AMENDED AND RESTATED EMPLOYMENT AGREEMENT

Exhibit 10.1

AMENDED AND RESTATED EMPLOYMENT AGREEMENT

This amended and restated Employment Agreement (the "Agreement"), entered into as of January 1, 2009, is between Insight Enterprises, Inc., a Delaware corporation (the "Company"), and Richard Fennessy (the "Executive").

This amended and restated Employment Agreement is entered into in the following context:

RECITALS

A. Executive is employed by Company pursuant to an Employment Agreement dated as of October 24, 2004 (the "Existing Employment Agreement").

B. Section 409A of the Internal Revenue Code of 1986, as amended (the "Code"), potentially applies to certain payments provided pursuant to the Existing Employment Agreement. The Existing Employment Agreement has been and shall continue to be administered in good faith compliance with the requirements of Section 409A of the Code from January 1, 2005 through December 31, 2008.

C. Company and Executive have decided to amend and restate the Existing Employment Agreement with this new Agreement, effective as of January 1, 2009, in order to satisfy the documentation requirements of Section 409A of the Code and to comply with the final regulations issued pursuant to Section 409A.

D. In this amended and restated Agreement, Company proposes and Executive agrees to certain changes that are intended to promote uniformity in the employment agreements entered into between Company and certain other executives and to clarify certain other provisions. Substantive changes also have been made in order to promote retention, positive morale and certainty among Company’s senior executives, including Executive. These changes also are intended to provide incentives that are in line with similar agreements provided to executives working in Company’s industry.

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 for a two-year term commencing as of January 1, 2009 and ending on December 31, 2010 (the "Initial Term"), unless sooner terminated in accordance with the provisions of this Agreement.

(b)  Renewal Term; Employment Period Defined . This Agreement is intended to provide for a constantly renewing (or "evergreen") two-year term. As a result, on each 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 from that day forward (a "Renewal Term"). Nevertheless, Company may notify Executive, or Executive may notify Company, at any time, that there shall be no renewal of this Agreement. If this notice of non-renewal is given, 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 of this Agreement 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 employs, engages and hires Executive as its President and Chief Executive Officer, and Executive accepts and agrees to such employment, engagement and hiring. Executive’s duties and authority during the Employment Period shall be such executive and managerial duties as the Board of Directors of Company (the "Board") shall reasonably determine. Executive will devote full time on behalf of Company, or such lesser amount of time as the Board may determine, reasonable absences because of illness, personal and family exigencies excepted. Except as otherwise required by applicable law, Executive shall be the only officer that reports directly to the Board.

(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 under this Agreement pursuant to its express terms. Executive’s ownership of or participation as an officer, director, consultant or employee of any entity (other than Company) must be disclosed to the Board. Additionally, Executive shall disclose to the Board any interest in a company that is engaged in a Competing Business as defined in Section 11, unless such interest constitutes less than five percent (5%) of the issued and outstanding equity of such company.

(c)  Seat on Board of Directors . Executive currently serves on the Board. Company will use best efforts to make such appointment continuous during the term of this Agreement.

(d)  Travel . Executive necessarily will be required to engage in reasonable travel in order to fulfill his duties under this Agreement. At the same time, Executive, without his consent, may not be required by the Board to substantially increase the amount of his travel as compared to the level of travel actually experienced in calendar year 2008. Executive will be deemed to have consented to any additional required travel in the absence of a specific written objection provided to the Board.

(e)  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 (the "1934 Act"), 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 at the rate of $750,000.00 per annum. 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 incentive compensation pursuant to one or more incentive compensation plans established by the Company from time to time (each, an "Incentive Compensation Plan"). The amount of the incentive compensation, 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 or pursuant to the Incentive Compensation Plan, or Incentive Compensation Plans, for the relevant time period. Company’s Compensation Committee is committed to offering cash bonus incentives for Executive on an annual basis. Executive will be targeted to receive the highest dollar value award each year. While there is no guarantee regarding the amount of the Incentive Compensation payments that will be made in any year, Company intends to provide Executive with an Incentive Compensation target opportunity of at least $1,000,000 per year, provided Executive reaches performance targets established for the year. For purposes of this Agreement, the terms "Incentive Compensation Plan" and "Incentive Compensation Plans" do not include any employee benefit, stock option, restricted stock or other equity-based plan.

(c)  Equity Compensation . Executive shall also be permitted to participate in such equity compensation plans as are adopted by the Committee from time to time. The Committee, with input from senior management (including Executive), shall review the equity compensation plan or formula in light of all relevant circumstances and business conditions, and shall, in its discretion and business judgment, determine whether to provide equity compensation for the following year and, if so, make a determination as to the appropriate equity formula or equity allocation for Executive for such following year. The equity formula shall be the same as that used for the most senior executives of Company whose incentive is based on Company-wide performance, though amount of equity participation, if any, shall be at the discretion of the Committee. The Committee is committed to equity incentives for its executives on an annual basis. Executive will be targeted to receive the largest incentive each year.

(d)  Benefit Plans . Executive will be entitled to participate in those benefit plans generally provided for Company’s executives in accordance with the terms of the applicable 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. Executive shall be entitled to D&O insurance and indemnification as provided by Company consistent with the coverage provided to other directors and officers. Executive shall be entitled to four (4) weeks vacation during the calendar year, and such additional vacation time as the Board shall approve, with such vacation to be carried over, scheduled and taken in accordance with Company’s standard vacation policies.

(e)  Life Insurance . Company shall acquire and be the owner of a life insurance policy on the life of Executive. Company and Executive shall enter into a separate split-dollar life insurance agreement pursuant to which Executive will be entitled to designate a beneficiary or beneficiaries for all or a portion of the proceeds of such life insurance policy. At a minimum, Executive shall be entitled to designate the beneficiary for life insurance proceeds equal to at least 1.75 times Executive’s current Base Salary. The level of life insurance shall be reviewed periodically and will be increased to reflect any significant cumulative increases in Executive’s Base Salary, as agreed to by Executive and Company.

(f)  Clawback . To the extent required by law or Company policy, Company may require Executive to repay to Company any bonus or other incentive-based or equity-based compensation paid to Executive. For example, in accordance with Section 304 of the Sarbanes-Oxley Act of 2002, if Company is required to restate its financial statements due to its material noncompliance, as a result of misconduct, with any financial reporting requirement under the federal securities laws, Executive may be required to repay any bonus or other incentive-based or equity-based compensation he receives from Company during the twelve-month period following the first public issuance or filing with the U.S. Securities and Exchange Commission of the financial document embodying such financial reporting requirement, as well as any profits he realizes from the sale of Company’s securities during this twelve-month period.

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)  Compensation . If Executive’s employment is terminated as a result of Executive’s death, or if Executive becomes Disabled, Executive, or Executive’s estate, as the case may be, shall be entitled to receive the Base Salary due to Executive through the date of Executive’s death or Disability. Executive or Executive’s estate, as the case may be, also shall be entitled to receive the following:

(1) A single lump sum payment equal to ninety (90) days of Executive’s Base Salary as in effect on the date of Executive’s death or Disability;

(2) With respect to any Incentive Compensation Plan with quarterly objectives, a single lump sum cash payment in an amount equal to a prorated portion (based on the number of calendar days that have elapsed during the quarter) of the payment to which Executive would be entitled under the Incentive Compensation Plan (had Executive’s death or Disability not occurred) for the quarter in which Executive died or became Disabled; and

(3) With respect to any Incentive Compensation Plan with annual objectives, a single lump sum cash payment in an amount equal to a prorated portion (based on the number of calendar days that have elapsed during the year) of the payment to which Executive would have been entitled (had Executive’s death or Disability not occurred) under the Incentive Compensation Plan for the calendar year in which Executive dies or becomes Disabled.

The payment to which Executive or Executive’s estate is entitled pursuant to paragraph (1) will be paid within thirty (30) days of Executive’s death or the effective date of Executive’s Disability, as the case may be. The payments to which Executive is entitled pursuant to paragraphs (2) and (3) shall be made within the time period described in the applicable Incentive Compensation Plan. In no event will the payments due pursuant to paragraphs (1), (2) or (3) be made later than March 15 of the year following the year in which Executive dies or the effective date of Executive’s Disability occurs.

(b)  Disability . The term "Disability" or "Disabled" means that Executive with or without any accommodation required by law, is, by reason of any medically determinable physical or mental impairment that can be expected to result in death or can be expected to last for a continuous period of not less than twelve (12) months, receiving income replacement benefits for a period of not less than three (3) months under an accident and health plan covering employees of Company. The effective date of Executive’s Disability is the last day of the third month for which Executive receives the income replacement benefits.

(c)  Termination of Employment . Unless otherwise prohibited by law, Executive’s employment shall terminate on the first business day following the effective date of Executive’s "Disability." Executive’s employment also shall terminate on the date of Executive’s death.

6.  TERMINATION BY COMPANY .

(a)  Termination for Cause . Company may terminate this Agreement and Executive’s employment at any time during the Initial Term or any Renewal Term for "Cause" upon written notice to Executive specifying the basis for the termination. 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 Plan 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 criminal conviction for any felony involving theft or embezzlement from Company or any affiliate;

(2) the criminal conviction for any felony involving moral turpitude that reflects adversely upon the standing of Company in the community;

(3) the criminal conviction for any felony involving fraud committed against Company, any affiliate or any individual or entity that provides goods or services to, receives goods or services from or otherwise deals with Company or any affiliate;

(4) acts by Executive that constitute repeated and material violations of this Agreement, any written employment policies of Company or any written directives of Company. A violation will not be considered to be "repeated" unless such violation has occurred more than once and after receipt of written notice from Company of such violation.

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 3(d)) due to Executive through the termination date, and Executive will not be entitled to, nor will Executive receive, any type of severance payment.

If Company terminates Executive for Cause, and it is later determined as provided in Section 18 of this Agreement that Cause did not exist, Company will pay Executive the amount he would have received under this Agreement if his employment had been terminated by Company without Cause, plus interest at the Prime Rate published by the Wall Street Journal on the date of termination. Such payments and interest shall be calculated as of the effective date of the initial termination. Payment shall be made within fifteen (15) days after such later determination is made.

(b)  Termination Without Cause . Company also may terminate this Agreement and Executive’s employment at any time during the Initial Term or any Renewal Term without Cause. Company may, in 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)  Base Salary . In the event Executive’s employment is terminated by Company without Cause, Executive shall receive a single lump sum cash payment in an amount equal to two (2) times Executive’s Base Salary as in effect on the date Executive’s employment is terminated to be paid within three (3) days (or sooner if required by law) following the termination of Executive’s employment. Executive shall have no duty to mitigate damages in order to receive the compensation described by this Section 6(c), 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 Plan payments for the quarter or year in which Executive’s employment is terminated or for any other periods. If Executive is terminated without Cause, Executive shall receive a single lump sum cash payment in an amount equal to the sum of the following:

(1) Two (2) times the annual compensation paid to Executive in the one (1) of the two (2) preceding years in which Executive received the higher annual compensation under all Incentive Compensation Plans (annual and quarterly) in which Executive participates as of the date his employment is terminated or, if an Incentive Compensation Plan was not in existence in the preceding year, two (2) times the annual compensation paid to Executive in the one (1) of the two (2) preceding years in which Executive received the higher annual compensation under a predecessor Incentive Compensation Plan; plus

(2) With respect to any Incentive Compensation Plan with quarterly objectives, a prorated portion (based on the number of calendar days that have elapsed during the quarter) of the payment to which Executive would be entitled under the Incentive Compensation Plan (had Executive’s employment not been terminated) for the quarter in which Executive’s employment is terminated; plus

(3) With respect to any Incentive Compensation Plan with annual objectives, a prorated portion (based on the number of calendar days that have elapsed during the year) of the payment to which Executive would be entitled under the Incentive Compensation Plan (had Executive’s employment not been terminated) for the year in which Executive’s employment is terminated.

The payments described in this Section 6(d) will be made at the time described in the applicable Incentive Compensation Plan, but in no event later than March 15 of the year following the year in which Executive’s termination without Cause occurs. Executive shall have no duty to mitigate damages in order to receive the compensation described by this Section 6(d), and the compensation shall not be reduced or offset by other income, payments or profits received by Executive from any source.

(e)  Welfare Benefit Continuation . If Executive’s employment is terminated by Company without Cause, and such employment termination qualifies as a Separation from Service, Executive shall be entitled to continue to receive life, disability, accident and group health and dental insurance benefits, at substantially the levels Executive was receiving immediately prior to Executive’s Separation from Service, for a period of time expiring upon the earlier of: (1) the end of the period of twenty-four (24) months following Executive’s Separation from Service, or (2) the day on which Executive becomes eligible to receive any substantially similar benefits under any plan or program of any other employer or source without being required to pay any premium with respect thereto. Company will satisfy the obligation to provide the health and dental insurance benefits pursuant to this Section 6(e) by either paying for or reimbursing Executive for the actual cost of COBRA coverage (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). Following the expiration of the COBRA continuation period, Company will reimburse Executive for the cost of comparable health and dental insurance benefits. Similarly, Company will reimburse Executive for the cost of comparable coverage for all other insurance benefits that are not subject to the COBRA continuation rules. It will be Executive’s responsibility to procure such benefits and Company will promptly reimburse Executive for the premiums for such benefits in the specified amount upon Executive’s submission of an invoice or other acceptable proof of payment. Company’s obligation under this paragraph will cease with respect to a particular type of coverage when and if Executive becomes eligible to receive substantially similar coverage with a successor employer.

(f)  Other Plans . Except to the extent specified in this Section 6 and as provided in this Section 6(f), termination of Executive’s employment 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. Executive shall have no duty to mitigate damages in order to receive the compensation described by this Section 6(f), and the compensation shall not be reduced or offset by other income, payments or profits received by Executive from any source.

7.  TERMINATION BY EXECUTIVE .

(a)  General . Executive may terminate this Agreement and his employment at any time, with or without "Good Reason." Company may, in its discretion, place Executive on a paid administrative leave prior to the actual date of termination of Executive’s employment. 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 . Executive may terminate this Agreement and his employment for Good Reason if Executive provides Company with written notice of the breach or action giving rise to Good Reason within ninety (90) days of the initial existence of such breach or action. For purposes of this Agreement, "Good Reason" shall mean and include each of the following (unless Executive has expressly agreed to such event in a signed writing):

(1) A material diminution in Executive’s authority, duties, or responsibilities. For example, if a Change in Control occurs and, following the Change in Control, Executive is required to report to an officer of the acquiring company, or to a subsidiary’s Board of Directors, Executive shall be deemed to have suffered a material diminution in his authority, duties or responsibilities. The prior sentence is not intended to provide an exclusive list of examples of actions or omissions that will result in a material diminution of Executive’s authority, duties, or responsibilities.

(2) A material change in the geographic location at which Executive must perform services.

(3) A material diminution in Executive’s Base Salary.

(4) Any action or inaction that constitutes a material breach of this Agreement by Company.

Notwithstanding any provisions of this Agreement to the contrary, none of the events described in this Section 7(b) will constitute Good Reason if, within thirty (30) days after Executive provides Company written notice specifying the occurrence or existence of the breach or action that Executive believes constitutes Good Reason, Company has fully corrected (or reversed) such breach or action. Executive’s employment will terminate on the day following the expiration of this thirty (30) day "cure period," unless Executive and Company agree to a later date not later than two (2) years following the initial existence of such breach or action. Executive shall be deemed to have waived Executive’s right to terminate for Good Reason with respect to any such breach or action if Executive does not notify Company in writing of such breach or action within ninety (90) days of the event that gives rise to such breach or action.

(c)  Effect of Termination by Executive for Good Reason . If Executive terminates this Agreement and his employment for Good Reason, it shall for all purposes be treated as a termination by Company without Cause and Executive shall be entitled to compensation in accordance with Section 6.

(d)  Effect of Termination by Executive Without Good Reason . If Executive terminates this Agreement and his employment 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 in accordance with Section 6.

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 (as defined in Section 8(c)) occurs, Executive shall be entitled to the lump-sum severance benefit provided in Section 8(b) if, prior to the expiration of twenty-four (24) months after the Change in Control, (1) Executive terminates his employment with Company for Good Reason in accordance with the requirements of Section 7(b), or (2) Company terminates Executive’s employment without Cause pursuant to Section 6(b). The full severance benefits provided by this Section 8 shall be payable regardless of the period remaining until the expiration of the Initial Term or any Renewal Term.

(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 the date of termination of Executive’s employment, Company will provide Executive