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    <link:label id="lab_us-gaap_ValuationAllowanceOfDeferredTaxAssetsMember_cfb90bce-8e06-40a0-9ae9-fd11ce415c88_terseLabel_en-US" xlink:label="lab_us-gaap_ValuationAllowanceOfDeferredTaxAssetsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Valuation allowance for deferred tax assets</link:label>
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    <link:label id="lab_us-gaap_RelatedPartyTransactionAmountsOfTransaction_410536af-dac5-4b73-a698-a23fe55b177f_terseLabel_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionAmountsOfTransaction" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Amount of related party transaction</link:label>
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    <link:label id="lab_us-gaap_TemporaryEquityLiquidationPreference_d0751ee9-edda-4092-b28a-6c854b59326f_terseLabel_en-US" xlink:label="lab_us-gaap_TemporaryEquityLiquidationPreference" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Temporary equity, liquidation preference</link:label>
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    <link:label id="lab_us-gaap_IncomeStatementAbstract_157dc472-0705-4baf-baf1-c8884ad8591a_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeStatementAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Income Statement [Abstract]</link:label>
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    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember_fb16c7eb-d2e8-4085-aaca-463180d550ba_terseLabel_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accumulated Other Comprehensive Income</link:label>
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    <link:label id="lab_root_WesternAllianceBankMember_244907ef-b6fa-4462-ac09-8bedd8c3fa27_terseLabel_en-US" xlink:label="lab_root_WesternAllianceBankMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Western Alliance Bank</link:label>
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    <link:label id="lab_us-gaap_RealizedInvestmentGainsLosses_eeea2dc4-d3e6-4318-952d-8eb7d44931be_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_RealizedInvestmentGainsLosses" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Realized gains on investments</link:label>
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    <link:label id="lab_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment_6461d68a-2750-4499-9da2-7d09c45bea7e_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Purchases of fixed assets</link:label>
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    <link:label id="lab_root_RelatedPartyTransactionShares_f9161e6a-d206-4fab-8e8f-ec08b924cc36_terseLabel_en-US" xlink:label="lab_root_RelatedPartyTransactionShares" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Related party transaction, shares (in shares)</link:label>
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    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsAccidentYearAxis_0a4e47e6-086f-433b-82dd-b25a0eea3653_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsAccidentYearAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-duration Insurance Contracts, Accident Year [Axis]</link:label>
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    <link:label id="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense_e17769a7-8004-46ba-ac13-f0cbf5f039b1_verboseLabel_en-US" xlink:label="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Amortization of deferred acquisition costs</link:label>
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    <link:label id="lab_root_TermLoanAMember_68d817b1-3c35-4599-8cf8-5df6d3f195d2_terseLabel_en-US" xlink:label="lab_root_TermLoanAMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Term Loan A</link:label>
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    <link:label id="lab_us-gaap_OperatingLossCarryforwardsTable_696b9d18-067e-4d5a-b01e-765bf4ecaa17_terseLabel_en-US" xlink:label="lab_us-gaap_OperatingLossCarryforwardsTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Operating Loss Carryforwards [Table]</link:label>
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    <link:label id="lab_dei_EntityDomain_0e2d0f85-74b6-4a8f-911a-16388a14fb7e_terseLabel_en-US" xlink:label="lab_dei_EntityDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity [Domain]</link:label>
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    <link:label id="lab_root_LiabilityForClaimsAndClaimsAdjustmentExpenseMember_739426a9-c05e-4689-baf6-f89e9f9ac747_terseLabel_en-US" xlink:label="lab_root_LiabilityForClaimsAndClaimsAdjustmentExpenseMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Loss and loss adjustment expenses</link:label>
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    <link:label id="lab_root_TermLoanBMember_1848b2ec-bc2c-4b20-95d7-adbbe6f966bc_terseLabel_en-US" xlink:label="lab_root_TermLoanBMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Term Loan B</link:label>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleTableTextBlock_3ee0f2eb-e68c-40e3-8d22-e28f9498a18b_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of AFS debt securities</link:label>
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    <link:label id="lab_root_ReallocatedTermLoanAMember_1e3858f3-613b-493d-afb9-4e7008c01789_terseLabel_en-US" xlink:label="lab_root_ReallocatedTermLoanAMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reallocated Term Loan A</link:label>
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    <link:label id="lab_root_OtherCertainRestrictedStockUnits2Member_3797746d-d40a-4887-94f9-d2c44b89d449_terseLabel_en-US" xlink:label="lab_root_OtherCertainRestrictedStockUnits2Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other Certain RSUs 2</link:label>
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    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtSecurities_7f3cf15a-be00-49f3-a2cd-494cc70d4293_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtSecurities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueInputsLevel3Member" xlink:to="lab_us-gaap_FairValueInputsLevel3Member" xlink:type="arc" order="1"/>
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    <link:label id="lab_us-gaap_RelatedPartyTransactionExpensesFromTransactionsWithRelatedParty_9d04a4f2-3c36-4486-b143-a8d99a3488e4_terseLabel_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionExpensesFromTransactionsWithRelatedParty" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Expenses with related party</link:label>
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    <link:label id="lab_us-gaap_EffectsOfReinsuranceTableTextBlock_5e43c63b-fb70-4aab-815a-ba2084ffd982_terseLabel_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of direct premiums written</link:label>
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    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue_de16e9eb-beaf-4716-967b-fa6b1f0ebe8f_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Due after one year through five years</link:label>
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    <link:label id="lab_us-gaap_FixedMaturitiesMember_499bcb44-7a04-4f88-92aa-050e2eba4fd4_terseLabel_en-US" xlink:label="lab_us-gaap_FixedMaturitiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fixed maturities</link:label>
    <link:label id="lab_us-gaap_FixedMaturitiesMember_label_en-US" xlink:label="lab_us-gaap_FixedMaturitiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fixed Maturities [Member]</link:label>
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    <link:label id="lab_us-gaap_LineOfCreditMember_4dca3f9f-7a1a-4696-9e1b-8a2fa5350673_terseLabel_en-US" xlink:label="lab_us-gaap_LineOfCreditMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Line of Credit</link:label>
    <link:label id="lab_us-gaap_LineOfCreditMember_label_en-US" xlink:label="lab_us-gaap_LineOfCreditMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Line of Credit [Member]</link:label>
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    <link:label id="lab_us-gaap_TemporaryEquityRedemptionPricePerShare_41d4d4b8-27a4-4cea-8bc0-3a406a8da628_terseLabel_en-US" xlink:label="lab_us-gaap_TemporaryEquityRedemptionPricePerShare" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Conversion price per share (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_TemporaryEquityRedemptionPricePerShare_label_en-US" xlink:label="lab_us-gaap_TemporaryEquityRedemptionPricePerShare" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Temporary Equity, Redemption Price Per Share</link:label>
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    <link:label id="lab_us-gaap_PostemploymentBenefitsAbstract_label_en-US" xlink:label="lab_us-gaap_PostemploymentBenefitsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Postemployment Benefits [Abstract]</link:label>
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    <link:label id="lab_us-gaap_SharebasedCompensationSharesAuthorizedUnderStockOptionPlansExercisePriceRangeOutstandingOptionsWeightedAverageExercisePriceBeginningBalance1_a34151bb-c0eb-479e-8f35-1f17296bb4fe_terseLabel_en-US" xlink:label="lab_us-gaap_SharebasedCompensationSharesAuthorizedUnderStockOptionPlansExercisePriceRangeOutstandingOptionsWeightedAverageExercisePriceBeginningBalance1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Options outstanding, weighted-average exercise price (in dollars per share)</link:label>
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    <link:label id="lab_us-gaap_PurchaseObligationDueAfterFifthYear_2f70f799-96a4-4aeb-ab0c-ec5fe22cca68_terseLabel_en-US" xlink:label="lab_us-gaap_PurchaseObligationDueAfterFifthYear" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">2026 and thereafter</link:label>
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    <link:label id="lab_us-gaap_PaymentsForRepurchaseOfCommonStock_0c8bd3d8-b68f-4757-b367-cfbf02b75c93_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsForRepurchaseOfCommonStock" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Purchases of treasury stock</link:label>
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    <link:label id="lab_us-gaap_FurnitureAndFixturesMember_a1708732-796c-4765-a3d2-574dc069cc4e_terseLabel_en-US" xlink:label="lab_us-gaap_FurnitureAndFixturesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Furniture</link:label>
    <link:label id="lab_us-gaap_FurnitureAndFixturesMember_label_en-US" xlink:label="lab_us-gaap_FurnitureAndFixturesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Furniture and Fixtures [Member]</link:label>
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    <link:label id="lab_dei_EntityAddressStateOrProvince_639afcfb-4326-4ae8-9348-8675921a636d_terseLabel_en-US" xlink:label="lab_dei_EntityAddressStateOrProvince" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Address, State or Province</link:label>
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    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Equity Instruments Other than Options, Vested in Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod" xlink:href="http://xbrl.fasb.org/us-gaap/2020/elts/us-gaap-2020-01-31.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod"/>
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    <link:label id="lab_us-gaap_IncomeTaxReconciliationIncomeTaxExpenseBenefitAtFederalStatutoryIncomeTaxRate_2da5c470-e16b-4eb1-8232-d1df6a3f29ee_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxReconciliationIncomeTaxExpenseBenefitAtFederalStatutoryIncomeTaxRate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statutory U.S. federal income tax benefit</link:label>
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    <link:label id="lab_us-gaap_ReinsuranceAccountingPolicy_1de36e2f-bf2d-43fd-8df5-b5dc938d3e4a_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceAccountingPolicy" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance</link:label>
    <link:label id="lab_us-gaap_ReinsuranceAccountingPolicy_label_en-US" xlink:label="lab_us-gaap_ReinsuranceAccountingPolicy" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance Accounting Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceAccountingPolicy" xlink:href="http://xbrl.fasb.org/us-gaap/2020/elts/us-gaap-2020-01-31.xsd#us-gaap_ReinsuranceAccountingPolicy"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceAccountingPolicy" xlink:to="lab_us-gaap_ReinsuranceAccountingPolicy" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RedeemableConvertiblePreferredStockMember_b8aec816-fd29-4bbe-8243-219fb4ef7c12_terseLabel_en-US" xlink:label="lab_us-gaap_RedeemableConvertiblePreferredStockMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Redeemable convertible preferred stock (as converted to common stock)</link:label>
    <link:label id="lab_us-gaap_RedeemableConvertiblePreferredStockMember_label_en-US" xlink:label="lab_us-gaap_RedeemableConvertiblePreferredStockMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Redeemable Convertible Preferred Stock [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RedeemableConvertiblePreferredStockMember" xlink:href="http://xbrl.fasb.org/us-gaap/2020/elts/us-gaap-2020-01-31.xsd#us-gaap_RedeemableConvertiblePreferredStockMember"/>
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    <link:label id="lab_us-gaap_InternalUseSoftwarePolicy_e1c8b913-93b0-438e-b9f4-2a756afd4ff9_terseLabel_en-US" xlink:label="lab_us-gaap_InternalUseSoftwarePolicy" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Internally Developed Software</link:label>
    <link:label id="lab_us-gaap_InternalUseSoftwarePolicy_label_en-US" xlink:label="lab_us-gaap_InternalUseSoftwarePolicy" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Internal Use Software, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InternalUseSoftwarePolicy" xlink:href="http://xbrl.fasb.org/us-gaap/2020/elts/us-gaap-2020-01-31.xsd#us-gaap_InternalUseSoftwarePolicy"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InternalUseSoftwarePolicy" xlink:to="lab_us-gaap_InternalUseSoftwarePolicy" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TemporaryEquitySharesIssued_660ed99b-ac57-4e44-abf7-2549b3481771_verboseLabel_en-US" xlink:label="lab_us-gaap_TemporaryEquitySharesIssued" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Temporary equity, shares issued (in shares)</link:label>
    <link:label id="lab_us-gaap_TemporaryEquitySharesIssued_de82d843-dab2-496a-ad7f-31a631674da2_terseLabel_en-US" xlink:label="lab_us-gaap_TemporaryEquitySharesIssued" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Shares issued (in shares)</link:label>
    <link:label id="lab_us-gaap_TemporaryEquitySharesIssued_label_en-US" xlink:label="lab_us-gaap_TemporaryEquitySharesIssued" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Temporary Equity, Shares Issued</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TemporaryEquitySharesIssued" xlink:href="http://xbrl.fasb.org/us-gaap/2020/elts/us-gaap-2020-01-31.xsd#us-gaap_TemporaryEquitySharesIssued"/>
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    <link:label id="lab_us-gaap_RetainedEarningsAccumulatedDeficit_3f7290d7-b827-4d6e-8153-753ddad6ea5e_terseLabel_en-US" xlink:label="lab_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accumulated loss</link:label>
    <link:label id="lab_us-gaap_RetainedEarningsAccumulatedDeficit_label_en-US" xlink:label="lab_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Retained Earnings (Accumulated Deficit)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:href="http://xbrl.fasb.org/us-gaap/2020/elts/us-gaap-2020-01-31.xsd#us-gaap_RetainedEarningsAccumulatedDeficit"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:to="lab_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesAllowance_8d82426f-3ce3-431f-b5cc-a8c1cbde1448_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesAllowance" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Provision for loss corridor</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesAllowance_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesAllowance" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance Recoverable, Allowance for Credit Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverablesAllowance" xlink:href="http://xbrl.fasb.org/us-gaap/2020/elts/us-gaap-2020-01-31.xsd#us-gaap_ReinsuranceRecoverablesAllowance"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverablesAllowance" xlink:to="lab_us-gaap_ReinsuranceRecoverablesAllowance" xlink:type="arc" order="1"/>
    <link:label id="lab_root_AssetAcquisitionPolicyPolicyTextBlock_5fa03029-e59c-4d18-b186-0b175f7a2276_terseLabel_en-US" xlink:label="lab_root_AssetAcquisitionPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Asset Acquisition</link:label>
    <link:label id="lab_root_AssetAcquisitionPolicyPolicyTextBlock_label_en-US" xlink:label="lab_root_AssetAcquisitionPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Asset Acquisition, Policy [Policy Text Block]</link:label>
    <link:label id="lab_root_AssetAcquisitionPolicyPolicyTextBlock_documentation_en-US" xlink:label="lab_root_AssetAcquisitionPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Asset Acquisition, Policy</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_AssetAcquisitionPolicyPolicyTextBlock" xlink:href="root-20201231.xsd#root_AssetAcquisitionPolicyPolicyTextBlock"/>
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    <link:label id="lab_root_LoansAndLeasesReceivableRelatedPartiesRecoursePortionPercentage_10eec29c-f9fd-4bed-ac9d-6e4ca472d878_terseLabel_en-US" xlink:label="lab_root_LoansAndLeasesReceivableRelatedPartiesRecoursePortionPercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Recourse portion percentage</link:label>
    <link:label id="lab_root_LoansAndLeasesReceivableRelatedPartiesRecoursePortionPercentage_label_en-US" xlink:label="lab_root_LoansAndLeasesReceivableRelatedPartiesRecoursePortionPercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Loans And Leases Receivable, Related Parties, Recourse Portion Percentage</link:label>
    <link:label id="lab_root_LoansAndLeasesReceivableRelatedPartiesRecoursePortionPercentage_documentation_en-US" xlink:label="lab_root_LoansAndLeasesReceivableRelatedPartiesRecoursePortionPercentage" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Loans And Leases Receivable, Related Parties, Recourse Portion Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_LoansAndLeasesReceivableRelatedPartiesRecoursePortionPercentage" xlink:href="root-20201231.xsd#root_LoansAndLeasesReceivableRelatedPartiesRecoursePortionPercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_LoansAndLeasesReceivableRelatedPartiesRecoursePortionPercentage" xlink:to="lab_root_LoansAndLeasesReceivableRelatedPartiesRecoursePortionPercentage" xlink:type="arc" order="1"/>
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    <link:label id="lab_srt_ScenarioForecastMember_8e03bf59-6ea9-4545-9c8f-49550a0f2310_terseLabel_en-US" xlink:label="lab_srt_ScenarioForecastMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Forecast</link:label>
    <link:label id="lab_srt_ScenarioForecastMember_label_en-US" xlink:label="lab_srt_ScenarioForecastMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Forecast [Member]</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ScenarioForecastMember" xlink:to="lab_srt_ScenarioForecastMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTable_56dc497e-b155-427c-8dba-da974bd77f13_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-duration Insurance Contracts, Claims Development [Table]</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTable_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-duration Insurance Contracts, Claims Development [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTable" xlink:href="http://xbrl.fasb.org/us-gaap/2020/elts/us-gaap-2020-01-31.xsd#us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTable" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueConcentrationOfRiskTextBlock_3bc212f5-4f0e-459d-adf4-00fe287b2a37_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueConcentrationOfRiskTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of credit ratings</link:label>
    <link:label id="lab_us-gaap_FairValueConcentrationOfRiskTextBlock_label_en-US" xlink:label="lab_us-gaap_FairValueConcentrationOfRiskTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value, Concentration of Risk [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueConcentrationOfRiskTextBlock" xlink:href="http://xbrl.fasb.org/us-gaap/2020/elts/us-gaap-2020-01-31.xsd#us-gaap_FairValueConcentrationOfRiskTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueConcentrationOfRiskTextBlock" xlink:to="lab_us-gaap_FairValueConcentrationOfRiskTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityVoluntaryFilers_fb51836d-477d-4d39-bb77-dbe2bc300884_terseLabel_en-US" xlink:label="lab_dei_EntityVoluntaryFilers" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Voluntary Filers</link:label>
    <link:label id="lab_dei_EntityVoluntaryFilers_label_en-US" xlink:label="lab_dei_EntityVoluntaryFilers" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Voluntary Filers</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityVoluntaryFilers" xlink:href="https://xbrl.sec.gov/dei/2020/dei-2020-01-31.xsd#dei_EntityVoluntaryFilers"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityVoluntaryFilers" xlink:to="lab_dei_EntityVoluntaryFilers" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TaxCreditCarryforwardAxis_b2f5f259-0d8e-406f-be7b-4fef64781fa0_terseLabel_en-US" xlink:label="lab_us-gaap_TaxCreditCarryforwardAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Tax Credit Carryforward [Axis]</link:label>
    <link:label id="lab_us-gaap_TaxCreditCarryforwardAxis_label_en-US" xlink:label="lab_us-gaap_TaxCreditCarryforwardAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Tax Credit Carryforward [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TaxCreditCarryforwardAxis" xlink:href="http://xbrl.fasb.org/us-gaap/2020/elts/us-gaap-2020-01-31.xsd#us-gaap_TaxCreditCarryforwardAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TaxCreditCarryforwardAxis" xlink:to="lab_us-gaap_TaxCreditCarryforwardAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceTextBlock_88881d07-f827-4d3d-908b-9c937f685d79_verboseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceTextBlock" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">REINSURANCE</link:label>
    <link:label id="lab_us-gaap_ReinsuranceTextBlock_fe195c63-9fa2-464e-a81d-107f5b99ebcf_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">GEOGRAPHICAL BREAKDOWN OF DIRECT WRITTEN PREMIUM</link:label>
    <link:label id="lab_us-gaap_ReinsuranceTextBlock_label_en-US" xlink:label="lab_us-gaap_ReinsuranceTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceTextBlock" xlink:href="http://xbrl.fasb.org/us-gaap/2020/elts/us-gaap-2020-01-31.xsd#us-gaap_ReinsuranceTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceTextBlock" xlink:to="lab_us-gaap_ReinsuranceTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CreditFacilityAxis_58b6e051-a381-437c-8091-afb86630690e_terseLabel_en-US" xlink:label="lab_us-gaap_CreditFacilityAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Credit Facility [Axis]</link:label>
    <link:label id="lab_us-gaap_CreditFacilityAxis_label_en-US" xlink:label="lab_us-gaap_CreditFacilityAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Credit Facility [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CreditFacilityAxis" xlink:href="http://xbrl.fasb.org/us-gaap/2020/elts/us-gaap-2020-01-31.xsd#us-gaap_CreditFacilityAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CreditFacilityAxis" xlink:to="lab_us-gaap_CreditFacilityAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_root_StockholdersEquityValueSettlementOfRelatedPartyLoan_8e87b260-a409-4258-b8a2-3e92ded43350_negatedTerseLabel_en-US" xlink:label="lab_root_StockholdersEquityValueSettlementOfRelatedPartyLoan" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Settlement of related party loan (Note 10)</link:label>
    <link:label id="lab_root_StockholdersEquityValueSettlementOfRelatedPartyLoan_label_en-US" xlink:label="lab_root_StockholdersEquityValueSettlementOfRelatedPartyLoan" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stockholders' Equity, Value, Settlement Of Related Party Loan</link:label>
    <link:label id="lab_root_StockholdersEquityValueSettlementOfRelatedPartyLoan_documentation_en-US" xlink:label="lab_root_StockholdersEquityValueSettlementOfRelatedPartyLoan" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stockholders' Equity, Value, Settlement Of Related Party Loan</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_StockholdersEquityValueSettlementOfRelatedPartyLoan" xlink:href="root-20201231.xsd#root_StockholdersEquityValueSettlementOfRelatedPartyLoan"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_StockholdersEquityValueSettlementOfRelatedPartyLoan" xlink:to="lab_root_StockholdersEquityValueSettlementOfRelatedPartyLoan" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue_d1485c35-4f62-4201-a4b5-8fb8b6be5ce3_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Due after 10 years</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Fair Value, Maturity, Allocated and Single Maturity Date, after Year 10</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue" xlink:href="http://xbrl.fasb.org/us-gaap/2020/elts/us-gaap-2020-01-31.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardFairValueAssumptionsExpectedVolatilityRateMinimum_9bccaca7-66fd-4f66-aa1c-191517d86078_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardFairValueAssumptionsExpectedVolatilityRateMinimum" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Volatility, min</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardFairValueAssumptionsExpectedVolatilityRateMinimum_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardFairValueAssumptionsExpectedVolatilityRateMinimum" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Fair Value Assumptions, Expected Volatility Rate, Minimum</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardFairValueAssumptionsExpectedVolatilityRateMinimum" xlink:href="http://xbrl.fasb.org/us-gaap/2020/elts/us-gaap-2020-01-31.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardFairValueAssumptionsExpectedVolatilityRateMinimum"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardFairValueAssumptionsExpectedVolatilityRateMinimum" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardFairValueAssumptionsExpectedVolatilityRateMinimum" xlink:type="arc" order="1"/>
    <link:label id="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsGross_a4369315-1068-4dc8-b2d9-c89408cd56e7_terseLabel_en-US" xlink:label="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsGross" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Direct</link:label>
    <link:label id="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsGross_label_en-US" xlink:label="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability For Unpaid Claims And Claims Adjustment Expense, Incurred Claims, Gross</link:label>
    <link:label id="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsGross_documentation_en-US" xlink:label="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsGross" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability For Unpaid Claims And Claims Adjustment Expense, Incurred Claims, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsGross" xlink:href="root-20201231.xsd#root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsGross" xlink:to="lab_root_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsGross" xlink:type="arc" order="1"/>
    <link:label id="lab_root_APICTenderOfferAndConversionOfUnitsValue_62438098-7f90-48da-93c7-d2b6a67c880c_terseLabel_en-US" xlink:label="lab_root_APICTenderOfferAndConversionOfUnitsValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Tender offer and subsequent conversion (Note 9)</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_root_APICTenderOfferAndConversionOfUnitsValue" xlink:href="root-20201231.xsd#root_APICTenderOfferAndConversionOfUnitsValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_root_APICTenderOfferAndConversionOfUnitsValue" xlink:to="lab_root_APICTenderOfferAndConversionOfUnitsValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet_f9618a43-5c26-42a8-8b30-15914e65e7ff_periodStartLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net loss and LAE reserves, January 1</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet_6f27573e-3926-4d37-8211-19f8f7ca3c71_periodEndLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net loss and LAE reserves, December 31</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet_99bd0709-2a6e-40e9-8456-364ca03d94ba_totalLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net loss and LAE reserves</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:href="http://xbrl.fasb.org/us-gaap/2020/elts/us-gaap-2020-01-31.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareBasicAndDiluted_1a323dde-384b-4602-9fcd-0c4d3cc692c8_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareBasicAndDiluted" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Loss per common share: basic and diluted (in dollars per share)</link:label>
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    <link:label id="lab_us-gaap_SeriesEPreferredStockMember_7146506a-055c-419b-ab2c-03cc0466f8aa_terseLabel_en-US" xlink:label="lab_us-gaap_SeriesEPreferredStockMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Series E Preferred Stock</link:label>
    <link:label id="lab_us-gaap_SeriesEPreferredStockMember_label_en-US" xlink:label="lab_us-gaap_SeriesEPreferredStockMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Series E Preferred Stock [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SeriesEPreferredStockMember" xlink:href="http://xbrl.fasb.org/us-gaap/2020/elts/us-gaap-2020-01-31.xsd#us-gaap_SeriesEPreferredStockMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SeriesEPreferredStockMember" xlink:to="lab_us-gaap_SeriesEPreferredStockMember" xlink:type="arc" order="1"/>
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    <link:label id="lab_stpr_OH_477203ea-082a-42fb-a311-cfece0abb91b_terseLabel_en-US" xlink:label="lab_stpr_OH" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ohio</link:label>
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    <link:label id="lab_us-gaap_LettersOfCreditOutstandingAmount_2af9d31b-7d60-48e3-9530-9090c6100102_terseLabel_en-US" xlink:label="lab_us-gaap_LettersOfCreditOutstandingAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Letters of credit outstanding</link:label>
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    <link:label id="lab_us-gaap_ConcentrationRiskByTypeAxis_2dbffdc0-2705-4a16-9785-9edc6055e2ea_terseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskByTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Concentration Risk Type [Axis]</link:label>
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    <link:label id="lab_root_LoansReceivableWeightedAverageInterestRateMember_20194c7b-bfaa-4c98-980d-25be442695ae_terseLabel_en-US" xlink:label="lab_root_LoansReceivableWeightedAverageInterestRateMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Weighted-average interest rate of loans receivable</link:label>
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    <link:label id="lab_us-gaap_EstimateOfFairValueFairValueDisclosureMember_c91a3baa-cd41-4d12-9544-c32816c1bfcd_terseLabel_en-US" xlink:label="lab_us-gaap_EstimateOfFairValueFairValueDisclosureMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Estimated Fair Value</link:label>
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    <link:label id="lab_us-gaap_RelatedPartyTransactionRate_72c1441f-a4ae-45ae-824c-83f757cfa384_terseLabel_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionRate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Interest rate</link:label>
    <link:label id="lab_us-gaap_RelatedPartyTransactionRate_label_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionRate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Related Party Transaction, Rate</link:label>
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    <link:label id="lab_srt_CondensedBalanceSheetStatementsCaptionsLineItems_b94b6f67-71bd-4cf4-ab9d-f8602a37e905_terseLabel_en-US" xlink:label="lab_srt_CondensedBalanceSheetStatementsCaptionsLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Condensed Balance Sheet Statements, Captions [Line Items]</link:label>
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    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardRequisiteServicePeriod1_8448a8d0-d85c-44e0-abbc-7f2fbb021091_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardRequisiteServicePeriod1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Service and performance period</link:label>
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    <link:label id="lab_us-gaap_LeaseAndRentalExpense_16b55b61-49a2-4910-96a3-c477476fa0d2_terseLabel_en-US" xlink:label="lab_us-gaap_LeaseAndRentalExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Rent expense</link:label>
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    <link:label id="lab_stpr_MO_22216e74-e102-46ba-9342-35ce6c3e739b_terseLabel_en-US" xlink:label="lab_stpr_MO" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Missouri</link:label>
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    <link:label id="lab_dei_LegalEntityAxis_6a24560d-d0c5-4786-8b30-14c2c7828420_terseLabel_en-US" xlink:label="lab_dei_LegalEntityAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Legal Entity [Axis]</link:label>
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    <link:label id="lab_root_CreditRatingConcentrationRiskMember_99990d83-9d75-4e76-9903-7c41e17a37ba_terseLabel_en-US" xlink:label="lab_root_CreditRatingConcentrationRiskMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Credit rating</link:label>
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    <link:label id="lab_us-gaap_LongTermDebt_e40fc5cc-18b7-47ea-8ad3-8c05416f07b7_verboseLabel_en-US" xlink:label="lab_us-gaap_LongTermDebt" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long-term debt and warrants</link:label>
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    <link:label id="lab_us-gaap_Investments_547b581f-8f9a-4d83-8f8c-ae7b49ae195d_totalLabel_en-US" xlink:label="lab_us-gaap_Investments" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total investments</link:label>
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    <link:label id="lab_us-gaap_NumberOfReportableSegments_03c0603c-24d3-44f0-891c-92c1f476b8b6_terseLabel_en-US" xlink:label="lab_us-gaap_NumberOfReportableSegments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Number of reportable segments</link:label>
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    <link:label id="lab_us-gaap_TemporaryEquityStockIssuedDuringPeriodValueNewIssues_db48ba75-2155-4de3-93ee-9c9a672ae717_terseLabel_en-US" xlink:label="lab_us-gaap_TemporaryEquityStockIssuedDuringPeriodValueNewIssues" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred stock&#8212;issued, net of issuance costs</link:label>
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    <link:label id="lab_us-gaap_ValuationAllowancesAndReservesChargedToCostAndExpense_298fa818-f469-47c4-91d7-7ac4da267f1d_terseLabel_en-US" xlink:label="lab_us-gaap_ValuationAllowancesAndReservesChargedToCostAndExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Charged to costs and expenses</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilitiesFairValueDisclosureAbstract" xlink:to="lab_us-gaap_LiabilitiesFairValueDisclosureAbstract" xlink:type="arc" order="1"/>
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    <link:label id="lab_stpr_GA_0a46dcd8-401f-4603-89a2-372b37187876_terseLabel_en-US" xlink:label="lab_stpr_GA" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Georgia</link:label>
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    <link:label id="lab_us-gaap_OtherLiabilitiesMember_b58c03e8-c413-40b2-aa39-a9e0d8ed2ffd_terseLabel_en-US" xlink:label="lab_us-gaap_OtherLiabilitiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other liabilities</link:label>
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    <link:label id="lab_us-gaap_CreditFacilityDomain_c66814d9-a6f3-4e45-837b-cc9a2fc22651_terseLabel_en-US" xlink:label="lab_us-gaap_CreditFacilityDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Credit Facility [Domain]</link:label>
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    <link:label id="lab_us-gaap_CapitalizedComputerSoftwareNet_8c8b3e72-7cb0-434c-8143-6af92c23f557_totalLabel_en-US" xlink:label="lab_us-gaap_CapitalizedComputerSoftwareNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Internally developed software, net</link:label>
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    <link:label id="lab_us-gaap_LongTermDebtFairValue_92bac5c4-0b5e-49d0-a139-b29226320847_terseLabel_en-US" xlink:label="lab_us-gaap_LongTermDebtFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long-term debt</link:label>
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