Jill Company, whether predicated on this Agreement or
otherwise, shall not constitute a defense to the enforcement by any J.Jill Company of such covenants. 

  
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 (h)    Executive has carefully read and considered the provisions of
this paragraph 7 and, having done so, agrees that the restrictive covenants in this paragraph 7 impose a fair and reasonable restraint on Executive and are reasonably required to protect the interests of the J.Jill Companies and their respective
officers, directors, employees, and equityholders. 
 8.    Trade Secrets and Confidential Information.

 (a)    For purposes of this paragraph 8, “Confidential Information” means any data or
information (other than Trade Secrets) that is valuable to the J.Jill Companies (or, if owned by someone else, is valuable to that third party) and not generally known to the public or to competitors in the industry, including, but not limited to,
any non-public information (regardless of whether in writing or retained as personal knowledge) pertaining to research and development; product costs, designs and processes; equityholder information; pricing,
cost, or profit factors; quality programs; annual budget and long-range business plans; marketing plans and methods; contracts and bids; business ideas and methods, store concepts, inventions, innovations, developments, graphic designs, website
designs, patterns, specifications, procedures, databases and personnel. “Trade Secret” means trade secret as defined by applicable state law. In the absence of such a definition, Trade Secret means information including, but not
limited to, any technical or nontechnical data, formula, pattern, compilation, program, device, method, technique, drawing, process, financial data, financial plan, product plan, list of actual or potential customers or suppliers or other
information similar to any of the foregoing, which (i) derives economic value, actual or potential, from not being generally known to, and not being readily ascertainable by proper means by, other persons who can derive economic value from its
disclosure or use and (ii) is the subject of efforts that are reasonable under the circumstances to maintain its secrecy. 

(b)    Executive acknowledges that in the course of his employment with the Company, he has received or will
receive and has had or will have access to Confidential Information and Trade Secrets of the J.Jill Companies, and that unauthorized or improper use or disclosure by Executive of such Confidential Information or Trade Secrets will cause serious and
irreparable harm to the J.Jill Companies. Accordingly, he is willing to enter into the covenants contained in paragraphs 7, 8, 9, 10, and 11 of this Agreement in order to provide the J.Jill Companies with what he considers to be reasonable
protection for its interests. 
 (c)    Executive hereby agrees to hold in confidence all Confidential
Information of the J.Jill Companies that came into his knowledge during his employment by the Company and will not disclose, publish or make use of such Confidential Information without the prior written consent of the Company for as long as the
information remains Confidential Information. 
 (d)    Executive hereby agrees to hold in confidence all Trade
Secrets of the J.Jill Companies that came into his knowledge during his employment by the Company and shall not disclose, publish, or make use of at any time after the date hereof such Trade Secrets without the prior written consent of the Company
for as long as the information remains a Trade Secret. 

  
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 (e)    Notwithstanding the foregoing, the provisions of this
paragraph will not apply to (i) information required to be disclosed by Executive in the ordinary course of his duties hereunder, or required to be disclosed by judicial or governmental proceedings, or (ii) Confidential Information or
Trade Secrets that otherwise becomes generally known in the industry or to the public through no act of Executive or any person or entity acting by or on Executive’s behalf or information which Executive can demonstrate to have had rightfully
in his possession prior to the date on which he first worked for the Company. 
 (f)    The parties agree that
the restrictions stated in this paragraph 8 are in addition to and not in lieu of protections afforded to trade secrets and confidential information under applicable state and federal law. Nothing in this Agreement is intended to or shall be
interpreted as diminishing or otherwise limiting any J.Jill Companies’ rights under applicable state or federal law to protect its trade secrets and Confidential Information. 

9.    Nondisparagement. During the Employment Term and thereafter, the Executive shall not, directly
or indirectly, take any action, or encourage others to take any action, to disparage or criticize the Company and/or its subsidiaries and affiliates or their respective employees, officers, directors, products, services, customers or owners. 

10.    Return of Company Property. All records, designs, patents, business plans, financial statements,
manuals, memoranda, customer lists, computer data, customer information, and other property or information delivered to or compiled by Executive by or on behalf of the J.Jill Companies, their representatives, vendors or customers shall be and remain
the property of the J.Jill Companies, and be subject at all times to its discretion and control. Upon the request of the Company and, in any event, upon the termination of Executive’s employment with the Company, Executive shall deliver all
such materials to the Company. 
 11.    Work Product and Inventions. 

(a)    Works. Executive acknowledges that Executive’s work on and contributions to documents, programs,
methodologies, protocols, and other expressions in any tangible medium (including, without limitation, all business ideas and methods, store concepts, inventions, innovations, developments, graphic designs (such as catalog designs, in-store signage and posters), web site designs, patterns, specifications, procedures or processes, market research, databases, works of authorship, products, and other works of creative authorship) which have been
or will be prepared by Executive, or to which Executive has contributed or will contribute, in connection with Executive’s services to any J.Jill Company (collectively, “Works”), are and will be within the scope of
Executive’s employment and part of Executive’s duties and responsibilities. Executive’s work on and contributions to the Works will be rendered and made by 

  
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Executive for, at the instigation of, and under the overall direction of any J.Jill Company, and are and at all times shall be regarded, together with the Works, as “work made for hire”
as that term is used in the United States Copyright Laws. However, to the extent that any court or agency should conclude that the Works (or any of them) do not constitute or qualify as a “work made for hire”, Executive hereby assigns,
grants, and delivers exclusively and throughout the world to the Company all rights, titles, and interests in and to any such Works, and all copies and versions, including all copyrights and renewals. Executive agrees to cooperate with the Company
and to execute and deliver to the Company and its successors and assigns, any assignments and documents the Company requests for the purpose of establishing, evidencing, and enforcing or defending its complete, exclusive, perpetual, and worldwide
ownership of all rights, titles, and interests of every kind and nature, including all copyrights, in and to the Works, and Executive constitutes and appoints the Company as its agent to execute and deliver any assignments or documents Executive
fails or refuses to execute and deliver, this power and agency being coupled with an interest and being irrevocable. Without limiting the preceding provisions of this paragraph 11(a), Executive agrees that the Company may edit and otherwise modify,
and use, publish and otherwise exploit, the Works in all media and in such manner as the Company, in its sole discretion, may determine. 

(b)    Inventions and Ideas. Executive shall disclose promptly to the Company (which shall receive it in
confidence), and only to the Company, any invention or idea of Executive in any way connected with Executive’s services or related to the Business of the J.Jill Companies, any J.Jill Company’s research or development, or demonstrably
anticipated research or development (developed alone or with others), conceived or made during the Term or within three (3) months thereafter and hereby assigns to the Company any such invention or idea. Executive agrees to cooperate with the
Company and sign all papers deemed necessary by the Company to enable it to obtain, maintain, protect and defend patents covering such inventions and ideas and to confirm the Company’s exclusive ownership of all rights in such inventions, ideas
and patents, and irrevocably appoints the Company as its agent to execute and deliver any assignments or documents Executive fails or refuses to execute and deliver promptly, this power and agency being coupled with an interest and being
irrevocable. This constitutes the Company’s written notification that this assignment does not apply to an invention for which no equipment, supplies, facility or trade secret information of any J.Jill Company was used and which was developed
entirely on Executive’s own time, unless (a) the invention relates (i) directly to the Business of the J.Jill Companies, or (ii) to actual or demonstrably anticipated research or development of any J.Jill Company, or (b) the
invention results from any work performed by Executive for any J.Jill Company. 
 12.    No Prior
Agreements. Executive hereby represents and warrants to the Company that the execution of this Agreement by Executive and his employment by the Company and the performance of his duties hereunder will not violate or be a breach of any
agreement with a former employer, client, or any other person or entity. 
 13.    Assignment; Binding
Effect. Executive understands that he has been selected for employment by the Company on the basis of his personal qualifications, 

  
 13 

 
experience, and skills. Executive agrees, therefore, that he cannot assign all or any portion of his performance under this Agreement. The Company may assign this Agreement to the purchaser of
substantially all of the assets of the Company, or to any subsidiary or parent company of the Company. Subject to the preceding two sentences, this Agreement shall be binding upon, inure to the benefit of, and be enforceable by the parties and their
respective heirs, legal representatives, successors, and assigns. 
 14.    Complete Agreement; Waiver;
Amendment. Executive has no oral representations, understandings, or agreements with the Company or any of its officers, directors, or representatives covering the same subject matter as this Agreement. This Agreement, the Rollover
Agreement, the Grant Agreement, and the Release are the final, complete, and exclusive statement of expression of the agreement between the Company and Executive with respect to the subject matter hereof (including, but not limited to, any severance
payments, change in control payments, and terms of employment) and cannot be varied, contradicted, or supplemented by evidence of any prior or contemporaneous oral or written agreements. This written Agreement may not be later modified except by a
further writing signed by a duly authorized officer of the Company or member of the Board and Executive, and no term of this Agreement may be waived except by a writing signed by the party waiving the benefit of such term. 

15.    Notice. Whenever any notice is required hereunder, it shall be given in writing addressed as follows:

  

			
	To the Company:	  	c/o Jill Acquisition LLC
		  	4 Batterymarch Park
		  	Quincy, MA 02169
		  	Attn: Chief Executive Officer

 To the Executive, to the most recent address the Company has on file for the Executive. 

16.    Severability; Headings. If any portion of this Agreement is held invalid or inoperative, the other
portions of this Agreement shall be deemed valid and operative and, so far as is reasonable and possible, effect shall be given to the intent manifested by the portion held invalid or inoperative. This severability provision shall be in addition to,
and not in place of, the provisions of paragraph 7(f) above. The paragraph and section headings are for reference purposes only and are not intended in any way to describe, interpret, define or limit the extent of the Agreement or of any part
hereof. 
 17.    Equitable Remedy. Because of the difficulty of measuring economic losses to any J.Jill
Company as a result of a breach of the covenants set forth in paragraphs 7 through 11, and because of the immediate and irreparable damage that would be caused to the J.Jill Companies for which monetary damages would not be a sufficient remedy, it
is hereby agreed that in addition to all other remedies that may be available to the J.Jill Companies , at law or in equity, each J.Jill Company shall be entitled to specific performance and any injunctive or other equitable relief as a remedy for
any breach or threatened breach by Executive of any provision of paragraphs 7 

  
 14 

 
through 11 of this Agreement. Each J.Jill Company may seek temporary and/or permanent injunctive relief for an alleged violation of paragraphs 7 through 11 of this Agreement without the necessity
of first arbitrating the matter pursuant to paragraph 18 of this Agreement and without the necessity of posting a bond. 

18.    Arbitration. Except for an action by any J.Jill Company for injunctive relief as described in
paragraph 17 of this Agreement, any disputes or controversies arising under or related to this Agreement or the Executive’s employment with the Company will be settled by binding arbitration in Boston, Massachusetts, through the use of and in
accordance with the applicable rules of the American Arbitration Association relating to arbitration of commercial disputes and pursuant to the Federal Arbitration Act. One neutral arbitrator shall hear the dispute. The determination and findings of
such arbitrator will be binding on all parties and may be enforced, if necessary, in any court of competent jurisdiction. The arbitrator shall be mutually acceptable to the parties and need not be selected from the AAA’s roster of arbitrators
if the parties can agree otherwise. If the parties are unable to agree on an arbitrator, then the arbitrator shall be selected pursuant to the AAA’s rules. Except as prohibited by applicable law, the prevailing party in any such arbitration, or
in any action to enforce this paragraph 18 or any arbitration award hereunder, shall be awarded and the nonprevailing party shall pay the prevailing party’s attorneys’ fees and related expenses and the nonprevailing party shall pay all
arbitration filing and administration fees as well as all fees and expenses of the arbitrator. 
 19.    Jointly
Drafted. The parties and their respective counsel have participated jointly in the negotiation and drafting of this Agreement. In the event that an ambiguity or question of intent or interpretation arises, this Agreement shall be construed
as if drafted jointly by the parties, and no presumption or burden of proof shall arise favoring or disfavoring any party by virtue of the authorship of any of the provisions of this Agreement. 

20.    Governing Law. This Agreement shall in all respects be governed by and construed in accordance with
the laws of the State of Delaware, not including the choice-of-law rules thereof. All parties hereby consent to the exclusive and sole jurisdiction and venue of the
state and federal courts located in Delaware for the litigation of disputes not subject to arbitration and waive any claims of improper venue, lack of personal jurisdiction, or lack of subject matter jurisdiction as to any such disputes. 

  
 15 

 IN WITNESS WHEREOF, each of the parties hereto have caused this Agreement to be duly
executed as of the date first written above. 
  

			
	JILL ACQUISITION LLC
		
		 	 /s/ Paula Bennett

		
	By:	 	 Paula Bennett

	Title:	 	President & CEO
	
	For purposes of paragraph 3(e) hereof, only
	
	JJILL TOPCO HOLDINGS, LP
		
		 	  

		
	By:	 	  

	Title:	 	  

  

	
	
	 /s/ David Biese

	DAVID BIESE

 [Signature Page to Employment Agreement – Biese, David] 

 
			
	For purposes of paragraph 3(e) hereof, only
	
	JJILL TOPCO HOLDINGS, LP
		
	By:	 	JJ Holdings GP, LLC
		 	its general partner
		
		 	 /s/ Glenn Miller

		
	By:	 	Glenn Miller
	Title:	 	Vice President and Secretary

  
 1

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