Kevin William O'Brien - May 1, 2023 Form 4 Insider Report for EngageSmart, Inc. (ESMT)

Role
President, Enterprise Solutions
Signature
/s/ Scott Semel, Attorney-in-Fact for Kevin William O'Brien
Stock symbol
ESMT
Transactions as of
May 1, 2023
Transactions value $
-$80,101
Form type
4
Date filed
5/3/2023, 05:24 PM
Previous filing
Apr 4, 2023
Next filing
Jun 21, 2023

Transactions Table

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Ownership Footnotes
transaction ESMT Common Stock Options Exercise $0 +10.6K +34.39% $0.00 41.3K May 1, 2023 Direct
transaction ESMT Common Stock Tax liability -$80.1K -4.69K -11.35% $17.09 36.6K May 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 -10.6K -8.33% $0.00 116K May 1, 2023 Common Stock 10.6K Direct F2, F3
* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id Content
F1 Represents the number of shares 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 have vested or will vest with respect to 25% of the shares on the first anniversary of the date of grant and then in equal installments on each of the 12 quarterly anniversaries thereafter. The RSUs have no expiration date.

Remarks:

President, Enterprise Solutions