Robert Paul Bennett - Sep 27, 2021 Form 4 Insider Report for EngageSmart, Inc. (ESMT)

Role
Chief Executive Officer, Director
Signature
By: /s/ Charles Kallenbach, Attorney-in-Fact for Robert P. Bennett
Stock symbol
ESMT
Transactions as of
Sep 27, 2021
Transactions value $
-$8,547,728
Form type
4
Date filed
9/29/2021, 08:10 PM
Previous filing
Sep 23, 2021
Next filing
Mar 29, 2022

Transactions Table

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Ownership Footnotes
transaction ESMT Common Stock Sale -$8.55M -351K -26.24% $24.38 986K Sep 27, 2021 Direct
holding ESMT Common Stock 2.55M Sep 27, 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
transaction ESMT Restricted Stock Unit Award $0 +38.5K $0.00 38.5K Sep 27, 2021 Common Stock 38.5K Direct F2, F3
* 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 Each restricted stock unit ("RSU") represents a contingent right to receive one share of common stock.
F3 The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date.