Robert Paul Bennett - Jan 1, 2022 Form 4/A - Amendment 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
Jan 1, 2022
Transactions value $
$830,408
Form type
4/A - Amendment
Date filed
3/29/2022, 06:58 PM
Date Of Original Report
Feb 15, 2022
Previous filing
Sep 29, 2021
Next filing
Feb 15, 2022

Transactions Table

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Ownership Footnotes
transaction ESMT Common Stock Options Exercise +2.4K +0.24% 988K Jan 1, 2022 Direct F1, F2
transaction ESMT Common Stock Tax liability -$20.1K -833 -0.08% $24.12 987K Jan 1, 2022 Direct
transaction ESMT Common Stock Options Exercise $851K +150K +15.2% $5.67 1.14M Feb 11, 2022 Direct F3
holding ESMT Common Stock 2.55M Jan 1, 2022 See footnote F4

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 -6.25% $0.00 36.1K Jan 1, 2022 Common Stock 2.4K Direct F2, F5
transaction ESMT Stock Option Options Exercise $0 +150K +50% $0.00 450K Feb 11, 2022 Common Stock 150K $5.67 Direct F6
* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id Content
F1 On February 15, 2022, the Reporting Person filed a Form 4 (the "Original Form 4") which inadvertently indicated that the date of earliest transaction required to be reported was 02/11/2022. The correct date of earliest transaction required to be reported is 01/01/2022. This amendment is being filed to correct the date of the earliest transaction required to be reported.
F2 Each restricted stock unit ("RSU") represents a contingent right to receive one share of common stock.
F3 The Original Form 4 inadvertently incorrectly stated the total number of shares of common stock directly beneficially owned by the Reporting Person. This amendment is being filed to correct the total number of shares of common stock directly beneficially owned by the Reporting Person.
F4 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.
F5 The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date.
F6 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.

Remarks:

Exhibit 24 - Power of Attorney.