Alex Constantinople - May 15, 2022 Form 4 Insider Report for Zendesk, Inc. (ZEN)

Role: Chief Marketing Officer
Signature: /s/ Albert Yeh via Power-of-Attorney for Alex Constantinople
Stock symbol: ZEN
Transactions as of: May 15, 2022
Transactions value $: -$265,590
Form type: 4
Date filed: 5/17/2022, 07:22 PM
Previous filing: Mar 2, 2022
Next filing: Jun 17, 2022

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	ZEN	Common Stock	Options Exercise		+6.11K	+2728.13%		6.34K	May 15, 2022	Direct	F1, F2
transaction	ZEN	Common Stock	Tax liability	-$216K	-2.11K	-33.37%	$102.15	4.22K	May 15, 2022	Direct	F3
transaction	ZEN	Common Stock	Options Exercise		+1.07K	+25.4%		5.29K	May 15, 2022	Direct	F1
transaction	ZEN	Common Stock	Tax liability	-$49.6K	-486	-9.18%	$102.15	4.81K	May 15, 2022	Direct	F3

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	ZEN	Restricted Stock Unit	Options Exercise	$0	-6.11K	-25%	$0.00	18.3K	May 15, 2022	Common Stock	6.11K		Direct	F1, F4
transaction	ZEN	Restricted Stock Unit	Options Exercise	$0	-1.07K	-6.25%	$0.00	16.1K	May 15, 2022	Common Stock	1.07K		Direct	F1, F5

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

Explanation of Responses:

Id	Content
F1	Restricted stock units convert into common stock on a one-for-one basis.
F2	Includes 224 shares acquired by the Reporting Person on May 13, 2022, pursuant to the Issuer's Employee Stock Purchase Plan in a transaction exempt under Rule 16b-3(c).
F3	Represents the number of shares withheld by the Issuer in satisfaction of tax withholding obligations in connection with the vesting of the restricted stock units listed in Table II. Such withholding is mandated by an election of the Issuer made in advance and does not represent a discretionary trade by the Reporting Person.
F4	1/4th of the shares issuable pursuant to the restricted stock units shall vest one year after the vesting commencement date of May 15, 2021, and an additional 1/48th of the shares issuable pursuant to the restricted stock units shall vest each month thereafter, subject to the Reporting Person's continuous service to the Issuer on each such date. Unvested shares are subject to acceleration upon the occurrence of certain events.
F5	1/48th of the shares issuable pursuant to the restricted stock units shall vest each month after the vesting commencement date of February 15, 2022, subject to cliff vesting for all months prior to the 1st anniversary, May 10, 2021, of the commencement of grantee's provision of services to the company or its subsidiaries, and the Reporting Person's continuous service to the Issuer on each such date. Unvested shares are subject to acceleration upon the occurrence of certain events.