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                <ns2:stateOrCountry>MA</ns2:stateOrCountry>
                <ns2:zipCode>02184</ns2:zipCode>
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            <issuerContactPhone>7818483733</issuerContactPhone>
            <nameOfPersonForWhoseAccountTheSecuritiesAreToBeSold>THE BENNETT FAMILY 2020 TRUSTU/A DTD 12/31/2020</nameOfPersonForWhoseAccountTheSecuritiesAreToBeSold>
            <relationshipsToIssuer>
                <relationshipToIssuer>Director</relationshipToIssuer>
                <relationshipToIssuer>Officer</relationshipToIssuer>
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            <securitiesClassTitle>COMMON</securitiesClassTitle>
            <brokerOrMarketmakerDetails>
                <name>Morgan Stanley Smith Barney LLC Executive Financial Services</name>
                <address>
                    <ns2:street1>1 New York Plaza</ns2:street1>
                    <ns2:street2>38th Fl.</ns2:street2>
                    <ns2:city>New York</ns2:city>
                    <ns2:stateOrCountry>NY</ns2:stateOrCountry>
                    <ns2:zipCode>10004</ns2:zipCode>
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            <noOfUnitsSold>42000</noOfUnitsSold>
            <aggregateMarketValue>801780.00</aggregateMarketValue>
            <noOfUnitsOutstanding>166743782</noOfUnitsOutstanding>
            <approxSaleDate>07/03/2023</approxSaleDate>
            <securitiesExchangeName>NYSE</securitiesExchangeName>
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            <natureOfAcquisitionTransaction>Previously Exercised Stock Options</natureOfAcquisitionTransaction>
            <nameOfPersonfromWhomAcquired>Issuer</nameOfPersonfromWhomAcquired>
            <isGiftTransaction>N</isGiftTransaction>
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            <paymentDate>01/03/2018</paymentDate>
            <natureOfPayment>Cash</natureOfPayment>
        </securitiesToBeSold>
        <nothingToReportFlagOnSecuritiesSoldInPast3Months>N</nothingToReportFlagOnSecuritiesSoldInPast3Months>
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                <name>10b5-1 Sales Plan for ROBERT P BENNETT</name>
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                    <ns2:street1>30 Braintree Hill Office Park, Suite 101</ns2:street1>
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                    <ns2:stateOrCountry>MA</ns2:stateOrCountry>
                    <ns2:zipCode>02184</ns2:zipCode>
                </address>
            </sellerDetails>
            <securitiesClassTitle>Common</securitiesClassTitle>
            <saleDate>04/05/2023</saleDate>
            <amountOfSecuritiesSold>14000</amountOfSecuritiesSold>
            <grossProceeds>241490.20</grossProceeds>
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        <securitiesSoldInPast3Months>
            <sellerDetails>
                <name>10b5-1 Sales Plan for THE ROBERT P BENNETT 2020 GRAT</name>
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                    <ns2:street1>30 Braintree Hill Office Park, Suite 101</ns2:street1>
                    <ns2:city>Braintree</ns2:city>
                    <ns2:stateOrCountry>MA</ns2:stateOrCountry>
                    <ns2:zipCode>02184</ns2:zipCode>
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        </securitiesSoldInPast3Months>
        <securitiesSoldInPast3Months>
            <sellerDetails>
                <name>10b5-1 Sales Plan for ROBERT P BENNETT</name>
                <address>
                    <ns2:street1>30 Braintree Hill Office Park, Suite 101</ns2:street1>
                    <ns2:city>Braintree</ns2:city>
                    <ns2:stateOrCountry>MA</ns2:stateOrCountry>
                    <ns2:zipCode>02184</ns2:zipCode>
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            <securitiesClassTitle>Common</securitiesClassTitle>
            <saleDate>04/04/2023</saleDate>
            <amountOfSecuritiesSold>14000</amountOfSecuritiesSold>
            <grossProceeds>255834.60</grossProceeds>
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        <securitiesSoldInPast3Months>
            <sellerDetails>
                <name>10b5-1 Sales Plan for THE BENNETT FAMILY 2020 TRUSTU/A DTD 12/31/20</name>
                <address>
                    <ns2:street1>30 Braintree Hill Office Park, Suite 101</ns2:street1>
                    <ns2:city>Braintree</ns2:city>
                    <ns2:stateOrCountry>MA</ns2:stateOrCountry>
                    <ns2:zipCode>02184</ns2:zipCode>
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            <securitiesClassTitle>Common</securitiesClassTitle>
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            <amountOfSecuritiesSold>14000</amountOfSecuritiesSold>
            <grossProceeds>255834.60</grossProceeds>
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        <securitiesSoldInPast3Months>
            <sellerDetails>
                <name>10b5-1 Sales Plan for THE ROBERT P BENNETT 2020 GRAT</name>
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                    <ns2:street1>30 Braintree Hill Office Park, Suite 101</ns2:street1>
                    <ns2:city>Braintree</ns2:city>
                    <ns2:stateOrCountry>MA</ns2:stateOrCountry>
                    <ns2:zipCode>02184</ns2:zipCode>
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            <grossProceeds>255834.60</grossProceeds>
        </securitiesSoldInPast3Months>
        <remarks>The securities to be sold were acquired from previously exercised stock options during the period of 1/3/2018 through 2/11/2019
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        <noticeSignature>
            <noticeDate>07/03/2023</noticeDate>
            <planAdoptionDates>
                <planAdoptionDate>09/09/2022</planAdoptionDate>
            </planAdoptionDates>
            <signature>/s/ Martha A. Bennett</signature>
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144
0001881869
XXXXXXXX
LIVE
0001863105
ENGAGESMART LLC
001-40835
30 Braintree Hill Office Park, Suite 101
Braintree
MA
02184
7818483733
THE BENNETT FAMILY 2020 TRUSTU/A DTD 12/31/2020
Director
Officer
COMMON
Morgan Stanley Smith Barney LLC Executive Financial Services
1 New York Plaza
38th Fl.
New York
NY
10004
42000
801780.00
166743782
07/03/2023
NYSE
Common
01/03/2018
Previously Exercised Stock Options
Issuer
N
42000
01/03/2018
Cash
N
10b5-1 Sales Plan for ROBERT P BENNETT
30 Braintree Hill Office Park, Suite 101
Braintree
MA
02184
Common
04/05/2023
14000
241490.20
10b5-1 Sales Plan for THE BENNETT FAMILY 2020 TRUSTU/A DTD 12/31/20
30 Braintree Hill Office Park, Suite 101
Braintree
MA
02184
Common
04/05/2023
14000
241490.20
10b5-1 Sales Plan for THE ROBERT P BENNETT 2020 GRAT
30 Braintree Hill Office Park, Suite 101
Braintree
MA
02184
Common
04/05/2023
14000
241490.20
10b5-1 Sales Plan for ROBERT P BENNETT
30 Braintree Hill Office Park, Suite 101
Braintree
MA
02184
Common
04/04/2023
14000
255834.60
10b5-1 Sales Plan for THE BENNETT FAMILY 2020 TRUSTU/A DTD 12/31/20
30 Braintree Hill Office Park, Suite 101
Braintree
MA
02184
Common
04/04/2023
14000
255834.60
10b5-1 Sales Plan for THE ROBERT P BENNETT 2020 GRAT
30 Braintree Hill Office Park, Suite 101
Braintree
MA
02184
Common
04/04/2023
14000
255834.60
The securities to be sold were acquired from previously exercised stock options during the period of 1/3/2018 through 2/11/2019
07/03/2023
09/09/2022
/s/ Martha A. Bennett