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

Signature
By: /s/ Scott Semel, Attorney-in-Fact for Robert P. Bennett
Stock symbol
ESMT
Transactions as of
Jan 1, 2023
Transactions value $
-$2,234,361
Form type
4
Date filed
1/4/2023, 08:19 PM
Previous filing
Oct 12, 2022
Next filing
Feb 7, 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 -0.21% $0.00 1.13M Jan 1, 2023 Direct
transaction ESMT Common Stock Tax liability -$14.7K -833 -0.07% $17.60 1.13M Jan 1, 2023 Direct F1
transaction ESMT Common Stock Sale -$495K -28K -2.48% $17.67 1.1M Jan 3, 2023 Direct F2, F3
transaction ESMT Common Stock Sale -$495K -28K -2.85% $17.67 953K Jan 3, 2023 The Robert P. Bennett 2020 Grantor Retained Annuity Trust F2, F4
transaction ESMT Common Stock Sale -$495K -28K -1.92% $17.67 1.43M Jan 3, 2023 The Bennett Family 2020 Trust F2, F5
transaction ESMT Common Stock Sale -$245K -14K -1.27% $17.51 1.09M Jan 4, 2023 Direct F2, F6
transaction ESMT Common Stock Sale -$245K -14K -1.47% $17.51 939K Jan 4, 2023 The Robert P. Bennett 2020 Grantor Retained Annuity Trust F2, F7
transaction ESMT Common Stock Sale -$245K -14K -0.98% $17.51 1.42M Jan 4, 2023 The Bennett Family 2020 Trust F2, 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 -8.33% $0.00 26.4K Jan 1, 2023 Common Stock 2.4K Direct F9, F10
* 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 The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan.
F3 The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $17.54 to $17.99. The Reporting Person undertakes to provide upon request 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 $17.55 to $18.00. The Reporting Person undertakes to provide upon request 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 price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $17.54 to $17.99. The Reporting Person undertakes to provide upon request 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.
F6 The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $17.29 to $17.92. The Reporting Person undertakes to provide upon request 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 price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $17.29 to $17.92. The Reporting Person undertakes to provide upon request 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.
F8 The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $17.29 to $17.92. The Reporting Person undertakes to provide upon request 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.