Exhibit 10.1

Execution Version

PURCHASE AND SETTLEMENT AGREEMENT

This PURCHASE AND SETTLEMENT AGREEMENT (this “Agreement”), is made and entered
into as of December 19, 2011, by and between Mattersight Corporation, a Delaware
corporation (the “Company”), and TCV III (GP), TCV III (Q), L.P., TCV III, L.P.,
TCV III Strategic Partners, L.P., TCV IV, L.P. and TCV IV Strategic Partners,
L.P. (collectively the “Sellers” and individually referred to as a “Seller”).

WHEREAS, the Sellers collectively own 1,872,805 shares (the “Shares”) of 7%
Series B Convertible Preferred Stock, par value $0.01 per share, of the Company
(the “Series B Stock”);

WHEREAS, the Company entered into that certain Acquisition Agreement dated as of
March 17, 2011 providing for the sale of assets used in the Integrated Contact
Solutions Business Unit (the “Asset Sale”) to a subsidiary of TeleTech Holdings,
Inc.;

WHEREAS, the Company and the Sellers held differing views regarding the effect
of the closing of the Asset Sale under the Certificate of Designations for the
Series B Stock;

WHEREAS, the parties submitted their dispute to arbitration in the Court of
Chancery of the State of Delaware (the “Arbitration”);

WHEREAS, the parties wish to settle the dispute and terminate the Arbitration;

WHEREAS, in connection with the settlement of the dispute and termination of the
Arbitration, the Sellers wish to sell to the Company, and the Company wishes to
purchase from the Sellers, the Shares, upon the terms and subject to the
conditions set forth herein;

NOW, THEREFORE, the parties hereby agree as follows:

1. Purchase and Sale

(a) Purchase Price. Upon the terms and subject to the conditions of this
Agreement, the Sellers agree to sell the Shares to the Company, and the Company
agrees to repurchase the Shares from the Sellers. The purchase price (the
“Purchase Price”) payable in respect of each of the Shares shall equal the sum
of (i) $5.10 per share plus an amount equal to the accrued but unpaid dividends
on the Series B Stock as of the Closing Date (the “Per Share Cash Amount”) and
(ii) $3.50 per share (the “Per Share Deferred Amount”), payable as follows:

(i) The aggregate Per Share Cash Amount shall be paid by the Company to the
Sellers on the Closing Date in cash by wire transfer of immediately available
funds to the account(s) designated prior to the Closing Date by the Sellers.

(ii) The aggregate Per Share Deferred Amount shall be paid by the Company
through the execution and delivery to the Sellers on the Closing Date of
promissory notes in the form attached hereto as Exhibit A (the “Notes”).

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(b) Closing.

(i) Timing. The purchase and sale of the Shares shall occur on December 20, 2011
(the “Closing Date”).

(ii) Deliveries. On the Closing Date: (A) the Sellers shall deliver to the
Company one or more original stock certificates representing the Shares,
together with an original duly executed stock power for each stock certificate
authorizing transfer of the Shares to the Company, in form and substance
reasonably satisfactory to the Company; (B) the Company shall pay to each Seller
its pro rata share of the aggregate Per Share Cash Amount, as set forth on
Schedule I attached hereto; and (C) the Company shall deliver to each Seller an
original duly executed Note, representing such Seller’s pro rata share of the
aggregate Per Share Deferred Amount, as set forth in Schedule I attached hereto.

(c) Legend Removal. In the event any Seller requests that the Company remove the
restrictive legends from the shares of common stock, par value $0.01 per share,
of the Company owned by any such Seller as of the date hereof, the Company
agrees to instruct the transfer agent to remove such legends upon receipt of an
opinion of counsel to the Seller to the effect that the removal of such legends
is in compliance with all applicable state and federal securities laws.

2. Representations of the Sellers. The Sellers severally represent and warrant
to, and covenant and agree with, the Company as of the date hereof and as of the
Closing Date, as follows:

(a) Power and Authority. The Sellers have all requisite power and authority to
execute and deliver this Agreement and to perform their obligations under this
Agreement.

(b) Binding Obligations. This Agreement constitutes the legal, valid, and
binding obligation of the Sellers, enforceable against each Seller in accordance
with its terms.

(c) No Violation. The execution, delivery, and performance of this Agreement by
the Sellers does not and shall not conflict with, violate, or cause a breach of
any agreement, contract, or instrument to which any Seller is a party or any
judgment, order, or decree to which any Seller is subject.

(d) Title. The Shares include all Series B Stock owned by the Sellers. The
Sellers own beneficially and of record and have good and marketable title to the
Shares as set forth on Schedule I hereto, free and clear of all liens, charges,
claims, security agreements, equities, options, pledges, and encumbrances. On
the Closing Date, the Company will acquire good title to the Shares, free and
clear of all liens, charges, claims, security agreements, equities, options,
pledges, and encumbrances.

(e) Acquisition of Notes Entirely for Own Account. The Notes are being issued to
Sellers in reliance upon the Sellers’ representations to the Company, which by
execution of this Agreement by the Sellers the Sellers hereby confirm, that the
Notes to be acquired by the Sellers will be acquired for investment for each
Seller’s own account, not as a nominee or agent, and not with a view to the
resale or distribution of any part thereof, and that each Seller has no present

 

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intention of selling, granting any participation in, or otherwise distributing
the same. By executing this Agreement, the Sellers further represent that they
do not presently have any contract, undertaking, agreement, or arrangement with
any person to sell, transfer, or grant participations to such person or to any
third person, with respect to the Notes.

(f) Access to Information. The Sellers have had an opportunity to ask the
Company and its officers questions and receive answers regarding the Company’s
business, management, and financial affairs, and the terms and conditions of the
purchase of the Shares, including the terms and conditions of the Notes, and
have had full access to such other information concerning the Company and its
operations and financial performance as the Sellers have requested. The Sellers
acknowledge that they have completed to their satisfaction their own due
diligence investigation with respect to all of the facts, laws, and
circumstances material to this Agreement or any provision hereof.

(g) Restricted Securities. The Sellers understand that the Notes have not been,
and will not be, registered under the Securities Act of 1933, as amended (the
“Act”), by virtue of §4(2) of the Act and the provisions of Regulation D
promulgated thereunder which depends upon, among other things, the bona fide
nature of the investment intent and the accuracy of the Sellers’ representations
as expressed herein. The Sellers understand that the Notes are “restricted
securities” under applicable U.S. federal and state securities laws and that,
pursuant to these laws, the Sellers must hold the Notes indefinitely unless they
are registered with the Securities and Exchange Commission and qualified by
state authorities, or an exemption from such registration and qualification
requirements is available. The Sellers acknowledge that the Company has no
obligation to register or qualify the Notes for resale. The Sellers further
acknowledge that if an exemption from registration or qualification is
available, it may be conditioned on various requirements including, but not
limited to, the time and manner of sale, the holding period for the Notes, and
requirements relating to the Company which are outside of the Sellers’ control,
and which the Company is under no obligation and may not be able to satisfy.

(h) No Public Market. The Sellers understand that no public market now exists
for the Notes, and that no public market may ever exist for the Notes.

(i) Legends. The Sellers understand that the Notes, and any securities issued in
respect of or exchange for the Notes, will bear the following legend:

THE SECURITIES REPRESENTED BY THIS INSTRUMENT HAVE BEEN ACQUIRED FOR INVESTMENT
AND HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR
UNDER ANY APPLICABLE STATE SECURITIES LAWS. THESE SECURITIES MAY NOT BE SOLD OR
TRANSFERRED IN THE ABSENCE OF SUCH REGISTRATION OR AN EXEMPTION THEREFROM UNDER
SAID ACT. IN ADDITION, THE TRANSFERABILITY OF THE SECURITIES REPRESENTED HEREBY
IS RESTRICTED AS SET FORTH IN SECTION 3 HEREOF.

 

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(j) Accredited Investor. Each of the Sellers is an “Accredited Investor” as
defined in Rule 501(a) of Regulation D of the Securities and Exchange Act of
1934, as amended.

(k) Sophisticated Party. Each of the Sellers (i) is a sophisticated entity with
respect to the sale of the Shares and receipt of the Notes, (ii) has adequate
information concerning the business and financial condition of Company to make
an informed decision regarding the sale of the Shares and receipt of the Notes
and (iii) has independently and without reliance upon the Company, and based on
such information as each Seller has deemed appropriate, made its own analysis
and decision to enter into this Agreement, except that the Sellers have relied
upon the Company’s express representations, warranties, covenants, agreements,
and indemnities in this Agreement. The Sellers acknowledge that the Company has
not given the Sellers any investment advice, credit information, or opinion on
whether the sale of the Shares or receipt of the Notes are prudent.

3. Representations of the Company.

The Company represents and warrants to, and covenants and agrees with the
Sellers, as of the date hereof and as of the Closing Date as follows:

(a) Corporate Power and Authority. The Company has all requisite corporate power
and authority, and has obtained all approvals and consents required to enter
into, to execute and deliver this Agreement and the Notes, and to perform its
obligations under this Agreement and the Notes. The Board of Directors of the
Company has duly approved this Agreement and the Notes and has duly authorized
the execution, delivery and performance of this Agreement and the Notes. No
other corporate proceedings on the part of the Company are necessary to approve
and authorize the execution and delivery of this Agreement and the Notes by the
Company, and the consummation of the transactions contemplated hereby or
thereby.

(b) Binding Obligations. This Agreement constitutes, and upon its execution and
delivery by the Company, each of the Notes will constitute, a legal, valid, and
binding obligation of the Company, enforceable against the Company in accordance
with its terms.

(c) No Violation. The execution, delivery, and performance of this Agreement and
the Notes by the Company does not and shall not (a) conflict with, violate, or
cause a breach of, (b) constitute a default under or give any person or entity
the right to exercise any remedy under or to accelerate the maturity or
performance of or to cancel, terminate or modify, or (c) require any
authorization, consent, approval, exemption or other action by or notice to any
court or other governmental body under, the provisions of the certificate of
incorporation or bylaws of the Company or any agreement, contract, or instrument
to which the Company is a party or by which any of its assets or bound or by
which any of its assets are affected, or any applicable law, statute, rule or
regulation, or any judgment, order, or decree to which the Company is subject.

(d) Proceedings. There is no pending or threatened action, arbitration, audit,
hearing, investigation, litigation or suit (whether civil, criminal,
administrative, investigative or informal) against the Company that challenges,
or may have the effect of preventing, delaying, making illegal or otherwise
interfering with, any of the transactions hereunder.

 

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(e) Certain Transactions. The Company is not currently in discussions regarding,
or receipt of any pending or current proposal with respect to, (1) a merger,
consolidation, business combination, recapitalization, liquidation, dissolution
or similar transaction of the Company, (2) any sale of a majority of the capital
stock of the Company, or (3) any other similar transaction or series of
transactions that would result in the Company ceasing to be registered.

4. Release.

(a) Seller Release. In further consideration of the agreements provided for
pursuant to this Agreement, and as a material inducement therefor, effective as
of the Closing Date, the Sellers and their respective affiliates, subsidiaries,
officers, directors, partners, members, equity holders, employees, predecessors,
successors, assigns, heirs, representatives, agents, insurers, and attorneys
(collectively, the “Seller Parties”), do hereby release, remise, and forever
discharge the Company and its affiliates, subsidiaries, officers, directors,
equity holders, employees, predecessors, successors, assigns, heirs,
representatives, agents, insurers, and attorneys (collectively, the “Company
Parties”) from any and all causes of action, sums of money, damages, attorneys’
fees, costs, losses, liabilities, accountings, claims, costs, awards, judgments,
and demands whatsoever (whether known or unknown, disclosed or undisclosed,
asserted or unasserted, direct or indirect, absolute or contingent, accrued or
unaccrued, and whether due or to become due, in law or equity, contract or tort,
or otherwise), arising from the beginning of time up to and including the
Closing Date, which the Seller Parties ever had, now have, or hereafter can,
shall, or may have against the Company Parties relating to the Shares and the
Sellers’ ownership of such Shares, including without limitation, the matters
that are the subject of the Arbitration.

(b) Company Release. In further consideration of the agreements provided for
pursuant to this Agreement, and as a material inducement therefor, effective as
of the Closing Date, the Company Parties do hereby release, remise, and forever
discharge the Seller Parties from any and all causes of action, sums of money,
damages, attorneys’ fees, costs, losses, liabilities, accountings, claims,
costs, awards, judgments, and demands whatsoever (whether known or unknown,
disclosed or undisclosed, asserted or unasserted, direct or indirect, absolute
or contingent, accrued or unaccrued, and whether due or to become due, in law or
equity, contract or tort, or otherwise), arising from the beginning of time up
to and including the Closing Date, which the Company Parties ever had, now have,
or hereafter can, shall, or may have against the Seller Parties relating to the
Shares and the Sellers’ ownership of such Shares, including without limitation,
the matters that are the subject of the Arbitration.

(c) Exclusions. It is expressly understood and agreed that the releases in
Sections 4(a) and 4(b) above, constitute general releases and shall be
interpreted liberally to effectuate the maximum protection to the released
parties allowed by law; provided, however, that nothing contained herein shall
be deemed to release any of the Company Parties or Seller Parties, as
applicable, from claims arising from, in connection with, or related to (a) any
breach of the terms and conditions of this Agreement, (b) any claims arising
under the Notes, or (c) any causes of action, sums of money, damages, attorneys’
fees, costs, losses, liabilities, accountings, claims, or demands whatsoever (in
law or equity, contract or tort, or otherwise), arising after the Closing Date.

 

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(d) No Admission of Wrongdoing. Each Party agrees that no term of this
Agreement, or any aspect of its negotiation or performance, including, without
limitation, any purchase or sale referenced herein, shall be deemed an admission
of liability or wrongdoing by any Party, such liability or wrongdoing being
expressly denied.

5. Termination.

(a) Arbitration. On or prior to December 27, 2011, the Parties jointly shall
submit a letter to the Honorable Leo E. Strine, Jr. of the Court of Chancery of
Delaware terminating the arbitration captioned TCV III, G.P. et al v.
Mattersight Corporation, Arbitration No. 002-CS.

(b) Dispute Resolution Agreement. On the Closing Date, the Dispute Resolution
Agreement dated April 26, 2011 between the Company and the Sellers shall
terminate in accordance with Section 14 of the Dispute Resolution Agreement.

6. Miscellaneous

(a) Fees and Expenses. Whether or not the transactions contemplated by this
Agreement shall be consummated, each of the parties hereto shall pay the fees
and expenses of its own counsel, accountants, and other experts and all other
expenses incurred by it in connection with the negotiation, preparation,
execution, and delivery of this Agreement and the consummation of the
transactions contemplated hereby and all other matters incident thereto;
provided, however, that in any action to enforce or interpret the terms of this
Agreement, the prevailing party (or parties) shall be entitled to an award of
reasonable attorneys’ fees and costs.

(b) Modification and Waiver. No amendment or modification of the terms or
provisions of this Agreement shall be binding unless the same shall be in
writing and duly executed by the parties hereto. No waiver of any of the
provisions of this Agreement shall be deemed to or shall constitute a waiver of
any other provision hereof. No delay on the part of any party in exercising any
right, power, or privilege hereunder shall operate as a waiver thereof.

(c) Severability. In case any provision in this Agreement shall be invalid,
illegal, or unenforceable, the validity, legality, and enforceability of the
remaining provisions shall not in any way be affected or impaired thereby.

(d) No Implied Rights. Nothing herein express or implied, is intended to or
shall be construed to confer upon or give to any person, firm, corporation, or
legal entity, other than the parties hereto and their affiliates, any interests,
rights, remedies, or other benefits with respect to or in connection with any
agreement or provision contained herein or contemplated hereby.

(e) No Presumption Against Drafter. Each of the parties hereto has jointly
participated in the negotiation and drafting of this Agreement. In the event of
an ambiguity or a question of intent arises, this Agreement shall be construed
as if drafted jointly by each of the parties hereto and no presumptions or
burdens of proof shall arise favoring any party by virtue of authorship of any
of the provisions of this Agreement.

 

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(f) Additional Documents. The Sellers and the Company agree to take any such
actions and execute any additional documentation necessary or desirable to carry
out the purposes of this Agreement.

(g) Notices. All notices, requests, demands and other communications regarding
this Agreement shall be in writing and delivered in person, sent by facsimile,
sent by electronic mail or sent by Registered or Certified U.S. Mail, Postage
Prepaid, Return Receipt Requested, and properly addressed as follows:

To the Company:

Mattersight Corporation

200 South Wacker Drive

Suite 820

Chicago, IL 60606

Fax: (775) 252-9987

Attention: Kelly D. Conway

With a copy (which shall not constitute notice) to:

Winston & Strawn LLP

35 West Wacker Drive

Chicago, IL 60601

Fax: (312) 558-5700

Attention: Steven J. Gavin, Esq.

To Sellers:

Technology Crossover Ventures

528 Ramona Street

Palo Alto, California 94301

Fax: (650) 614-8222

Attention: Carla S. Newell

With a copy (which shall not constitute notice) to:

Richards, Layton & Finger, P.A.

920 N. King Street

Wilmington, Delaware 19801

Fax: (302) 498-7772

Attention: Gregory V. Varallo

Any notice so addressed shall be deemed to be given: if delivered by hand, on
the date of such delivery; if sent by facsimile, on the date of proof of
transmission; if sent by electronic mail, on the date of proof of receipt; if
mailed by overnight courier, on the first business day following the date of
such mailing; and if mailed by registered or certified mail, on the third
business day after the date of such mailing.

 

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(h) Governing Law. This Agreement shall be governed by and construed in
accordance with the laws of the State of Delaware.

(i) Waiver of Jury Trial. THE COMPANY AND THE SELLERS HEREBY IRREVOCABLY WAIVE
ANY AND ALL RIGHT TO TRIAL BY JURY IN ANY LEGAL PROCEEDING ARISING OUT OF OR
RELATING TO THIS AGREEMENT.

(j) Consent to Jurisdiction, Etc. Each of the Company and the Sellers agree that
any suit, action, or proceeding seeking to enforce any provision of, or based on
any matter arising out of or in connection with, this Agreement shall be brought
only to the exclusive jurisdiction of the Courts of Chancery of the State of
Delaware or, if under applicable law exclusive jurisdiction over the matter is
vested in the federal courts, the federal courts located in the State of
Delaware, and each of the Company and the Sellers hereby consents to the
jurisdiction of such courts (and of the appropriate appellate courts therefrom)
in any such suit, action, or proceeding and irrevocably waives, to the fullest
extent permitted by law, any objection it may now or hereafter have to the
laying of the venue of any such suit, action, or proceeding in any such court or
that any such suit, action, or proceeding which is brought in any such court has
been brought in an inconvenient forum. The Company and the Sellers agree that,
after a legal dispute is before a court as specified in this Section 6(i), and
during the pendency of such dispute before such court, all actions, suits, or
proceedings with respect to such dispute or any other dispute, including without
limitation, any counterclaim, cross-claim, or interpleader, shall be subject to
the exclusive jurisdiction of such court. Process in any such suit, action, or
proceeding may be served on either the Company or the Sellers anywhere in the
world, whether within or without the jurisdiction of any such court. Each of the
Company and the Sellers hereto agrees that a final judgment in any action, suit,
or proceeding described in this Section 6(i) after the expiration of any period
permitted for appeal and subject to any stay during appeal shall be conclusive
and may be enforced in other jurisdictions by suit on the judgment or in any
other manner provided by applicable laws.

(k) Counterparts. This Agreement may be executed in one or more counterparts,
each of which shall be deemed to be an original, but all of which shall
constitute one and the same instrument.

(l) Entire Agreement. This Agreement represents the entire agreement and
understandings between the parties concerning the purchase and sale of the
Shares pursuant hereto and supersedes and replaces any and all prior agreements
and understandings.

(m) Voluntary Execution of Agreement. This Agreement is executed voluntarily and
without any duress or undue influence on the parties hereto. The parties
acknowledge that they: (i) have read this Agreement; (ii) have been represented
in the preparation, negotiation, and execution of this Agreement by legal
counsel of their own choice; (iii) understand the terms and consequences of this
Agreement and of the release it contains; and (iv) are fully aware of the legal
and binding effect of this Agreement.

 

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

 

MATTERSIGHT CORPORATION By:   /s/ Kelly D. Conway Name: Kelly D. Conway Title:
President and Chief Executive Officer

 

TCV III (GP)

By: Technology Crossover Management III,

LLC, its general partner

By:   /s/ Frederic D. Fenton Name: Frederic D. Fenton Title: Attorney-in-Fact

 

TCV III (Q), L.P.

By: Technology Crossover Management III,

LLC, its general partner

By:   /s/ Frederic D. Fenton Name: Frederic D. Fenton Title: Attorney-in-Fact

 

TCV III, L.P.

By: Technology Crossover Management III,

LLC, its general partner

By:   /s/ Frederic D. Fenton Name: Frederic D. Fenton Title: Attorney-in-Fact

 

TCV III Strategic Partners, L.P.

By: Technology Crossover Management III,

LLC, its general partner

By:   /s/ Frederic D. Fenton Name: Frederic D. Fenton Title: Attorney-in-Fact

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TCV IV, L.P.

By: Technology Crossover Management IV,

LLC, its general partner

By:   /s/ Frederic D. Fenton Name: Frederic D. Fenton Title: Attorney-in-Fact

 

TCV IV Strategic Partners, L.P.

By: Technology Crossover Management IV,

LLC, its general partner

By:   /s/ Frederic D. Fenton Name: Frederic D. Fenton Title: Attorney-in-Fact

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Schedule I

 

Seller    Number of Shares of
Series B Stock held
by Seller      Pro Rata Share of
Aggregate  Per Share
Cash Amount1      Pro Rata Share of
Aggregate Per
Share Deferred
Amount2  

TCV III (GP)

     2,285       $ 12,043.24       $ 7,997.50   

TCV III (Q), L.P.

     288,422       $ 1,520,147.38       $ 1,009,477.00   

TCV III, L.P.

     10,852       $ 57,196.19       $ 37,982.00   

TCV III Strategic Partners, L.P.

     13,057       $ 68,817.79       $ 45,699.50   

TCV IV, L.P.

     1,501,673       $ 7,914,667.66       $ 5,255,855.50   

TCV IV Strategic Partners, L.P.

     56,516       $ 297,871.35       $ 197,806.00      

 

 

    

 

 

    

 

 

 

TOTAL

     1,872,805       $ 9,870,743.61       $ 6,554,817.50      

 

 

    

 

 

    

 

 

 

 

1 

Represents $5.10 per share plus an amount equal to the accrued but unpaid
dividends on the Series B Stock through December 19, 2011.

2 

Represents $3.50 per share