Cassandra Hudson - Jul 1, 2023 Form 4 Insider Report for EngageSmart, Inc. (ESMT)

Role
Chief Financial Officer
Signature
By: /s/ Scott Semel, Attorney-in-Fact for Cassandra E. Hudson
Stock symbol
ESMT
Transactions as of
Jul 1, 2023
Transactions value $
-$90,200
Form type
4
Date filed
7/6/2023, 09:40 PM
Previous filing
Jun 27, 2023
Next filing
Oct 3, 2023

Transactions Table

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Ownership Footnotes
transaction ESMT Common Stock Options Exercise $0 +3.61K +6.33% $0.00 60.5K Jul 1, 2023 Direct
transaction ESMT Common Stock Tax liability -$30.5K -1.6K -2.64% $19.09 58.9K Jul 1, 2023 Direct F1
transaction ESMT Common Stock Options Exercise $0 +7.05K +11.96% $0.00 66K Jul 1, 2023 Direct
transaction ESMT Common Stock Tax liability -$59.7K -3.13K -4.74% $19.09 62.9K Jul 1, 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 ESMT Restricted Stock Units Options Exercise $0 -3.61K -10% $0.00 32.5K Jul 1, 2023 Common Stock 3.61K Direct F2, F3
transaction ESMT Restricted Stock Units Options Exercise $0 -7.05K -6.67% $0.00 98.6K Jul 1, 2023 Common Stock 7.05K Direct F2, F4
* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id Content
F1 Represents the number of common stock withheld to satisfy the tax withholding obligation in connection with the vesting of certain previously reported restricted stock units ("RSUs").
F2 Each RSU represents a contingent right to receive one share of common stock.
F3 The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date.
F4 The RSUs vest in 16 equal quarterly installments commencing on April 1, 2023 and have no expiration date.