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Filing Details

Issuer

Cik	Name	Symbol	Sector (SIC)	IRS No
1863105	Engagesmart Inc.	ESMT	Services-Prepackaged Software (7372)	000000000

Insiders

Cik	Name	Reported Address	Insider Title	Director	Officer	Large Shareholder	Other
1881869	Paul Robert Bennett	C/O Engagesmart, Inc. 30 Braintree Hill Office Park, Suite 101 Braintree MA 02184	Chief Executive Officer	Yes	Yes	No	No

Reported Non-Derivative Transactions

Sec. Name	Acquisiton - Disposition	Date	Amount	Price	Remaning Holdings	Equity Swap Involved	Form Type	Code	Nature of Ownership	Explanation
Common Stock	Disposition	2023-03-03	230,433	$18.19	855,330	No	4	S	Direct
Common Stock	Disposition	2023-03-07	34,892	$18.19	820,438	No	4	S	Direct

Equity Swap Involved	Form Type	Code	Nature of Ownership	Explanation
No	4	S	Direct
No	4	S	Direct

Reported Non-Derivative Holdings

Sec. Name	Remaning Holdings	Nature of Ownership	Explanation
Common Stock	2,354,978	Indirect	See Footnote

Footnotes

This amount represents a public offering price of $19.00 per share of common stock of EngageSmart, Inc. (the "Common Stock"), less an underwriting discount of $0.8075 per share for shares sold in an underwritten public offering.
Represents (i) 938,978 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) 1,416,000 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.