Robert Paul Bennett - Jul 5, 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
Jul 5, 2023
Transactions value $
-$1,431,275
Form type
4
Date filed
7/14/2023, 08:47 PM
Previous filing
Jul 6, 2023
Next filing
Oct 3, 2023

Transactions Table

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Ownership Footnotes
transaction ESMT Common Stock Sale -$519K -28K -3.34% $18.53 810K Jul 5, 2023 Direct F1, F2
transaction ESMT Common Stock Sale -$519K -28K -3.34% $18.53 810K Jul 5, 2023 The Robert P. Bennett 2020 Grantor Retained Annuity Trust F1, F3
transaction ESMT Common Stock Sale -$519K -28K -2.06% $18.53 1.33M Jul 5, 2023 The Bennett Family 2020 Trust F1, F4
transaction ESMT Common Stock Options Exercise $125K +22.1K +2.73% $5.67 833K Jul 12, 2023 Direct

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 Stock Option Options Exercise $0 -22.1K -4.91% $0.00 428K Jul 12, 2023 Common Stock 22.1K $5.67 Direct F5
* 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 The sales reported in this Form 4 were effected pursuant to Rule 10b5-1 trading plans, each dated September 9, 2022.
F2 The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.25 to $18.75. 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.
F3 The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.25 to $18.75. 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.
F4 The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.25 to $18.75. 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 stock option vested and became exercisable with respect to 25% of the underlying shares on February 2, 2022 and will vest with respect to the remaining shares in twelve equal quarterly installments beginning on April 1, 2022, subject to the Reporting Person's continued service to the Issuer through each vesting date.