Document:

EX-10.1

EMPLOYMENT AGREEMENT

This Employment Agreement (the “Agreement”), which shall be effective as of December 16,
2007, is between Insight Enterprises, Inc., a Delaware corporation (“Company”), and Glynis A. Bryan
(“Executive”).

RECITAL

Company has decided to offer Executive an employment agreement, the terms and provisions of
which are set forth below.

In exchange for valuable consideration, the receipt and sufficiency of which is hereby
acknowledged, the parties agree as follows:

1. TERMS OF AGREEMENT.

(a) Initial Term. Executive shall be employed by Company for the duties set forth in Section
2, below, for a two-year term, commencing as of December 17, 2007 and ending on December 17, 2009
(the “Initial Term”), unless sooner terminated in accordance with the provisions of this Agreement.

(b) Renewal Term; Employment Period Defined. On each successive day after the commencement of
the Initial Term, without further action on the part of Company or Executive, this Agreement shall
be automatically renewed for a new two-year term dated effective and beginning upon each such
successive day (a “Renewal Term”); provided, however, that Company may notify Executive, or
Executive may notify Company, at any time, that there shall be no renewal of this Agreement, and in
the event of such notice, the Agreement shall immediately cease to renew and shall terminate
naturally at the end of the then current Renewal Term. No severance or other post-termination
compensation will be due or payable in the event of a termination resulting from non-renewal. The
period of time commencing as of the date hereof and ending on the effective date of the termination
of employment of Executive under this or any successor Agreement shall be referred to as the
“Employment Period.”

2. POSITION AND DUTIES.

(a) Job Duties. Company does hereby employ, engage and hire Executive as its Chief Financial
Officer, and Executive does hereby accept and agree to such employment, engagement, and hiring.
Executive’s duties and authority during the Employment Period shall be such executive and
managerial duties as the Chief Executive Officer of Company, or Chief Executive Officer’s designee,
shall reasonably determine. Executive will devote full time on behalf of Company, or such lesser
amount of time as the Chief Executive Officer, or Chief Executive Officer’s designee, may
determine, reasonable absences because of illness, personal and family exigencies excepted.

(b) Best Efforts. Executive agrees that at all times during the Employment Period Executive
will faithfully, and to the best of Executive’s ability, experience and talents, perform the duties
that may be required of and from Executive and fulfill Executive’s responsibilities hereunder
pursuant to the express terms hereof. Executive’s participation as an officer, director,
consultant or employee of any entity (other than Company) must be disclosed to Company and the
Board of Directors of Company. Additionally, Executive shall disclose to Company and the Board of
Directors of Company any interest in a company that is engaged in a Competing Business as defined
in Section 10, below, unless such interest constitutes less than 1% of the issued and outstanding
equity of such company.

(c) Section 16. If, at the time Executive’s employment is terminated for any reason,
Executive is a person designated to file pursuant to Section 16 under the Securities Exchange Act
of 1934, Executive will provide to Company a written representation in a form acceptable to Company
that all reportable pre-termination securities transactions relating to Executive have been
reported.

3. COMPENSATION.

(a) Base Salary. Company shall pay Executive a “Base Salary” in consideration for Executive’s
services to Company, payable as nearly as possible in equal semi-monthly installments or in such
other installments as are customary from time to time for Company’s executives. The Base Salary
may be adjusted from time to time in accordance with the procedures established by Company for
salary adjustments for executives, provided that the Base Salary shall not be reduced.

(b) Incentive Compensation. Executive shall be eligible for an incentive bonus pursuant to
one or more incentive compensation plans established by the Company from time to time (each, an
“Incentive Compensation Plan”). The amount of such incentive bonus, if any, shall be based on the
extent to which Executive or Company, or any combination of Executive, Company and Company’s direct
and indirect subsidiaries, achieve objectives set forth in the Incentive Compensation Plan, or
Incentive Compensation Plans, for the relevant time period. For purposes of this Agreement,
Incentive Compensation Plan, and Incentive Compensation Plans, does not include any employee
benefit, stock option, restricted stock or other equity-based plan, and the benefits under such
plans shall be governed by their respective plan documents.

(c) Incentive and Benefit Plans. Executive will be entitled to participate in those benefit
plans generally provided for Company’s executives in the same or a similar tier of management, in
accordance with the terms of such benefit plans. Additionally, Executive shall be entitled to
participate in any other benefit plans made available generally to employees of Company from time
to time, including but not limited to, any savings plan, life insurance plan and health insurance
plan, all subject to any restrictions specified in, or amendments made to, such plans.

4. BUSINESS EXPENSES.

Company will reimburse Executive for any and all necessary, customary and usual expenses which
are incurred by Executive on behalf of Company, provided Executive provides Company with receipts
to substantiate the business expense in accordance with Company’s policies or otherwise reasonably
justifies the expense to Company.

5. DEATH OR DISABILITY.

(a) Death. This Agreement shall terminate upon Executive’s death, but Executive’s estate
shall be entitled to receive the Base Salary for ninety (90) days following the date of Executive’s
death. Company shall also pay to Executive’s estate (1) with respect to any Incentive Compensation
Plan with quarterly objectives, the sum of (i) a prorated portion of any incentive compensation to
which Executive would have been entitled (had Executive not died) for the quarter in which
Executive died and (ii) the amount of incentive compensation for the last completed quarter prior
to the date of Executive’s death, plus (2) with respect to any Incentive Compensation Plan with
annual objectives, a prorated bonus for the year in which the Executive died, each to be calculated
as soon as reasonably practicable, allowing Company a sufficient amount of time to calculate such
amount.

(b) Disability. This Agreement shall also terminate in the event of Executive’s “Disability.”
For purposes of this Agreement, “Disability” means the inability of Executive to perform
Executive’s essential job duties, with or without a reasonable accomodation, for a period of thirty
(30) consecutive days or for sixty (60) days within any period of one-hundred and eighty (180) days
due to a physical or mental injury or illness that occurs while Executive is actively employed by
Company. Any dispute concerning whether Disability has occurred will be determined by a physician
selected by Company. If this Agreement is terminated due to Executive’s Disability, Executive
shall receive the Base Salary for ninety (90) days following the date of termination and (1) with
respect to any Incentive Compensation Plan with quarterly objectives, the sum of (i) a prorated
portion of any incentive compensation to which Executive would have been entitled (had termination
not occurred) for the quarter in which this Agreement is terminated due to Executive’s disability
and (ii) the amount of incentive compensation for the last completed quarter prior to the date of
termination, plus (2) with respect to any Incentive Compensation Plan with annual objectives, a
prorated bonus for the year in which termination occurs, each to be calculated as soon as
reasonably practicable, allowing Company a sufficient amount of time to calculate such amount.

6. TERMINATION BY COMPANY.

(a) Termination for Cause. Company may terminate this Agreement at any time during the
Initial Term or any Renewal Term for “Cause” upon written notice to Executive. If Company
terminates this Agreement for “Cause,” Executive’s Base Salary shall immediately cease, and
Executive shall not be entitled to severance payments, incentive compensation payments or any other
payments or benefits pursuant to this Agreement, except for any vested rights pursuant to any
benefit plans in which Executive participates and any accrued compensation, accrued and unused
vacation pay and similar items. For purposes of this Agreement, the term “Cause” shall mean the
termination of Executive’s employment by Company for one or more of the following reasons: (1) the
misappropriation (or attempted misappropriation) of any of Company’s funds or property; (2) the
conviction of, or the entering of a guilty plea or plea of no contest with respect to, a felony or
misdemeanor which involves moral turpitude or a fraudulent act; (3) willful and significant or
repeated neglect of duties (after notice and opportunity to cure); (4) acts of material dishonesty,
disloyalty or insubordination toward Company; (5) material violation of Company’s Values or any
material policy with respect to Company’s business or operations (after notice and opportunity to
cure); (6) significant and repeated deficiencies with respect to performance objectives assigned by
the Chief Executive Officer of Company (after notice and opportunity to cure); (7) insolvency of
Company; or (8) Executive’s material breach of this Agreement. If Executive is terminated for
Cause, Company shall be obligated to pay Executive only the Base Salary (from Section 3(a)) and
benefits (from Section 4) due to Executive through the termination date, and Executive will not be
entitled to, nor will Executive receive, any type of severance payment.

(b) Termination Without Cause. Company also may terminate Executive’s employment at any time
during the Initial Term or any Renewal Term without Cause. Company may, at its discretion, place
Executive on a paid administrative leave prior to the actual date of termination set by Company.
During the administrative leave, Company may bar Executive’s access to Company’s offices or
facilities if reasonably necessary to the smooth operation of Company, or may provide Executive
with access subject to such reasonable terms and conditions as Company chooses to impose.

(c) Continued Compensation. Should Executive’s employment by Company be terminated without
Cause, Executive shall receive as a lump sum within three (3) business days (or sooner if required
by law) following such termination the total amount of Executive’s base salary for the remainder of
the Initial Term or current Renewal Term. Executive shall have no duty to mitigate damages in
order to receive the compensation described by this Subsection, and the compensation shall not be
reduced or offset by other income, payments or profits received by Executive from any source.

(d) Incentive Compensation. If Executive is terminated for Cause, Executive shall not be
entitled to receive any incentive compensation payments for the quarter in which Executive’s
employment is terminated or for any other periods. If Executive is terminated without Cause,
Executive shall receive, in a lump sum, an amount equal to (1) with respect to any Incentive
Compensation Plan with quarterly objectives, the sum of (i) a prorated bonus for the quarter in
which the termination takes place and (ii) four times Executive’s highest quarterly bonus of the
quarterly bonuses for the four most recently completed quarters, plus (2) with respect to any
Incentive Compensation Plan with annual objectives, a prorated bonus for the year in which the
termination takes place, each to be paid as soon as reasonably practicable, allowing Company a
sufficient amount of time to calculate such amount, but not later than March 15 of the year
following the year in which termination takes place. Executive shall have no duty to mitigate
damages in order to receive the compensation described by this Subsection, and the compensation
shall not be reduced or offset by other income, payments or profits received by Executive from any
source.

(e) Other Plans. Except to the extent specified in this Section 6 and as provided in this
Subsection (e), termination of this Agreement shall not affect Executive’s participation in,
distributions from, and vested rights under, any employee benefit, stock option, restricted stock
or other equity-based plan of, or maintained by or for, Company, which benefits will be governed by
the terms of those respective plans, in the event of Executive’s termination of employment.

7. TERMINATION BY EXECUTIVE.

(a) General. Executive may terminate this Agreement at any time, with or without “Good
Reason” by providing Company with thirty (30) days advance written notice. Company may, at its
discretion, place Executive on a paid administrative leave during all or any part of any such
notice period. During the administrative leave, Company may bar Executive’s access to Company’s
offices or facilities if reasonably necessary to the smooth operation of Company, or may provide
Executive with access subject to such reasonable terms and conditions as Company chooses to impose.

(b) Good Reason Defined. For purposes of this Agreement, “Good Reason” shall mean and include
(after notice and an opportunity to cure) each of the following (unless Executive has expressly
agreed to such event in a signed writing): (1) assignment of Executive to a position other than
Chief Financial Officer; (2) any material act or acts of dishonesty by Company directed toward or
affecting Executive; (3) any illegal act or instruction directly affecting Executive by Company,
which is not withdrawn after the Company is notified of the illegality by Executive; or (4)
Company’s material breach of this Agreement.

(c) Effect of Good Reason Termination. If Executive terminates this Agreement for Good Reason
(as defined in Section 7(b)), it shall for all purposes be treated as a termination by Company
without Cause.

(d) Effect of Termination without Good Reason. If Executive terminates this Agreement without
Good Reason, while the termination shall not be characterized as a termination for Cause, it shall
for all purposes, result in the same compensation as a termination for Cause.

8. CHANGE IN CONTROL OF COMPANY.

(a) Continued Eligibility to Receive Benefits. Company considers the maintenance of a sound
and vital management to be essential to protecting and enhancing the best interests of Company and
its shareholders. In furtherance of such goal and in further consideration of Executive’s
continued employment with Company, if a Change in Control occurs, Executive shall be entitled to a
lump-sum severance benefit provided in subparagraph (b) of this Section 8 if, prior to the
expiration of twenty-four (24) months after the Change in Control, Executive notifies Company of
Executive’s intent to terminate employment with Company for Good Reason or Company terminates
Executive’s employment without Cause. If Executive triggers the application of this Section by
terminating employment for Good Reason, Executive must do so within sixty (60) days following
Executive’s receipt of notice of the occurrence of the last event that constitutes Good Reason. The
full severance benefits provided by this Section shall be payable regardless of the period
remaining until the expiration of the Agreement without renewal.

(b) Receipt of Benefits. If Executive is entitled to receive a severance benefit pursuant to
Section 8(a) hereof:

	 	(1)	 	within ten (10) days following Executive’s last day
of work, Company will provide Executive with a lump sum payment equal to
(A) two (2) times the greater of Executive’s highest annualized Base
Salary in effect on any date during the Term of this Agreement plus (B)
an amount equal to two times the higher annual bonus that would have been
awarded, based on the method of calculation then in effect, during the
one of the two immediately preceding fiscal years which would produce the
higher award.

	 	(2)	 	Executive shall be vested in any and all
equity-based plans and agreements of Company in which Executive had an
interest, vested or contingent. If applicable law prohibits such vesting,
then Company shall pay Executive an amount equal to the value of benefits
and rights that would have, but for such prohibition, been vested in
Executive.

	 	(3)	 	Executive shall be compensated in a manner selected
by Company to provide for life, disability, accident and group health and
dental insurance benefits, at substantially the levels Executive was
receiving immediately prior to her termination, for a period of time
expiring upon the earlier of (i) the end of the period of 42 months
following termination of Executive’s employment or (ii) the day on which
Executive becomes eligible to receive any substantially similar
continuing health care benefits under any plan or program of any other
employer or source without being required to pay any premium with respect
thereto. At Company’s option, Company may satisfy the obligation to
provide the benefits pursuant to this Section by either (A) paying for or
reimbursing Executive at reasonable intervals for the actual cost of such
benefits (and Executive shall cooperate with Company in all respects in
securing and maintaining such benefits, including exercising all
appropriate COBRA elections and complying with all terms and conditions
of such coverage in a manner to minimize the cost), (B) payment of a lump
sum in the amount of the present value, discounted at Company’s effective
borrowing rate, of the premiums for such benefits for the continuing
coverage period (which shall be calculated based on the conclusive
presumption that the cost or premiums will remain constant at the rate
existing for COBRA coverage immediately following termination), or (C) a
combination of the foregoing options (for example, Company may elect to
pay Executive’s premiums during the period of time covered by COBRA, and
thereafter pay a lump sum to cover the present value of the remaining
cost).

Executive shall have no duty to mitigate damages in order to receive the compensation
described by this Subsection. If Executive is entitled to receive the payments called for by this
Section 8(b), Executive’s right to receive the compensation provided by Section 6(c) or 7(c) shall
be reduced to the extent of such payments.

(c) Change in Control Defined. For purposes of this Agreement, a “Change in Control” means
any one or more of the following events:

	 	(1)	 	a change of control of the Company through a
transaction or series of transactions, such that any person (as that term
is used in Section 13 and 14(d)(2) of the Securities Exchange Act of 1934
(“1934 Act”)), excluding affiliates of the Company as of the Effective
Date, is or becomes the beneficial owner (as that term is used in Section
13(d) of the 1934 Act) directly or indirectly, of securities of the
Company representing 30% or more of the combined voting power of the
Company’s then outstanding securities;

	 	(2)	 	any merger, consolidation or liquidation of the
Company in which the Company is not the continuing or surviving company
or pursuant to which stock would be converted into cash, securities or
other property, other than a merger of the Company in which the holders
of the shares of stock immediately before the merger have the same
proportionate ownership of common stock of the surviving company
immediately after the merger;

	 	(3)	 	the shareholders of the Company approve any plan or
proposal for the liquidation or dissolution of the Company; or

	 	(4)	 	substantially all of the assets of the Company are
sold or otherwise transferred to parties that are not within a
“controlled group of corporations” (as defined in Section 1563 of the
Internal Revenue Code of 1986, as amended (the “Code”)) in which the
Company is a member at the Relevant Date.

(d) Notice of Termination by Executive. Any termination by Executive under this Section 8
shall be communicated by written notice to Company, which notice shall set forth generally the
facts and circumstances claimed to provide a basis for such termination.

(e) Gross-Up Allowance.

(1) General Rules. The Code places significant tax consequences on Executive and Company if
the total payments made to Executive due, or deemed due, to a Change in Control exceed prescribed
limits. For example, if Executive’s “Base Period Income” (as defined below) is $100,000 and
Executive’s “Total Payments” exceed 299% of such Base Period Income (the “Cap”), Executive will be
subject to an excise tax under Section 4999 of the Code of 20% of all amounts paid to him in excess
of $100,000. In other words, if Executive’s Cap is $299,999, she will not be subject to an excise
tax if she receives exactly $299,999. If Executive receives $300,000, she will be subject to an
excise tax of $40,000 (20% of $200,000). In the event such a consequence occurs, for any reason,
due to this Agreement or otherwise, Company shall pay to Executive a “gross-up allowance” equal in
amount to the sum of (i) the excise tax liability of Executive on the Total Payments, and (ii) all
the total excise, income, and payroll tax liability of Executive on the “gross-up allowance,”
further increased by all additional excise, and income, and payroll tax liability thereon, which
increase shall be part of the “gross-up allowance” for purpose of computing the gross-up allowance.
Company shall indemnify and hold Executive harmless from such additional tax liability for the
income and payroll tax arising from the “gross-up allowance” and all excise tax arising with
respect to compensation and other payments made to Executive under this Agreement and excise,
income, and payroll tax on the gross-up allowance, and all penalties and interest thereon. The
purpose and effect of the gross-up allowance is to cause Executive to have the same net
compensation after income, excise, and payroll taxes that Executive would have if there was no tax
under Code § 4999.

(2) Special Definitions. For purposes of this Section, the following specialized terms will
have the following meanings:

(i) “Base Period Income”. “Base Period Income” is an amount equal to
Executive’s “annualized includable compensation” for the “base period”
as defined in Sections 28OG(d)(1) and(2)of the Code and the regulations
adopted thereunder. Generally, Executive’s “annualized includable
compensation” is the average of her annual taxable income from the
Company for the “base period,” which is the five calendar years prior
to the year in which the Change of Control occurs.

(ii) “Cap” or “280G Cap”. “Cap” or “28OG Cap” shall mean an amount
equal to 2.99 times Executive’s “Base Period Income.” This is the
maximum amount which she may receive without becoming subject to the
excise tax imposed by Section 4999 of the Code or which Company may pay
without loss of deduction under Section 28OG of the Code.

(iii) “Total Payments”. The “Total Payments” include any “payments in
the nature of compensation” (as defined in Section 280G of the Code and
the regulations adopted thereunder), made pursuant to this Agreement or
otherwise, to or for Executive’s benefit, the receipt of which is
contingent or deemed contingent on a Change of Control and to which
Section 28OG of the Code applies.

(f) Effect of Repeal. In the event that the provisions of Sections 28OG and 4999 of the Code
are repealed without succession, this Section shall be of no further force or effect.

(g) Employment by Successor. For purposes of this Agreement, employment by a successor of
Company or a successor of any subsidiary of Company that has assumed this Agreement shall be
considered to be employment by Company or one of its subsidiaries. As a result, if Executive is
employed by such a successor following a Change in Control, Executive will not be entitled to
receive the benefits provided by Section 8 unless Executive’s employment with the successor is
subsequently terminated without Cause within twenty-four (24) months following the Change in
Control or Executive terminates employment for Good Reason.

9. CONFIDENTIALITY.

Because of Executive’s knowledge of and participation in executive issues and decisions as a
result of Executive’s present and former executive positions, for purposes of Sections 9 and 10 of
this Agreement, “Company” shall be interpreted to include Company and all of its direct and
indirect subsidiaries.

Executive covenants and agrees to hold in strictest confidence, and not disclose to any
person, firm or company, without the express written consent of Company, any and all of Company’s
confidential data, including but not limited to information and documents concerning Company’s
business, clients, and suppliers, market methods, files, trade secrets, or other “know-how” or
techniques or information not of a published nature or generally known (for the duration they are
not published or generally known) which shall come into Executive’s possession, knowledge, or
custody concerning the business of Company, except as such disclosure may be required by law or in
connection with Executive’s employment hereunder or except as such matters may have been known to
Executive at the time of Executive’s employment by Company. This covenant and agreement of
Executive shall survive this Agreement and continue to be binding upon Executive after the
expiration or termination of this Agreement, whether by passage of time or otherwise so long as
such information and data shall be treated as confidential by Company.

10. RESTRICTIVE COVENANTS.

(a) Covenant Not To Compete. In consideration of Company’s agreements contained herein and
the payments to be made by it to Executive pursuant hereto, Executive agrees that, for a period of
time equal to the time remaining in the Initial Term or any Renewal Term (or if, but only if, a
court or tribunal of final authority finds that this period is unenforceable because it is
unreasonably long, then, if it would shorten the duration, for six months) following the
termination of Executive’s employment for any reason and so long as Company is continuously not in
material default of its obligations to provide payments or employment-type benefits to Executive
hereunder or under any other agreement, covenant, or obligation, Executive will not, without prior
written consent of Company, consult with or act as an advisor to another company about activity
which is a “Competing Business” of such company in the Restricted Territory, as defined below. For
purposes of this Agreement, Executive shall be deemed to be engaged in a “Competing Business” if,
in any capacity, including proprietor, shareholder, partner, officer, director or employee,
Executive engages or participates, directly or indirectly, in the operation, ownership or
management of the activity of any proprietorship, partnership, company or other business entity
which activity is competitive with the then actual business in which Company and its operating
subsidiaries and affiliates are engaged on the date of, or any business contemplated by such
entities’ business plans in effect on the date of notice of, Executive’s termination of employment.
Nothing in this Subsection is intended to limit Executive’s ability to own equity in a public
company constituting less than one percent (1%) of the outstanding equity of such company, when
Executive is not actively engaged in the management thereof.

(b) Non-Solicitation. Executive recognizes that Company’s clients are valuable and
proprietary resources of Company. Accordingly, Executive agrees that for a period of time
following the termination of Executive’s employment for any reason equal to the time remaining in
the Initial Term or any Renewal Term (or if, but only if, a court or tribunal of final authority
finds that this period is unenforceable because it is unreasonably long, then, if it would shorten
the duration, for six months), and only so long as Company is continuously not in material default
of its obligations to provide payments or employment-type benefits to Executive hereunder or under
any other agreement, covenant, or obligation, Executive will not directly or indirectly, through
Executive’s own efforts or through the efforts of another person or entity, solicit business in the
Restricted Territory for or in connection with any Competing Business from any individual or entity
which obtained products or services from Company at any time during Executive’s employment with
Company, Executive will not solicit business for or in connection with a Competing Business from
any individual or entity which may have been solicited by Executive on behalf of Company, and
Executive will not solicit, hire or engage employees of Company who would have the skills and
knowledge necessary to enable or assist efforts by Executive to engage in a Competing Business.

(c) Restricted Territory. Executive and Company understand and agree that Company’s business
is not geographically restricted and is unrelated to the physical location of Company facilities or
the physical location of any Competing Business, due to extensive use of the Internet, telephones,
facsimile transmissions and other means of electronic information and product distribution.
Executive and Company further understand and agree that Executive will, in part, work toward
expanding Company’s markets and geographic business territories and will be compensated for
performing this work on behalf of Company.

Accordingly, Company has a protectable business interest in, and the parties intend the
Restricted Territory to encompass, each and every location from which Exectutive could engage in a
Competing Business in any country, state, province, county or other political subdivision in which
Company has clients, employees, suppliers, distributors or other business partners or operations.
If, but only if, this Restricted Territory is held to be invalid on the ground that it is
unreasonably broad, the Restricted Territory shall include each location from which Executive can
conduct business in any of the following locations: each state in the United States in which
Company conducts sales or operations, each province within Canada in which Company conducts sales
or operations, and each political subdivision of the United Kingdom in which Company conducts sales
or operations. If, but only if, this Restricted Territory is held to be invalid on the grounds
that it is unreasonably broad, then the Restricted Territory shall be any location within a fifty
(50) mile radius of any Company office.

(d) Remedies; Reasonableness. Executive acknowledges and agrees that a breach by Executive of
the provisions of this Section 10 will constitute such damage as will be irreparable and the exact
amount of which will be impossible to ascertain and, for that reason, agrees that Company will be
entitled to an injunction to be issued by any court of competent jurisdiction restraining and
enjoining Executive from violating the provisions of this Section. The right to an injunction shall
be in addition to and not in lieu of any other remedy available to Company for such breach or
threatened breach, including the recovery of damages from Executive.

Executive expressly acknowledges and agrees that: (1) the Restrictive Covenants contained
herein are reasonable as to time and geographical area and do not place any unreasonable burden
upon Executive; (2) the general public will not be harmed as a result of enforcement of these
Restrictive Covenants; and (3) Executive understands and hereby agrees to each and every term and
condition of the Restrictive Covenants set forth in this Agreement.

Executive also expressly acknowledges and agrees that Executive’s covenants and agreements in
this Section 10 shall survive this Agreement and continue to be binding upon Executive after the
expiration or termination of this Agreement, whether by passage of time or otherwise.

11. BENEFIT AND BINDING EFFECT.

This Agreement shall inure to the benefit of and be binding upon Company, its successors and
assigns, including, but not limited to, any company, person, or other entity which may acquire all
or substantially all of the assets and business of Company or any company with or into which
Company may be consolidated or merged, and Executive, Executive’s heirs, executors, administrators,
and legal representatives, provided that the obligations of Executive may not be delegated.

12. FREEDOM FROM RESTRICTIONS.

Executive represents and warrants that Executive has not entered into any agreement, whether
express, implied, oral, or written, that poses an impediment to Executive’s employment by Company
including Executive’s compliance with the terms of this Agreement. In particular, Executive is not
subject to a valid, pre-existing non-competition agreement which prohibits Executive from
fulfilling Executive’s job duties as set out in Section 2(a) of this Agreement, and no restrictions
or limitations exist respecting Executive’s ability to perform fully Executive’s obligations to
Company, including Executive’s compliance with the terms of this Agreement.

13. THIRD-PARTY TRADE SECRETS.

During the term of this Agreement, Executive agrees not to copy, refer to, or in any way use,
information that is proprietary to any third party (including any previous employer). Executive
represents and warrants that Executive has not improperly taken any documents, listings, hardware,
software, discs, or any other tangible medium that embodies proprietary information from any third
party, and that Executive does not intend to copy, refer to, or in any way use, information that is
proprietary to any third party in performing duties for Company.

14. NOTICES.

All notices hereunder shall be in writing and delivered personally or sent by United States
registered or certified mail, postage prepaid and return receipt requested:

	 	 	 
	If to Company, to:

	 	Insight Enterprises, Inc.

Attn: Chief Executive Officer

1305 West Auto Drive

Tempe, Arizona 85284
	With a copy to:

	 	Insight Enterprises, Inc.

Attn: Legal Department

1305 West Auto Drive

Tempe, Arizona 85284
	If to Executive, to:

	 	Glynis A. Bryan

6814 North First Place

Phoenix, Arizona 85012

Either party may change the address to which notices are to be sent to it by giving ten (10) days
written notice of such change of address to the other party in the manner above provided for giving
notice. Notices will be considered delivered on personal delivery or on the date of deposit in the
United States mail in the manner provided for giving notice by mail.

	 	15.	 	NONDELEGABILITY OF EXECUTIVE’S RIGHTS AND COMPANY ASSIGNMENT RIGHTS.

The obligations, rights and benefits of Executive hereunder are personal and may not be
delegated, assigned or transferred in any manner whatsoever, nor are such obligations, rights or
benefits subject to involuntary alienation, assignment or transfer. Upon reasonable notice to
Executive, Company may transfer Executive to an affiliate of Company, which affiliate shall assume
the obligations of Company under this Agreement. This Agreement shall be assigned automatically to
any entity merging with or acquiring Company or its business.

16. SEVERABILITY.

If any term or provision of this Agreement is declared by a court or tribunal of competent
jurisdiction to be invalid or unenforceable for any reason, this Agreement shall remain in full
force and effect, and either (1) the invalid or unenforceable provision shall be modified to the
minimum extent necessary to make it valid and enforceable or (2) if such a modification is not
possible, this Agreement shall be interpreted as if such invalid or unenforceable provision were
not a part hereof.

17. ARBITRATION.

The parties agree that any and all disputes arising out of the terms of this Agreement, their
interpretation, or Executive’s employment or compensation, shall be subject to binding arbitration
in Maricopa County, Arizona, before the American Arbitration Association under its National Rules
for the Resolution of Employment Disputes, or by a judge to be mutually agreed upon. The parties
agree that the prevailing party in any arbitration shall be entitled to injunctive relief in any
court of competent jurisdiction to enforce the arbitration award. The parties agree that if
Company initiates the arbitral proceedings, it shall advance the costs of the arbitration. If
Executive initiates the arbitral proceedings, Executive shall pay the greater of $200.00 or the
initial filing fee Executive would have had to pay if Executive had initiated the case in Maricopa
County courts. Company shall advance the remaining arbitration costs. The prevailing party in any
arbitration shall be awarded its reasonable attorney’s fees and costs.

18. COUNTERPARTS.

This Agreement may be executed in counterparts, each of which shall be deemed to be an
original, but which together shall constitute one and the same instrument.

19. ENTIRE AGREEMENT.

The entire understanding and agreement between the parties has been incorporated into this
Agreement, and this Agreement supersedes all other agreements and understandings between Executive
and Company with respect to the relationship of Executive with Company, except with respect to
other continuing or future stock option, health, benefit and similar plans or agreements.

20. GOVERNING LAW.

This Agreement and Executive’s employment shall be governed in all respects by the laws of the
State of Arizona as governs transactions occurring entirely within Arizona among Arizona residents,
except as preempted by Federal Law.

21. DEFINITIONS.

Throughout this Agreement, certain defined terms will be identified by the capitalization of
the first letter of the defined word or the first letter of each substantive word in a defined
phrase. Whenever used, these terms will be given the indicated meaning.

22. TERMINATION OF EMPLOYMENT.

The termination of this Agreement by either party also shall result in the termination of
Executive’s employment relationship with Company in the absence of an express written agreement
providing to the contrary. Neither party intends that any oral employment relationship continue
after the termination of this Agreement.

23. TIME IS OF THE ESSENCE.

Company and Executive agree that time is of the essence with respect to the duties and
performance of the covenants and promises of this Agreement.

24. CONSTRUCTION. 

This Agreement is the result of negotiation between Company and Executive and both have had
the opportunity to have this Agreement reviewed by their legal counsel and other advisors.
Accordingly, this Agreement shall not be construed for or against Company or Executive, regardless
of which party drafted the provision at issue. The language in all parts of this Agreement shall
in all cases be construed as a whole according to its fair meaning and not strictly for or against
either party. The Section headings contained in this Agreement are for reference purposes only and
will not affect the meaning or interpretation of this Agreement in any way. Whenever the words
“include,” “includes,” or “including” are used in the Agreement, they shall be deemed to be
followed by the words “without limitation.”

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Company:

Insight Enterprises, Inc.,

a Delaware corporation

By: /s/ Richard A. Fennessy

Name: Rich Fennessy

Title: Chief Executive Officer

Executive:

/s/ Glynis A. Bryan

Glynis A. Bryan

2EX-10.2

[Insight Letterhead]

November 16, 2007

Glynis A. Bryan

6814 North First Place

Phoenix, Arizona 85012

Dear Glynis:

We are pleased to offer you the position of Chief Financial Officer of Insight Enterprises, Inc.
(“Insight”). This position will report to directly to me, and your anticipated start date will be
December 17, 2007.

Your compensation will consist of an annual base salary of $400,000, to be paid on an
exempt/semi-monthly pay schedule. In addition, you will be eligible for a mix of annual and
quarterly incentive compensation. The target annual incentive compensation for the remainder of
2007 (prorated for the remainder of the year) and for 2008 is $425,000. In addition, you will
receive four (4) weeks of vacation.

We plan to award you an option to purchase 200,000 shares of the common stock of Insight (the
“Option”). The exercise price for the Option will be the closing price for IEI’s common stock on
the grant date, which will be your first day of employment with Insight. The Option will vest,
subject to continued employment, evenly over a three-year period with a term of five years from the
date of grant. We also plan to award you 15,000 service-based restricted stock units (“RSUs”), and
the RSUs will vest, subject to continued employment, evenly over a three-year period measured from
the grant date. The RSUs will be granted on the 10th day of the month following the
month in which you commence employment with Insight. The terms and conditions of the Option and
RSUs will be governed by separate award agreements and applicable plan documents. You will also be
eligible to participate in any equity programs that are made available to executives within the
company, typically on an annual basis.

You will be eligible for enrollment in Insight’s 401(k) plan and for other benefits (i.e., medical,
dental, etc.) as of the first day of the month following the month in which you commence employment
with Insight. All other benefits will be outlined during your orientation.

It is Insight’s understanding that you are not under a covenant restricting your ability to enter
into an employment relationship with Insight. You may also have had access to confidential
information, trade secrets, and/or intellectual property while employed by any prior employers
(“Prior Employer Proprietary Information”). Insight has a policy that prohibits the use of any
Prior Employer Proprietary Information, unless Insight has been explicitly authorized to do so by
the owner of such Prior Employer Proprietary Information or it is otherwise proper for Insight to
use such information.

1

This offer is contingent upon approval by the Compensation Committee of Insight’s Board of
Directors and upon execution and delivery of the enclosed Employment Agreement. Employment is also
contingent upon you successfully passing a background check and drug screen.

I am very excited about your joining the executive team at Insight. If the previously mentioned
terms of employment are acceptable to you, please sign in the space provided below before the end
of the day on Thursday, November 8, 2007.

Sincerely,

/s/ Richard A. Fennessy

Richard A. Fennessy

Chief Executive Officer

I accept the offer of employment as stated by Insight.

	 	 	 
	/s/ Glynis A. Bryan

Glynis A. Bryan

	 	11/16/07

Date

2

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