Scott N. Semel - Oct 1, 2023 Form 4 Insider Report for EngageSmart, Inc. (ESMT)

Role
Chief Legal Officer
Signature
/s/ Scott Semel
Stock symbol
ESMT
Transactions as of
Oct 1, 2023
Transactions value $
-$72,122
Form type
4
Date filed
10/3/2023, 04:34 PM
Previous filing
Jul 6, 2023
Next filing
Jan 3, 2024

Transactions Table

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Ownership Footnotes
transaction ESMT Common Stock Options Exercise $0 +6.71K +23.39% $0.00 35.4K Oct 1, 2023 Direct
transaction ESMT Common Stock Tax liability -$44K -2.45K -6.92% $17.99 32.9K Oct 1, 2023 Direct F1
transaction ESMT Common Stock Options Exercise $0 +3.52K +10.7% $0.00 36.4K Oct 1, 2023 Direct
transaction ESMT Common Stock Tax liability -$28.1K -1.56K -4.29% $17.99 34.9K Oct 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 -6.71K -9.09% $0.00 67.1K Oct 1, 2023 Common Stock 6.71K Direct F2, F3
transaction ESMT Restricted Stock Units Options Exercise $0 -3.52K -7.14% $0.00 45.8K Oct 1, 2023 Common Stock 3.52K 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 with respect to 25% of the shares on April 1, 2023 and then in equal installments on each of the 12 quarterly anniversaries thereafter. The RSUs have no expiration date.
F4 The RSUs vest in 16 equal quarterly installments commencing on April 1, 2023 and have no expiration date.