Robert Paul Bennett - 26 Jan 2024 Form 4 Insider Report for EngageSmart, Inc.

Role
Chief Executive Officer, Director
Signature
/s/ Scott Semel, Attorney-in-Fact for Robert P. Bennett
Issuer symbol
N/A
Transactions as of
26 Jan 2024
Net transactions value
-$69,036,501
Form type
4
Filing time
29 Jan 2024, 17:30:45 UTC
Previous filing
03 Jan 2024
Next filing
22 Jul 2024
SEC
View on sec.gov

Transactions Table

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Ownership Footnotes
transaction ESMT Common Stock Disposed to Issuer $19,773,330 -859,710 -100% $23.00 0 26 Jan 2024 Direct F1
transaction ESMT Common Stock Disposed to Issuer $18,627,171 -809,877 -100% $23.00 0 26 Jan 2024 The Robert P. Bennett 2020 Grantor Retained Annuity Trust F1
transaction ESMT Common Stock Disposed to Issuer $30,636,000 -1,332,000 -100% $23.00 0 26 Jan 2024 The Bennett Family 2020 Trust 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 Units Disposed to Issuer -249,352 -100% 0 26 Jan 2024 Common Stock 249,352 Direct F2, F3
transaction ESMT Option to Purchase Common Stock Disposed to Issuer -427,911 -100% 0 26 Jan 2024 Common Stock 427,911 $5.67 Direct F4
* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Robert Paul Bennett is no longer subject to Section 16 filing requirements. Form 4 or Form 5 obligations may continue.

Explanation of Responses:

Id Content
F1 This Form 4 reports securities disposed of under the Agreement and Plan of Merger (the "Merger Agreement"), dated October 23, 2023, among EngageSmart, Inc. (the "Company"), Icefall Parent, Inc. ("Parent"), and Icefall Merger Sub, LLC ("Merger Sub"), under which Merger Sub was merged with and into the Company (the "Merger"), with the Company continuing as the surviving corporation in the Merger. At the effective time of the Merger (the "Effective Time"), each issued and outstanding share of common stock of the Company ("Shares") was cancelled and converted into the right to receive $23.00 in cash (the "Per Share Price") without interest thereon.
F2 Each Company restricted stock unit ("Company RSUs") represented a contingent right to receive one Share upon vesting of the Company RSU.
F3 Under the Merger Agreement, at the Effective Time, each Company RSU reported in this Form 4 was cancelled and converted into the contingent right to receive from Parent or the Company a converted cash award (a "Converted Cash Award") with respect to an aggregate amount in cash equal in value to (A) the total number of Shares subject to such Company RSU immediately prior to the Effective Time multiplied by (B) the Per Share Price, which Converted Cash Award will remain subject to the same vesting terms and conditions of the corresponding Company RSU.
F4 Under the Merger Agreement, at the Effective Time, each option to purchase Shares (a "Company Option") that was reported in this Form 4 was cancelled and converted into the right to receive an amount (without interest) in cash equal in value to (A) the total number of Shares subject to such Company Option multiplied by (B) the excess, if any, of the Per Share Price over the exercise price per Share underlying such Company Option.