Document:

exv10w44

Exhibit 10.44

TRUSTWAVE HOLDINGS, INC.

2011 EMPLOYEE STOCK PURCHASE PLAN

Article I

Purpose and Scope of the Plan

1.1 Purpose. The Trustwave Holdings, Inc. 2011 Employee Stock Purchase Plan is intended to
encourage employee participation in the ownership and economic progress of the Company.

1.2 Definitions. Unless the context clearly indicates otherwise, the following terms have the
meaning set forth below:

“Board of Directors” or “Board” shall mean the Board of Directors of the Company.

“Code” shall mean the Internal Revenue Code of 1986, as amended from time to time, together
with any applicable regulations issued thereunder.

“Committee” shall mean the Board, or a committee designated by the Board to administer the
Plan, which Committee shall administer the Plan as provided in Section 1.3 hereof.

“Company” shall mean Trustwave Holdings, Inc., a corporation organized under the laws of
the State of Delaware, or any successor corporation.

“Compensation” shall mean the fixed salary or base hourly wage paid by the Company to an
Employee as reported by the Company to the United States government (or other applicable
government) for income tax purposes, including an Employee’s portion of salary deferral
contributions pursuant to Section 401(k) of the Code and any amount excludable pursuant to Section
125 of the Code, but excluding any commissions, bonus, fee, overtime pay, severance pay, expenses,
stock option or other equity incentive income, or other special payment or any credit or benefit
under any employee plan maintained by the Company.

“Continuous Service” shall mean the period of time, uninterrupted by a termination of
employment (other than a termination as a result of a transfer of employment among the Company or a
Designated Subsidiary), that an Employee has been employed by the Company or a Designated
Subsidiary (or any combination of the foregoing) immediately preceding an Option Period. Such
period of time shall include any approved leave of absence.

“Designated Subsidiary” shall mean any subsidiary of the Company that has been designated
by the Committee to participate in the Plan.

“Employee” shall mean any full-time or part-time employee of the Company or a Designated
Subsidiary who customarily works for the Company or Designated Subsidiary, as the case may be, for
a minimum of twenty (20) hours per week.

“Exercise Date” shall mean the last business day of each Option Period.

“Fair Market Value” of a share of Stock means the fair market value of such Stock
determined by such methods or procedures as shall be established from time to time by the
Committee. Unless otherwise determined by the Committee in good faith, the per share Fair Market
Value as of a particular date shall mean (i) the closing price per share of Stock on the national
securities exchange on which the Stock is principally traded, for the last preceding date on which
there was a sale of such Stock on such exchange,

 

 

or (ii) if the shares of Stock are then traded in an over-the-counter market, the average of the
closing bid and asked prices for the shares of Stock in such over-the-counter market for the last
preceding date on which there was a sale of such Stock in such market, or (iii) if the shares of
Stock are not then listed on a national securities exchange or traded in an over-the-counter
market, such value as the Committee, in its sole discretion, shall determine.

“Option Period” or “Period” shall mean such duration (not to exceed twenty-seven
(27) months) as shall be determined by the Committee prior to the beginning of such Option Period.
Unless the Committee determines otherwise before the beginning of the Option Period, Option Periods
shall commence at six (6)-month intervals on each April 1 and October 1 (or the next business day,
if such date is not a business day) over the term of the Plan, and each Option Period shall last
for six (6) months, ending on March 31 or September 30, as the case may be (or the next business
day, if such date is not a business day). Accordingly, unless the Committee determines otherwise,
two separate Option Periods shall commence in each calendar year during which the Plan remains in
existence. The initial Option Period shall commence on October 1, 2011, subject to the Company’s
prior registration of the Stock on Form S-1.

“Option Price” shall mean the purchase price of a share of Stock hereunder as provided in
Section 3.1 hereof.

“Participant” shall mean any Employee who (i) is eligible to participate in the Plan under
Section 2.1 hereof and (ii) elects to participate.

“Plan” shall mean the Company’s 2011 Employee Stock Purchase Plan, as the same may be
amended from time to time.

“Plan Account” or “Account” shall mean an account established and maintained in the
name of each Participant.

“Plan Manager” shall mean any Employee appointed pursuant to Section 1.3 hereof.

“Stock” means shares of the common stock, par value $0.01 per share, of the Company.

1.3 Administration of Plan. Subject to oversight by the Board of Directors or the Board’s
Compensation Committee, the Committee shall have the authority to administer the Plan and to make
and adopt rules and regulations not inconsistent with the provisions of the Plan or the Code. Its
interpretations and decisions in respect of the Plan shall, subject to the aforesaid, be final and
conclusive. The Committee shall have the authority to appoint an Employee as Plan Manager and to
delegate to the Plan Manager such authority with respect to the administration of the Plan as the
Committee, in its sole discretion, deems advisable from time to time.

1.4 Effective Date of Plan. The Plan shall become effective on the date established for that
purpose by the Committee, if, prior to that date, the Plan (i) has been adopted by the Board of
Directors of the Company and (ii) has been approved by an affirmative vote of a majority of the
shares of the Company’s Stock present, in person or by proxy and entitled to vote on the proposal,
at a meeting at which a quorum is present; provided, however, that such stockholder approval occurs
on a date no later than twelve (12) months following the date the Plan is so adopted.

1.5 Termination of Plan. The Plan shall continue in effect through and including September 30,
2021, unless terminated prior thereto pursuant to Section 4.3 hereof, or by the Board of
Directors or the Compensation Committee of the Board, each of which shall have the right to
terminate the Plan at any time. Upon any such termination, the balance, if any, in each
Participant’s Account shall be refunded to

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him, or otherwise disposed of in accordance with the policies and procedures prescribed by the
Committee in cases where such a refund may not be possible.

Article II

Participation

2.1 Eligibility. Participation in the Plan is limited to Employees who meet the requirements of
this Section 2.1. Each Employee who, on the start date of an Option Period, will have at
least ninety (90) days of Continuous Service may become a Participant by completing the enrollment
procedures prescribed by, or on behalf of, the Committee or the Plan Manager, as revised from time
to time. No Employee may participate in the Plan if such Employee, immediately after the end of an
Option Period, would be deemed for purposes of Section 423(b)(3) of the Code to possess five
percent (5%) or more of the total combined voting power or value of all classes of stock of the
Company or any subsidiary. The Committee may, prior to the commencement of an Option Period,
exclude from participation any Employee who, at the time of the commencement of the Option Period,
is an officer of the Company subject to the reporting requirements of Section 16(a) of the
Securities Exchange Act of 1934.

2.2 Payroll Deductions. Payment for shares of Stock purchased hereunder shall be made by
authorized payroll deductions from each payment of Compensation in accordance with instructions
received from a Participant. Such deductions shall be expressed as a whole number percentage which
shall be at least one percent (1%) but not more than ten percent (10%). A Participant may not
increase the deduction during an Option Period; provided that no more than once per Option
Period, a Participant may decrease the deduction. Notwithstanding the foregoing, a Participant may
change the percentage deduction for any subsequent Option Period by filing notice thereof with the
Company prior to the date on which such Option Period commences. Any amount remaining in the
Participant’s Account after the purchase of Stock shall be refunded without interest; provided that
any amounts remaining in a Participant’s Account that were insufficient to acquire a full share of
Stock shall be carried forward to the next Option Period, unless otherwise requested in writing by
the Participant. Any Participant who discontinues payroll deductions during an Option Period may
again become a Participant for a subsequent Option Period upon completion of the enrollment
procedures prescribed by, or on behalf of, the Committee or the Plan Manager, as revised from time
to time. Amounts deducted from a Participant’s Compensation pursuant to this Section 2.2 shall be
credited to such Participant’s Account. A Participant may not make any additional payments into
such Account.

Article III

Purchase of Shares

3.1 Option Price. The Option Price per share of the Stock sold to Participants hereunder shall be
eighty-five percent (85%) of the lesser of (a) the Fair Market Value of such share on the Exercise
Date of an Option Period or (b) the Fair Market Value of such share on the first day of the
applicable Option Period (or, in each case, such greater percentage as is determined by the
Committee in advance of an Option Period), but in no event shall the Option Price per share be less
than the par value of the Stock.

3.2 Purchase of Shares. On each Exercise Date, the amount in a Participant’s Account shall be
charged with the aggregate Option Price of the largest number of whole shares of Stock that can be
purchased with such amount. Unless otherwise provided by the Committee, the number of shares of
Stock purchased by each Participant on the Exercise Date shall be deposited into an account
established in the Participant’s name with the stock brokerage or other financial services firm
designated by the Committee. The balance, if any, in such Account shall be carried forward to the
next succeeding Option Period; provided that any payroll deductions accumulated in a Participant’s
Account that are not applied

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toward the purchase of shares on an Exercise Date due to limitations imposed by this Plan shall be
returned to the Participant.

3.3 Limitations on Purchase.

          3.3.1 Notwithstanding any provisions of the Plan to the contrary, no Employee shall be granted
an option under the Plan if, immediately after the grant, such Employee’s right to purchase shares
under all employee stock purchase plans (as described in Section 423 of the Code) of the Company
and any subsidiary of the Company would accrue at a rate per Option Period which exceeds the lesser
of: (a) twenty-five thousand dollars ($25,000) or (b) an amount equal to ten percent (10%) of the
Employee’s annualized base salary in effect at the start of such Option Period, in each case, of
the Fair Market Value of such shares (determined at the time such option is granted); provided,
however, that for any calendar year in which such option would be outstanding at any time, an
Employee’s right to purchase shares under all employee stock purchase plans (as described in
Section 423 of the Code) of the Company and any subsidiary of the Company may not accrue at a rate
which exceeds twenty-five thousand dollars ($25,000) in the aggregate (as determined at the time
such option is granted).

          3.3.2 To the extent necessary to comply with Section 423(b)(8) of the Code and the limitations
on purchase in this Section 3.3, a Participant’s payroll deductions may be decreased to
zero percent (0%) during any Option Period which is scheduled to end during any calendar year, such
that the aggregate of all payroll deductions accumulated with respect to such Option Period and any
other Option Period ending within the same calendar year is no greater than twenty-five thousand
dollars ($25,000). Payroll deductions shall re-commence at the rate provided for by the
Participant’s prior election at the beginning of the first Option Period which is scheduled to end
in the following calendar year, unless suspended by the Participant pursuant to Section 2.2
of the Plan. Subject to the limits imposed under this Section 3.3, the maximum number of
shares of Stock that may be purchased by each Participant in any Option Period shall be 5,000
shares.

3.4 Transferability of Rights. Rights to purchase shares hereunder shall be exercisable only by
the Participant. Such rights shall not be transferable.

Article IV

Provisions Relation to Common Stock

4.1 Stock Reserved; Delivery of Stock. A maximum of 300,000 shares of Stock may be purchased under
the Plan, of which up to 60,000 shares of Stock may be purchased under the Plan per Option Period
(in each case, subject to adjustment in accordance with Section 4.2 hereof). Subject to
the limitation in the preceding sentence, as determined by the Committee in its sole discretion,
any shares of Stock purchased under the Plan may be either newly issued shares, existing treasury
shares, or new purchases in the open market.

4.2 Adjustment for Changes in Stock. In the event that adjustments are made in the number of
outstanding shares of Stock or such shares are exchanged for a different class of stock of the
Company or for shares of stock of any other corporation by reason of merger, consolidation, stock
dividend, extraordinary cash dividend, stock split or otherwise, the Committee may make appropriate
adjustments in (i) the number and class of shares or other securities that may be reserved for
purchase, or purchased, hereunder, and (ii) the Option Price. All such adjustments shall be made
in the sole discretion of the Committee, and its decision shall be binding and conclusive. The
existence of the Plan and any options granted hereunder shall not affect in any way the right or
power of the Board of Directors or the shareholders of the Company to make or authorize any
adjustment, recapitalization, reorganization or other change in the Company’s capital structure or
its business, any merger or consolidation of the

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Company or a subsidiary, any issue of debt, preferred or prior preference stock ahead of or
affecting Stock, the authorization or issuance of additional shares of Stock, the dissolution or
liquidation of the Company or any subsidiary, any sale or transfer of all or part of the Company’s
or a subsidiary’s assets or business or any other corporate act or proceeding. The Board of
Directors may at any time terminate an Option Period then in progress and provide, in its
discretion, that Participants’ then outstanding Account balances shall be used to purchase shares
pursuant to Article III or returned to the applicable Participants.

4.3 Insufficient Shares. If the aggregate funds available for the purchase of Stock on any
Exercise Date would cause an issuance of shares in excess of the number provided for in Section
4.1 hereof, (i) the Committee shall proportionately reduce the number of shares which would
otherwise be purchased by each Participant in order to eliminate such excess and (ii) the Plan
shall automatically terminate immediately after such Exercise Date.

4.4 Confirmation. Confirmation of each purchase of Stock hereunder shall be made available to the
Participant in either written or electronic format. A record of purchases shall be maintained by
appropriate entries on the books of the Company. Unless otherwise determined by the Committee,
shares of Stock delivered to a Participant hereunder may not be assigned, transferred, pledged or
otherwise disposed of in any way by the Participant during the six (6) month period following such
delivery to the Participant (other than by will or the laws of descent and distribution) and the
shares of Stock shall bear an appropriate legend substantially in the following form:

“The anticipation, alienation, attachment, sale, transfer, assignment,
pledge, encumbrance or charge of the shares of stock represented hereby
are subject to the terms and conditions of the Trustwave Holdings, Inc.
2011 Employee Stock Purchase Plan (the “Plan”), including, without
limitation, the restriction that the shares may not be assigned,
transferred, pledged or otherwise disposed of in any way during the six
(6) month period following the date of delivery of such shares. A copy
of the Plan is on file at the principal office of Trustwave Holdings,
Inc.”

4.5 Rights as Shareholders. The shares of Stock purchased by a Participant on an Exercise Date
shall, for all purposes, be deemed to have been issued and sold as of the close of business on such
Exercise Date. Prior to that time, none of the rights or privileges of a shareholder of the
Company shall exist with respect to such shares.

Article V

Termination of Participation

5.1 Voluntary Withdrawal. A Participant may withdraw from the Plan at any time by filing notice of
withdrawal prior to the close of business on the date immediately preceding the applicable Exercise
Date. Upon withdrawal, the entire amount, if any, in a Participant’s Account shall be refunded to
him without interest. Any Participant who withdraws from the Plan may again become a Participant
in accordance with Section 2.1 hereof.

5.2 Termination of Eligibility. If a Participant ceases to be eligible under Section 2.1
hereof for any reason, the dollar amount and the number of unissued shares in such Participant’s
Account will be refunded or distributed to the Participant, or in the case of death, the
Participant’s designated beneficiary or estate, or otherwise disposed of in accordance with
policies and procedures prescribed by the Committee in cases where such a refund or distribution
may not be possible.

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Article VI

General Provisions

6.1 Notices. Any notice which a Participant files pursuant to the Plan shall be made on forms
prescribed by the Committee and shall be effective only when received by the Company.

6.2 Condition of Employment. Neither the creation of the Plan nor participation therein shall be
deemed to create any right of continued employment or in any way affect the right of the Company or
a Designated Subsidiary to terminate an Employee.

6.3 Withholding of Taxes. Each Participant shall, no later than the date as of which the value of
an option under the Plan and/or shares of Stock first becomes includible in the income of the
Participant for income tax purposes, pay to the Company, or make arrangements satisfactory to the
Committee regarding payment of, any taxes of any kind required by law to be withheld with respect
to such option or shares of Stock. The obligations of the Company under the Plan shall be
conditioned upon the making of such payments or arrangements, and the Company shall, to the extent
permitted by law, have the right to deduct any such taxes from any payment of any kind otherwise
due to the Participant. In particular, to the extent a Participant is subject to taxation under
U.S. Federal income tax law, if the Participant makes a disposition, within the meaning of Section
424(c) of the Code of any share or shares of Stock issued to Participant pursuant to Participant’s
exercise of an option, and such disposition occurs within the two-year period commencing on the day
after the first date of the Option Period or within the one-year period commencing on the day after
the Exercise Date, Participant shall, within ten (10) days of such disposition, notify the Company
thereof and thereafter immediately deliver to the Company any amount of Federal, state or local
income taxes and other amounts which the Company informs the Participant the Company may be
required to withhold.

6.4 Amendment of the Plan. The Board of Directors or the Board’s Compensation Committee may at any
time, or from time to time, amend the Plan in any respect, except that, without approval of the
shareholders, no amendment may increase the aggregate number of shares reserved under the Plan
other than as provided in Section 4.2 hereof, materially increase the benefits accruing to
Participants or materially modify the requirements as to eligibility for participation in the Plan.
Any amendment of the Plan must be made in accordance with applicable provisions of the Code and/or
any regulations issued thereunder, any other applicable law or regulations, and the requirements of
the principal exchange upon which the Stock is listed.

6.5 Application of Funds. All funds received by the Company by reason of purchases of Stock
hereunder may be used for any corporate purpose.

6.6 Legal Restrictions. The Company shall not be obligated to sell shares of Stock hereunder if
counsel to the Company determines that such sale would violate any applicable law or regulation.

6.7 Gender. Whenever used herein, use of any gender shall be applicable to both genders.

6.8 Conditions Upon Issuance of Shares.

     6.8.1 If at any time the Committee shall determine, in its discretion, that the listing,
registration and/or qualification of shares of Stock upon any securities exchange or under any
state or Federal law, or the consent or approval of any governmental regulatory body, is necessary
or desirable as a condition of, or in connection with, the sale or purchase of shares of Stock
hereunder, no option may be exercised or paid in whole or in part unless and until such listing,
registration, qualification, consent and/or approval

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shall have been effected or obtained, or otherwise provided for, free of any conditions not
acceptable to the Committee.

     6.8.2 If at any time counsel to the Company shall be of the opinion that any sale or delivery
of shares of Stock pursuant to an option is or may be in the circumstances unlawful, contravene the
requirements of any stock exchange, or result in the imposition of excise taxes on the Company or
any subsidiary under the statutes, rules or regulations of any applicable jurisdiction, the Company
shall have no obligation to make such sale or delivery, or to make any application or to effect or
to maintain any qualification or registration under the Securities Act of 1933, as amended, or
otherwise with respect to shares of Stock or options and the right to exercise any option shall be
suspended until, in the opinion of such counsel, such sale or delivery shall be lawful or will not
result in the imposition of excise taxes on the Company or any subsidiary.

     6.8.3 The Committee, in its absolute discretion, may impose such restrictions on the ownership
and transferability of the shares of Stock purchasable or otherwise receivable by any person under
any option as it deems appropriate. The certificates evidencing such shares may include any legend
that the Committee deems appropriate to reflect any such restrictions.

6.9 Governing Law. The Plan and all rights and obligations thereunder shall be constructed and
enforced in accordance with the laws of the State of Delaware and any applicable provisions of the
Code and the related regulations.

6.10 Unfunded Status of Plan. The Plan shall be an unfunded plan. The Committee may authorize the
creation of trusts or other arrangements to meet the obligations created under the Plan to deliver
Stock or make payments, provided that the existence of such trusts or other arrangements is
consistent with the unfunded status of the Plan.

7exv10w45

Exhibit 10.45

	 	 	 

	

	 	Trustwave Holdings Inc.
	 	70 West Madison Street, Suite 1050
	 	Chicago, IL 60602

July 13, 2011

Mr. Richard Kiphart

c/o William Blair & Company, L.L.C

222 West Adams Street

Chicago, Illinois 60606

Financial Technology Ventures II (Q), L.P.

Financial Technology Ventures II, L.P.

c/o Mr. Richard Garman

555 California Street, Suit 2900

San Francisco, California 94104

Dear Sirs:

     This letter shall confirm our agreement that you have agreed, subject to the terms hereof, to
consent, and you will take all such necessary action to effect, (i) the conversion of all of the
respective shares of the Series A Preferred Stock (the “Preferred Stock”) of Trustwave
Holdings, Inc., a Delaware corporation (the “Company”) of which you are a beneficial owner
into shares of the Company’s Common Stock on a share-for-share basis in connection with the initial
public offering of the Company’s Common Stock in the manner and as contemplated by the Company’s
Registration Statement on Form S-1 (SEC No. 333-173661) (the “IPO”) and (ii) an amendment
to that certain Stockholders’ Agreement, dated as of March 14, 2005, by and among the Company and
the investors named therein, as amended to the date hereof, and to the certain Investor Rights
Agreement, dated March 14, 2005, by and among the Company and the investors named therein, as
amended to the date hereof, to provide in each case that the IPO shall constitute a “Qualified
Public Offering” as such term is used in such agreements (the “Amendments”). In
consideration for such agreement, the Company has agreed to make a cash payment on account of such
Preferred Stock in the aggregate amount of $7,822,023.67, of which Financial Technology Ventures II
(Q), L.P and Financial Technology Ventures II, L.P. will receive in the aggregate $4,602,284.34 and
Mr. Kiphart and those members of his immediate family who own shares of Preferred Stock will
receive an aggregate of $3,219,739.33. The conversion of the Preferred Stock, which will be
immediately followed by a one-for-four reverse stock split, and the related payments contemplated
by this letter will be made on, and subject to, the substantially concurrent closing of the IPO.
Each of the Amendments shall provide that it shall be effective upon the closing of the IPO.

     This letter agreement will be governed by and construed in accordance with the Laws of the
State of New York applicable to contracts made and to be performed within the State of New York.
This letter agreement may be executed in multiple counterparts (including by means of

	 	 	 

	70 W. Madison St.

	 	Tel 312 873 7500
	Suite 1050

	 	Fax 312 443 8028
	Chicago IL 60602

	 	www.trustwave.com

 

 

	 	 	 

	

	 	Trustwave Holdings Inc.
	 	70 West Madison Street, Suite 1050
	 	Chicago, IL 60602

telecopied signature pages or electronic transmission in portable document format (pdf)), each of which shall
be an original, but all of which together shall constitute one instrument. In addition, this
letter agreement will terminate in the event the IPO is not consummated by October 31, 2011.

     Please indicate your agreement with the foregoing by executing this letter in the space
provided

*           *           *           *

	 	 	 

	70 W. Madison St.

	 	Tel 312 873 7500
	Suite 1050

	 	Fax 312 443 8028
	Chicago IL 60602

	 	www.trustwave.com

 

 

	 	 	 

	 

	 	Very truly yours,
	 
	 	 
	 

	 	/s/ Robert J. McCullen
 
 Robert
J. McCullen
	 

	 	Chief Executive Officer & President

	 	 	 

	70 W. Madison St.

	 	Tel 312 873 7500
	Suite 1050

	 	Fax 312 443 8028
	Chicago IL 60602

	 	www.trustwave.com

 

 

	 	 	 	 	 

	 	 	Agreed to and Authorized By:
	 
	 	 	 	 
	 	 	Financial Technology Ventures II (Q), L.P.
	 	 	By: Financial Technology Management, II, LLC
	 
	 	 	 	 
	 

	 	By:
	 	/s/ Richard Garman
 
 Name:
Richard Garman
	 

	 	 	 	Title: Managing Member
	 
	 	 	 	 
	 	 	Financial Technology Ventures II, L.P.
	 	 	By: Financial Technology Management, II, LLC
	 
	 	 	 	 
	 

	 	By:
	 	/s/ Richard Garman
 
 Name:
Richard Garman
	 

	 	 	 	Title: Managing Member
	 
	 	 	 	 

	 	 	 

	 

	 	/s/ Richard P. Kiphart
 
 Richard
Kiphart

	 	 	 

	70 W. Madison St.

	 	Tel 312 873 7500
	Suite 1050

	 	Fax 312 443 8028
	Chicago IL 60602

	 	www.trustwave.com

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