Robert Paul Bennett - 11 Feb 2022 Form 4 Insider Report for EngageSmart, Inc.

Reporting relationship: Chief Executive Officer, Director
Issuer ticker: N/A
Reported as of: 11 Feb 2022
Net transaction value: +$830,408
SEC form: 4
Accepted by SEC: 15 Feb 2022, 20:40:29 UTC
Prior SEC filing: 29 Mar 2022
Next SEC filing: 05 Apr 2022
Source filing: View source filing
Reporting owner signature: By: /s/ Charles Kallenbach, Attorney-in-Fact for Robert P. Bennett

Key filing fact

Robert Paul Bennett filed Form 4 for EngageSmart, Inc. on 15 Feb 2022.

Key facts

This page summarizes Robert Paul Bennett's Form 4 filing for EngageSmart, Inc..
5 reported transactions and 2 derivative rows are listed below.
Accepted by SEC: 15 Feb 2022, 20:40.

Change

Previous filing in this sequence was filed on 29 Mar 2022.
Current net transaction value: +$830,408.

Research use

This tells you what this filing adds before you inspect full transaction and derivative tables.
You can trace every row back to the original SEC filing document.

Evidence

Filed on Form 4

Ownership activity is grounded in SEC Form 4 disclosures.

View source filing

Reported non-derivative transactions

Shares, units, or other non-derivative securities reported in this filing.

ESMT transaction

Common Stock

Options Exercise

Transaction value
Shares: +2,403
Change %: +0.24%
Price
Shares after: 987,992
Date: 01 Jan 2022
Ownership: Direct
Footnotes: F1

ESMT transaction

Common Stock

Tax liability

Transaction value: $20,092
Shares: -833
Change %: -0.08%
Price: $24.12
Shares after: 987,159
Date: 01 Jan 2022
Ownership: Direct

ESMT transaction

Common Stock

Options Exercise

Transaction value: $850,500
Shares: +150,000
Change %: +15%
Price: $5.67
Shares after: 1,135,589
Date: 11 Feb 2022
Ownership: Direct

ESMT holding

Common Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after: 2,550,000
Date: 11 Feb 2022
Ownership: See footnote
Footnotes: F2

Reported derivative securities

Options, warrants, convertible securities, or similar derivative positions disclosed in the filing.

ESMT transaction Derivative

Restricted Stock Units

Options Exercise

Transaction value: $0
Shares: -2,403
Change %: -6.2%
Price: $0.000000
Shares after: 36,058
Date: 01 Jan 2022
Ownership: Direct
Underlying class: Common Stock
Underlying amount: 2,403
Exercise price
Footnotes: F1, F3

ESMT transaction Derivative

Stock Option

Options Exercise

Transaction value: $0
Shares: +150,000
Change %: +50%
Price: $0.000000
Shares after: 450,000
Date: 11 Feb 2022
Ownership: Direct
Underlying class: Common Stock
Underlying amount: 150,000
Exercise price: $5.67
Footnotes: F4

^* marks a reported price that did not pass the local price check.

Additional SEC filing notes

Filing notes and footnotes

Explanation of responses 4 footnotes

Footnote F1

Each restricted stock unit ("RSU") represents a contingent right to receive one share of common stock.

Footnote F2

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.

Footnote F3

The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date.

Footnote F4

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.