Robert Paul Bennett - Apr 1, 2023 Form 4 Insider Report for EngageSmart, Inc. (ESMT)

Role
Chief Executive Officer, Director
Signature
/s/ Scott Semel, Attorney-in-Fact for Robert P. Bennett
Stock symbol
ESMT
Transactions as of
Apr 1, 2023
Transactions value $
-$916,045
Form type
4
Date filed
4/4/2023, 09:51 PM
Previous filing
Mar 7, 2023
Next filing
Apr 6, 2023

Transactions Table

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Ownership Footnotes
transaction ESMT Common Stock Options Exercise $0 +2.4K +0.28% $0.00 868K Apr 1, 2023 Direct F1
transaction ESMT Common Stock Tax liability -$13.6K -706 -0.08% $19.25 867K Apr 1, 2023 Direct F2
transaction ESMT Common Stock Options Exercise $0 +19.4K +2.23% $0.00 887K Apr 1, 2023 Direct
transaction ESMT Common Stock Tax liability -$109K -5.69K -0.64% $19.25 881K Apr 1, 2023 Direct F2
transaction ESMT Common Stock Sale -$264K -14K -1.59% $18.88 867K Apr 3, 2023 Direct F3, F4
transaction ESMT Common Stock Sale -$264K -14K -1.57% $18.88 880K Apr 3, 2023 The Robert P. Bennett 2020 Grantor Retained Annuity Trust F5, F6
transaction ESMT Common Stock Sale -$264K -14K -0.99% $18.88 1.4M Apr 3, 2023 The Bennett Family 2020 Trust F7, F8

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 -9.09% $0.00 24K Apr 1, 2023 Common Stock 2.4K Direct F9, F10
transaction ESMT Restricted Stock Units Options Exercise $0 -19.4K -6.25% $0.00 291K Apr 1, 2023 Common Stock 19.4K Direct F9, F11
* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Buy Plan / Sale Plan: These are also open market purchases/sales of shares, but in this case the transaction is part of a trading plan. Rule 10b5-1 allows insiders to setup a trading plan to buy/sell stocks over a certain period of time. Since the purchases/sales are predetermined, this protects the insiders from violating insider trading law.

Transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c).

Explanation of Responses:

Id Content
F1 Includes 45,101 shares previously held through the Robert P. Bennett 2020 Grantor Retained Annuity Trust, of which the Reporting Person serves as the sole trustee, which were distributed to the Reporting Person on January 31, 2023 and are now owned directly by the Reporting Person.
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 The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan dated September 9, 2022.
F4 The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.71 to $19.06. The Reporting Person undertakes to provide upon request from the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote.
F5 The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan dated September 9, 2022.
F6 The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.73 to $19.06. The Reporting Person undertakes to provide upon request from the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote.
F7 The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan dated September 9, 2022.
F8 The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.72 to $19.06. The Reporting Person undertakes to provide upon request from the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote.
F9 Each RSU represents a contingent right to receive one share of common stock.
F10 The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date.
F11 The RSUs vest in 16 equal quarterly installments commencing on April 1, 2023 and have no expiration date.