Robert Paul Bennett - Jul 1, 2022 Form 4 Insider Report for EngageSmart, Inc. (ESMT)

Role
Chief Executive Officer, Director
Signature
By: /s/ Scott Semel, Attorney-in-Fact for Robert P. Bennett
Stock symbol
ESMT
Transactions as of
Jul 1, 2022
Transactions value $
-$17,499
Form type
4
Date filed
7/6/2022, 06:12 PM
Previous filing
Apr 5, 2022
Next filing
Oct 4, 2022

Transactions Table

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Ownership Footnotes
transaction ESMT Common Stock Options Exercise $0 +2.4K +0.21% $0.00 1.17M Jul 1, 2022 Direct F1
transaction ESMT Common Stock Tax liability -$17.5K -1.07K -0.09% $16.40 1.17M Jul 1, 2022 Direct F2
holding ESMT Common Stock 2.52M Jul 1, 2022 See footnote F3

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 -2.4K -7.14% $0.00 31.3K Apr 1, 2022 Common Stock 2.4K Direct F4, F5
* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id Content
F1 Includes 27,022 shares of common stock received as annuity payment from The Robert P. Bennett 2020 Grantor Retained Annuity Trust, of which the Reporting Person serves as the sole trustee.
F2 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").
F3 Represents (i) 1,022,978 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.
F4 Each RSU represents a contingent right to receive one share of common stock.
F5 The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date.