Document:

EX-10.5

 Exhibit 10.5 
 RESTRICTED STOCK AWARD 
 Mattersight Corporation, a
Delaware corporation (the “Company”), hereby grants to the individual whose name appears below (the “Participant”), pursuant to the provisions of the Mattersight Corporation 1999 Stock Incentive Plan (the
“Plan”), a Restricted Stock Award (this “Award”) of shares of its Common Stock, $0.01 par value per share (the “Restricted Shares”), as set forth below but only upon and subject to the terms and conditions set forth
herein, in the Plan, and in Annex I hereto. 
 All terms and conditions set forth in Annex I and the Plan are
deemed to be incorporated herein in their entirety. All capitalized terms used in this Award and not otherwise defined herein have the respective meanings assigned to them in Annex I or the Plan. 

Participant’s Name: 
 Number of Restricted Shares Subject to Award: 
 Date of
Award Grant (“Award Date”): 
 Vesting Provisions: 

(a) The Participant’s Restricted Shares will become vested in sixteen (16) equal quarterly increments equal to
6.25% of the Restricted Shares, beginning            , 2012, and ending            , 2015, provided that the Participant is
employed by the Company on such dates. If the application of this paragraph (a) would result in the Participant vesting in a fraction of a share of Common Stock, such fractional share of Common Stock shall be rounded up to the next whole share,
in which case adjustments may be made to future vesting increments to prevent exceeding the total number of Restricted Shares subject to the Award, as provided above. 

(b) If the Participant’s employment or service with the Company terminates for any reason other than death,
Disability or Retirement before all of the Participant’s Restricted Shares have become vested under this Award, then the Restricted Shares that have not become vested will be forfeited on and after the effective date of the termination.

 (c) If the Participant’s employment or service with the Company is terminated on account of the
Participant’s death or Disability, all Restricted Shares that have not otherwise vested under this Award will then become fully vested as of the date of such event. For purposes of this Award, “Disability” means a physical or mental
condition of a Participant resulting from a bodily injury, disease, or mental disorder that renders the Participant eligible for benefits under the Company’s long-term disability plan (as in effect as of the date of the Participant’s
termination of employment and regardless of whether the Participant is otherwise eligible for benefits under such plan), as determined by the Company in its sole discretion. 

(d) If the Participant’s employment or service with the Company terminates by reason of the Participant’s
retirement with the Company’s approval at age 55 or greater and with at least 5 years of continuous service with the Company or with the Company and its predecessor on a combined and uninterrupted basis (“Retirement”), an
additional 20% of the Restricted Shares subject to this Award (but not in excess of the remaining number of Restricted Shares not yet vested under this Award) will then become fully vested as of the date of the Participant’s Retirement.

 (e) Notwithstanding the foregoing, if the Participant terminates employment or service with the Company
because he or she has become employed by an affiliate or subsidiary of the Company, then the Participant shall continue to vest in the Restricted Shares in accordance with the vesting schedule set forth in the preceding paragraph, and the
Participant’s cessation of employment or service with the Company shall not be deemed a forfeiture event hereunder. 
 (f) The Board of Directors will have the right to determine, in its sole discretion, how a Participant’s leave of absence will affect the terms of this Award, including the vesting of Restricted
Shares hereunder. 
 (g) The Company will not have any further obligations to the Participant under this Award if
the Participant’s Restricted Shares are forfeited as provided herein. 

  

					
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 General: 

This Award is subject to the provisions of the Plan, and will be interpreted in accordance therewith. In the event of a
discrepancy between this Award, or any other material describing this Award or the Restricted Shares awarded hereunder, and the actual terms of the Plan, the Plan will govern in all respects. A copy of the Plan is available upon request by
contacting the General Counsel and Corporate Secretary at the Company’s Chicago, Illinois office. 
 IN
WITNESS WHEREOF, this Award has been executed as of the Award Date set forth above. 
  

			
	 MATTERSIGHT CORPORATION

		
	 By:
	 	 

		 	 Kelly D. Conway

	 Its: President and Chief Executive Officer

  

					
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	  	Page 2	  	Restricted Stock Award

 Annex I 
 to 
 Restricted Stock Award 

1. Meaning of Certain Terms. As used herein, the following terms have the meanings set forth below.
“Board” means the Company’s Board of Directors. “Code” means the Internal Revenue Code of 1986, as amended. References to this “Award”, the “Restricted Shares”, and “herein” are deemed to
include the Restricted Stock Award and this Annex I to the Restricted Stock Award taken as a whole. This Annex I and the Restricted Stock Award are deemed to be one and the same instrument. The term “employment” shall have the meanings set
forth in Section 1.4 of the Plan. Other capitalized terms used herein without definition shall have the respective meanings set forth in the Restricted Stock Award or the Plan, as appropriate. 

2. Stock Certificates. Stock certificates will not be issued for the Restricted Shares. Rather, the Company will cause its
transfer agent to maintain a book entry for the Restricted Shares in the Participant’s name. The Restricted Shares will be maintained in a book entry until they are either forfeited or vested. The Participant’s right to receive
this Award hereunder is contingent upon the Participant’s execution and delivery to the Company of all stock powers or other instruments of assignment (including a power of attorney), each endorsed in blank with a guarantee of signature if
deemed necessary or appropriate by the Company, which would permit transfer to the Company of all or a portion of the Restricted Shares in the event such Restricted Shares are forfeited in whole or in part. The Company, or its transfer agent, will
release the Restricted Shares, as and when provided by Section 4 hereof. 
 3. Rights as Stockholder. On and after
the Award Date, and except to the extent provided in Section 8 hereof, the Participant will be entitled to all of the rights of a stockholder with respect to the Restricted Shares, including the right to vote the Restricted Shares, the right to
receive dividends and other distributions payable with respect to the Restricted Shares, and the right to participate in any capital adjustment applicable to all holders of Common Stock; provided, however, that a distribution with respect to
shares of Common Stock, other than a regular cash dividend, will be deposited with the Company and will be subject to the same restrictions as the Restricted Shares. If the Participant forfeits any rights he or she may have under this Award, the
Participant shall, on the day following the event of forfeiture, no longer have any rights as a stockholder with respect to the forfeited portion of the Restricted Shares or any interest therein (or with respect to any Restricted Shares not then
vested), and the Participant shall no longer be entitled to receive dividends on such stock or vote the Restricted Shares as of any record date occurring thereafter. 
 4. Terms and Conditions of Distribution. The Company, or its transfer agent, will transfer the vested portion of the Restricted Shares to a brokerage account established by the Company on behalf of
the Participant as soon as practicable after the Restricted Shares become vested. If the Participant dies before the Company has distributed any portion of vested Restricted Shares, the Company will transfer that portion of the vested Restricted
Shares to a brokerage account established by the Company on behalf of the beneficiary designated by the Participant on a form provided by the Company for this purpose. If the Participant failed to designate a beneficiary, the Company will distribute
certificates for the Restricted Shares in accordance with the Participant’s will or, if the Participant did not have a will, the Restricted Shares will be distributed in accordance with the laws of descent and distribution. The Company will
distribute certificates for any undistributed portion of vested Restricted Shares no later than six months after the Participant’s death. 
 The Committee (as defined in Section 7) may require the Participant, or the alternate recipient identified in the preceding paragraph, will be required to satisfy any potential federal, state, local
or other tax withholding liability. Such liability must be satisfied at the time the Restricted Shares become “substantially vested” (as defined in the regulations issued under Section 83 of the Code). In order to satisfy the
withholding, the Company shall withhold whole shares of Common Stock which would otherwise be delivered having an aggregate Fair Market Value, determined as of the Tax Date in an amount necessary to satisfy the amount of applicable taxes required to
be withheld; provided, however, that in the event the Participant is subject to Section 16 of the Exchange Act, the Committee may require that the method of satisfying such an obligation be in compliance with Section 16 and the
rules and regulations thereunder. 
 The Company will not make any distribution under this Section 4 before
the first date any portion of the Restricted Shares may be distributed to the Participant without penalty or forfeiture under federal or state laws or regulations governing short swing trading of securities. In determining whether a distribution
would result in such a penalty or forfeiture, the Company and the Committee may rely upon information reasonably available to them or upon representations of the Participant’s legal or personal representative. 

  

					
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 5. No Right to Continue Employment or Service. Nothing in the Plan or this Award will
be construed as creating any right in the Participant to continued employment or service with the Company, or as altering or amending the existing terms and conditions of the Participant’s employment or service. 

6. Nontransferability. No interest of the Participant or any designated beneficiary in or under this Award will be assignable or
transferable by voluntary or involuntary act or by operation of law, other than as set forth in Section 4 hereof. Distribution of Restricted Shares will be made only to the Participant; or, if the Committee has been provided with evidence
acceptable to it that the Participant is legally incompetent, the Participant’s personal representative; or, if the Participant is deceased, to the designated beneficiary or other appropriate recipient in accordance with Section 4 hereof.
The Committee may require personal receipts or endorsements of a Participant’s personal representative, designated beneficiary, or designated alternate recipient. Any effort to otherwise assign or transfer the rights under this Award will be
wholly ineffective, and will be grounds for termination by the Committee of all rights of the Participant and his or her beneficiary in and under this Award. 
 7. Administration. The Compensation Committee of the Board of Directors of the Company (the “Committee”) has the authority to manage and supervise the administration of the Plan. The
Participant’s rights under this Award are expressly subject to the terms and conditions of the Plan, including any required continued shareholder approval of the Plan, and to any guidelines the Committee adopts from time to time that are not
inconsistent with the Plan. 
 8. Interpretation; Governing Law. Any interpretation by the Committee of the terms and
conditions of the Plan, this Award, or any guidelines adopted as described in Section 7 hereof will be final. This Award and all determinations made and actions taken pursuant hereto, to the extent not otherwise governed by the Code or the laws
of the United States, will be governed by the laws of the State of Delaware and construed in accordance therewith without giving effect to the principles of conflicts of law, to the extent such principles would result in the application of another
state’s laws. 
 9. Binding Effect. This Award will be binding upon and will inure to the benefit of the Company and
the Participant and their respective heirs, executors, administrators, legal representatives, successors, and assigns. 
 10.
Amendment and Waiver. The provisions of this Award may be amended or waived only with the prior written consent of the Company and the Participant, and no course of conduct or failure or delay in enforcing the provisions of this Award will
affect the validity, binding effect or enforceability of this Award. 

  

					
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	 1999 Stock Incentive Plan
	  		  	Rev. 8/27/12

  

Exhibit 10.8 

Mattersight Corporation 
 Non-Statutory 
 Stock Option Agreement 

Mattersight Corporation, a Delaware corporation (the “Company”), hereby grants to the individual whose name
appears below (the “Optionholder”), pursuant to the provisions of the Mattersight Corporation 1999 Stock Incentive Plan (the “Plan”), an option to purchase from the Company (the “Option”) such number of shares of
its Common Stock, $0.01 par value (“Stock”), as set forth below at the price per share set forth below, but only upon and subject to the terms and conditions set forth herein, in the Plan, and in Annex I hereto. The Option is a
non-statutory stock option, which means it is not intended to qualify as an “incentive stock option” under Code Section 422. 
 All terms and conditions set forth in Annex I and the Plan are deemed to be incorporated herein in their entirety. All capitalized terms used in this Agreement and not otherwise defined herein have the
respective meanings assigned to them in Annex I or the Plan. 
 Optionholder’s Name: 

Number of Shares 
 Subject to Option: 
 Exercise Price 

Per Share: 
 Date of Option Grant 
 (“Option Date”):

 Exercise Provisions: 

(a) The Option will become exercisable as follows: (i) one (1) increment equal to 25% of the shares subject to
the Option on August 31, 2013, and (ii) twelve (12) equal quarterly increments equal to 6.25% of the shares subject to the Option, beginning November 30, 2013 and ending August 31, 2016; provided that Optionholder is
employed by the Company on such dates and (iii) as otherwise provided pursuant to paragraphs (b) through (f) of this Agreement or Section 6.8 of the Plan. 

(b) If, on or after the Option Date, the Optionholder’s employment or service with the Company terminates for any
reason whatsoever (including, without limitation, involuntary termination by the Company) other than death, Disability, or Retirement, the Option will remain exercisable with respect to the number of shares subject to the Option that are exercisable
as of the effective date of the Optionholder’s termination of employment or service with the Company and may thereafter be exercised for a period of ninety (90) days from the effective date of the Optionholder’s termination of
employment or service or until the Expiration Date, whichever period is shorter, after which the Option will terminate in its entirety. The Option shall terminate as of the effective date of the Optionholder’s termination of employment or
service with respect to any shares subject thereto that are not exercisable as of such employment or service termination date. 

  
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	 1999 Stock Incentive Plan
	  		  	Rev. 8/27/12

  

(c) If the Optionholder’s employment or service with the Company terminates by reason of the Optionholder’s
death, the Option will become exercisable as of the date of death with respect to any or all of the shares subject to the Option. The Option may thereafter be exercised by the Optionholder’s legal representative for a period of one
(1) year from the date of death or until the Expiration Date, whichever period is shorter, after which the Option will terminate in its entirety. 
 (d) If the Optionholder’s employment or service with the Company terminates by reason of the Optionholder’s Disability, the Option will become exercisable as of the effective date of such
termination with respect to any or all of the shares subject to the Option. The Option may thereafter be exercised for a period of ninety (90) days from the effective date of such termination or until the Expiration Date, whichever period is
shorter, after which the Option will terminate in its entirety. For purposes of this Award, “Disability” means a physical or mental condition of a Participant resulting from a bodily injury, disease or mental disorder that renders the
Participant eligible for benefits under the Company’s long-term disability plan (as in effect as of the date of the Participant’s termination of employment and regardless of whether the Participant is otherwise eligible for benefits under
such plan), as determined by the Company in its sole discretion. 
 (e) If the Optionholder’s employment or
service with the Company terminates by reason of the Optionholder’s retirement after the Optionholder has completed five (5) years of service as an employee of the Company and is at least 55 years of age (“Retirement”), the
Option will remain exercisable with respect to the number of shares subject to the Option that are exercisable as of the effective date of the Optionholder’s Retirement, and may thereafter be exercised for a period of two (2) years from
the effective date of the Optionholder’s Retirement or until the Expiration Date, whichever period is shorter, after which the Option will terminate in its entirety. The Option shall terminate as of the effective date of the Optionholder’s
Retirement with respect to any shares subject thereto that are not exercisable as of such Retirement effective date. 
 (f) If the Optionholder dies following the termination of the Optionholder’s employment or service with the Company, the Option will be exercisable only to the extent that it is exercisable on the
date of the Optionholder’s death and may thereafter be exercised only for that period of time for which the Option is exercisable immediately prior to the Optionholder’s death. 

  
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	 1999 Stock Incentive Plan
	  		  	Rev. 8/27/12

  

General: 
 This Agreement is subject to the provisions of the Plan, and will be interpreted in accordance therewith. In the event of a discrepancy between this Agreement, or any other material describing this
Agreement or the Option awarded hereunder, and the actual terms of the Plan, the Plan will govern in all respects. A copy of the Plan is available upon request by contacting the General Counsel and Corporate Secretary at the Company’s Chicago,
Illinois office. 
 IN WITNESS WHEREOF, this Agreement has been executed as the Option Date set forth above.

  

			
	 Mattersight Corporation

		
	 By:
	 	 

		 	 Kelly D. Conway

	 Its: President & Chief Executive Officer

  
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	 1999 Stock Incentive Plan
	  		  	Rev. 8/27/12

  

Annex I 

to 

Stock Option Agreement 
 1. Meaning of Certain Terms. As used herein, the following terms have the meanings set forth below. “Board” means the Company’s Board of Directors. “Code” means the
Internal Revenue Code of 1986, as amended. References to this “Agreement,” the “Option” and “herein” are deemed to include the Stock Option Agreement and this Annex I to Stock Option Agreement taken as a whole. This
Annex I and the Stock Option Agreement are deemed to be one and the same instrument. The term “employment” shall have the meanings set forth in Section 1.4 of the Plan. Other capitalized terms used herein without definition shall have
the respective meanings set forth in the Stock Option Agreement or the Plan, as appropriate. 
 2. Time and
Manner of Exercise of Option. 
 2.1. Term and Termination of Option. The maximum term of the Option
will be the date which is ten (10) years after the Option Date (the “Expiration Date”). The Option will terminate, to the extent not exercised or earlier terminated pursuant to the terms of this Agreement, on its Expiration Date.
Notwithstanding any other term of this Agreement, in no event may the Option be exercised, in whole or in part, after the Expiration Date or its earlier termination. 

2.2. Exercisability of Option. The Option will become exercisable on the date or dates as set forth in this
Agreement. 
 2.3. Manner of Exercise. The Option may be exercised in whole or in part by the
Optionholder in the manner described in or established by the Committee pursuant to Section 2.1(c) of the Plan. 
 2.4 Tax Withholding. The Company will be entitled to withhold, or secure payment from the Optionholder in lieu of withholding, the amount of any Federal, state, local or other withholding taxes due
upon exercise of the Option, in accordance with Section 6.9 of the Plan. 
 3. Miscellaneous
Provisions. 
 3.1. Option Confers No Rights as Stockholder. Neither the Optionholder nor any other
person has or will have any rights as a security holder of the Company or any successor with respect to any shares of Common Stock or other securities which are or become subject to the Option hereunder unless and until the Optionholder becomes a
holder of record with respect to such shares of Common Stock or other securities following proper exercise of the Option. 
 3.2. Option Confers No Rights to Continue Employment or Service. In no event will the granting of the Option or its acceptance by the Optionholder confer upon the Optionholder any right to
continued employment or service with the Company, or any subsidiary or affiliate of the Company, or affect in any manner the right of the Company, or its subsidiary or affiliate, to terminate the employment or service of the Optionholder at any time
without liability hereunder. 

  
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	 1999 Stock Incentive Plan
	  		  	Rev. 8/27/12

  

3.3. Designation as Nonqualified Stock Option. The Option is hereby designated as a non-statutory stock option and
shall not constitute an “incentive stock option” within the meaning of section 422 of the Code; this Agreement will be interpreted and treated consistently with such designation. 

3.4. Decisions of the Committee. Subject to Section 1.3 of the Plan, the Committee has the right to resolve
all questions which may arise in connection with the Option or its exercise. Any interpretation, determination or other action made or taken by the Committee regarding the Plan or this Agreement shall be final, binding, and conclusive. 

3.5. Non-transferability. Except as and to the extent otherwise expressly permitted by Section 6.8 of the
Plan, the Option may not be transferred, assigned, or pledged. 
 3.6 Conformity with Plan. The Option is
intended to conform in all respects with, and is subject to all applicable provisions of, the Plan, which is incorporated herein by reference. In the event of any discrepancy between the Option, or a document that describes or explains the Option,
and the Plan, the Plan will govern in all respects. 
 3.7. Successors. This Agreement will be binding
upon and inure to the benefit of any successor or successors of the Company and any person or persons who acquire any rights under Section 6.8 of the Plan. 

3.8. Notices. All notices, requests or other communications relating to the exercise of this Option (including,
without limitation, the “cashless exercise” thereof or tax withholdings relating thereto) will be made in writing in such form and substance, and provided in accordance with such procedures, as may be prescribed by the Committee from time
to time and then in effect. Any other notices, requests or other communications provided for in this Agreement will be made in writing either (1) by actual delivery to the party entitled thereto, or (2) by mailing in the U.S. mails,
postage prepaid, to the last known address of the party entitled thereto. Any such other notices will be deemed to be received, in case (1), on the date of its actual receipt by the party entitled thereto and, in case (2), three (3) days after
the date of its mailing. 
 3.9. Governing Law. This Agreement, and all determinations made and actions
taken pursuant thereto, to the extent not otherwise governed by the Code or the laws of the United States, will be governed by the laws of the State of Delaware and construed in accordance therewith, without giving effect to principles of conflicts
of laws, to the extent such principles would result in the application of another state’s laws. 

  
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