<?xml version="1.0" encoding="UTF-8"?>

<!--XBRL Document Created with Wdesk from Workiva-->
<!--Copyright 2022 Workiva-->
<!--r:05ec8d61-e8b8-4793-9784-89a6c4a42e47,g:c703e724-b7bf-4666-a001-89040a8cd8eb-->
<xs:schema xmlns:xs="http://www.w3.org/2001/XMLSchema" xmlns:link="http://www.xbrl.org/2003/linkbase" xmlns:root="http://www.joinroot.com/20211231" xmlns:xbrli="http://www.xbrl.org/2003/instance" xmlns:dtr-types="http://www.xbrl.org/dtr/type/2020-01-21" attributeFormDefault="unqualified" elementFormDefault="qualified" targetNamespace="http://www.joinroot.com/20211231">
  <xs:import namespace="http://fasb.org/srt/2021-01-31" schemaLocation="https://xbrl.fasb.org/srt/2021/elts/srt-2021-01-31.xsd"/>
  <xs:import namespace="http://fasb.org/us-gaap/2021-01-31" schemaLocation="https://xbrl.fasb.org/us-gaap/2021/elts/us-gaap-2021-01-31.xsd"/>
  <xs:import namespace="http://www.w3.org/1999/xlink" schemaLocation="http://www.xbrl.org/2003/xlink-2003-12-31.xsd"/>
  <xs:import namespace="http://www.xbrl.org/2003/instance" schemaLocation="http://www.xbrl.org/2003/xbrl-instance-2003-12-31.xsd"/>
  <xs:import namespace="http://www.xbrl.org/2003/linkbase" schemaLocation="http://www.xbrl.org/2003/xbrl-linkbase-2003-12-31.xsd"/>
  <xs:import namespace="http://www.xbrl.org/dtr/type/2020-01-21" schemaLocation="https://www.xbrl.org/dtr/type/2020-01-21/types.xsd"/>
  <xs:import namespace="http://xbrl.sec.gov/dei/2021q4" schemaLocation="https://xbrl.sec.gov/dei/2021q4/dei-2021q4.xsd"/>
  <xs:import namespace="http://xbrl.sec.gov/stpr/2021" schemaLocation="https://xbrl.sec.gov/stpr/2021/stpr-2021.xsd"/>
  <xs:annotation>
    <xs:appinfo>
      <link:linkbaseRef xmlns:xlink="http://www.w3.org/1999/xlink" xlink:arcrole="http://www.w3.org/1999/xlink/properties/linkbase" xlink:href="root-20211231_lab.xml" xlink:role="http://www.xbrl.org/2003/role/labelLinkbaseRef" xlink:type="simple"/>
      <link:linkbaseRef xmlns:xlink="http://www.w3.org/1999/xlink" xlink:arcrole="http://www.w3.org/1999/xlink/properties/linkbase" xlink:href="root-20211231_pre.xml" xlink:role="http://www.xbrl.org/2003/role/presentationLinkbaseRef" xlink:type="simple"/>
      <link:linkbaseRef xmlns:xlink="http://www.w3.org/1999/xlink" xlink:arcrole="http://www.w3.org/1999/xlink/properties/linkbase" xlink:href="root-20211231_cal.xml" xlink:role="http://www.xbrl.org/2003/role/calculationLinkbaseRef" xlink:type="simple"/>
      <link:linkbaseRef xmlns:xlink="http://www.w3.org/1999/xlink" xlink:arcrole="http://www.w3.org/1999/xlink/properties/linkbase" xlink:href="root-20211231_def.xml" xlink:role="http://www.xbrl.org/2003/role/definitionLinkbaseRef" xlink:type="simple"/>
      <link:roleType id="COVERPAGE" roleURI="http://www.joinroot.com/role/COVERPAGE">
        <link:definition>0001001 - Document - COVER PAGE</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="AUDITINFORMATION" roleURI="http://www.joinroot.com/role/AUDITINFORMATION">
        <link:definition>0002002 - Document - AUDIT INFORMATION</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="CONSOLIDATEDBALANCESHEETS" roleURI="http://www.joinroot.com/role/CONSOLIDATEDBALANCESHEETS">
        <link:definition>1001003 - Statement - CONSOLIDATED BALANCE SHEETS</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="CONSOLIDATEDBALANCESHEETSParenthetical" roleURI="http://www.joinroot.com/role/CONSOLIDATEDBALANCESHEETSParenthetical">
        <link:definition>1002004 - Statement - CONSOLIDATED BALANCE SHEETS (Parenthetical)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="CONSOLIDATEDSTATEMENTSOFOPERATIONSANDCOMPREHENSIVELOSS" roleURI="http://www.joinroot.com/role/CONSOLIDATEDSTATEMENTSOFOPERATIONSANDCOMPREHENSIVELOSS">
        <link:definition>1003005 - Statement - CONSOLIDATED STATEMENTS OF OPERATIONS AND COMPREHENSIVE LOSS</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="CONSOLIDATEDSTATEMENTSOFREDEEMABLECONVERTIBLEPREFERREDSTOCKANDSTOCKHOLDERSEQUITYDEFICIT" roleURI="http://www.joinroot.com/role/CONSOLIDATEDSTATEMENTSOFREDEEMABLECONVERTIBLEPREFERREDSTOCKANDSTOCKHOLDERSEQUITYDEFICIT">
        <link:definition>1004006 - Statement - CONSOLIDATED STATEMENTS OF REDEEMABLE CONVERTIBLE PREFERRED STOCK AND STOCKHOLDERS&#8217; EQUITY (DEFICIT)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="CONSOLIDATEDSTATEMENTSOFCASHFLOWS" roleURI="http://www.joinroot.com/role/CONSOLIDATEDSTATEMENTSOFCASHFLOWS">
        <link:definition>1005007 - Statement - CONSOLIDATED STATEMENTS OF CASH FLOWS</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="NATUREOFBUSINESS" roleURI="http://www.joinroot.com/role/NATUREOFBUSINESS">
        <link:definition>2101101 - Disclosure - NATURE OF BUSINESS</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="NATUREOFBUSINESSDetails" roleURI="http://www.joinroot.com/role/NATUREOFBUSINESSDetails">
        <link:definition>2402401 - Disclosure - NATURE OF BUSINESS (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="BASISOFPRESENTATIONANDSUMMARYOFSIGNIFICANTACCOUNTINGPOLICIES" roleURI="http://www.joinroot.com/role/BASISOFPRESENTATIONANDSUMMARYOFSIGNIFICANTACCOUNTINGPOLICIES">
        <link:definition>2103102 - Disclosure - BASIS OF PRESENTATION AND SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="BASISOFPRESENTATIONANDSUMMARYOFSIGNIFICANTACCOUNTINGPOLICIESPolicies" roleURI="http://www.joinroot.com/role/BASISOFPRESENTATIONANDSUMMARYOFSIGNIFICANTACCOUNTINGPOLICIESPolicies">
        <link:definition>2204201 - Disclosure - BASIS OF PRESENTATION AND SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES (Policies)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="BASISOFPRESENTATIONANDSUMMARYOFSIGNIFICANTACCOUNTINGPOLICIESTables" roleURI="http://www.joinroot.com/role/BASISOFPRESENTATIONANDSUMMARYOFSIGNIFICANTACCOUNTINGPOLICIESTables">
        <link:definition>2305301 - Disclosure - BASIS OF PRESENTATION AND SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES (Tables)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="BASISOFPRESENTATIONANDSUMMARYOFSIGNIFICANTACCOUNTINGPOLICIESAdditionalInformationDetails" roleURI="http://www.joinroot.com/role/BASISOFPRESENTATIONANDSUMMARYOFSIGNIFICANTACCOUNTINGPOLICIESAdditionalInformationDetails">
        <link:definition>2406402 - Disclosure - BASIS OF PRESENTATION AND SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES - Additional Information (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="BASISOFPRESENTATIONANDSUMMARYOFSIGNIFICANTACCOUNTINGPOLICIESSupplementalCashFlowDetails" roleURI="http://www.joinroot.com/role/BASISOFPRESENTATIONANDSUMMARYOFSIGNIFICANTACCOUNTINGPOLICIESSupplementalCashFlowDetails">
        <link:definition>2407403 - Disclosure - BASIS OF PRESENTATION AND SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES - Supplemental Cash Flow (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="BASISOFPRESENTATIONANDSUMMARYOFSIGNIFICANTACCOUNTINGPOLICIESCashCashEquivalentsandRestrictedCashDetails" roleURI="http://www.joinroot.com/role/BASISOFPRESENTATIONANDSUMMARYOFSIGNIFICANTACCOUNTINGPOLICIESCashCashEquivalentsandRestrictedCashDetails">
        <link:definition>2408404 - Disclosure - BASIS OF PRESENTATION AND SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES- Cash, Cash Equivalents and Restricted Cash (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="BASISOFPRESENTATIONANDSUMMARYOFSIGNIFICANTACCOUNTINGPOLICIESInternallyDevelopedSoftwareDetails" roleURI="http://www.joinroot.com/role/BASISOFPRESENTATIONANDSUMMARYOFSIGNIFICANTACCOUNTINGPOLICIESInternallyDevelopedSoftwareDetails">
        <link:definition>2409405 - Disclosure - BASIS OF PRESENTATION AND SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES - Internally Developed Software (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="BASISOFPRESENTATIONANDSUMMARYOFSIGNIFICANTACCOUNTINGPOLICIESFixedAssetsDetails" roleURI="http://www.joinroot.com/role/BASISOFPRESENTATIONANDSUMMARYOFSIGNIFICANTACCOUNTINGPOLICIESFixedAssetsDetails">
        <link:definition>2410406 - Disclosure - BASIS OF PRESENTATION AND SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES - Fixed Assets (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="BASISOFPRESENTATIONANDSUMMARYOFSIGNIFICANTACCOUNTINGPOLICIESEmployeeShareBasedCompensationDetails" roleURI="http://www.joinroot.com/role/BASISOFPRESENTATIONANDSUMMARYOFSIGNIFICANTACCOUNTINGPOLICIESEmployeeShareBasedCompensationDetails">
        <link:definition>2411407 - Disclosure - BASIS OF PRESENTATION AND SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES - Employee Share-Based Compensation (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="BASISOFPRESENTATIONANDSUMMARYOFSIGNIFICANTACCOUNTINGPOLICIESASUsDetails" roleURI="http://www.joinroot.com/role/BASISOFPRESENTATIONANDSUMMARYOFSIGNIFICANTACCOUNTINGPOLICIESASUsDetails">
        <link:definition>2412408 - Disclosure - BASIS OF PRESENTATION AND SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES - ASUs (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="INVESTMENTS" roleURI="http://www.joinroot.com/role/INVESTMENTS">
        <link:definition>2113103 - Disclosure - INVESTMENTS</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="INVESTMENTSTables" roleURI="http://www.joinroot.com/role/INVESTMENTSTables">
        <link:definition>2314302 - Disclosure - INVESTMENTS (Tables)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="INVESTMENTSAmortizedCostandFairValueDetails" roleURI="http://www.joinroot.com/role/INVESTMENTSAmortizedCostandFairValueDetails">
        <link:definition>2415409 - Disclosure - INVESTMENTS - Amortized Cost and Fair Value (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="INVESTMENTSOtherinvestmentsDetails" roleURI="http://www.joinroot.com/role/INVESTMENTSOtherinvestmentsDetails">
        <link:definition>2416410 - Disclosure - INVESTMENTS- Other investments (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="INVESTMENTSUnrealizedLossesDetails" roleURI="http://www.joinroot.com/role/INVESTMENTSUnrealizedLossesDetails">
        <link:definition>2417411 - Disclosure - INVESTMENTS - Unrealized Losses (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="INVESTMENTSContractualMaturityDetails" roleURI="http://www.joinroot.com/role/INVESTMENTSContractualMaturityDetails">
        <link:definition>2418412 - Disclosure - INVESTMENTS - Contractual Maturity (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="INVESTMENTSNetInvestmentIncomeDetails" roleURI="http://www.joinroot.com/role/INVESTMENTSNetInvestmentIncomeDetails">
        <link:definition>2419413 - Disclosure - INVESTMENTS - Net Investment Income (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="INVESTMENTSCreditRatingsDetails" roleURI="http://www.joinroot.com/role/INVESTMENTSCreditRatingsDetails">
        <link:definition>2420414 - Disclosure - INVESTMENTS - Credit Ratings (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="INVESTMENTSSpecialDepositsDetails" roleURI="http://www.joinroot.com/role/INVESTMENTSSpecialDepositsDetails">
        <link:definition>2421415 - Disclosure - INVESTMENTS - Special Deposits (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="FAIRVALUEOFFINANCIALINSTRUMENTS" roleURI="http://www.joinroot.com/role/FAIRVALUEOFFINANCIALINSTRUMENTS">
        <link:definition>2122104 - Disclosure - FAIR VALUE OF FINANCIAL INSTRUMENTS</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="FAIRVALUEOFFINANCIALINSTRUMENTSTables" roleURI="http://www.joinroot.com/role/FAIRVALUEOFFINANCIALINSTRUMENTSTables">
        <link:definition>2323303 - Disclosure - FAIR VALUE OF FINANCIAL INSTRUMENTS (Tables)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="FAIRVALUEOFFINANCIALINSTRUMENTSBalanceSheetGroupingDetails" roleURI="http://www.joinroot.com/role/FAIRVALUEOFFINANCIALINSTRUMENTSBalanceSheetGroupingDetails">
        <link:definition>2424416 - Disclosure - FAIR VALUE OF FINANCIAL INSTRUMENTS - Balance Sheet Grouping (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="FAIRVALUEOFFINANCIALINSTRUMENTSLongTermDebtDetails" roleURI="http://www.joinroot.com/role/FAIRVALUEOFFINANCIALINSTRUMENTSLongTermDebtDetails">
        <link:definition>2425417 - Disclosure - FAIR VALUE OF FINANCIAL INSTRUMENTS - Long Term Debt (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="LOSSANDLOSSADJUSTMENTEXPENSERESERVES" roleURI="http://www.joinroot.com/role/LOSSANDLOSSADJUSTMENTEXPENSERESERVES">
        <link:definition>2126105 - Disclosure - LOSS AND LOSS ADJUSTMENT EXPENSE RESERVES</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="LOSSANDLOSSADJUSTMENTEXPENSERESERVESTables" roleURI="http://www.joinroot.com/role/LOSSANDLOSSADJUSTMENTEXPENSERESERVESTables">
        <link:definition>2327304 - Disclosure - LOSS AND LOSS ADJUSTMENT EXPENSE RESERVES (Tables)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="LOSSANDLOSSADJUSTMENTEXPENSERESERVESScheduleofReserveBalanceDetails" roleURI="http://www.joinroot.com/role/LOSSANDLOSSADJUSTMENTEXPENSERESERVESScheduleofReserveBalanceDetails">
        <link:definition>2428418 - Disclosure - LOSS AND LOSS ADJUSTMENT EXPENSE RESERVES-Schedule of Reserve Balance (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="LOSSANDLOSSADJUSTMENTEXPENSERESERVESDetails" roleURI="http://www.joinroot.com/role/LOSSANDLOSSADJUSTMENTEXPENSERESERVESDetails">
        <link:definition>2429419 - Disclosure - LOSS AND LOSS ADJUSTMENT EXPENSE RESERVES (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="LOSSANDLOSSADJUSTMENTEXPENSERESERVESLAEbyAccidentYearDetails" roleURI="http://www.joinroot.com/role/LOSSANDLOSSADJUSTMENTEXPENSERESERVESLAEbyAccidentYearDetails">
        <link:definition>2430420 - Disclosure - LOSS AND LOSS ADJUSTMENT EXPENSE RESERVES - LAE by Accident Year (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="LOSSANDLOSSADJUSTMENTEXPENSERESERVESReconciliationDetails" roleURI="http://www.joinroot.com/role/LOSSANDLOSSADJUSTMENTEXPENSERESERVESReconciliationDetails">
        <link:definition>2431421 - Disclosure - LOSS AND LOSS ADJUSTMENT EXPENSE RESERVES - Reconciliation (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="LOSSANDLOSSADJUSTMENTEXPENSERESERVESHistoricalClaimsDetails" roleURI="http://www.joinroot.com/role/LOSSANDLOSSADJUSTMENTEXPENSERESERVESHistoricalClaimsDetails">
        <link:definition>2432422 - Disclosure - LOSS AND LOSS ADJUSTMENT EXPENSE RESERVES - Historical Claims (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="REINSURANCE" roleURI="http://www.joinroot.com/role/REINSURANCE">
        <link:definition>2133106 - Disclosure - REINSURANCE</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="REINSURANCETables" roleURI="http://www.joinroot.com/role/REINSURANCETables">
        <link:definition>2334305 - Disclosure - REINSURANCE (Tables)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="REINSURANCEDetails" roleURI="http://www.joinroot.com/role/REINSURANCEDetails">
        <link:definition>2435423 - Disclosure - REINSURANCE (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="LONGTERMDEBT" roleURI="http://www.joinroot.com/role/LONGTERMDEBT">
        <link:definition>2136107 - Disclosure - LONG-TERM DEBT</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="LONGTERMDEBTTables" roleURI="http://www.joinroot.com/role/LONGTERMDEBTTables">
        <link:definition>2337306 - Disclosure - LONG-TERM DEBT (Tables)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="LONGTERMDEBTNarrativeDetails" roleURI="http://www.joinroot.com/role/LONGTERMDEBTNarrativeDetails">
        <link:definition>2438424 - Disclosure - LONG-TERM DEBT - Narrative (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="LONGTERMDEBTScheduleOfDebtDetails" roleURI="http://www.joinroot.com/role/LONGTERMDEBTScheduleOfDebtDetails">
        <link:definition>2439425 - Disclosure - LONG-TERM DEBT - Schedule Of Debt (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="LEASES" roleURI="http://www.joinroot.com/role/LEASES">
        <link:definition>2140108 - Disclosure - LEASES</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="LEASESTables" roleURI="http://www.joinroot.com/role/LEASESTables">
        <link:definition>2341307 - Disclosure - LEASES (Tables)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="LEASESNarrativeDetails" roleURI="http://www.joinroot.com/role/LEASESNarrativeDetails">
        <link:definition>2442426 - Disclosure - LEASES - Narrative (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="LEASESFutureLeasePaymentsDetails" roleURI="http://www.joinroot.com/role/LEASESFutureLeasePaymentsDetails">
        <link:definition>2443427 - Disclosure - LEASES - Future Lease Payments (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="LEASESFutureLeasePaymentsDetails_1" roleURI="http://www.joinroot.com/role/LEASESFutureLeasePaymentsDetails_1">
        <link:definition>2443427 - Disclosure - LEASES - Future Lease Payments (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="LEASESOperatingLeaseMaturitiesDetails" roleURI="http://www.joinroot.com/role/LEASESOperatingLeaseMaturitiesDetails">
        <link:definition>2444428 - Disclosure - LEASES - Operating Lease Maturities (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="INCOMETAXES" roleURI="http://www.joinroot.com/role/INCOMETAXES">
        <link:definition>2145109 - Disclosure - INCOME TAXES</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="INCOMETAXESTables" roleURI="http://www.joinroot.com/role/INCOMETAXESTables">
        <link:definition>2346308 - Disclosure - INCOME TAXES (Tables)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="INCOMETAXESIncomeTaxExpenseBenefitDetails" roleURI="http://www.joinroot.com/role/INCOMETAXESIncomeTaxExpenseBenefitDetails">
        <link:definition>2447429 - Disclosure - INCOME TAXES - Income Tax Expense (Benefit) (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="INCOMETAXESEffectiveIncomeTaxReconciliationDetails" roleURI="http://www.joinroot.com/role/INCOMETAXESEffectiveIncomeTaxReconciliationDetails">
        <link:definition>2448430 - Disclosure - INCOME TAXES - Effective Income Tax Reconciliation (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="INCOMETAXESDeferredTaxAssetsandLiabilitiesDetails" roleURI="http://www.joinroot.com/role/INCOMETAXESDeferredTaxAssetsandLiabilitiesDetails">
        <link:definition>2449431 - Disclosure - INCOME TAXES - Deferred Tax Assets and Liabilities (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="INCOMETAXESAdditionalInformationDetails" roleURI="http://www.joinroot.com/role/INCOMETAXESAdditionalInformationDetails">
        <link:definition>2450432 - Disclosure - INCOME TAXES - Additional Information (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="CAPITALSTOCK" roleURI="http://www.joinroot.com/role/CAPITALSTOCK">
        <link:definition>2151110 - Disclosure - CAPITAL STOCK</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="CAPITALSTOCKDetails" roleURI="http://www.joinroot.com/role/CAPITALSTOCKDetails">
        <link:definition>2452433 - Disclosure - CAPITAL STOCK (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="SHAREBASEDCOMPENSATION" roleURI="http://www.joinroot.com/role/SHAREBASEDCOMPENSATION">
        <link:definition>2153111 - Disclosure - SHARE-BASED COMPENSATION</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="SHAREBASEDCOMPENSATIONTables" roleURI="http://www.joinroot.com/role/SHAREBASEDCOMPENSATIONTables">
        <link:definition>2354309 - Disclosure - SHARE-BASED COMPENSATION (Tables)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="SHAREBASEDCOMPENSATIONNarrativeDetails" roleURI="http://www.joinroot.com/role/SHAREBASEDCOMPENSATIONNarrativeDetails">
        <link:definition>2455434 - Disclosure - SHARE-BASED COMPENSATION - Narrative (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="SHAREBASEDCOMPENSATIONScheduleofWarrantsDetails" roleURI="http://www.joinroot.com/role/SHAREBASEDCOMPENSATIONScheduleofWarrantsDetails">
        <link:definition>2456435 - Disclosure - SHARE-BASED COMPENSATION- Schedule of Warrants (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="SHAREBASEDCOMPENSATIONSharebasedCompensationExpenseDetails" roleURI="http://www.joinroot.com/role/SHAREBASEDCOMPENSATIONSharebasedCompensationExpenseDetails">
        <link:definition>2457436 - Disclosure - SHARE-BASED COMPENSATION - Share-based Compensation Expense (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="SHAREBASEDCOMPENSATIONRSUActivityDetails" roleURI="http://www.joinroot.com/role/SHAREBASEDCOMPENSATIONRSUActivityDetails">
        <link:definition>2458437 - Disclosure - SHARE-BASED COMPENSATION - RSU Activity (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="SHAREBASEDCOMPENSATIONOptionActivityDetails" roleURI="http://www.joinroot.com/role/SHAREBASEDCOMPENSATIONOptionActivityDetails">
        <link:definition>2459438 - Disclosure - SHARE-BASED COMPENSATION - Option Activity (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="SHAREBASEDCOMPENSATIONExercisePriceRangeDetails" roleURI="http://www.joinroot.com/role/SHAREBASEDCOMPENSATIONExercisePriceRangeDetails">
        <link:definition>2460439 - Disclosure - SHARE-BASED COMPENSATION - Exercise Price Range (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="COMMITMENTSANDCONTINGENCIES" roleURI="http://www.joinroot.com/role/COMMITMENTSANDCONTINGENCIES">
        <link:definition>2161112 - Disclosure - COMMITMENTS AND CONTINGENCIES</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="COMMITMENTSANDCONTINGENCIESTables" roleURI="http://www.joinroot.com/role/COMMITMENTSANDCONTINGENCIESTables">
        <link:definition>2362310 - Disclosure - COMMITMENTS AND CONTINGENCIES (Tables)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="COMMITMENTSANDCONTINGENCIESDetails" roleURI="http://www.joinroot.com/role/COMMITMENTSANDCONTINGENCIESDetails">
        <link:definition>2463440 - Disclosure - COMMITMENTS AND CONTINGENCIES (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="OTHERCOMPREHENSIVELOSSINCOMEANDACCUMULATEDOTHERCOMPREHENSIVEINCOME" roleURI="http://www.joinroot.com/role/OTHERCOMPREHENSIVELOSSINCOMEANDACCUMULATEDOTHERCOMPREHENSIVEINCOME">
        <link:definition>2164113 - Disclosure - OTHER COMPREHENSIVE (LOSS) INCOME AND ACCUMULATED OTHER COMPREHENSIVE INCOME</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="OTHERCOMPREHENSIVELOSSINCOMEANDACCUMULATEDOTHERCOMPREHENSIVEINCOMETables" roleURI="http://www.joinroot.com/role/OTHERCOMPREHENSIVELOSSINCOMEANDACCUMULATEDOTHERCOMPREHENSIVEINCOMETables">
        <link:definition>2365311 - Disclosure - OTHER COMPREHENSIVE (LOSS) INCOME AND ACCUMULATED OTHER COMPREHENSIVE INCOME (Tables)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="OTHERCOMPREHENSIVELOSSINCOMEANDACCUMULATEDOTHERCOMPREHENSIVEINCOMEDetails" roleURI="http://www.joinroot.com/role/OTHERCOMPREHENSIVELOSSINCOMEANDACCUMULATEDOTHERCOMPREHENSIVEINCOMEDetails">
        <link:definition>2466441 - Disclosure - OTHER COMPREHENSIVE (LOSS) INCOME AND ACCUMULATED OTHER COMPREHENSIVE INCOME (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="LOSSPERSHARE" roleURI="http://www.joinroot.com/role/LOSSPERSHARE">
        <link:definition>2167114 - Disclosure - LOSS PER SHARE</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="LOSSPERSHARETables" roleURI="http://www.joinroot.com/role/LOSSPERSHARETables">
        <link:definition>2368312 - Disclosure - LOSS PER SHARE (Tables)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="LOSSPERSHAREDetails" roleURI="http://www.joinroot.com/role/LOSSPERSHAREDetails">
        <link:definition>2469442 - Disclosure - LOSS PER SHARE (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="LOSSPERSHAREScheduleofAntiDilutiveSecuritiesDetails" roleURI="http://www.joinroot.com/role/LOSSPERSHAREScheduleofAntiDilutiveSecuritiesDetails">
        <link:definition>2470443 - Disclosure - LOSS PER SHARE - Schedule of Anti-Dilutive Securities (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="STATUTORYFINANCIALINFORMATION" roleURI="http://www.joinroot.com/role/STATUTORYFINANCIALINFORMATION">
        <link:definition>2171115 - Disclosure - STATUTORY FINANCIAL INFORMATION</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="STATUTORYFINANCIALINFORMATIONTables" roleURI="http://www.joinroot.com/role/STATUTORYFINANCIALINFORMATIONTables">
        <link:definition>2372313 - Disclosure - STATUTORY FINANCIAL INFORMATION (Tables)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="STATUTORYFINANCIALINFORMATIONDetails" roleURI="http://www.joinroot.com/role/STATUTORYFINANCIALINFORMATIONDetails">
        <link:definition>2473444 - Disclosure - STATUTORY FINANCIAL INFORMATION (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="GEOGRAPHICALBREAKDOWNOFGROSSWRITTENPREMIUM" roleURI="http://www.joinroot.com/role/GEOGRAPHICALBREAKDOWNOFGROSSWRITTENPREMIUM">
        <link:definition>2174116 - Disclosure - GEOGRAPHICAL BREAKDOWN OF GROSS WRITTEN PREMIUM</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="GEOGRAPHICALBREAKDOWNOFGROSSWRITTENPREMIUMTables" roleURI="http://www.joinroot.com/role/GEOGRAPHICALBREAKDOWNOFGROSSWRITTENPREMIUMTables">
        <link:definition>2375314 - Disclosure - GEOGRAPHICAL BREAKDOWN OF GROSS WRITTEN PREMIUM (Tables)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="GEOGRAPHICALBREAKDOWNOFGROSSWRITTENPREMIUMDetails" roleURI="http://www.joinroot.com/role/GEOGRAPHICALBREAKDOWNOFGROSSWRITTENPREMIUMDetails">
        <link:definition>2476445 - Disclosure - GEOGRAPHICAL BREAKDOWN OF GROSS WRITTEN PREMIUM (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="SUBSEQUENTEVENTS" roleURI="http://www.joinroot.com/role/SUBSEQUENTEVENTS">
        <link:definition>2177117 - Disclosure - SUBSEQUENT EVENTS</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="SUBSEQUENTEVENTSDetails" roleURI="http://www.joinroot.com/role/SUBSEQUENTEVENTSDetails">
        <link:definition>2478446 - Disclosure - SUBSEQUENT EVENTS (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="ScheduleIICondensedCombinedFinancialInformationofRegistrant" roleURI="http://www.joinroot.com/role/ScheduleIICondensedCombinedFinancialInformationofRegistrant">
        <link:definition>2179118 - Disclosure - Schedule II: Condensed Combined Financial Information of Registrant</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="ScheduleIICondensedCombinedFinancialInformationofRegistrantBalanceSheetDetails" roleURI="http://www.joinroot.com/role/ScheduleIICondensedCombinedFinancialInformationofRegistrantBalanceSheetDetails">
        <link:definition>2480447 - Disclosure - Schedule II: Condensed Combined Financial Information of Registrant - Balance Sheet (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="ScheduleIICondensedCombinedFinancialInformationofRegistrantBalanceSheetAdditionalDetails" roleURI="http://www.joinroot.com/role/ScheduleIICondensedCombinedFinancialInformationofRegistrantBalanceSheetAdditionalDetails">
        <link:definition>2481448 - Disclosure - Schedule II: Condensed Combined Financial Information of Registrant - Balance Sheet Additional (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="ScheduleIICondensedCombinedFinancialInformationofRegistrantStatementofOperationsandComprehensiveLossDetails" roleURI="http://www.joinroot.com/role/ScheduleIICondensedCombinedFinancialInformationofRegistrantStatementofOperationsandComprehensiveLossDetails">
        <link:definition>2482449 - Disclosure - Schedule II: Condensed Combined Financial Information of Registrant - Statement of Operations and Comprehensive Loss (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="ScheduleIICondensedCombinedFinancialInformationofRegistrantStatementofCashFlowsDetails" roleURI="http://www.joinroot.com/role/ScheduleIICondensedCombinedFinancialInformationofRegistrantStatementofCashFlowsDetails">
        <link:definition>2483450 - Disclosure - Schedule II: Condensed Combined Financial Information of Registrant - Statement of Cash Flows (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="ScheduleIICondensedCombinedFinancialInformationofRegistrantAdditionalInformationDetails" roleURI="http://www.joinroot.com/role/ScheduleIICondensedCombinedFinancialInformationofRegistrantAdditionalInformationDetails">
        <link:definition>2484451 - Disclosure - Schedule II: Condensed Combined Financial Information of Registrant - Additional Information (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="ScheduleVValuationandQualifyingAccounts" roleURI="http://www.joinroot.com/role/ScheduleVValuationandQualifyingAccounts">
        <link:definition>2185119 - Disclosure - Schedule V: Valuation and Qualifying Accounts</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
      <link:roleType id="ScheduleVValuationandQualifyingAccountsDetails" roleURI="http://www.joinroot.com/role/ScheduleVValuationandQualifyingAccountsDetails">
        <link:definition>2486452 - Disclosure - Schedule V: Valuation and Qualifying Accounts (Details)</link:definition>
        <link:usedOn>link:presentationLink</link:usedOn>
        <link:usedOn>link:calculationLink</link:usedOn>
        <link:usedOn>link:definitionLink</link:usedOn>
      </link:roleType>
    </xs:appinfo>
  </xs:annotation>
  <xs:element id="root_ShareBasedCompensationArrangementByShareBasedPaymentAwardBaseNumberOfOptionsIssuable" abstract="false" name="ShareBasedCompensationArrangementByShareBasedPaymentAwardBaseNumberOfOptionsIssuable" nillable="true" xbrli:periodType="instant" substitutionGroup="xbrli:item" type="xbrli:sharesItemType"/>
  <xs:element id="root_TechnologyAndDevelopmentExpenseMember" abstract="true" name="TechnologyAndDevelopmentExpenseMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="root_StockIssuedDuringPeriodSharesWarrantsExercised" abstract="false" name="StockIssuedDuringPeriodSharesWarrantsExercised" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="xbrli:sharesItemType"/>
  <xs:element id="root_DebtSecuritiesAvailableForSaleCurrentMember" abstract="true" name="DebtSecuritiesAvailableForSaleCurrentMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="root_TemporaryEquityAndStockholdersEquityNoteDisclosureTextBlock" abstract="false" name="TemporaryEquityAndStockholdersEquityNoteDisclosureTextBlock" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:textBlockItemType"/>
  <xs:element id="root_OtherCertainRestrictedStockUnits3Member" abstract="true" name="OtherCertainRestrictedStockUnits3Member" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="root_ClassOfWarrantOrRightNumberOfTranches" abstract="false" name="ClassOfWarrantOrRightNumberOfTranches" nillable="true" xbrli:periodType="instant" substitutionGroup="xbrli:item" type="xbrli:integerItemType"/>
  <xs:element id="root_ReinsuranceRecoverableProvisionForSlidingScaleCommission" abstract="false" name="ReinsuranceRecoverableProvisionForSlidingScaleCommission" nillable="true" xbrli:periodType="instant" xbrli:balance="credit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_NonvestedSharesSubjectToRepurchaseMember" abstract="true" name="NonvestedSharesSubjectToRepurchaseMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseLossAdjustmentExpenseNet" abstract="false" name="LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseLossAdjustmentExpenseNet" nillable="true" xbrli:periodType="instant" xbrli:balance="credit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_PaymentOfInterestPaidInKindOperatingActivities" abstract="false" name="PaymentOfInterestPaidInKindOperatingActivities" nillable="true" xbrli:periodType="duration" xbrli:balance="credit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_LiabilityForClaimsAndClaimsAdjustmentExpenseMember" abstract="true" name="LiabilityForClaimsAndClaimsAdjustmentExpenseMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="root_TermLoanAMember" abstract="true" name="TermLoanAMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="root_LiabilityForClaimsAndClaimsAdjustmentExpenseGross" abstract="false" name="LiabilityForClaimsAndClaimsAdjustmentExpenseGross" nillable="true" xbrli:periodType="instant" xbrli:balance="credit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_ClassOfWarrantOrRightGrantDateFairValuePerShare" abstract="false" name="ClassOfWarrantOrRightGrantDateFairValuePerShare" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:perShareItemType"/>
  <xs:element id="root_CatlinIndemnityCompanyMember" abstract="true" name="CatlinIndemnityCompanyMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="root_LineOfCreditFacilityFeeOnAverageDailyAmountPercentage" abstract="false" name="LineOfCreditFacilityFeeOnAverageDailyAmountPercentage" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:percentItemType"/>
  <xs:element id="root_OtherCertainRestrictedStockUnits2Member" abstract="true" name="OtherCertainRestrictedStockUnits2Member" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="root_LongTermWarrantMember" abstract="true" name="LongTermWarrantMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="root_BookOverdraftPolicyPolicyTextBlock" abstract="false" name="BookOverdraftPolicyPolicyTextBlock" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:textBlockItemType"/>
  <xs:element id="root_LeaseholdImprovementsNonCash" abstract="false" name="LeaseholdImprovementsNonCash" nillable="true" xbrli:periodType="duration" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_TermLoanMember" abstract="true" name="TermLoanMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="root_EarlyExerciseDepositLiability" abstract="false" name="EarlyExerciseDepositLiability" nillable="true" xbrli:periodType="instant" xbrli:balance="credit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_FeeIncome" abstract="false" name="FeeIncome" nillable="true" xbrli:periodType="duration" xbrli:balance="credit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_TermLoanBMember" abstract="true" name="TermLoanBMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="root_TemporaryEquityStockIssuedDuringPeriodSharesConversionOfPreferredStock" abstract="false" name="TemporaryEquityStockIssuedDuringPeriodSharesConversionOfPreferredStock" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="xbrli:sharesItemType"/>
  <xs:element id="root_AssetAcquisitionRecognizedIdentifiableAssetsAcquiredCashCashEquivalentsAndInvestmentIncome" abstract="false" name="AssetAcquisitionRecognizedIdentifiableAssetsAcquiredCashCashEquivalentsAndInvestmentIncome" nillable="true" xbrli:periodType="instant" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_AssetAcquisitionRecognizedIdentifiableAssetsAcquiredIndefiniteLivedIntangibleAssets" abstract="false" name="AssetAcquisitionRecognizedIdentifiableAssetsAcquiredIndefiniteLivedIntangibleAssets" nillable="true" xbrli:periodType="instant" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_RootIncMember" abstract="true" name="RootIncMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="root_OtherInsuranceExpenseMember" abstract="true" name="OtherInsuranceExpenseMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="root_StandardPoorsAAPlusAAAAMinusAMinusOneRatingMember" abstract="true" name="StandardPoorsAAPlusAAAAMinusAMinusOneRatingMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="root_StandardPoorsAPlusAAMinusRatingMember" abstract="true" name="StandardPoorsAPlusAAMinusRatingMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="root_LineOfCreditFacilityFrontingFeePercentage" abstract="false" name="LineOfCreditFacilityFrontingFeePercentage" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:percentItemType"/>
  <xs:element id="root_RegulatoryAssetRequirementSpecialDepositsFairValue" abstract="false" name="RegulatoryAssetRequirementSpecialDepositsFairValue" nillable="true" xbrli:periodType="instant" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_NetIncomeLossAttributableToParentBeforeIncomeLossFromSubsidiariesAfterTax" abstract="false" name="NetIncomeLossAttributableToParentBeforeIncomeLossFromSubsidiariesAfterTax" nillable="true" xbrli:periodType="duration" xbrli:balance="credit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_APICTenderOfferAndConversionOfUnitsValue" abstract="false" name="APICTenderOfferAndConversionOfUnitsValue" nillable="true" xbrli:periodType="duration" xbrli:balance="credit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_IntercompanyPayable" abstract="false" name="IntercompanyPayable" nillable="true" xbrli:periodType="instant" xbrli:balance="credit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_InvestmentAgreementTermOfAgreement" abstract="false" name="InvestmentAgreementTermOfAgreement" nillable="true" xbrli:periodType="instant" substitutionGroup="xbrli:item" type="xbrli:durationItemType"/>
  <xs:element id="root_OtherInsuranceExpensePolicyPolicyTextBlock" abstract="false" name="OtherInsuranceExpensePolicyPolicyTextBlock" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:textBlockItemType"/>
  <xs:element id="root_RootInsuranceCompanyMember" abstract="true" name="RootInsuranceCompanyMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAbstract" abstract="true" name="LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAbstract" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="xbrli:stringItemType"/>
  <xs:element id="root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCeded" abstract="false" name="LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCeded" nillable="true" xbrli:periodType="duration" xbrli:balance="credit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_StockIssuanceCostsNonCash" abstract="false" name="StockIssuanceCostsNonCash" nillable="true" xbrli:periodType="duration" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_TemporaryEquitySharesTenderOffer" abstract="false" name="TemporaryEquitySharesTenderOffer" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="xbrli:sharesItemType"/>
  <xs:element id="root_ProceedsFromSimpleAgreementForFutureEquity" abstract="false" name="ProceedsFromSimpleAgreementForFutureEquity" nillable="true" xbrli:periodType="duration" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_APICShareBasedPaymentArrangementRecognitionAndExerciseShares" abstract="false" name="APICShareBasedPaymentArrangementRecognitionAndExerciseShares" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="xbrli:sharesItemType"/>
  <xs:element id="root_OperatingLossCarryforwardsNotSubjectToExpiration" abstract="false" name="OperatingLossCarryforwardsNotSubjectToExpiration" nillable="true" xbrli:periodType="instant" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_ShareBasedCompensationArrangementByShareBasedPaymentAwardIncreaseInNumberOfSharesAvailableForGrantPercentageOfSharesOutstanding" abstract="false" name="ShareBasedCompensationArrangementByShareBasedPaymentAwardIncreaseInNumberOfSharesAvailableForGrantPercentageOfSharesOutstanding" nillable="true" xbrli:periodType="instant" substitutionGroup="xbrli:item" type="dtr-types:percentItemType"/>
  <xs:element id="root_ConversionOfStock" abstract="false" name="ConversionOfStock" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="xbrli:sharesItemType"/>
  <xs:element id="root_TemporaryEquityStockIssuedDuringPeriodValueConversionOfSimpleAgreementForFutureEquity" abstract="false" name="TemporaryEquityStockIssuedDuringPeriodValueConversionOfSimpleAgreementForFutureEquity" nillable="true" xbrli:periodType="duration" xbrli:balance="credit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_OtherInsuranceExpenseIncome" abstract="false" name="OtherInsuranceExpenseIncome" nillable="true" xbrli:periodType="duration" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_AmendedTermLoanBMember" abstract="true" name="AmendedTermLoanBMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="root_UnearnedPremiumsNet" abstract="false" name="UnearnedPremiumsNet" nillable="true" xbrli:periodType="instant" xbrli:balance="credit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_StockholdersEquityValueSettlementOfRelatedPartyLoan" abstract="false" name="StockholdersEquityValueSettlementOfRelatedPartyLoan" nillable="true" xbrli:periodType="duration" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_ReclassificationOfDeferredRentAndLeaseLiabilities" abstract="false" name="ReclassificationOfDeferredRentAndLeaseLiabilities" nillable="true" xbrli:periodType="duration" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseLossesNet" abstract="false" name="LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseLossesNet" nillable="true" xbrli:periodType="instant" xbrli:balance="credit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_CededCommissionsMaximumAmountDueWithReturnOfUnpaidPremiums" abstract="false" name="CededCommissionsMaximumAmountDueWithReturnOfUnpaidPremiums" nillable="true" xbrli:periodType="instant" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_AssetAcquisitionPolicyPolicyTextBlock" abstract="false" name="AssetAcquisitionPolicyPolicyTextBlock" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:textBlockItemType"/>
  <xs:element id="root_CreditRatingConcentrationRiskMember" abstract="true" name="CreditRatingConcentrationRiskMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="root_TechnologyAndDevelopmentExpense" abstract="false" name="TechnologyAndDevelopmentExpense" nillable="true" xbrli:periodType="duration" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_ClassOfWarrantOrRightAdditionalWarrantToPurchaseSharesPercent" abstract="false" name="ClassOfWarrantOrRightAdditionalWarrantToPurchaseSharesPercent" nillable="true" xbrli:periodType="instant" substitutionGroup="xbrli:item" type="dtr-types:percentItemType"/>
  <xs:element id="root_RootPropertyAndCasualtyMember" abstract="true" name="RootPropertyAndCasualtyMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="root_OperatingLossCarryforwardsSubjectToExpiration" abstract="false" name="OperatingLossCarryforwardsSubjectToExpiration" nillable="true" xbrli:periodType="instant" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_A2020EmployeeStockPurchasePlanMember" abstract="true" name="A2020EmployeeStockPurchasePlanMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="root_StandardPoorsBBBPlusBBBBBBMinusRatingMember" abstract="true" name="StandardPoorsBBBPlusBBBBBBMinusRatingMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="root_CarvanaMember" abstract="true" name="CarvanaMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="root_A2020EquityIncentivePlanMember" abstract="true" name="A2020EquityIncentivePlanMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="root_AssumedUnearnedPremiums" abstract="false" name="AssumedUnearnedPremiums" nillable="true" xbrli:periodType="instant" xbrli:balance="credit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_EffectiveIncomeTaxOperatingLossCarryforwardsStateAndLocalAmount" abstract="false" name="EffectiveIncomeTaxOperatingLossCarryforwardsStateAndLocalAmount" nillable="true" xbrli:periodType="duration" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_CapitalizedComputerSoftwareAmortizationPeriod" abstract="false" name="CapitalizedComputerSoftwareAmortizationPeriod" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="xbrli:durationItemType"/>
  <xs:element id="root_DeferredTaxAssetsNondeductibleAccruals" abstract="false" name="DeferredTaxAssetsNondeductibleAccruals" nillable="true" xbrli:periodType="instant" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_ReinsuranceRecoverableProvisionForLossCorridor" abstract="false" name="ReinsuranceRecoverableProvisionForLossCorridor" nillable="true" xbrli:periodType="instant" xbrli:balance="credit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_IntercompanyReceivable" abstract="false" name="IntercompanyReceivable" nillable="true" xbrli:periodType="instant" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_GrossWrittenPremiumsMember" abstract="true" name="GrossWrittenPremiumsMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="root_OtherCertainRestrictedStockUnits1Member" abstract="true" name="OtherCertainRestrictedStockUnits1Member" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="root_FeeAndOtherIncomePolicyPolicyTextBlock" abstract="false" name="FeeAndOtherIncomePolicyPolicyTextBlock" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:textBlockItemType"/>
  <xs:element id="root_ShareBasedCompensationAwardTrancheFourMemberMember" abstract="true" name="ShareBasedCompensationAwardTrancheFourMemberMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="root_ExercisePriceRangeThreeMember" abstract="true" name="ExercisePriceRangeThreeMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="root_TreasuryStockAcquiredNonCash" abstract="false" name="TreasuryStockAcquiredNonCash" nillable="true" xbrli:periodType="duration" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_TemporaryEquityIssuanceCostRelatingToStockAndWarrant" abstract="false" name="TemporaryEquityIssuanceCostRelatingToStockAndWarrant" nillable="true" xbrli:periodType="duration" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_IncreaseDecreaseInIntercompanyAssetsAndLiabilitiesNet" abstract="false" name="IncreaseDecreaseInIntercompanyAssetsAndLiabilitiesNet" nillable="true" xbrli:periodType="duration" xbrli:balance="credit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfAdditionalSharesAuthorizedAnnualIncreaseOutstandingShares" abstract="false" name="ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfAdditionalSharesAuthorizedAnnualIncreaseOutstandingShares" nillable="true" xbrli:periodType="instant" substitutionGroup="xbrli:item" type="xbrli:sharesItemType"/>
  <xs:element id="root_AllOtherStatesMember" abstract="true" name="AllOtherStatesMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="root_ExercisePriceRangeOneMember" abstract="true" name="ExercisePriceRangeOneMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="root_PaymentOfInterestAndFeesDebt" abstract="false" name="PaymentOfInterestAndFeesDebt" nillable="true" xbrli:periodType="duration" xbrli:balance="credit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_RegulatoryAssetRequirementSpecialDepositsAmortizedCost" abstract="false" name="RegulatoryAssetRequirementSpecialDepositsAmortizedCost" nillable="true" xbrli:periodType="instant" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_OtherComprehensiveIncomeLossFromSubsidiariesNetOfTax" abstract="false" name="OtherComprehensiveIncomeLossFromSubsidiariesNetOfTax" nillable="true" xbrli:periodType="duration" xbrli:balance="credit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_APICShareBasedPaymentArrangementIncreaseForCostRecognitionWarrants" abstract="false" name="APICShareBasedPaymentArrangementIncreaseForCostRecognitionWarrants" nillable="true" xbrli:periodType="duration" xbrli:balance="credit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_DirectAndAssumedUnearnedPremiums" abstract="false" name="DirectAndAssumedUnearnedPremiums" nillable="true" xbrli:periodType="instant" xbrli:balance="credit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_CommonStockVotingRightsVotes" abstract="false" name="CommonStockVotingRightsVotes" nillable="true" xbrli:periodType="instant" substitutionGroup="xbrli:item" type="xbrli:integerItemType"/>
  <xs:element id="root_TemporaryEquityStockIssuedDuringPeriodSharesNewIssues" abstract="false" name="TemporaryEquityStockIssuedDuringPeriodSharesNewIssues" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="xbrli:sharesItemType"/>
  <xs:element id="root_StockIssuedDuringPeriodSharesConversionOfCommonStock" abstract="false" name="StockIssuedDuringPeriodSharesConversionOfCommonStock" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="xbrli:sharesItemType"/>
  <xs:element id="root_EffectiveIncomeTaxOperatingLossCarryforwardsStateAndLocalPercent" abstract="false" name="EffectiveIncomeTaxOperatingLossCarryforwardsStateAndLocalPercent" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:percentItemType"/>
  <xs:element id="root_FairValueAdjustmentSimpleAgreementForFutureEquity" abstract="false" name="FairValueAdjustmentSimpleAgreementForFutureEquity" nillable="true" xbrli:periodType="duration" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_ProceedsFromIssuanceOfLongTermDebtAndWarrants" abstract="false" name="ProceedsFromIssuanceOfLongTermDebtAndWarrants" nillable="true" xbrli:periodType="duration" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAssumed" abstract="false" name="LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAssumed" nillable="true" xbrli:periodType="duration" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_UnearnedPremiumsNetAbstract" abstract="true" name="UnearnedPremiumsNetAbstract" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="xbrli:stringItemType"/>
  <xs:element id="root_TemporaryEquityStockIssuedDuringPeriodSharesConversionOfSimpleAgreementForFutureEquity" abstract="false" name="TemporaryEquityStockIssuedDuringPeriodSharesConversionOfSimpleAgreementForFutureEquity" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="xbrli:sharesItemType"/>
  <xs:element id="root_TenderOfferMember" abstract="true" name="TenderOfferMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="root_StockholdersEquitySharesSettlementOfRelatedPartyLoan" abstract="false" name="StockholdersEquitySharesSettlementOfRelatedPartyLoan" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="xbrli:sharesItemType"/>
  <xs:element id="root_WarrantsToPurchaseCommonStockMember" abstract="true" name="WarrantsToPurchaseCommonStockMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="root_LiabilityForClaimsAndClaimsAdjustmentExpenseLossAndLAEReservesAssumed" abstract="false" name="LiabilityForClaimsAndClaimsAdjustmentExpenseLossAndLAEReservesAssumed" nillable="true" xbrli:periodType="instant" xbrli:balance="credit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_AmendedTermLoanAMember" abstract="true" name="AmendedTermLoanAMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="root_AuditInformationAbstract" abstract="true" name="AuditInformationAbstract" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="xbrli:stringItemType"/>
  <xs:element id="root_PaymentsForAssetAcquisitions" abstract="false" name="PaymentsForAssetAcquisitions" nillable="true" xbrli:periodType="duration" xbrli:balance="credit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_DeferredTaxAssetExcessCedingCommission" abstract="false" name="DeferredTaxAssetExcessCedingCommission" nillable="true" xbrli:periodType="instant" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_ShortTermWarrantMember" abstract="true" name="ShortTermWarrantMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="root_ExercisePriceRangeTwoMember" abstract="true" name="ExercisePriceRangeTwoMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="root_ShareBasedCompensationAwardTrancheFiveMemberMember" abstract="true" name="ShareBasedCompensationAwardTrancheFiveMemberMember" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:domainItemType"/>
  <xs:element id="root_ClassOfWarrantOrRightExpirationPeriod" abstract="false" name="ClassOfWarrantOrRightExpirationPeriod" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="xbrli:durationItemType"/>
  <xs:element id="root_PurchaseObligationToBePaidAfterYearFour" abstract="false" name="PurchaseObligationToBePaidAfterYearFour" nillable="true" xbrli:periodType="instant" xbrli:balance="credit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_TemporaryEquityStockIssuedDuringPeriodValueConversionOfPreferredStock" abstract="false" name="TemporaryEquityStockIssuedDuringPeriodValueConversionOfPreferredStock" nillable="true" xbrli:periodType="duration" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_ScheduleOfCapitalizedComputerSoftwareTableTextBlock" abstract="false" name="ScheduleOfCapitalizedComputerSoftwareTableTextBlock" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="dtr-types:textBlockItemType"/>
  <xs:element id="root_NumberOfStatesInWhichEntityOperatesAutoPoliciesWritten" abstract="false" name="NumberOfStatesInWhichEntityOperatesAutoPoliciesWritten" nillable="true" xbrli:periodType="instant" substitutionGroup="xbrli:item" type="xbrli:integerItemType"/>
  <xs:element id="root_ShareBasedPaymentArrangementNoncashExpenseTenderOffer" abstract="false" name="ShareBasedPaymentArrangementNoncashExpenseTenderOffer" nillable="true" xbrli:periodType="duration" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsGross" abstract="false" name="LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsGross" nillable="true" xbrli:periodType="duration" xbrli:balance="debit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_APICTenderOfferAndConversionOfUnitsShares" abstract="false" name="APICTenderOfferAndConversionOfUnitsShares" nillable="true" xbrli:periodType="duration" substitutionGroup="xbrli:item" type="xbrli:sharesItemType"/>
  <xs:element id="root_NetIncomeLossAttributableToParentBeforeIncomeLossFromSubsidiariesNetOfTax" abstract="false" name="NetIncomeLossAttributableToParentBeforeIncomeLossFromSubsidiariesNetOfTax" nillable="true" xbrli:periodType="duration" xbrli:balance="credit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
  <xs:element id="root_InvestmentsInSubsidiaries" abstract="false" name="InvestmentsInSubsidiaries" nillable="true" xbrli:periodType="instant" xbrli:balance="credit" substitutionGroup="xbrli:item" type="xbrli:monetaryItemType"/>
</xs:schema>
