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

Role
President, Enterprise Solutions Exhibit 24 - Power of Attorney
Signature
By: /s/ Scott Semel, Attorney-in-Fact for Kevin William O'Brien
Stock symbol
ESMT
Transactions as of
Feb 1, 2023
Transactions value $
-$251,494
Form type
4
Date filed
2/3/2023, 08:48 PM
Previous filing
Feb 3, 2022
Next filing
Feb 7, 2023

Transactions Table

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Ownership Footnotes
transaction ESMT Common Stock Options Exercise $0 +42.3K $0.00 42.3K Feb 1, 2023 Direct
transaction ESMT Common Stock Tax liability -$251K -12.7K -30.1% $19.77 29.5K Feb 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 Unit Options Exercise $0 -42.3K -25% $0.00 127K Feb 1, 2023 Common Stock 42.3K 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 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 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 Exhibit 24 - Power of Attorney