Jonathan Cole Seltzer - Oct 1, 2023 Form 4 Insider Report for EngageSmart, Inc. (ESMT)

Role
President, SMB Solutions
Signature
/s/ Scott Semel, Attorney-in-Fact for Jonathan C. Seltzer
Stock symbol
ESMT
Transactions as of
Oct 1, 2023
Transactions value $
-$83,844
Form type
4
Date filed
10/3/2023, 04:38 PM
Previous filing
Sep 6, 2023
Next filing
Nov 3, 2023

Transactions Table

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Ownership Footnotes
transaction ESMT Common Stock Options Exercise $0 +1.2K $0.00 1.2K Oct 1, 2023 Direct
transaction ESMT Common Stock Tax liability -$10.7K -596 -49.58% $17.99 606 Oct 1, 2023 Direct F1
transaction ESMT Common Stock Options Exercise $0 +2.11K +348.84% $0.00 2.72K Oct 1, 2023 Direct
transaction ESMT Common Stock Tax liability -$18.9K -1.05K -38.57% $17.99 1.67K Oct 1, 2023 Direct F1
transaction ESMT Common Stock Options Exercise $10.6K +3.5K +209.46% $3.02* 5.17K Oct 2, 2023 Direct
transaction ESMT Common Stock Sale -$64.8K -3.5K -67.69% $18.52 1.67K Oct 2, 2023 Direct F2, F3

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 -1.2K -11.11% $0.00 9.62K Oct 1, 2023 Common Stock 1.2K Direct F4, F5
transaction ESMT Restricted Stock Units Options Exercise $0 -2.11K -7.14% $0.00 27.5K Oct 1, 2023 Common Stock 2.11K Direct F4, F6
transaction ESMT Stock Option Options Exercise $0 -3.5K -1.61% $0.00 213K Oct 2, 2023 Common Stock 3.5K $3.02 Direct F7
* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Buy Plan / Sale Plan: These are also open market purchases/sales of shares, but in this case the transaction is part of a trading plan. Rule 10b5-1 allows insiders to setup a trading plan to buy/sell stocks over a certain period of time. Since the purchases/sales are predetermined, this protects the insiders from violating insider trading law.

Transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c).

Explanation of Responses:

Id Content
F1 Represents the number of shares of common stock withheld to satisfy the tax withholding obligation in connection with the vesting of certain previously reported restricted stock units ("RSUs").
F2 The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan dated March 15, 2023.
F3 The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.23 to $18.68. The Reporting Person undertakes to provide upon request from the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote.
F4 Each RSU represents a contingent right to receive one share of common stock.
F5 The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date.
F6 The RSUs vest in 16 equal quarterly installments commencing on April 1, 2023 and have no expiration date.
F7 The stock option vested and became exercisable with respect to 25% of the shares on November 1, 2020 and vests with respect to the remaining shares in twelve equal quarterly installments beginning on January 1, 2021.