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Bennett Robert Paul

Disclosed activity across 2 companies

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47765
SEC CIK
0001881869

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Reported relationships

Latest disclosed role at each company.

CompanyLast reported asReport datePublished
FORRESTER RESEARCH, INC.FORR · Entity 412DirectorMay 12, 2026May 13, 2026

Disclosed balances

About these balances

Latest available filing per company, not a reconstructed current portfolio. Matching sequences show the last reported balance with all source rows expandable; grouping alone does not establish account ownership. Do not add unresolved positions together. Filings may omit unchanged positions, and amendments may correct only part of an older disclosure. Jointly reported shares are not necessarily this owner's personal holdings.

FORRESTER RESEARCH, INC.

Report date May 12, 2026 · Filed May 13, 2026

Security / awardOwnership accountDisclosed shares / unitsDisclosure context
Common StockSEC Table I · non-derivativeDirect27,305 Reported balance After 2026-05-12 transaction · row 1
1 source row

Row 1 · 2026-05-12 · Grant · Acquired 8,000 · Balance 27,305

F1: The securities awarded on May 12, 2026 are in the form of Restricted Stock Units issued pursuant to the Forrester Research, Inc. Amended and Restated Equity Incentive Plan that entitle the reporting person, upon vesting, to receive one share of common stock per Restricted Stock Unit. The Restricted Stock Units will vest and convert into common stock in four equal and consecutive installments. The first tranche will vest on September 1, 2026, with an equal number of shares vesting on each of December 1, 2026 and March 1, 2027, and the balance of the shares vesting on June 1, 2027.

Filing footnotes · ownership attribution and instrument terms

F1: The securities awarded on May 12, 2026 are in the form of Restricted Stock Units issued pursuant to the Forrester Research, Inc. Amended and Restated Equity Incentive Plan that entitle the reporting person, upon vesting, to receive one share of common stock per Restricted Stock Unit. The Restricted Stock Units will vest and convert into common stock in four equal and consecutive installments. The first tranche will vest on September 1, 2026, with an equal number of shares vesting on each of December 1, 2026 and March 1, 2027, and the balance of the shares vesting on June 1, 2027.

Past disclosures · reporting ended (1)

No longer tracked through insider filings. These historical balances do not imply present ownership or a zero position.

EngageSmart, Inc.

Report date January 26, 2024 · Filed January 29, 2024

Section 16 reporting ended · disclosed 2024-01-29. Current position is not established by this disclosure.

Security / awardOwnership accountDisclosed shares / unitsDisclosure context
Common StockSEC Table I · non-derivativeDirect0 Reported balance After 2024-01-26 transaction · row 1
1 source row

Row 1 · 2024-01-26 · Disposition to issuer · Disposed 859,710 · Balance 0

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.

Common StockSEC Table I · non-derivativeIndirectThe Robert P. Bennett 2020 Grantor Retained Annuity Trust0 Reported balance After 2024-01-26 transaction · row 2 Account identity is unresolved; indirect or unspecified ownership is not merged.
1 source row

Row 2 · 2024-01-26 · Disposition to issuer · Disposed 809,877 · Balance 0

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.

Common StockSEC Table I · non-derivativeIndirectThe Bennett Family 2020 Trust0 Reported balance After 2024-01-26 transaction · row 3 Account identity is unresolved; indirect or unspecified ownership is not merged.
1 source row

Row 3 · 2024-01-26 · Disposition to issuer · Disposed 1,332,000 · Balance 0

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.

Restricted Stock UnitsSEC Table II · derivative / convertible securityDirect0 Reported balance After 2024-01-26 transaction · row 4 Instrument identity requires review; Table II rows are not merged.
1 source row

Row 4 · 2024-01-26 · Disposition to issuer · Disposed 249,352 · Balance 0

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.

Option to Purchase Common StockSEC Table II · derivative / convertible security · Conversion / exercise price $5.67Direct0 Reported balance After 2024-01-26 transaction · row 5 Instrument identity requires review; Table II rows are not merged.
1 source row

Row 5 · 2024-01-26 · Disposition to issuer · Disposed 427,911 · Balance 0

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.

Filing footnotes · ownership attribution and instrument terms

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.

Transaction history

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Purchases/sales include open-market and private transactions. Plan disclosure applies to the filing; individual rows may differ. “Not disclosed” is not “unplanned.”

The cutoff filters transaction history only. Company summaries and owner relationships show the latest available disclosures. Parser corrections can improve historical records.

Transaction dateCompanyActivity / securityShares / unitsReported priceReported valueDetails
May 12, 2026 Filed May 13, 2026 17:58 UTC FORRESTER RESEARCH, INC. FORR · Entity 412 GrantCommon Stock 8,000 $0.00 $0.00
Disclosure

SEC source: 0001193125-26-221244 · ownership.xml · nonDerivative · entry 1

Bennett Robert Paul · CIK 0001881869 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 27,305

F1 · shares: The securities awarded on May 12, 2026 are in the form of Restricted Stock Units issued pursuant to the Forrester Research, Inc. Amended and Restated Equity Incentive Plan that entitle the reporting person, upon vesting, to receive one share of common stock per Restricted Stock Unit. The Restricted Stock Units will vest and convert into common stock in four equal and consecutive installments. The first tranche will vest on September 1, 2026, with an equal number of shares vesting on each of December 1, 2026 and March 1, 2027, and the balance of the shares vesting on June 1, 2027.

Read SEC document
June 02, 2025 Filed Jun 3, 2025 18:55 UTC FORRESTER RESEARCH, INC. FORR · Entity 412 GrantCommon Stock 8,000 $0.00 $0.00
Disclosure

SEC source: 0000950170-25-080798 · ownership.xml · nonDerivative · entry 1

Bennett Robert Paul · CIK 0001881869 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 19,305

F1 · shares: The securities awarded on June 2, 2025 are in the form of Restricted Stock Units issued pursuant to the Forrester Research, Inc. Amended and Restated Equity Incentive Plan that entitle the reporting person, upon vesting, to receive one share of common stock per Restricted Stock Unit. The Restricted Stock Units will vest and convert into common stock in four equal and consecutive installments. The first tranche will vest on September 1, 2025, with an equal number of shares vesting on each of December 1, 2025 and March 1, 2026, and the balance of the shares vesting on June 1, 2026.

Read SEC document
February 28, 2025 Filed Mar 3, 2025 17:13 UTC FORRESTER RESEARCH, INC. FORR · Entity 412 GrantCommon Stock 4,000 $10.99 $43,947.20
Disclosure

SEC source: 0000950170-25-030491 · ownership.xml · nonDerivative · entry 1

Bennett Robert Paul · CIK 0001881869 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 11,305

F1 · price: This transaction was executed in multiple trades at prices ranging from $10.90 to $11.08. The price reported above reflects the weighted average sale price. The reporting person hereby undertakes to provide upon request to the SEC staff, the issuer or a security holder of the issuer full information regarding the number of shares and prices at which the transaction was effected.

Read SEC document
August 01, 2024 Filed Aug 5, 2024 16:58 UTC FORRESTER RESEARCH, INC. FORR · Entity 412 GrantCommon Stock 6,305 $0.00 $0.00
Disclosure

SEC source: 0000950170-24-090547 · ownership.xml · nonDerivative · entry 1

Bennett Robert Paul · CIK 0001881869 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,305

F1 · shares: The securities awarded on August 1, 2024 are in the form of Restricted Stock Units issued pursuant to the Forrester Research, Inc. Amended and Restated Equity Incentive Plan that entitle the reporting person, upon vesting, to receive one share of common stock per Restricted Stock Unit. The Restricted Stock Units will vest and convert into common stock in four equal and consecutive installments. The first tranche will vest on September 1, 2024, with an equal number of shares vesting on each of December 1, 2024 and March 1, 2025, and the balance of the shares vesting on June 1, 2025.

Read SEC document
January 26, 2024 Filed Jan 29, 2024 22:30 UTC EngageSmart, Inc. ESMT · Entity 94837 Disposition to issuerOption to Purchase Common Stock · Derivative 427,911 Not disclosed Strike: $5.67 Not disclosed
Disclosure

SEC source: 0000950170-24-008415 · ownership.xml · derivative · entry 5

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 427,911 shares

Expires not disclosed

F4 · price: 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.

F4 · derivative.exercise_date: 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.

F4 · derivative.expiration_date: 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.

Read SEC document
January 26, 2024 Filed Jan 29, 2024 22:30 UTC EngageSmart, Inc. ESMT · Entity 94837 Disposition to issuerRestricted Stock Units · Derivative 249,352 Not disclosed Not disclosed
Disclosure

SEC source: 0000950170-24-008415 · ownership.xml · derivative · entry 4

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 249,352 shares

Expires not disclosed

F2 · derivative.exercise_price: Each Company restricted stock unit ("Company RSUs") represented a contingent right to receive one Share upon vesting of the Company RSU.

F3 · price: 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.

F3 · derivative.exercise_date: 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.

F3 · derivative.expiration_date: 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.

Read SEC document
January 26, 2024 Filed Jan 29, 2024 22:30 UTC EngageSmart, Inc. ESMT · Entity 94837 Disposition to issuerCommon Stock 1,332,000 $23.00 $30,636,000.00
Disclosure

SEC source: 0000950170-24-008415 · ownership.xml · nonDerivative · entry 3

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Indirect · The Bennett Family 2020 Trust

Disclosed balance after: 0

F1 · price: 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.

Read SEC document
January 26, 2024 Filed Jan 29, 2024 22:30 UTC EngageSmart, Inc. ESMT · Entity 94837 Disposition to issuerCommon Stock 809,877 $23.00 $18,627,171.00
Disclosure

SEC source: 0000950170-24-008415 · ownership.xml · nonDerivative · entry 2

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Indirect · The Robert P. Bennett 2020 Grantor Retained Annuity Trust

Disclosed balance after: 0

F1 · price: 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.

Read SEC document
January 26, 2024 Filed Jan 29, 2024 22:30 UTC EngageSmart, Inc. ESMT · Entity 94837 Disposition to issuerCommon Stock 859,710 $23.00 $19,773,330.00
Disclosure

SEC source: 0000950170-24-008415 · ownership.xml · nonDerivative · entry 1

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

F1 · price: 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.

Read SEC document
January 01, 2024 Filed Jan 4, 2024 01:40 UTC EngageSmart, Inc. ESMT · Entity 94837 Exercise / conversionRestricted Stock Units · Derivative 19,377 $0.00 $0.00
Disclosure

SEC source: 0000950170-24-001408 · ownership.xml · derivative · entry 8

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 232,525

Underlying: Common Stock · 19,377 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · derivative.exercise_price: Each RSU represents a contingent right to receive one share of common stock.

F4 · derivative.exercise_date: The RSUs vest in 16 equal quarterly installments commencing on April 1, 2023 and have no expiration date.

F4 · derivative.expiration_date: The RSUs vest in 16 equal quarterly installments commencing on April 1, 2023 and have no expiration date.

Read SEC document
January 01, 2024 Filed Jan 4, 2024 01:40 UTC EngageSmart, Inc. ESMT · Entity 94837 Exercise / conversionRestricted Stock Units · Derivative 2,404 $0.00 $0.00
Disclosure

SEC source: 0000950170-24-001408 · ownership.xml · derivative · entry 7

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 16,827

Underlying: Common Stock · 2,404 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · derivative.exercise_price: Each RSU represents a contingent right to receive one share of common stock.

F3 · derivative.exercise_date: The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date.

F3 · derivative.expiration_date: The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date.

Read SEC document
January 01, 2024 Filed Jan 4, 2024 01:40 UTC EngageSmart, Inc. ESMT · Entity 94837 Tax withholdingCommon Stock 5,938 $22.90 $135,980.20
Disclosure

SEC source: 0000950170-24-001408 · ownership.xml · nonDerivative · entry 4

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 859,710

F1 · kind: 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").

Read SEC document
January 01, 2024 Filed Jan 4, 2024 01:40 UTC EngageSmart, Inc. ESMT · Entity 94837 Exercise / conversionCommon Stock 19,377 $0.00 $0.00
Disclosure

SEC source: 0000950170-24-001408 · ownership.xml · nonDerivative · entry 3

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 865,648

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

Read SEC document
January 01, 2024 Filed Jan 4, 2024 01:40 UTC EngageSmart, Inc. ESMT · Entity 94837 Tax withholdingCommon Stock 833 $22.90 $19,075.70
Disclosure

SEC source: 0000950170-24-001408 · ownership.xml · nonDerivative · entry 2

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 846,271

F1 · kind: 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").

Read SEC document
January 01, 2024 Filed Jan 4, 2024 01:40 UTC EngageSmart, Inc. ESMT · Entity 94837 Exercise / conversionCommon Stock 2,404 $0.00 $0.00
Disclosure

SEC source: 0000950170-24-001408 · ownership.xml · nonDerivative · entry 1

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 847,104

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

Read SEC document
October 01, 2023 Filed Oct 3, 2023 20:30 UTC EngageSmart, Inc. ESMT · Entity 94837 Exercise / conversionRestricted Stock Units · Derivative 19,377 $0.00 $0.00
Disclosure

SEC source: 0000950170-23-051559 · ownership.xml · derivative · entry 8

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 251,902

Underlying: Common Stock · 19,377 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · derivative.exercise_price: Each RSU represents a contingent right to receive one share of common stock.

F4 · derivative.exercise_date: The RSUs vest in 16 equal quarterly installments commencing on April 1, 2023 and have no expiration date.

F4 · derivative.expiration_date: The RSUs vest in 16 equal quarterly installments commencing on April 1, 2023 and have no expiration date.

Read SEC document
October 01, 2023 Filed Oct 3, 2023 20:30 UTC EngageSmart, Inc. ESMT · Entity 94837 Exercise / conversionRestricted Stock Units · Derivative 2,404 $0.00 $0.00
Disclosure

SEC source: 0000950170-23-051559 · ownership.xml · derivative · entry 7

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 19,231

Underlying: Common Stock · 2,404 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · derivative.exercise_price: Each RSU represents a contingent right to receive one share of common stock.

F3 · derivative.exercise_date: The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date.

F3 · derivative.expiration_date: The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date.

Read SEC document
October 01, 2023 Filed Oct 3, 2023 20:30 UTC EngageSmart, Inc. ESMT · Entity 94837 Tax withholdingCommon Stock 8,594 $17.99 $154,606.06
Disclosure

SEC source: 0000950170-23-051559 · ownership.xml · nonDerivative · entry 4

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 844,700

F1 · kind: 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").

Read SEC document
October 01, 2023 Filed Oct 3, 2023 20:30 UTC EngageSmart, Inc. ESMT · Entity 94837 Exercise / conversionCommon Stock 19,377 $0.00 $0.00
Disclosure

SEC source: 0000950170-23-051559 · ownership.xml · nonDerivative · entry 3

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 853,294

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

Read SEC document
October 01, 2023 Filed Oct 3, 2023 20:30 UTC EngageSmart, Inc. ESMT · Entity 94837 Tax withholdingCommon Stock 1,067 $17.99 $19,195.33
Disclosure

SEC source: 0000950170-23-051559 · ownership.xml · nonDerivative · entry 2

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 833,917

F1 · kind: 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").

Read SEC document
October 01, 2023 Filed Oct 3, 2023 20:30 UTC EngageSmart, Inc. ESMT · Entity 94837 Exercise / conversionCommon Stock 2,404 $0.00 $0.00
Disclosure

SEC source: 0000950170-23-051559 · ownership.xml · nonDerivative · entry 1

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 834,984

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

Read SEC document
July 12, 2023 Filed Jul 15, 2023 00:47 UTC EngageSmart, Inc. ESMT · Entity 94837 Exercise / conversionStock Option · Derivative 22,089 $0.00 Strike: $5.67 $0.00
Disclosure

SEC source: 0000950170-23-033088 · ownership.xml · derivative · entry 5

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 427,911

Underlying: Common Stock · 22,089 shares

Expires 2031-02-01

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F5 · derivative.exercise_date: 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.

Read SEC document
July 12, 2023 Filed Jul 15, 2023 00:47 UTC EngageSmart, Inc. ESMT · Entity 94837 Exercise / conversionCommon Stock 22,089 $5.67 $125,244.63
Disclosure

SEC source: 0000950170-23-033088 · ownership.xml · nonDerivative · entry 4

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 832,580

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

Read SEC document
July 05, 2023 Filed Jul 15, 2023 00:47 UTC EngageSmart, Inc. ESMT · Entity 94837 SaleCommon Stock 28,000 $18.53 $518,840.00
Disclosure

SEC source: 0000950170-23-033088 · ownership.xml · nonDerivative · entry 3

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: Plan reported

Ownership: Indirect · The Bennett Family 2020 Trust

Disclosed balance after: 1,332,000

F1 · kind: The sales reported in this Form 4 were effected pursuant to Rule 10b5-1 trading plans, each dated September 9, 2022.

F4 · price: The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.25 to $18.75. 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.

Read SEC document
July 05, 2023 Filed Jul 15, 2023 00:47 UTC EngageSmart, Inc. ESMT · Entity 94837 SaleCommon Stock 28,000 $18.53 $518,840.00
Disclosure

SEC source: 0000950170-23-033088 · ownership.xml · nonDerivative · entry 2

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: Plan reported

Ownership: Indirect · The Robert P. Bennett 2020 Grantor Retained Annuity Trust

Disclosed balance after: 809,877

F1 · kind: The sales reported in this Form 4 were effected pursuant to Rule 10b5-1 trading plans, each dated September 9, 2022.

F3 · price: The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.25 to $18.75. 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.

Read SEC document
July 05, 2023 Filed Jul 15, 2023 00:47 UTC EngageSmart, Inc. ESMT · Entity 94837 SaleCommon Stock 28,000 $18.53 $518,840.00
Disclosure

SEC source: 0000950170-23-033088 · ownership.xml · nonDerivative · entry 1

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 810,491

F1 · kind: The sales reported in this Form 4 were effected pursuant to Rule 10b5-1 trading plans, each dated September 9, 2022.

F2 · price: The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.25 to $18.75. 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.

Read SEC document
July 03, 2023 Filed Jul 7, 2023 01:39 UTC EngageSmart, Inc. ESMT · Entity 94837 SaleCommon Stock 14,000 $18.67 $261,380.00
Disclosure

SEC source: 0000950170-23-032120 · ownership.xml · nonDerivative · entry 7

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: Plan reported

Ownership: Indirect · The Bennett Family 2020 Trus

Disclosed balance after: 1,360,000

F2 · kind: The sales reported in this Form 4 were effected pursuant to Rule 10b5-1 trading plans, each dated September 9, 2022.

F5 · price: The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.49 to $18.99. 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.

Read SEC document
July 03, 2023 Filed Jul 7, 2023 01:39 UTC EngageSmart, Inc. ESMT · Entity 94837 SaleCommon Stock 14,000 $18.67 $261,380.00
Disclosure

SEC source: 0000950170-23-032120 · ownership.xml · nonDerivative · entry 6

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: Plan reported

Ownership: Indirect · The Robert P. Bennett 2020 Grantor Retained Annuity Trust

Disclosed balance after: 837,877

F1 · kind: 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").

F4 · price: The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.49 to $18.99. 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.

Read SEC document
July 03, 2023 Filed Jul 7, 2023 01:39 UTC EngageSmart, Inc. ESMT · Entity 94837 SaleCommon Stock 14,000 $18.67 $261,380.00
Disclosure

SEC source: 0000950170-23-032120 · ownership.xml · nonDerivative · entry 5

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 838,491

F2 · kind: The sales reported in this Form 4 were effected pursuant to Rule 10b5-1 trading plans, each dated September 9, 2022.

F3 · price: The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.49 to $18.99. 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.

Read SEC document
July 01, 2023 Filed Jul 7, 2023 01:39 UTC EngageSmart, Inc. ESMT · Entity 94837 Exercise / conversionRestricted Stock Units · Derivative 19,377 $0.00 $0.00
Disclosure

SEC source: 0000950170-23-032120 · ownership.xml · derivative · entry 9

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 271,279

Underlying: Common Stock · 19,377 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F6 · derivative.exercise_price: Each RSU represents a contingent right to receive one share of common stock.

F8 · derivative.exercise_date: The RSUs vest in 16 equal quarterly installments commencing on April 1, 2023 and have no expiration date.

F8 · derivative.expiration_date: The RSUs vest in 16 equal quarterly installments commencing on April 1, 2023 and have no expiration date.

Read SEC document
July 01, 2023 Filed Jul 7, 2023 01:39 UTC EngageSmart, Inc. ESMT · Entity 94837 Exercise / conversionRestricted Stock Units · Derivative 2,404 $0.00 $0.00
Disclosure

SEC source: 0000950170-23-032120 · ownership.xml · derivative · entry 8

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 21,635

Underlying: Common Stock · 2,404 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F6 · derivative.exercise_price: Each RSU represents a contingent right to receive one share of common stock.

F7 · derivative.exercise_date: The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date.

F7 · derivative.expiration_date: The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date.

Read SEC document
July 01, 2023 Filed Jul 7, 2023 01:39 UTC EngageSmart, Inc. ESMT · Entity 94837 Tax withholdingCommon Stock 7,509 $19.09 $143,346.81
Disclosure

SEC source: 0000950170-23-032120 · ownership.xml · nonDerivative · entry 4

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 852,491

F1 · kind: 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").

Read SEC document
July 01, 2023 Filed Jul 7, 2023 01:39 UTC EngageSmart, Inc. ESMT · Entity 94837 Exercise / conversionCommon Stock 19,377 $0.00 $0.00
Disclosure

SEC source: 0000950170-23-032120 · ownership.xml · nonDerivative · entry 3

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 860,000

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

Read SEC document
July 01, 2023 Filed Jul 7, 2023 01:39 UTC EngageSmart, Inc. ESMT · Entity 94837 Tax withholdingCommon Stock 706 $19.09 $13,477.54
Disclosure

SEC source: 0000950170-23-032120 · ownership.xml · nonDerivative · entry 2

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 840,623

F1 · kind: 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").

Read SEC document
July 01, 2023 Filed Jul 7, 2023 01:39 UTC EngageSmart, Inc. ESMT · Entity 94837 Exercise / conversionCommon Stock 2,404 $0.00 $0.00
Disclosure

SEC source: 0000950170-23-032120 · ownership.xml · nonDerivative · entry 1

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 841,329

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

Read SEC document
April 05, 2023 Filed Apr 7, 2023 01:06 UTC EngageSmart, Inc. ESMT · Entity 94837 SaleCommon Stock 166 $18.07 $2,999.62
Disclosure

SEC source: 0000899243-23-010942 · doc4.xml · nonDerivative · entry 9

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: Plan reported

Ownership: Indirect · The Bennett Family 2020 Trust

Disclosed balance after: 1,374,000

F1 · kind: Each of the sales reported in this Form 4 were effected pursuant to Rule 10b5-1 trading plans, each dated September 9, 2022.

F10 · price: The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $17.88 to $18.17. 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.

Read SEC document
April 05, 2023 Filed Apr 7, 2023 01:06 UTC EngageSmart, Inc. ESMT · Entity 94837 SaleCommon Stock 13,834 $17.24 $238,498.16
Disclosure

SEC source: 0000899243-23-010942 · doc4.xml · nonDerivative · entry 8

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: Plan reported

Ownership: Indirect · The Bennett Family 2020 Trust

Disclosed balance after: 1,374,166

F1 · kind: Each of the sales reported in this Form 4 were effected pursuant to Rule 10b5-1 trading plans, each dated September 9, 2022.

F9 · price: The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $16.88 to $17.83. 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.

Read SEC document
April 05, 2023 Filed Apr 7, 2023 01:06 UTC EngageSmart, Inc. ESMT · Entity 94837 SaleCommon Stock 167 $18.07 $3,017.69
Disclosure

SEC source: 0000899243-23-010942 · doc4.xml · nonDerivative · entry 7

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: Plan reported

Ownership: Indirect · The Robert P. Bennett 2020 Grantor Retained Annuity Trust

Disclosed balance after: 851,877

F1 · kind: Each of the sales reported in this Form 4 were effected pursuant to Rule 10b5-1 trading plans, each dated September 9, 2022.

F8 · price: The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $17.88 to $18.17. 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.

Read SEC document
April 05, 2023 Filed Apr 7, 2023 01:06 UTC EngageSmart, Inc. ESMT · Entity 94837 SaleCommon Stock 13,833 $17.24 $238,480.92
Disclosure

SEC source: 0000899243-23-010942 · doc4.xml · nonDerivative · entry 6

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: Plan reported

Ownership: Indirect · The Robert P. Bennett 2020 Grantor Retained Annuity Trust

Disclosed balance after: 852,044

F1 · kind: Each of the sales reported in this Form 4 were effected pursuant to Rule 10b5-1 trading plans, each dated September 9, 2022.

F7 · price: The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $16.88 to $17.83. 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.

Read SEC document
April 05, 2023 Filed Apr 7, 2023 01:06 UTC EngageSmart, Inc. ESMT · Entity 94837 SaleCommon Stock 167 $18.07 $3,017.69
Disclosure

SEC source: 0000899243-23-010942 · doc4.xml · nonDerivative · entry 5

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 838,925

F1 · kind: Each of the sales reported in this Form 4 were effected pursuant to Rule 10b5-1 trading plans, each dated September 9, 2022.

F6 · price: The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $17.88 to $18.17. 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.

Read SEC document
April 05, 2023 Filed Apr 7, 2023 01:06 UTC EngageSmart, Inc. ESMT · Entity 94837 SaleCommon Stock 13,833 $17.24 $238,480.92
Disclosure

SEC source: 0000899243-23-010942 · doc4.xml · nonDerivative · entry 4

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 839,092

F1 · kind: Each of the sales reported in this Form 4 were effected pursuant to Rule 10b5-1 trading plans, each dated September 9, 2022.

F5 · price: The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $16.88 to $17.83. 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.

Read SEC document
April 04, 2023 Filed Apr 7, 2023 01:06 UTC EngageSmart, Inc. ESMT · Entity 94837 SaleCommon Stock 14,000 $18.27 $255,780.00
Disclosure

SEC source: 0000899243-23-010942 · doc4.xml · nonDerivative · entry 3

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: Plan reported

Ownership: Indirect · The Bennett Family 2020 Trust

Disclosed balance after: 1,388,000

F1 · kind: Each of the sales reported in this Form 4 were effected pursuant to Rule 10b5-1 trading plans, each dated September 9, 2022.

F4 · price: The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.05 to $18.84. 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.

Read SEC document
April 04, 2023 Filed Apr 7, 2023 01:06 UTC EngageSmart, Inc. ESMT · Entity 94837 SaleCommon Stock 14,000 $18.27 $255,780.00
Disclosure

SEC source: 0000899243-23-010942 · doc4.xml · nonDerivative · entry 2

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: Plan reported

Ownership: Indirect · The Robert P. Bennett 2020 Grantor Retained Annuity Trust

Disclosed balance after: 865,877

F1 · kind: Each of the sales reported in this Form 4 were effected pursuant to Rule 10b5-1 trading plans, each dated September 9, 2022.

F3 · price: The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.05 to $18.84. 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.

Read SEC document
April 04, 2023 Filed Apr 7, 2023 01:06 UTC EngageSmart, Inc. ESMT · Entity 94837 SaleCommon Stock 14,000 $18.27 $255,780.00
Disclosure

SEC source: 0000899243-23-010942 · doc4.xml · nonDerivative · entry 1

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 852,925

F1 · kind: Each of the sales reported in this Form 4 were effected pursuant to Rule 10b5-1 trading plans, each dated September 9, 2022.

F2 · price: The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.05 to $18.84. 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.

Read SEC document
April 03, 2023 Filed Apr 5, 2023 01:51 UTC EngageSmart, Inc. ESMT · Entity 94837 SaleCommon Stock 14,000 $18.88 $264,320.00
Disclosure

SEC source: 0000899243-23-010611 · doc4.xml · nonDerivative · entry 7

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: Plan reported

Ownership: Indirect · The Bennett Family 2020 Trust

Disclosed balance after: 1,402,000

F7 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan dated September 9, 2022.

F8 · price: The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.72 to $19.06. 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.

Read SEC document
April 03, 2023 Filed Apr 5, 2023 01:51 UTC EngageSmart, Inc. ESMT · Entity 94837 SaleCommon Stock 14,000 $18.88 $264,320.00
Disclosure

SEC source: 0000899243-23-010611 · doc4.xml · nonDerivative · entry 6

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: Plan reported

Ownership: Indirect · The Robert P. Bennett 2020 Grantor Retained Annuity Trust

Disclosed balance after: 879,877

F5 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan dated September 9, 2022.

F6 · price: The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.73 to $19.06. 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.

Read SEC document
April 03, 2023 Filed Apr 5, 2023 01:51 UTC EngageSmart, Inc. ESMT · Entity 94837 SaleCommon Stock 14,000 $18.88 $264,320.00
Disclosure

SEC source: 0000899243-23-010611 · doc4.xml · nonDerivative · entry 5

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 866,925

F3 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan dated September 9, 2022.

F4 · price: The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.71 to $19.06. 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.

Read SEC document
April 01, 2023 Filed Apr 5, 2023 01:51 UTC EngageSmart, Inc. ESMT · Entity 94837 Exercise / conversionRestricted Stock Units · Derivative 19,377 $0.00 $0.00
Disclosure

SEC source: 0000899243-23-010611 · doc4.xml · derivative · entry 9

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 290,656

Underlying: Common Stock · 19,377 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F9 · derivative.exercise_price: Each RSU represents a contingent right to receive one share of common stock.

F11 · derivative.exercise_date: The RSUs vest in 16 equal quarterly installments commencing on April 1, 2023 and have no expiration date.

F11 · derivative.expiration_date: The RSUs vest in 16 equal quarterly installments commencing on April 1, 2023 and have no expiration date.

Read SEC document
April 01, 2023 Filed Apr 5, 2023 01:51 UTC EngageSmart, Inc. ESMT · Entity 94837 Exercise / conversionRestricted Stock Units · Derivative 2,403 $0.00 $0.00
Disclosure

SEC source: 0000899243-23-010611 · doc4.xml · derivative · entry 8

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 24,039

Underlying: Common Stock · 2,403 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F9 · derivative.exercise_price: Each RSU represents a contingent right to receive one share of common stock.

F10 · derivative.exercise_date: The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date.

F10 · derivative.expiration_date: The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date.

Read SEC document
April 01, 2023 Filed Apr 5, 2023 01:51 UTC EngageSmart, Inc. ESMT · Entity 94837 Tax withholdingCommon Stock 5,688 $19.25 $109,494.00
Disclosure

SEC source: 0000899243-23-010611 · doc4.xml · nonDerivative · entry 4

Bennett Robert Paul · CIK 0001881869 · Director · Chief Executive Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 880,925

F2 · kind: Represents the number of common stock withheld to satisfy the tax withholding obligation in connection with the vesting of certain previously reported restricted stock units ("RSUs").

Read SEC document

Value uses the disclosed total when available, otherwise shares × reported transaction price. It is not an estimate of exercise cash cost or investment performance.