Robert Paul Bennett - 01 Apr 2022 Form 4 Insider Report for EngageSmart, Inc.

Signature
By: /s/ Scott Semel, Attorney-in-Fact for Robert P. Bennett
Issuer symbol
N/A
Transactions as of
01 Apr 2022
Net transactions value
-$23,538
Form type
4
Filing time
05 Apr 2022, 21:08:58 UTC
Previous filing
15 Feb 2022
Next filing
06 Jul 2022

Transactions Table

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Ownership Footnotes
transaction ESMT Common Stock Options Exercise $0 +2,404 +0.21% $0.000000 1,139,563 01 Apr 2022 Direct
transaction ESMT Common Stock Tax liability $23,538 -1,067 -0.09% $22.06 1,138,496 01 Apr 2022 Direct F1
holding ESMT Common Stock 2,550,000 01 Apr 2022 See footnote F2

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 -2,404 -6.7% $0.000000 33,654 01 Apr 2022 Common Stock 2,404 Direct F3, 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 Represents (i) 1,050,000 shares of common stock held by The Robert P. Bennett 2020 Grantor Retained Annuity Trust, of which the Reporting Person serves as the sole trustee, and (ii) 1,500,000 shares of common stock held by The Bennett Family 2020 Trust, of which John Burgess and Martha Bennett, the Reporting Person's spouse, serve as trustees. John Burgess and Martha Bennett, the Reporting Person's spouse, may be deemed to share voting and dispositive power with respect to the shares held by The Bennett Family 2020 Trust.
F3 Each RSU represents a contingent right to receive one share of common stock.
F4 The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date.