<?xml version="1.0"?>
<edgarSubmission>

    <schemaVersion>X0706</schemaVersion>

    <submissionType>D</submissionType>

    <testOrLive>LIVE</testOrLive>

    <primaryIssuer>
        <cik>0001574465</cik>
        <entityName>Insight Venture Partners (Cayman) VIII, L.P.</entityName>
        <issuerAddress>
            <street1>Insight Venture Associates VIII, L.P.</street1>
            <street2>309 UGLAND HOUSE</street2>
            <city>GRAND CAYMAN</city>
            <stateOrCountry>E9</stateOrCountry>
            <stateOrCountryDescription>CAYMAN ISLANDS</stateOrCountryDescription>
            <zipCode>KY1-1104</zipCode>
        </issuerAddress>
        <issuerPhoneNumber>212-230-9200</issuerPhoneNumber>
        <jurisdictionOfInc>CAYMAN ISLANDS</jurisdictionOfInc>
        <issuerPreviousNameList>
            <value>None</value>
        </issuerPreviousNameList>
        <edgarPreviousNameList>
            <value>None</value>
        </edgarPreviousNameList>
        <entityType>Limited Partnership</entityType>
        <yearOfInc>
            <withinFiveYears>true</withinFiveYears>
            <value>2013</value>
        </yearOfInc>
    </primaryIssuer>

    <relatedPersonsList>
        <relatedPersonInfo>
            <relatedPersonName>
                <firstName>Jeffrey</firstName>
                <lastName>Horing</lastName>
            </relatedPersonName>
            <relatedPersonAddress>
                <street1>680 Fifth Avenue</street1>
                <street2>8th Floor</street2>
                <city>New York</city>
                <stateOrCountry>NY</stateOrCountry>
                <stateOrCountryDescription>NEW YORK</stateOrCountryDescription>
                <zipCode>10019</zipCode>
            </relatedPersonAddress>
            <relatedPersonRelationshipList>
                <relationship>Director</relationship>
            </relatedPersonRelationshipList>
            <relationshipClarification>Sole Director of the General Partner of the General Partner of the Issuer</relationshipClarification>
        </relatedPersonInfo>
    </relatedPersonsList>

    <offeringData>
        <industryGroup>
            <industryGroupType>Pooled Investment Fund</industryGroupType>
            <investmentFundInfo>
                <investmentFundType>Private Equity Fund</investmentFundType>
                <is40Act>false</is40Act>
            </investmentFundInfo>
        </industryGroup>
        <issuerSize>
            <revenueRange>Decline to Disclose</revenueRange>
        </issuerSize>
        <federalExemptionsExclusions>
            <item>06</item>
            <item>3C</item>
            <item>3C.7</item>
        </federalExemptionsExclusions>
        <typeOfFiling>
            <newOrAmendment>
                <isAmendment>false</isAmendment>
            </newOrAmendment>
            <dateOfFirstSale>
                <value>2013-04-11</value>
            </dateOfFirstSale>
        </typeOfFiling>
        <durationOfOffering>
            <moreThanOneYear>false</moreThanOneYear>
        </durationOfOffering>
        <typesOfSecuritiesOffered>
            <isEquityType>true</isEquityType>
            <isPooledInvestmentFundType>true</isPooledInvestmentFundType>
        </typesOfSecuritiesOffered>
        <businessCombinationTransaction>
            <isBusinessCombinationTransaction>false</isBusinessCombinationTransaction>
            <clarificationOfResponse></clarificationOfResponse>
        </businessCombinationTransaction>
        <minimumInvestmentAccepted>0</minimumInvestmentAccepted>
        <salesCompensationList>
            <recipient>
                <recipientName>Warren H. Spar</recipientName>
                <recipientCRDNumber>2357369</recipientCRDNumber>
                <associatedBDName>Sparring Partners Capital LLC</associatedBDName>
                <associatedBDCRDNumber>133780</associatedBDCRDNumber>
                <recipientAddress>
                    <street1>420 Lexington Avenue, Suite 2458</street1>
                    <city>New York</city>
                    <stateOrCountry>NY</stateOrCountry>
                    <stateOrCountryDescription>NEW YORK</stateOrCountryDescription>
                    <zipCode>10170</zipCode>
                </recipientAddress>
                <statesOfSolicitationList>
                    <state>IL</state>
                    <description>ILLINOIS</description>
                    <state>WA</state>
                    <description>WASHINGTON</description>
                    <state>NY</state>
                    <description>NEW YORK</description>
                    <state>VA</state>
                    <description>VIRGINIA</description>
                    <state>TX</state>
                    <description>TEXAS</description>
                    <state>CA</state>
                    <description>CALIFORNIA</description>
                    <state>FL</state>
                    <description>FLORIDA</description>
                    <state>MD</state>
                    <description>MARYLAND</description>
                    <state>PA</state>
                    <description>PENNSYLVANIA</description>
                    <state>MA</state>
                    <description>MASSACHUSETTS</description>
                    <state>OR</state>
                    <description>OREGON</description>
                </statesOfSolicitationList>
                <foreignSolicitation>false</foreignSolicitation>
            </recipient>
            <recipient>
                <recipientName>David Choi</recipientName>
                <recipientCRDNumber>2277222</recipientCRDNumber>
                <associatedBDName>Sparring Partners Capital LLC</associatedBDName>
                <associatedBDCRDNumber>133780</associatedBDCRDNumber>
                <recipientAddress>
                    <street1>420 Lexington Avenue, Suite 2458</street1>
                    <city>New York</city>
                    <stateOrCountry>NY</stateOrCountry>
                    <stateOrCountryDescription>NEW YORK</stateOrCountryDescription>
                    <zipCode>10170</zipCode>
                </recipientAddress>
                <statesOfSolicitationList>
                    <state>WA</state>
                    <description>WASHINGTON</description>
                </statesOfSolicitationList>
                <foreignSolicitation>false</foreignSolicitation>
            </recipient>
        </salesCompensationList>
        <offeringSalesAmounts>
            <totalOfferingAmount>Indefinite</totalOfferingAmount>
            <totalAmountSold>417490000</totalAmountSold>
            <totalRemaining>Indefinite</totalRemaining>
            <clarificationOfResponse>This is an offering of a parallel fund with Insight Venture Partners VIII, L.P.</clarificationOfResponse>
        </offeringSalesAmounts>
        <investors>
            <hasNonAccreditedInvestors>false</hasNonAccreditedInvestors>
            <totalNumberAlreadyInvested>19</totalNumberAlreadyInvested>
        </investors>
        <salesCommissionsFindersFees>
            <salesCommissions>
                <dollarAmount>1350000</dollarAmount>
                <isEstimate>true</isEstimate>
            </salesCommissions>
            <findersFees>
                <dollarAmount>0</dollarAmount>
            </findersFees>
            <clarificationOfResponse>The commission estimate is the maximum total amount agreed by the parties to be paid in connection with sales of interests in this Issuer and for two parallel funds if specified amounts are invested.</clarificationOfResponse>
        </salesCommissionsFindersFees>
        <useOfProceeds>
            <grossProceedsUsed>
                <dollarAmount>0</dollarAmount>
            </grossProceedsUsed>
            <clarificationOfResponse></clarificationOfResponse>
        </useOfProceeds>
        <signatureBlock>
            <authorizedRepresentative>false</authorizedRepresentative>
            <signature>
                <issuerName>Insight Venture Partners (Cayman) VIII, L.P.</issuerName>
                <signatureName>Jeffrey Horing</signatureName>
                <nameOfSigner>Jeffrey Horing</nameOfSigner>
                <signatureTitle>See Clarification box in Item #3 Above</signatureTitle>
                <signatureDate>2013-04-24</signatureDate>
            </signature>
        </signatureBlock>
    </offeringData>
</edgarSubmission>
