Samuel C. Cowley - Feb 20, 2023 Form 4 Insider Report for INSIGHT ENTERPRISES INC (NSIT)

Role: Gen'l Counsel & Secretary
Signature: Lisanne Steinheiser, by Power of Attorney, for Samuel C. Cowley
Stock symbol: NSIT
Transactions as of: Feb 20, 2023
Transactions value $: -$367,544
Form type: 4
Date filed: 2/22/2023, 03:32 PM
Previous filing: Dec 13, 2022
Next filing: Mar 15, 2023

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	NSIT	Common Stock	Options Exercise	$0	+868	+3.37%	$0.00	26.6K	Feb 20, 2023	Direct
transaction	NSIT	Common Stock	Tax liability	-$33.4K	-256	-0.96%	$130.52	26.4K	Feb 20, 2023	Direct	F1
transaction	NSIT	Common Stock	Options Exercise	$0	+1.02K	+3.86%	$0.00	27.4K	Feb 20, 2023	Direct
transaction	NSIT	Common Stock	Tax liability	-$56.9K	-436	-1.59%	$130.52	27K	Feb 20, 2023	Direct	F1
transaction	NSIT	Common Stock	Options Exercise	$0	+2.55K	+9.44%	$0.00	29.5K	Feb 20, 2023	Direct
transaction	NSIT	Common Stock	Tax liability	-$97.1K	-744	-2.52%	$130.52	28.8K	Feb 20, 2023	Direct	F1
transaction	NSIT	Common Stock	Options Exercise	$0	+718	+2.5%	$0.00	29.5K	Feb 20, 2023	Direct
transaction	NSIT	Common Stock	Tax liability	-$40.1K	-307	-1.04%	$130.52	29.2K	Feb 20, 2023	Direct	F1
transaction	NSIT	Common Stock	Options Exercise	$0	+1.26K	+4.31%	$0.00	30.4K	Feb 20, 2023	Direct
transaction	NSIT	Common Stock	Tax liability	-$45.7K	-350	-1.15%	$130.52	30.1K	Feb 20, 2023	Direct	F1
transaction	NSIT	Common Stock	Options Exercise	$0	+752	+2.5%	$0.00	30.8K	Feb 20, 2023	Direct
transaction	NSIT	Common Stock	Tax liability	-$27.3K	-209	-0.68%	$130.52	30.6K	Feb 20, 2023	Direct	F1
transaction	NSIT	Common Stock	Options Exercise	$0	+1K	+3.27%	$0.00	31.6K	Feb 20, 2023	Direct
transaction	NSIT	Common Stock	Tax liability	-$36.4K	-279	-0.88%	$130.52	31.4K	Feb 20, 2023	Direct	F1
transaction	NSIT	Common Stock	Options Exercise	$0	+846	+2.7%	$0.00	32.2K	Feb 20, 2023	Direct
transaction	NSIT	Common Stock	Tax liability	-$30.7K	-235	-0.73%	$130.52	32K	Feb 20, 2023	Direct	F1

Derivative Securities (e.g., puts, calls, warrants, options, convertible securities)

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Underlying Class	Amount	Exercise Price	Ownership	Footnotes
transaction	NSIT	Restricted Stock Units	Options Exercise	$0	-868	-100%	$0.00^*	0	Feb 20, 2023	Common Stock	868		Direct	F2, F3
transaction	NSIT	Restricted Stock Units	Options Exercise	$0	-1.02K	-50%	$0.00	1.02K	Feb 20, 2023	Common Stock	1.02K		Direct	F2, F4
transaction	NSIT	Restricted Stock Units	Options Exercise	$0	-2.55K	-100%	$0.00^*	0	Feb 20, 2023	Common Stock	2.55K		Direct	F2, F5
transaction	NSIT	Restricted Stock Units	Options Exercise	$0	-718	-33.33%	$0.00	1.44K	Feb 20, 2023	Common Stock	718		Direct	F2, F6
transaction	NSIT	Restricted Stock Units	Options Exercise	$0	-1.26K	-50%	$0.00	1.26K	Feb 20, 2023	Common Stock	1.26K		Direct	F2, F7
transaction	NSIT	Restricted Stock Units	Options Exercise	$0	-1K	-33.34%	$0.00	2K	Feb 20, 2023	Common Stock	1K		Direct	F2, F8
transaction	NSIT	Restricted Stock Units	Options Exercise	$0	-752	-50.03%	$0.00	751	Feb 20, 2023	Common Stock	752		Direct	F2, F9
transaction	NSIT	Restricted Stock Units	Options Exercise	$0	-846	-33.36%	$0.00	1.69K	Feb 20, 2023	Common Stock	846		Direct	F2, F10
transaction	NSIT	Restricted Stock Units	Award	$0	+3.07K		$0.00	3.07K	Feb 20, 2023	Common Stock	3.07K		Direct	F2, F11
transaction	NSIT	Restricted Stock Units	Award	$0	+2.3K		$0.00	2.3K	Feb 20, 2023	Common Stock	2.3K		Direct	F2, F12
transaction	NSIT	Restricted Stock Units	Award	$0	+2.3K		$0.00	2.3K	Feb 20, 2023	Common Stock	2.3K		Direct	F2, F13

* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id	Content
F1	Insight Enterprises, Inc. has withheld the number of whole shares necessary to satisfy the minimum statutory tax withholding obligations. The value of the vested shares (and the taxable income) is calculated based on the closing price on the vesting date or next preceding trading date in the case that the vesting date is a non-trading date.
F2	Each restricted stock unit represents a contingent right to receive one share of Common Stock of Insight Enterprises, Inc.
F3	The restricted stock units were granted on February 20, 2019 with vesting to occur in four equal annual installments beginning February 20, 2020.
F4	The restricted stock units were granted on February 20, 2020 with vesting to occur in four equal annual installments beginning February 20, 2021.
F5	The number of restricted stock units increases or decreases with the Company's performance against specific objectives defined in advance of the grant date, and the restricted stock units will vest in three equal annual installments beginning February 20, 2021.
F6	The restricted stock units were granted on February 20, 2021 with vesting to occur in four equal annual installments beginning February 20, 2022.
F7	The number of restricted stock units increases or decreases with the Company's performance against specific objectives defined in advance of the grant date, and the restricted stock units will vest in three equal annual installments beginning February 20, 2022.
F8	The restricted stock units were granted on February 20, 2022 with vesting to occur in three equal annual installments beginning February 20, 2023.
F9	The restricted stock units were granted on February 20, 2022 with vesting to occur in two equal annual installments beginning February 20, 2023.
F10	The number of restricted stock units increases or decreases with the Company's performance against specific objectives defined in advance of the grant date, and the restricted stock units will vest in three equal annual installments beginning February 20, 2023.
F11	The restricted stock units were granted on February 20, 2023 with vesting to occur in three equal annual installments beginning February 20, 2024.
F12	The number of restricted stock units increases or decreases with the Company's performance against specific objectives defined in advance of the grant date, and the restricted stock units will vest in three equal annual installments beginning February 20, 2024.
F13	The number of restricted stock units increases or decreases with the Company performance over a three year measurement period against a specific objective defined in advance of the grant date, and, subject to achievement of the specific objective, the restricted stock units will vest when the results are determined in 2026.