Document:

Executive Severance Agreement

 EXHIBIT 10.39 
 Confidential treatment has been requested for portions of this exhibit. The copy filed herewith omits the information subject to the confidentiality request. Omissions are designated as [*****]. A
complete version of this exhibit has been filed separately with the Securities and Exchange Commission. 
 EXECUTIVE SEVERANCE
AGREEMENT 
 By this Executive Severance Agreement dated and effective as of January 8, 2012 (“Agreement”),
Sears Holdings Corporation and its affiliates and subsidiaries (“Sears”), and Ronald D. Boire (“Executive”), intending to be legally bound, and for good and valuable consideration, agree as follows: 

1. Effect of Severance. 
 (a) Severance Benefits. If Executive is involuntarily terminated without “Cause” or Executive voluntarily terminates Executive’s employment for “Good Reason” (as such terms
are defined in Section 2 below), Executive shall be entitled to the benefits described in subsection (i), (ii) and (iii) below (collectively referred to herein as “Severance Benefits”). Executive shall not be entitled to the
Severance Benefits if Executive’s employment terminates for any other reason, including due to death or “Disability” (as defined in Section 2 below). Executive shall also not be entitled to Severance Benefits if Executive does
not meet all of the other requirements under this Agreement, including under subsection 4(g). 
 i.
Continuation of Salary. 
 1. Sears or the appropriate “Sears Affiliate” (as defined in
Section 2 below) shall pay Executive a cash severance equal to the sum of (A) plus (B). 
 (A)
Executive’s annual base salary rate as of the date Executive’s employment terminates (“Date of Termination”). Subject to subsection (a)(i)(2) below, payment of such amount (“Salary Continuation”) shall commence on
Executive’s “Separation from Service” (as defined in Section 2 below) and shall be paid in substantially equal installments on each regular salary payroll date for a period of twelve (12) months following Date of Termination
(“Salary Continuation Period”), except as otherwise provided in this Agreement. 
 (B) A bonus payable
under the Sears Holdings Corporation Annual Incentive Plan (“AIP”) (subject to proration as defined herein), provided that Executive was employed at least six (6) months of the then current AIP performance period (as defined therein)
as of Executive’s Date of Termination and only to the extent an incentive award would have been payable to Executive under the terms of the such AIP but for incurring a Date of Termination (“Bonus”). For purposes of calculating the
Bonus, the incentive award to which Executive otherwise would 

 
have been entitled to under the AIP shall be subject to a fraction, the numerator of which shall be the number of full days on active payroll during the applicable performance period (as defined
in the AIP) and the denominator of which shall be the number of full days in such performance period. Subject to subsection (a)(i)(2) below, any Bonus shall be payable as of the payment date for the AIP and shall be paid in substantially equal
installments on each regular salary payroll date for the remainder of the Salary Continuation Period, except as otherwise provided in this Agreement. In the event the payment date for the AIP occurs after the Salary Continuation Period, such Bonus
shall be payable in a one-time, single lump sum payment to Executive, subject to applicable withholding in accordance with Section 18 below, except as otherwise provided in this Agreement. 

Notwithstanding the foregoing, the Sears or Sears Affiliate obligations under this subsection (a)(i)(1) shall be reduced
on a dollar-for-dollar basis (but not below zero), by the amount, if any, of fees, salary or wages that Executive earns from a subsequent employer (including those arising from self-employment) during the Salary Continuation Period. For avoidance of
doubt, Executive shall not be obligated to seek affirmatively or accept an employment, contractor, consulting or other arrangement in order to mitigate Salary Continuation and Bonus. Further, to the extent Executive does not execute and timely
submit the applicable General Release and Waiver (in accordance with subsection 4(g) below) by the deadline specified therein, Salary Continuation and Bonus payments shall terminate and forever lapse, and Executive shall be required to reimburse
Sears for any portion of the Salary Continuation and Bonus paid during the Salary Continuation Period. 
 2.
Notwithstanding anything in this subsection (a)(i) to the contrary, if the Salary Continuation and Bonus payable to Executive in accordance with subsection (a)(i)(1) above during the first six (6) months after Executive’s Separation from
Service would exceed the “Section 409A Threshold” and if as of the date of the Separation from Service Executive is a “Specified Employee” (as such terms are defined in Section 2 below), then, payment shall be made to
Executive on each regular salary payroll date during the first six (6) months of the Salary Continuation Period until the aggregate amount received equals the Section 409A Threshold. Any portion of the Salary Continuation and Bonus in
excess of the Section 409A Threshold that would otherwise be paid during such first six (6) months or any portion of the Salary Continuation and/or Bonus that is otherwise subject to Section 409A, shall instead be paid to Executive in
a lump sum payment on the date that is six (6) months and one (1) day after the date of Executive’s Separation from Service. 

  

					
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 3. All Salary Continuation and Bonus payments (described under this
subsection (a)(i)) will terminate and forever lapse if Executive is employed by a “Sears Competitor” or “Sears Vendor” (as such terms are defined in subsection 4(c)(ii) and 4(d)(ii) herein, respectively) during the Salary
Continuation Period or in the event of Executive’s breach of this Agreement (in accordance with Section 10 below), and Executive shall be required to reimburse Sears for any portion of the Salary Continuation and Bonus paid during the
Salary Continuation Period. 
 ii. Continuation of Benefits. 

1. During the Salary Continuation Period, Executive will be entitled to participate in all benefit
plans and programs (except as specified in this subsection (a)(ii)), on the same terms (including payment of all or a portion of the cost of coverage by Sears or a Sears Affiliate) as a similarly situated active associate, in which Executive was
eligible to participate on the Date of Termination (subject to the terms and conditions and continued availability of such plans and programs); provided, however, that Executive will not be eligible to participate in the long-term disability plan
(as of the 15th day following the Date of Termination),
health care flexible spending account (except on an after-tax basis and only through the earlier of the end of Salary Continuation Period or the calendar year in which the Separation from Service occurs), Sears paid life insurance and the Sears
Holdings 401(k) Savings Plan (or any other defined contribution plan sponsored by Sears or a Sears Affiliate) during the Salary Continuation Period. Without limiting the generality of the foregoing sentence, Executive and Executive’s eligible
dependents shall be entitled to continue to participate, as active participants, in Sears medical and dental plans (subject to the terms and conditions and continued availability of such plans) during the Salary Continuation Period. Upon the
expiration of the Salary Continuation Period, Executive and his eligible dependents shall be eligible to elect COBRA continuation coverage under the Sears medical and dental plans. 

2. If Executive does not timely execute and submit the applicable General Release and Waiver (in accordance with
subsection 4(g) herein) by the deadline specified therein, Executive shall be required to reimburse Sears for the portion of the cost of the coverage referred to under subsection (a)(ii)(1) immediately above paid by Sears during the Salary
Continuation Period, and Executive shall instead be eligible for COBRA continuation coverage under the Sears medical and dental plans as of Executive’s Date of Termination. 

3. Subject to subsection (a)(ii)(4) immediately below, in the event Executive provides services to another employer and
becomes covered by (and not merely eligible for) such employer’s health benefits plan or program, the medical and dental benefits provided by Sears hereunder shall be secondary to such employer’s health benefits plan or program in
accordance with the terms of the Sears health benefit plans. 

  

					
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 4. All of the benefits described in this subsection (a)(ii) will terminate
and forever lapse if Executive is employed by a Sears Competitor or Sears Vendor during the Salary Continuation Period or in the event of Executive’s breach (in accordance with Section 10 below), and Executive shall be required to
reimburse Sears for any portion of the cost of the coverage referred to under subsection (a)(ii)(1) immediately above paid by Sears during the Salary Continuation Period, and Executive shall instead be eligible for COBRA continuation coverage under
the Sears medical and dental plans as of Executive’s Severance from Service date. 
 iii.
Outplacement. As of Executive’s Separation from Service, Executive will be immediately eligible for reasonable outplacement services at the expense of Sears or the appropriate Sears Affiliate. Sears and Executive will mutually agree on
which outplacement firm, among current vendors used by Sears, will provide these services. Such services will be provided for up to twelve (12) months from the Separation from Service or until employment is obtained, whichever occurs first.
Outplacement benefits described in this subsection (a)(iii) will terminate and forever lapse if Executive is employed by a Sears Competitor or Sears Vendor or in the event of Executive’s breach (in accordance with Section 10 below).

 iv. Other. 
 1 In addition to the foregoing Severance Benefits, a lump sum payment will be made to Executive within ten (10) business days following the Date of Termination in an amount equal to the sum of any
base salary and any vacation benefits that have accrued through the Date of Termination to the extent not already paid and any unreimbursed business expenses. No vacation will accrue during the Salary Continuation Period. Further, if Executive is
involuntarily terminated other than for Cause and such Date of Termination occurs after the end of the performance period for the immediately prior AIP and prior to the payment date for such performance period, Executive shall be paid, outside of
such annual incentive plan, an amount equivalent to the target bonus Executive would have been entitled to, if any, under such AIP in the form of a one-time, single lump sum payment, subject to applicable withholding in accordance with
Section 18 below. 
 2. Notwithstanding the foregoing and anything herein to the contrary, in the event of
Executive’s death during the Salary Continuation Period, any unpaid portion of the Salary Continuation and/or Bonus payable in accordance with subsection (a)(i) above shall be paid in a lump sum, within sixty (60) days of death (and no
later than amounts would have been paid absent death), to Executive’s estate, and any eligible dependents who are covered dependents as of the date of death shall incur a qualifying event under COBRA as a result of such death. 

  

					
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 (b) Impact of Termination on Certain Other Plans/Programs.

 i. Annual Incentive Plan. Except as provided herein, upon Executive’s Date of Termination,
Executive’s entitlement to any award under the applicable annual incentive plan (“AIP”) sponsored by Sears, shall be determined in accordance with the terms and conditions of the AIP document regarding termination of employment.

 ii. Long-Term Incentive Program(s). Upon Executive’s Date of Termination, Executive’s
entitlement to any award granted to Executive under a long-term incentive program (“LTIP”) sponsored by Sears, shall be determined in accordance with the terms and conditions of the award letter and the LTIP document regarding termination
of employment. 
 iii. Stock Plan. Upon Executive’s Date of Termination, Executive’s entitlement
to any unvested options, restricted stock or other equity award granted to Executive under a stock plan sponsored by Sears shall be determined in accordance with the terms and conditions of the applicable award agreement and the stock plan document
regarding termination of employment. 
 (c) Post-Termination Forfeiture of Severance Benefits. If Sears
determines after Executive’s Date of Termination that Executive engaged in activity during employment with Sears that Sears determines constituted Cause, Sears will provide Executive with written notice specifying such breach, which notice will
specifically identify the manner in which Sears or the Sears Affiliates believes that Executive has materially breached his duties and responsibilities. Executive shall immediately cease to be eligible for Severance Benefits and shall be required to
reimburse Sears for any portion of the Salary Continuation and Bonus paid to Executive and for the cost of other Severance Benefits received by Executive during the Salary Continuation Period. 

2. Definitions. For purposes of this Agreement, each capitalized term in this Agreement is either defined in the section, exhibit
or appendix in which it first appears or in this Section 2. The following capitalized terms shall have the definitions as set forth below: 
 (a) “Cause” shall mean (i) a material breach by Executive (other than a breach resulting from Executive’s incapacity due to a Disability) of Executive’s duties and
responsibilities which breach is demonstrably willful and deliberate on Executive’s part, is committed in bad faith or without reasonable belief that such breach is in the best interests of Sears or the Sears Affiliates and is not remedied in a
reasonable period of time after receipt of written notice from Sears specifying such breach, which notice specifically identifies the manner in which Sears or the Sears Affiliates believes that Executive has materially breached his duties and
responsibilities; (ii) the commission by Executive of a felony; or (iii) dishonesty or willful misconduct in connection with Executive’s employment. 

(b) “Disability” shall mean disability as defined under the Sears long-term disability plan (regardless
of whether the Executive is a participant under such plan). 
 (c) “Good Reason” shall mean,
without Executive’s written consent, (i) a reduction of more than ten percent (10%) in the sum of Executive’s annual base salary and target AIP bonus from those in effect as of the date of this Agreement;
(ii)

  

					
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Executive’s mandatory relocation to an office more than fifty (50) miles from the primary location at which Executive is required to perform Executive’s duties immediately prior to
the date of this Agreement; (iii) the failure of Sears or the Sears Affiliates to pay any undisputed amount due under this Agreement; (iv) a material diminution of Executive’s title, duties or responsibilities unrelated to (A) an
organizational or a corporate restructuring or (B) Executive’s performance; or (v) any other action or inaction that constitutes a material breach of the terms of this Agreement, including failure of a successor company to assume or
fulfill the obligations under this Agreement. In each case, Executive must provide Sears with written notice of the facts giving rise to a claim that “Good Reason” exists for purposes of this Agreement, within thirty (30) days of
the date Executive knows (or reasonably should have known) of the existence of such Good Reason event, and Sears shall have a right to remedy such event within sixty (60) days after receipt of Executive’s written
notice (“the sixty (60) day period”). If Sears remedies the Good Reason event within the sixty (60) day period, the Good Reason event (and Executive’s right to receive any benefit under this
Agreement on account of termination of employment for Good Reason) shall cease to exist. If Sears does not remedy the Good Reason event within the sixty (60) day period, and Executive does not incur a termination of employment within
thirty (30) days following the earlier of: (y) the date Sears notifies Executive that it does not intend to remedy the Good Reason or does not agree that there has been a Good Reason event, or (z) the expiration of the sixty
(60) day period, the Good Reason event (or any claim of Good Reason) shall cease to exist. Notwithstanding the foregoing, if Executive fails to provide written notice to Sears of the facts giving rise to a claim of Good Reason within
thirty (30) days of the date Executive knows (or reasonably should have known) of the existence of such Good Reason the initial existence of such Good Reason event, the Good Reason event (and Executive’s right to
receive any benefit under this Agreement on account of termination of employment for Good Reason) shall cease to exist as of the thirty-first (31st) day following the later of its occurrence or Executive’s knowledge thereof. 

(d) “Sears Affiliate” shall mean any person with whom Sears is considered to be a single employer under
Code Section 414 (b) and all persons with whom Sears would be considered a single employer under Code Section 414 (c), substituting “50%” for the “80%” standard that would otherwise apply. 

(e) “Section 409A Threshold” shall mean an amount equal to two times the lesser of
(i) Executive’s base salary for services provided to Sears and any Sears Affiliate as an employee for the calendar year preceding the calendar year in which Executive has a Separation from Service; or (ii) the maximum amount that may
be taken into account under a qualified plan in accordance with Code Section 401(a)(17) for the calendar year in which the Executive has a Separation from Service. In all events, this amount shall be limited to the amount specified under
Treasury Regulation Section 1.409A-1(b)(9)(iii)(A) or any successor thereto. 
 (f) “Separation from
Service” shall mean a “separation from service” with Sears (including any Sears Affiliate) within the meaning of Code Section 409A (and regulations issued thereunder). Notwithstanding anything herein to the contrary, the fact
that Executive is treated as having incurred a Separation from Service under Code Section 409A and the terms of this Agreement shall not be determinative, or in any way 

  

					
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affect the analysis, of whether Executive has retired, terminated employment, separated from service, incurred a severance from employment or become entitled to a distribution, under the terms of
any retirement plan (including pension plans and 401(k) savings plans) maintained by Sears (including by a Sears Affiliate). 
 (g) “Specified Employee” shall mean a “specified employee” under Code Section 409A (and regulations issued thereunder), which shall be determined in accordance with the
provisions of Supplement A to the Supplemental Retirement Income Plan (as amended and restated effective January 1, 2008). 

3. Intellectual Property Rights. Executive acknowledges that Executive’s development, work or research on any and all
inventions or expressions of ideas, that may or may not be eligible for patent, copyright, trademark or trade secret protection, hereafter made or conceived solely or jointly within the scope of employment at Sears or any Sears Affiliate, provided
such invention or expression of an idea relates to the business of Sears or any Sears Affiliate, or relates to actual or demonstrably anticipated research or development of Sears or any Sears Affiliate, or results from any work performed by
Executive for or on behalf of Sears or any Sears Affiliate, are hereby assigned to Sears, including Executive’s entire rights, title and interest. Executive will promptly disclose such invention or expression of an idea to Executive’s
management and will, upon request, promptly execute a specific written assignment of title to Sears. If Executive currently holds any inventions or expressions of an idea, regardless of whether they were published or filed with the U.S. Patent and
Trademark Office or the U.S. Copyright Office, or is under contract to not so assign, Executive will list them on the last page of this Agreement. 
 4. Protective Covenants. Executive acknowledges that this Agreement provides for additional consideration beyond what Sears or any Sears Affiliate is otherwise obligated to pay. In consideration of
the opportunity for the Severance Benefits, and other good and valuable consideration, Executive agrees to the following: 
 (a) Non-Disclosure of Sears Confidential Information. Executive acknowledges and agrees to be bound by the following, whether or not Executive receives any Severance Benefits under this Agreement:

 i. Non-Disclosure. 

1. Executive will not, during the term of Executive’s employment with Sears or any Sears Affiliate or thereafter,
and other than in the performance of his duties and obligations during his employment with Sears or as required by law or legal process, and except as Sears may otherwise consent or direct in writing, reveal or disclose, sell, use, lecture upon or
publish any “Sears Confidential Information” (as defined in subsection 4(a)(ii) below) until such time as the information becomes publicly known other than as a result of its disclosure, directly or indirectly, by Executive; and

 2. Executive understands that if Executive possesses any proprietary information of another person or company
as a result of prior employment or otherwise, Sears expects and requires that Executive will honor any and all legal obligations that Executive has to that person or company with respect to proprietary information, and Executive will refrain from
any unauthorized use or disclosure of such information. 

  

					
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 ii. Sears Confidential Information. For purposes of this Agreement,
“Sears Confidential Information” means trade secrets and non-public information which Sears or any Sears Affiliate designates as being confidential or which, under the circumstances, should be treated as confidential, including, without
limitation, any information received in confidence or developed by Sears or any Sears Affiliate, its long and short term goals, vendor and supply agreements, databases, methods, programs, techniques, business information, financial information,
marketing and business plans, proprietary software, personnel information and files, client information, pricing, and other information relating to the business of Sears or any Sears Affiliate that is not known generally to the public or in the
industry. Sears Confidential Information shall not include any information that is (1) generally known to the industry or the public or (2) required by law or judicial process to be disclosed. 

iii. Return of Sears Property. All documents and other property that relate to the business of Sears or any Sears
Affiliate are the exclusive property of Sears, even if Executive authored or created them. Executive agrees to return all such documents that Executive knowingly has and tangible property to Sears upon termination of employment or at such earlier
time as Sears may request Executive to do so. 
 iv. Conflict of Interest. During Executive’s
employment with Sears or any Sears Affiliate and during any Salary Continuation Period, except as may be approved in writing by Sears, neither Executive nor members of Executive’s immediate family (which shall refer to Executive, any spouse or
any child) will knowingly have financial investments or other interests or relationships with Sears’ or any Sears Affiliate’s customers, suppliers or competitors which might impair Executive’s independence of judgment on behalf of the
Company. Also during Executive’s employment with Sears or any Sears Affiliate and during any Salary Continuation Period, Executive agrees further not to knowingly engage in any activity in competition with Sears or any Sears Affiliate and will
avoid any outside activity that could adversely affect the independence and objectivity of Executive’s judgment, interfere with the timely and effective performance of Executive’s duties and responsibilities to Sears or any Sears
Affiliate, discredit Sears or any Sears Affiliate or otherwise conflict with the best interests of Sears or any Sears Affiliate. 
 (b) Non-Solicitation of Employees. During Executive’s employment with Sears or any Sears Affiliate and for twelve (12) months following Executive’s Date of Termination, whether or
not Executive receives any Severance Benefits under this Agreement, Executive will not, directly or indirectly, solicit or encourage any person to leave her/his employment with Sears or any Sears Affiliate or assist in any way with the hiring of any
Sears or any Sears Affiliate employee by any future employer or other entity. 

  

					
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 (c) Non-Competition. Executive acknowledges that as a result of
Executive’s position at Sears or any Sears Affiliate, Executive has learned or developed, or will learn or develop, Sears Confidential Information and that use or disclosure of Sears Confidential Information is likely to occur if Executive were
to render advice or services to any Sears Competitor. 
 i. Therefore, for twelve (12) months following
Executive’s Date of Termination, whether or not Executive receives any Severance Benefits under this Agreement, Executive will not, directly or indirectly, aid, assist, participate in, consult with, render services for, accept a position with,
become employed by, or otherwise enter into any relationship with (other than having a passive ownership interest in or being a customer of) any Sears Competitor. 

ii. For purposes of this Agreement, “Sears Competitor” means: 

1. Those companies listed on Appendix A, each of which Executive acknowledges is a Sears Competitor, whether or
not it falls within the categories in subsection (ii)(2) immediately below, and further acknowledges that this is not an exclusive list of Sears Competitors and is not intended to limit the generality of subsection (ii)(2) immediately below; and

 2. Any party (A) engaged in any retail business (whether in a department store, specialty store,
discount store, direct marketing, or electronic commerce or other business format), that consists of selling furniture, appliances, electronics, hardware, lawn/garden, auto parts, food/consumables, toys, seasonal, fitness/sporting goods, apparel
and/or pharmacy products, or providing home improvement, product repair and/or home services, with combined annual revenue in excess of $1 billion, or (B) a party engaged in any other line of business, in which Sears (including any Sears
Affiliate) has commenced business prior to the end of Executive’s employment, having annual gross sales in that line of business in excess of $100 million. 
 iii. Executive acknowledges that Sears shall have the right to propose modifications to Appendix A periodically to include (1) emergent Competitors in Sears existing lines of business and
(2) Competitors in lines of business that are new for Sears, in each case, with the prior written consent of Executive, which consent shall not be unreasonably withheld. 

iv. Executive further acknowledges that Sears (or Sears Affiliates) does business throughout the United States, Puerto
Rico, U.S. Virgin Islands, Guam and Canada and that this non-compete provision applies in any state or province (as applicable) of the United States, Puerto Rico, U.S. Virgin Islands, Guam and Canada, in which Sears does business. 

(d) Restriction on Post-Employment Affiliation with Sears Vendors. Executive acknowledges that as a result of
Executive’s position at Sears or any Sears Affiliate, Executive has learned or developed, or will learn or develop, Sears Confidential Information and that use or disclosure of Sears Confidential Information is likely to occur if Executive were
to render advice or services to any “Sears Vendor” (as defined herein). 

  

					
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 i. Therefore, for twelve (12) months from Executive’s Date of
Termination, whether or not Executive receives any Severance Benefits under this Agreement, Executive will not, directly or indirectly, aid, assist, participate in, consult with, render services for, accept a position with, become employed by, or
otherwise enter into any relationship with (other than having a passive ownership interest in or being a customer of) any Sears Vendor. 
 ii. For purposes of this Agreement, “Sears Vendor” means, the vendors, if any, listed in Appendix A as well as any vendor with combined annual gross sales of services or merchandise to
Sears in excess of $200 million. 
 (e) Compliance with Protective Covenants. Executive will provide Sears
with such information as Sears may from time to time reasonably request to determine Executive’s compliance with this Section 4. Executive authorizes Sears to contact Executive’s future employers and other entities with which
Executive has any business relationship to determine Executive’s compliance with this Agreement or to communicate the contents of this Agreement to such employers and entities. Executive releases Sears, Sears Affiliates, their agents and
employees, from all liability for any damage arising from any such contacts or communications. 
 (f)
Necessity and Reasonableness. Executive agrees that the restrictions set forth herein are necessary to prevent the use and disclosure of Sears Confidential Information and to otherwise protect the legitimate business interests of Sears and
Sears Affiliates. Executive further agrees and acknowledges that the provisions of this Agreement are reasonable. 
 (g) General Release and Waiver. Upon Executive’s Date of Termination (whether initiated by Sears or Executive in accordance with subsection 1(a) above) potentially entitling Executive to
Severance Benefits, Executive will execute a binding general release and waiver of claims in a form to be provided by Sears (“General Release and Waiver”), which is incorporated by reference under this Agreement. This General Release and
Waiver will be in a form substantially similar to the attached sample. If the General Release and Waiver is not signed within the time required by the waiver or is signed but subsequently revoked, Executive will not continue to receive any Severance
Benefits otherwise payable under subsection 1(a) above. Further, Executive shall be obligated to reimburse Sears for any portion of (i) the Salary Continuation paid during the Salary Continuation Period under subsection (1)(a)(i) herein,
and (ii) the cost for the benefits provided during the Salary Continuation Period under subsection (1)(a)(ii) herein. A sample of this General Release and Waiver is provided as Exhibit A to this Agreement. Upon Executive’s
executing the General Release and Waiver, Sears agrees to sign a binding general release and waiver of claims against Executive, which shall exclude claims provided for under any applicable compensation or benefit agreement or plan document and
claims regarding compliance with this Agreement and shall be subject to the Sears corporate charter and bylaws. 

  

					
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 (h) Exception Request. Notwithstanding the foregoing, Executive may
request a waiver or a specific exception to the non-competition provisions of this Agreement by written request to the Senior Vice President and President, Talent & Human Capital Services or Senior Vice President, General Counsel and
Corporate Secretary (or the equivalent) of Sears. Such a request will be given reasonable consideration and may be granted, in whole or in part, or denied at Sears’ absolute discretion. 

5. Irreparable Harm. Executive acknowledges that irreparable harm would result from any breach by Executive of the provisions of
this Agreement, including without limitation subsections 4(a), 4(b), 4(c) and 4(d), and that monetary damages alone would not provide adequate relief for any such breach. Accordingly, if Executive breaches or threatens to breach this Agreement,
Executive consents to injunctive relief in favor of Sears without the necessity of Sears posting a bond. Moreover, any award of injunctive relief shall not preclude Sears from seeking or recovering any lawful compensatory damages which may have
resulted from a breach of this Agreement, including a forfeiture of any future payments and a return of any payments and benefits already received by Executive. 
 6. Non-Disparagement. Executive will not take any actions that would reasonably be expected to be detrimental to the interests of Sears or any Sears Affiliate, nor make derogatory statements,
either written or oral to any third party, or otherwise publicly disparage Sears or any Sears Affiliate, its products, services, or present or former employees, officers or directors, and will not authorize others to make derogatory or disparaging
statements on Executive’s behalf. Sears shall not authorize and shall take reasonable measures to prevent its present or former officers and directors from making derogatory or disparaging statements regarding Executive to any third party. This
provision does not and is not intended to preclude Executive from entering into any relationship with a Sears Competitor or Sears Vendor after such relationship is permissible under subsection 4(c) or 4(d), respectively, nor does it preclude
Executive from providing truthful testimony in response to legal process or governmental inquiry. 
 7. Cooperation.
Executive agrees, without receiving additional compensation, to fully and completely cooperate with Sears to the extent that such cooperation does not materially and unreasonably interfere with Executive’s subsequent employment, both during and
after the period of employment with Sears or any Sears Affiliate (including any Salary Continuation Period), with respect to matters that relate to Executive’s period of employment, in all investigations, potential litigation or litigation in
which Sears is involved or may become involved other than any such investigations, potential litigation or litigation between Sears and Executive. Sears will reimburse Executive for reasonable travel and out-of-pocket expenses incurred in connection
with any such investigations, potential litigation or litigation. 
 8. Future Enforcement or Remedy. Any waiver, or
failure to seek enforcement or remedy for any breach or suspected breach, of any provision of this Agreement by Sears or Executive in any instance shall not be deemed a waiver of such provision in the future. 

9. Acting as Witness. Executive agrees that both during and after the period of employment with Sears or any Sears Affiliate
(including any Salary Continuation Period), Executive will not voluntarily act as a witness, consultant or expert for any person or party in any action against or involving Sears or any Sears Affiliate or corporate relative of Sears, unless subject
to judicial enforcement to appear as a fact witness only. 

  

					
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 10. Breach by Executive. In the event of a breach by Executive of any of the
provisions of this Agreement, including without limitation the non-competition provisions (Section 4) and the non-disparagement provision (Section 6) of this Agreement, the obligation of Sears or any Sears Affiliate to pay Salary Continuation, Bonus
or to provide other Severance Benefits under this Agreement will immediately cease and any Salary Continuation and Bonus payments already received and the value of any other Severance Benefits already received will be returned by Executive to Sears.

 11. Severability. If any provision(s) of this Agreement shall be found invalid, illegal, or unenforceable, in whole or
in part, then such provision(s) shall be modified or restricted so as to effectuate as nearly as possible in a valid and enforceable way the provisions hereof, or shall be deemed excised from this Agreement, as the case may require, and this
Agreement shall be construed and enforced to the maximum extent permitted by law, as if such provision(s) had been originally incorporated herein as so modified or restricted or as if such provision(s) had not been originally incorporated herein, as
the case may be. 
 12. Governing Law. This Agreement will be governed under the internal laws of the state of Illinois
without regard to principles of conflicts of laws. Executive agrees that the state and federal courts located in the state of Illinois shall have exclusive jurisdiction in any action, lawsuit or proceeding based on or arising out of this Agreement,
and Executive hereby: (a) submits to the personal jurisdiction of such courts; (b) consents to the service of process in connection with any action, suit, or proceeding against Executive; and (c) waives any other requirement (whether
imposed by statute, rule of court, or otherwise) with respect to personal jurisdiction, venue or service of process. 
  

13. Right to Jury. Executive agrees to waive any right to a jury trial on any claim contending that this Agreement or the General
Release and Waiver is illegal or unenforceable in whole or in part, and Executive agrees to try any claims brought in a court or tribunal without use of a jury or advisory jury. Further, should any claim arising out of Executive’s employment,
termination of employment or Salary Continuation Period (if any) be found by a court or tribunal of competent jurisdiction to not be released by the General Release and Waiver, Executive agrees to try such claim to the court or tribunal without use
of a jury or advisory jury. 
 14. Employment-at-Will. This Agreement does not constitute a contract of employment, and
Executive acknowledges that Executive’s employment with Sears or any Sears Affiliate is terminable “at-will” by either party with or without cause and with or without notice. 

15. Other Plans, Programs, Policies and Practices. If any provision of this Agreement conflicts with any other plan, programs,
policy, practice or other Sears document, then the provisions of this Agreement will control, except as otherwise precluded by law. Executive shall not be eligible for any benefits under the Sears Holdings Corporation Master Transition Pay Plan or
the Kmart Corporation Master Severance Pay Plan or any successor severance plan or program. 

  

					
		 	12	  	12/31/2011

 16. Entire Agreement. This Agreement, including any exhibits or appendices hereto,
contains and comprises the entire understanding and agreement between Executive and Sears (including any Sears Affiliate) and fully supersedes any and all prior agreements or understandings between Executive and Sears with respect to the subject
matter contained herein, and may be amended only by a writing signed by Executive and the Chief Executive Officer, Senior Vice President and President, Talent & Human Capital Services or Senior Vice President, General Counsel and Corporate
Secretary (or equivalent) of Sears. 
 17. Confidentiality. Executive agrees that the existence and terms of the
Agreement, including any compensation paid to Executive, and discussions with Sears (including any Sears Affiliate) regarding this Agreement, shall be considered confidential and shall not be disclosed or communicated in any manner except:
(a) as required by law or legal process; (b) to Executive’s spouse or domestic partner, or (c) to Executive’s financial/legal advisors, all of whom shall agree to keep such information confidential; provided, however, that
Executive may disclose to any prospective future employer the provisions of Section 4 of this Agreement to the extent Executive obtains such employer’s agreement to maintain the confidentiality of the terms of Section 4. 

18. Tax Withholding. Any compensation paid or provided to Executive under this Agreement shall be subject to any applicable
federal, state or local income and employment tax withholding requirements. 
 19. Notices. All notices and other
communications hereunder shall be in writing and shall be given by hand delivery to the other parties or by registered or certified mail, return receipt requested, postage prepaid, addressed as follows: 

 

					
	If to the Executive:	 	At the most recent address on file at Sears.
		
	If to Sears:	 	     Sears Holdings Corporation
     3333 Beverly Road

    Hoffman Estates, Illinois 60179

		 	     Attention to both:
	 	 Senior Vice President and President, Talent & Human Capital Services
 Senior Vice President, General Counsel and Corporate Secretary

 20. Assignment. Sears may assign its rights under this Agreement to any successor in interest,
whether by merger, consolidation, sale of assets, or otherwise. This Agreement shall be binding whether it is between Sears and Executive or between any successor or assignee of Sears or affiliate thereof and Executive. This Agreement, and all of
Executive’s rights and duties hereunder, shall not be assignable or delegable by Executive; provided, however, that if Executive shall die, all amounts then payable to Executive hereunder shall be paid in accordance with the terms of this
Agreement to Executive’s devisee, legatee or other designee or, if there be no such devisee, legatee or designee, to Executive’s estate. 
 21. Section 409A Compliance. To the extent that a payment or benefit under this Agreement is subject to Code Section 409A, it is intended that this Agreement as applied to that payment or
benefit comply with the requirements of Code Section 409A, and the Agreement shall be administered and interpreted consistent with this intent. Each payment of Salary Continuation and Bonus on each regular salary payroll date, and each other
payment of other Severance Benefits occurring on a particular date, shall be treated as a separate “payment,” as defined in Treasury Regulations Section 1.409A-2(b)(2), for purposes of Code Section 409A. 

22. Counterparts. This Agreement may be executed in one or more counterparts, which together shall constitute a valid and binding
agreement. 

  

					
		 	13	  	12/31/2011

 IN WITNESS WHEREOF, Executive and Sears, by its duly authorized representative, have
executed this Agreement on the dates stated below, effective as of the date first set forth 
 above. 

 

									
		 	EXECUTIVE	 		 	SEARS HOLDINGS CORPORATION
					
		 	/s/ Ronald D. Boire	 		 	BY:	 	/s/ Dane A. Drobny
		 	Ronald D. Boire	 		 	 Dane A. Drobny
 Senior Vice President, General Counsel and Corporate Secretary

					
		 	1/1/2012	 		 	 	 	12/31/11
		 	Date	 		 	Date	 	

  

					
		 	14	  	12/31/2011

 EXHIBIT A 
 NOTICE: YOU MAY CONSIDER THIS GENERAL RELEASE AND WAIVER FOR UP TO TWENTY-ONE (21) DAYS. YOU MAY NOT SIGN IT UNTIL ON OR AFTER YOUR LAST DAY OF WORK. IF YOU DECIDE TO SIGN IT, YOU MAY REVOKE THE
GENERAL RELEASE AND WAIVER WITHIN SEVEN (7) DAYS AFTER SIGNING. ANY REVOCATION WITHIN THIS PERIOD MUST BE IMMEDIATELY SUBMITTED IN WRITING TO GENERAL COUNSEL, SEARS HOLDINGS CORPORATION, 3333 BEVERLY ROAD, HOFFMAN ESTATES, IL 60179. YOU
MAY WISH TO CONSULT WITH AN ATTORNEY BEFORE SIGNING THIS DOCUMENT. 
 GENERAL RELEASE AND WAIVER 

In consideration for the benefits that I will receive under the attached Executive Severance Agreement, I, and any person acting by,
through, or under me hereby release Sears Holdings Corporation, its current and former agents, subsidiaries, affiliates, employees, officers, stockholders, successors, and assigns (“Sears”) from any and all claims arising out of my
employment or the termination thereof. This General Release and Waiver is to be broadly construed to encompass all claims of any kind or character whatsoever, whether known or unknown, based upon any matter occurring prior to my execution of this
General Release and Waiver and including, but without limiting the generality of the foregoing, any and all claims under the Age Discrimination in Employment Act (“ADEA”), Title VII of the Civil Rights Act of 1964, Section 1981 of the
Civil Rights Act of 1866, the Americans with Disabilities Act (“ADA”), the Employee Retirement Income Security Act (“ERISA”), the Worker Adjustment and Retraining Notification Act (“WARN”), the Family and Medical Leave
Act (“FMLA”) and any other federal, state or local constitution, statute, regulation, or ordinance, and any and all common law claims including, but not limited to, claims for wrongful or retaliatory discharge, intentional infliction of
emotional distress, negligence, defamation, invasion of privacy, and breach of contract. This General Release and Waiver does not apply to any claims or rights that may arise after the date that I signed this General Release and Waiver. I understand
that Sears is not admitting to any violation of my rights or any duty or obligation owed to me. 
 Excluded from this General
Release and Waiver are any claims which cannot be waived by law, including but not limited to (1) the right to file a charge with or participate in an investigation conducted by certain government agencies, and (2) any rights or claims to
benefits accrued under benefit plans maintained by Sears pursuant to ERISA. I do, however, waive my right to any monetary recovery should any agency or other third party pursue any claims on my behalf. I represent and warrant that I have not filed
any complaint, charge, or lawsuit against Sears with any governmental agency and/or any court. 
 I have read this General
Release and Waiver and I understand its legal and binding effect. I am acting voluntarily and of my own free will in executing this General Release and Waiver. 
 I have had the opportunity to seek, and I was advised in writing to seek, legal counsel prior to signing this General Release and Waiver. 

 I was given at least twenty-one (21) days to consider signing this General Release and
Waiver. Any immaterial modification of this General Release and Waiver does not restart the twenty-one (21) day consideration period. 
 GENERAL RELEASE AND WAIVER (continued) 
 I understand that, if I sign the
General Release and Waiver, I can change my mind and revoke it within seven (7) days after signing it by notifying the General Counsel of Sears in writing at Sears Holdings Corporation, 3333 Beverly Road, Hoffman Estates, Illinois 60179. I
understand that this General Release and Waiver will not be effective until after this seven (7) day revocation period has expired. 
  

							
		 		 	
				
	Date: SAMPLE ONLY—DO NOT DATE	 	Signed by:	 		 	SAMPLE ONLY—DO NOT SIGN
		 	  
 Witness by:
	 		 	SAMPLE ONLY—DO NOT SIGN
		 		 		 	

 Page 2 of 2 
 Return both pages of the signed General Release and Waiver 

			
	Executive: Ronald A. Boire	  	Date: January 8, 2012

 Appendix A 
 Executive Severance Agreement 

The following companies (including affiliates and subsidiaries within the same controlled group of corporations) are included within the
definition of “Sears Competitors”, as referred to under subsection 4(c)(ii)(1) of the Executive Severance Agreement: 

[*****] 
  

	[*****]    	Confidential material redacted and filed separately with the Securities and Exchange Commission.Letter to William K. Phelan

 EXHIBIT 10.40 
 [SEARS HOLDINGS LETTERHEAD] 
 September 7, 2011 

Mr. William K. Phelan 
 Senior Vice
President, Controller and Chief Accounting Officer 
 Dear Bill, 
 To acknowledge the individual contributions you have made to the Company and the critical role you play in our future success, you have been selected to receive a retention award and an annual base salary
increase effective August 16, 2011, subject to you signing a new Executive Severance Agreement. 
 The key elements of your new
compensation package are as follows: 
  

																	
	 	  	Current	 	 	New	 
	 Salary
	  	$	450,000	  	  				 	$	525,000	  	  			
	 AIP Target
	  	 	315,000	  	  	 	70	% 	 	 	367,500	  	  	 	70	% 
	 Total Targeted Cash Comp
	  	$	765,000	  	  				 	$	892,500	  	  			
	 LTIP Target*
	  	 	675,000	  	  	 	150	% 	 	 	787,500	  	  	 	150	% 
	 Total Targeted Direct Comp
	  	$	1,440,000	  	  				 	$	1,680,000	  	  			

  

	*	2011 LTIP Target Award will equal 100% of $450,000, your base salary in effect as of April 27, 2011. 

 

	 	•	 	 As noted, your annual incentive opportunity will remain at 70% of your base salary under Sears Holdings Annual Incentive Plan (“AIP”). Any
incentive payable under the 2011 AIP will be prorated based on the amount of time spent at each salary level through January 28, 2012, the last day of Sears Holdings 2011 fiscal year. Any annual incentive payable with respect to a fiscal
year will be paid by April 15th of the following
fiscal year, provided that you are actively employed at the payment date. 

  

	 	•	 	 You will continue to be eligible to participate in the Sears Holdings Corporation 2011 Long-Term Incentive Program (“2011”) at 150% of your
base salary in effect as of April 27, 2011 (the effective date of the 2011 LTIP, not based on your increased annual base salary). Any reward under the 2011 LTIP will continue to be determined based on the achievement of the financial goals
(100% SHC LTIP EBITDA). Further details regarding your 2011 LTIP will be provided to you in the near future. 

 In addition,
you will receive a retention award equal to $400,000 at the time of grant. The award is based 50% on a cash award and 50% on a restricted stock award, both of which will vest in installments over the next three years. The grant date for the
restricted stock award is September 1, 2011, determined by dividing the restricted stock award amount by the reported closing price of a share of the Company’s common stock on the grant date, rounded to the nearest (up or down) whole
share. The award amounts and payment/vesting schedule are as follows: 
  

	 	•	 	 Cash Award: $200,000 

  

	 	•	 	 September 1, 2012: $50,000 payable 

  

	 	•	 	 September 1, 2013: $50,000 payable 

  

	 	•	 	 September 1, 2014: $100,000 payable 

  

	 	•	 	 Restricted Stock Award: $200,000 (Note: Due to rounding, the actual award amount may vary slightly based on the number of shares granted.)

  

	 	•	 	 September 1, 2012: $50,000 vests 

  

	 	•	 	 September 1, 2013: $50,000 vests 

  

	 	•	 	 September 1, 2014: $100,000 vests 

 Mr. William K. Phelan 
 September 7, 2011 
 Page 2 
 Attached is a Retention Award Agreement for your signature, setting out the specific terms of this retention award. 
 As noted above, this award is contingent upon your signing a new Executive Severance Agreement (“Agreement”). If your employment with SHC is terminated by SHC (other than for Cause, death or
Disability) or by you for Good Reason (as such capitalized terms are defined in the Agreement), you will receive twelve (12) months of salary continuation, equal to your base salary at the time of termination, the second six (6) months of
the salary continuation will be subject to mitigation. Under the Agreement, you agree, among other things, not to disclose confidential information and for twelve (12) months following employment not to solicit employees. You also agree
not to aid, assist or render services for any “Sears Competitor” or “Sears Vendor” (as such terms are defined in the Agreement) for twelve (12) months following termination of employment. The non-disclosure,
non-solicitation, non-compete and non-affiliation provisions apply regardless of whether you are eligible for severance benefits under this Agreement. 
 Bill, we are excited about the important contributions you will continue to make to the company as a member of the Executive Leadership Team. If you need additional information or clarification, please
call. 
 In acknowledgement and acceptance of this increase in compensation, please sign below and return this letter along with your signed
Executive Severance Agreement and Retention Award Agreement to me. 
 Sincerely, 
 /s/ J. David Works 
 J. David Works 

 
  

							
	Accepted:	 		 	
				
	/s/ William K. Phelan	 		 		 	9/07/2012
	William K. Phelan	 		 		 	Date

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