Robert Paul Bennett - Sep 23, 2021 Form 3 Insider Report for EngageSmart, Inc. (ESMT)

Role
Chief Executive Officer, Director
Signature
/s/ Charles Kallenbach, Attorney-in-Fact for Robert P. Bennett
Stock symbol
ESMT
Transactions as of
Sep 23, 2021
Transactions value $
$0
Form type
3
Date filed
9/23/2021, 07:50 PM
Next filing
Sep 29, 2021

Transactions Table

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Ownership Footnotes
holding ESMT Common Stock 1.34M Sep 23, 2021 Direct
holding ESMT Common Stock 2.55M Sep 23, 2021 See Footnote F1

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
holding ESMT Stock Option Sep 23, 2021 Common Stock 600K $5.67 Direct F2
* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id Content
F1 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.
F2 The stock option will vest and become exercisable with respect to 25% of the shares on February 2, 2022 and will vest with respect to the remaining shares in twelve equal quarterly installments beginning on April 1, 2022.

Remarks:

Exhibit 24 - Power of Attorney.