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        <filerInfo>
            <filer>
                <filerCredentials>
                    <cik>0001906605</cik>
                    <ccc>XXXXXXXX</ccc>
                </filerCredentials>
            </filer>
            <liveTestFlag>LIVE</liveTestFlag>



        </filerInfo>
    </headerData>
    <formData>
        <issuerInfo>
            <issuerCik>0001863105</issuerCik>
            <issuerName>ENGAGESMART, INC.</issuerName>
            <secFileNumber>001-40835</secFileNumber>
            <issuerAddress>
                <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>
            </issuerAddress>
            <issuerContactPhone>(781) 848-3733</issuerContactPhone>
            <nameOfPersonForWhoseAccountTheSecuritiesAreToBeSold>KEVIN W O'BRIEN</nameOfPersonForWhoseAccountTheSecuritiesAreToBeSold>
            <relationshipsToIssuer>
                <relationshipToIssuer>Officer</relationshipToIssuer>
            </relationshipsToIssuer>
        </issuerInfo>
        <securitiesInformation>
            <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 Floor</ns2:street2>
                    <ns2:city>New York</ns2:city>
                    <ns2:stateOrCountry>NY</ns2:stateOrCountry>
                    <ns2:zipCode>10004</ns2:zipCode>
                </address>
            </brokerOrMarketmakerDetails>
            <noOfUnitsSold>3000</noOfUnitsSold>
            <aggregateMarketValue>54949.80</aggregateMarketValue>
            <noOfUnitsOutstanding>167360463</noOfUnitsOutstanding>
            <approxSaleDate>10/02/2023</approxSaleDate>
            <securitiesExchangeName>NYSE</securitiesExchangeName>
        </securitiesInformation>
        <securitiesToBeSold>
            <securitiesClassTitle>COMMON</securitiesClassTitle>
            <acquiredDate>02/01/2023</acquiredDate>
            <natureOfAcquisitionTransaction>Restricted Stock</natureOfAcquisitionTransaction>
            <nameOfPersonfromWhomAcquired>ISSUER</nameOfPersonfromWhomAcquired>
            <isGiftTransaction>N</isGiftTransaction>
            <amountOfSecuritiesAcquired>3000</amountOfSecuritiesAcquired>
            <paymentDate>02/01/2023</paymentDate>
            <natureOfPayment>Not Applicable</natureOfPayment>
        </securitiesToBeSold>
        <nothingToReportFlagOnSecuritiesSoldInPast3Months>N</nothingToReportFlagOnSecuritiesSoldInPast3Months>
        <securitiesSoldInPast3Months>
            <sellerDetails>
                <name>KEVIN W O'BRIEN</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>
                </address>
            </sellerDetails>
            <securitiesClassTitle>Common</securitiesClassTitle>
            <saleDate>09/01/2023</saleDate>
            <amountOfSecuritiesSold>3000</amountOfSecuritiesSold>
            <grossProceeds>53478.30</grossProceeds>
        </securitiesSoldInPast3Months>
        <securitiesSoldInPast3Months>
            <sellerDetails>
                <name>KEVIN W O'BRIEN</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>
                </address>
            </sellerDetails>
            <securitiesClassTitle>Common</securitiesClassTitle>
            <saleDate>08/01/2023</saleDate>
            <amountOfSecuritiesSold>3000</amountOfSecuritiesSold>
            <grossProceeds>56489.10</grossProceeds>
        </securitiesSoldInPast3Months>
        <securitiesSoldInPast3Months>
            <sellerDetails>
                <name>KEVIN W O'BRIEN</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>
                </address>
            </sellerDetails>
            <securitiesClassTitle>Common</securitiesClassTitle>
            <saleDate>07/03/2023</saleDate>
            <amountOfSecuritiesSold>3000</amountOfSecuritiesSold>
            <grossProceeds>56504.10</grossProceeds>
        </securitiesSoldInPast3Months>
        <noticeSignature>
            <noticeDate>10/02/2023</noticeDate>
            <planAdoptionDates>
                <planAdoptionDate>03/17/2023</planAdoptionDate>
            </planAdoptionDates>
            <signature>/s/ Kevin William O'Brien</signature>
        </noticeSignature>
    </formData>
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144
0001906605
XXXXXXXX
LIVE
0001863105
ENGAGESMART, INC.
001-40835
30 BRAINTREE HILL OFFICE PARK  SUITE 101
BRAINTREE
MA
02184
(781) 848-3733
KEVIN W O'BRIEN
Officer
Common
Morgan Stanley Smith Barney LLC Executive Financial Services
1 New York Plaza
38th Floor
New York
NY
10004
3000
54949.80
167360463
10/02/2023
NYSE
COMMON
02/01/2023
Restricted Stock
ISSUER
N
3000
02/01/2023
Not Applicable
N
KEVIN W O'BRIEN
30 BRAINTREE HILL OFFICE PARK  SUITE 101
BRAINTREE
MA
02184
Common
09/01/2023
3000
53478.30
KEVIN W O'BRIEN
30 BRAINTREE HILL OFFICE PARK  SUITE 101
BRAINTREE
MA
02184
Common
08/01/2023
3000
56489.10
KEVIN W O'BRIEN
30 BRAINTREE HILL OFFICE PARK  SUITE 101
BRAINTREE
MA
02184
Common
07/03/2023
3000
56504.10
10/02/2023
03/17/2023
/s/ Kevin William O'Brien