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

<!--XBRL Document Created with the Workiva Platform-->
<!--Copyright 2025 Workiva-->
<!--r:da61596d-4f07-4117-b37c-0acd14f707ca,g:5f5a8fb6-4894-4f26-94e0-9e09b654b9ef-->
<link:linkbase xmlns:link="http://www.xbrl.org/2003/linkbase" xmlns:xlink="http://www.w3.org/1999/xlink" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xsi:schemaLocation="http://www.xbrl.org/2003/linkbase http://www.xbrl.org/2003/xbrl-linkbase-2003-12-31.xsd">
  <link:roleRef roleURI="http://www.gooseheadinsurance.com/role/CondensedConsolidatedStatementsofOperationsUnaudited" xlink:type="simple" xlink:href="gshd-20250630.xsd#CondensedConsolidatedStatementsofOperationsUnaudited"/>
  <link:calculationLink xlink:role="http://www.gooseheadinsurance.com/role/CondensedConsolidatedStatementsofOperationsUnaudited" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_592de81c-196b-430d-9e1e-777c7f087db2" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingIncomeLoss_00c223ee-b235-4fc4-bb95-cbacbfcaed85" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_OperatingIncomeLoss"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_592de81c-196b-430d-9e1e-777c7f087db2" xlink:to="loc_us-gaap_OperatingIncomeLoss_00c223ee-b235-4fc4-bb95-cbacbfcaed85" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestExpenseNonoperating_9c80a723-d8bc-433b-9744-f2341c7da427" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_InterestExpenseNonoperating"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_592de81c-196b-430d-9e1e-777c7f087db2" xlink:to="loc_us-gaap_InterestExpenseNonoperating_9c80a723-d8bc-433b-9744-f2341c7da427" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NonoperatingIncomeExpense_d4151090-b716-46b7-8670-2239ae3389b6" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_NonoperatingIncomeExpense"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_592de81c-196b-430d-9e1e-777c7f087db2" xlink:to="loc_us-gaap_NonoperatingIncomeExpense_d4151090-b716-46b7-8670-2239ae3389b6" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProfitLoss_641ce39f-2f91-4df5-9641-1aab2bcffa0b" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ProfitLoss"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_58dd6398-dd8b-4a60-a4d9-9b38389b9e8e" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_ProfitLoss_641ce39f-2f91-4df5-9641-1aab2bcffa0b" xlink:to="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_58dd6398-dd8b-4a60-a4d9-9b38389b9e8e" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxExpenseBenefit_321d4682-ceb6-4486-99a0-029475ac95a1" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncomeTaxExpenseBenefit"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_ProfitLoss_641ce39f-2f91-4df5-9641-1aab2bcffa0b" xlink:to="loc_us-gaap_IncomeTaxExpenseBenefit_321d4682-ceb6-4486-99a0-029475ac95a1" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLoss_129065cc-97bb-4ce6-9d6b-84865a710e6d" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_NetIncomeLoss"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProfitLoss_16924e25-c6bb-42b0-9a2c-dff29829784b" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ProfitLoss"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_129065cc-97bb-4ce6-9d6b-84865a710e6d" xlink:to="loc_us-gaap_ProfitLoss_16924e25-c6bb-42b0-9a2c-dff29829784b" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLossAttributableToNoncontrollingInterest_187dd2d1-75e0-4690-86dd-8a83711187f7" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_NetIncomeLossAttributableToNoncontrollingInterest"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_129065cc-97bb-4ce6-9d6b-84865a710e6d" xlink:to="loc_us-gaap_NetIncomeLossAttributableToNoncontrollingInterest_187dd2d1-75e0-4690-86dd-8a83711187f7" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingExpenses_c6d11479-186c-420a-bb68-7619b28f20b6" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_OperatingExpenses"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LaborAndRelatedExpense_9ff16cdf-681d-4d12-a7fc-b3115b9d8187" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LaborAndRelatedExpense"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingExpenses_c6d11479-186c-420a-bb68-7619b28f20b6" xlink:to="loc_us-gaap_LaborAndRelatedExpense_9ff16cdf-681d-4d12-a7fc-b3115b9d8187" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GeneralAndAdministrativeExpense_de0e64ee-b3ad-4e76-b18e-46eb8411f137" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_GeneralAndAdministrativeExpense"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingExpenses_c6d11479-186c-420a-bb68-7619b28f20b6" xlink:to="loc_us-gaap_GeneralAndAdministrativeExpense_de0e64ee-b3ad-4e76-b18e-46eb8411f137" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProvisionForDoubtfulAccounts_ed3fac2c-e934-401d-9e61-e4392999e357" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ProvisionForDoubtfulAccounts"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingExpenses_c6d11479-186c-420a-bb68-7619b28f20b6" xlink:to="loc_us-gaap_ProvisionForDoubtfulAccounts_ed3fac2c-e934-401d-9e61-e4392999e357" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_gshd_DepreciationDepletionAndAmortizationExcludingDebtIssuanceCostAmortization_6981ee54-8a5d-4bb7-82cb-6c3d96774466" xlink:href="gshd-20250630.xsd#gshd_DepreciationDepletionAndAmortizationExcludingDebtIssuanceCostAmortization"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingExpenses_c6d11479-186c-420a-bb68-7619b28f20b6" xlink:to="loc_gshd_DepreciationDepletionAndAmortizationExcludingDebtIssuanceCostAmortization_6981ee54-8a5d-4bb7-82cb-6c3d96774466" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingIncomeLoss_047c9c97-180d-4c77-a708-647d859a2484" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_OperatingIncomeLoss"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Revenues_3736be27-b0cd-4dec-916d-2ed05371f761" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_Revenues"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingIncomeLoss_047c9c97-180d-4c77-a708-647d859a2484" xlink:to="loc_us-gaap_Revenues_3736be27-b0cd-4dec-916d-2ed05371f761" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingExpenses_2b1fad64-b92a-482f-b19f-818e89b814b0" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_OperatingExpenses"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingIncomeLoss_047c9c97-180d-4c77-a708-647d859a2484" xlink:to="loc_us-gaap_OperatingExpenses_2b1fad64-b92a-482f-b19f-818e89b814b0" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.gooseheadinsurance.com/role/CondensedConsolidatedBalanceSheetsUnaudited" xlink:type="simple" xlink:href="gshd-20250630.xsd#CondensedConsolidatedBalanceSheetsUnaudited"/>
  <link:calculationLink xlink:role="http://www.gooseheadinsurance.com/role/CondensedConsolidatedBalanceSheetsUnaudited" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetsCurrent_9b8fd58f-e48c-46bb-a53d-027d7d367f09" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AssetsCurrent"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashAndCashEquivalentsAtCarryingValue_e6e3f946-2794-4d0d-a32d-e5c14dc799b6" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CashAndCashEquivalentsAtCarryingValue"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_AssetsCurrent_9b8fd58f-e48c-46bb-a53d-027d7d367f09" xlink:to="loc_us-gaap_CashAndCashEquivalentsAtCarryingValue_e6e3f946-2794-4d0d-a32d-e5c14dc799b6" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestrictedCashCurrent_888b941f-ac37-416b-9586-0679d736406b" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_RestrictedCashCurrent"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_AssetsCurrent_9b8fd58f-e48c-46bb-a53d-027d7d367f09" xlink:to="loc_us-gaap_RestrictedCashCurrent_888b941f-ac37-416b-9586-0679d736406b" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_gshd_AccountsReceivableNetCurrentCommissionsAndAgencyFeesReceivable_06f2bc86-fb4a-4794-a81f-f08b5a46e47c" xlink:href="gshd-20250630.xsd#gshd_AccountsReceivableNetCurrentCommissionsAndAgencyFeesReceivable"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_AssetsCurrent_9b8fd58f-e48c-46bb-a53d-027d7d367f09" xlink:to="loc_gshd_AccountsReceivableNetCurrentCommissionsAndAgencyFeesReceivable_06f2bc86-fb4a-4794-a81f-f08b5a46e47c" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_gshd_AccountsReceivableNetCurrentFranchiseReceivable_0a220456-19e5-4fd2-a05b-d99aaee78012" xlink:href="gshd-20250630.xsd#gshd_AccountsReceivableNetCurrentFranchiseReceivable"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_AssetsCurrent_9b8fd58f-e48c-46bb-a53d-027d7d367f09" xlink:to="loc_gshd_AccountsReceivableNetCurrentFranchiseReceivable_0a220456-19e5-4fd2-a05b-d99aaee78012" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PrepaidExpenseCurrent_0a3a7738-bae2-416d-b07a-6abe79f724bb" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PrepaidExpenseCurrent"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_AssetsCurrent_9b8fd58f-e48c-46bb-a53d-027d7d367f09" xlink:to="loc_us-gaap_PrepaidExpenseCurrent_0a3a7738-bae2-416d-b07a-6abe79f724bb" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Assets_4c6971bd-3abb-4679-890f-c088b59d20da" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_Assets"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetsCurrent_b2e3d259-5e57-4af4-afde-54d3a490445f" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AssetsCurrent"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_4c6971bd-3abb-4679-890f-c088b59d20da" xlink:to="loc_us-gaap_AssetsCurrent_b2e3d259-5e57-4af4-afde-54d3a490445f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_gshd_AccountsReceivableNetNoncurrentFranchiseReceivable_26bb798b-d370-4153-8388-ce1664e7c2be" xlink:href="gshd-20250630.xsd#gshd_AccountsReceivableNetNoncurrentFranchiseReceivable"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_4c6971bd-3abb-4679-890f-c088b59d20da" xlink:to="loc_gshd_AccountsReceivableNetNoncurrentFranchiseReceivable_26bb798b-d370-4153-8388-ce1664e7c2be" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentNet_c86c492b-e0ef-4e45-bd2f-dce62a820452" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PropertyPlantAndEquipmentNet"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_4c6971bd-3abb-4679-890f-c088b59d20da" xlink:to="loc_us-gaap_PropertyPlantAndEquipmentNet_c86c492b-e0ef-4e45-bd2f-dce62a820452" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseRightOfUseAsset_15bc1f2b-17e9-41f3-8300-701276e21ba0" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_OperatingLeaseRightOfUseAsset"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_4c6971bd-3abb-4679-890f-c088b59d20da" xlink:to="loc_us-gaap_OperatingLeaseRightOfUseAsset_15bc1f2b-17e9-41f3-8300-701276e21ba0" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IntangibleAssetsNetExcludingGoodwill_ff085324-b067-4c9c-ad53-5dcba848b393" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IntangibleAssetsNetExcludingGoodwill"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_4c6971bd-3abb-4679-890f-c088b59d20da" xlink:to="loc_us-gaap_IntangibleAssetsNetExcludingGoodwill_ff085324-b067-4c9c-ad53-5dcba848b393" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredIncomeTaxAssetsNet_b1a1d224-1c70-46bc-a9cd-038d68e93b15" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DeferredIncomeTaxAssetsNet"/>
    <link:calculationArc order="6" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_4c6971bd-3abb-4679-890f-c088b59d20da" xlink:to="loc_us-gaap_DeferredIncomeTaxAssetsNet_b1a1d224-1c70-46bc-a9cd-038d68e93b15" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherAssetsNoncurrent_f08d43b4-7f93-46d9-850f-0d9c675f9ee3" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_OtherAssetsNoncurrent"/>
    <link:calculationArc order="7" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_4c6971bd-3abb-4679-890f-c088b59d20da" xlink:to="loc_us-gaap_OtherAssetsNoncurrent_f08d43b4-7f93-46d9-850f-0d9c675f9ee3" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquity_7d2b14b9-136a-47da-9560-835112d406ad" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_StockholdersEquity"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockValue_dd588091-5646-4653-ae2d-2de88fd674e7" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CommonStockValue"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_StockholdersEquity_7d2b14b9-136a-47da-9560-835112d406ad" xlink:to="loc_us-gaap_CommonStockValue_dd588091-5646-4653-ae2d-2de88fd674e7" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdditionalPaidInCapital_6c8cb828-27a1-48b1-9ccf-f45263becc85" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AdditionalPaidInCapital"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_StockholdersEquity_7d2b14b9-136a-47da-9560-835112d406ad" xlink:to="loc_us-gaap_AdditionalPaidInCapital_6c8cb828-27a1-48b1-9ccf-f45263becc85" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RetainedEarningsAccumulatedDeficit_eb97e4ab-34d0-4eac-bb92-df673c3a3e65" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_RetainedEarningsAccumulatedDeficit"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_StockholdersEquity_7d2b14b9-136a-47da-9560-835112d406ad" xlink:to="loc_us-gaap_RetainedEarningsAccumulatedDeficit_eb97e4ab-34d0-4eac-bb92-df673c3a3e65" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesAndStockholdersEquity_f2949702-8116-46f6-9c88-8b48669d85c5" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LiabilitiesAndStockholdersEquity"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Liabilities_b7f0da82-9f16-420e-bea8-7825cdd03151" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_Liabilities"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesAndStockholdersEquity_f2949702-8116-46f6-9c88-8b48669d85c5" xlink:to="loc_us-gaap_Liabilities_b7f0da82-9f16-420e-bea8-7825cdd03151" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterest_5825a812-0801-42ed-8381-3d73db8cb354" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterest"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesAndStockholdersEquity_f2949702-8116-46f6-9c88-8b48669d85c5" xlink:to="loc_us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterest_5825a812-0801-42ed-8381-3d73db8cb354" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesCurrent_76d483a2-7c41-4ea4-9b18-4513fa2c1c3e" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LiabilitiesCurrent"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrent_34cbed06-2c76-428a-bdb4-616fe24a1ffd" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AccountsPayableAndAccruedLiabilitiesCurrent"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesCurrent_76d483a2-7c41-4ea4-9b18-4513fa2c1c3e" xlink:to="loc_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrent_34cbed06-2c76-428a-bdb4-616fe24a1ffd" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_gshd_PremiumsPayableCurrent_7a48e8bb-29c3-49f0-89b9-3ca7e3fe5941" xlink:href="gshd-20250630.xsd#gshd_PremiumsPayableCurrent"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesCurrent_76d483a2-7c41-4ea4-9b18-4513fa2c1c3e" xlink:to="loc_gshd_PremiumsPayableCurrent_7a48e8bb-29c3-49f0-89b9-3ca7e3fe5941" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseLiabilityCurrent_33d60d5f-3482-4631-b8c0-dac495dbcb21" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_OperatingLeaseLiabilityCurrent"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesCurrent_76d483a2-7c41-4ea4-9b18-4513fa2c1c3e" xlink:to="loc_us-gaap_OperatingLeaseLiabilityCurrent_33d60d5f-3482-4631-b8c0-dac495dbcb21" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ContractWithCustomerLiabilityCurrent_50cb77b6-7733-49e0-8e6c-113706dffeca" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ContractWithCustomerLiabilityCurrent"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesCurrent_76d483a2-7c41-4ea4-9b18-4513fa2c1c3e" xlink:to="loc_us-gaap_ContractWithCustomerLiabilityCurrent_50cb77b6-7733-49e0-8e6c-113706dffeca" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtCurrent_bac0edaa-28b9-4b85-87c9-8cb7a6ed1fe4" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LongTermDebtCurrent"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesCurrent_76d483a2-7c41-4ea4-9b18-4513fa2c1c3e" xlink:to="loc_us-gaap_LongTermDebtCurrent_bac0edaa-28b9-4b85-87c9-8cb7a6ed1fe4" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_gshd_LiabilitiesUnderTaxReceivableAgreementCurrent_af20169c-b302-4399-a5ce-b3a6d1398402" xlink:href="gshd-20250630.xsd#gshd_LiabilitiesUnderTaxReceivableAgreementCurrent"/>
    <link:calculationArc order="6" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesCurrent_76d483a2-7c41-4ea4-9b18-4513fa2c1c3e" xlink:to="loc_gshd_LiabilitiesUnderTaxReceivableAgreementCurrent_af20169c-b302-4399-a5ce-b3a6d1398402" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Liabilities_b84d891c-b7a6-4181-808d-f04db0158d6f" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_Liabilities"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesCurrent_7422d9ed-7012-4b8b-b155-5435495ed789" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LiabilitiesCurrent"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_Liabilities_b84d891c-b7a6-4181-808d-f04db0158d6f" xlink:to="loc_us-gaap_LiabilitiesCurrent_7422d9ed-7012-4b8b-b155-5435495ed789" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseLiabilityNoncurrent_c132187c-d197-406d-8663-be31cb760aba" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_OperatingLeaseLiabilityNoncurrent"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_Liabilities_b84d891c-b7a6-4181-808d-f04db0158d6f" xlink:to="loc_us-gaap_OperatingLeaseLiabilityNoncurrent_c132187c-d197-406d-8663-be31cb760aba" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtNoncurrent_080d6e13-3d35-499e-9498-8a5254d313a9" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LongTermDebtNoncurrent"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_Liabilities_b84d891c-b7a6-4181-808d-f04db0158d6f" xlink:to="loc_us-gaap_LongTermDebtNoncurrent_080d6e13-3d35-499e-9498-8a5254d313a9" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ContractWithCustomerLiabilityNoncurrent_ffcece9b-1fac-4550-9c14-1763e81da188" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ContractWithCustomerLiabilityNoncurrent"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_Liabilities_b84d891c-b7a6-4181-808d-f04db0158d6f" xlink:to="loc_us-gaap_ContractWithCustomerLiabilityNoncurrent_ffcece9b-1fac-4550-9c14-1763e81da188" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_gshd_LiabilitiesUnderTaxReceivableAgreementNoncurrent_0012f0b7-7220-4382-a59a-62bd10ec71fa" xlink:href="gshd-20250630.xsd#gshd_LiabilitiesUnderTaxReceivableAgreementNoncurrent"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_Liabilities_b84d891c-b7a6-4181-808d-f04db0158d6f" xlink:to="loc_gshd_LiabilitiesUnderTaxReceivableAgreementNoncurrent_0012f0b7-7220-4382-a59a-62bd10ec71fa" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterest_d4789433-8971-4602-8ccf-5dfcb789bf9f" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterest"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquity_120f4761-d0d9-47c6-a360-eafdd2fd7664" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_StockholdersEquity"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterest_d4789433-8971-4602-8ccf-5dfcb789bf9f" xlink:to="loc_us-gaap_StockholdersEquity_120f4761-d0d9-47c6-a360-eafdd2fd7664" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MinorityInterest_b45f680c-22e9-42b3-95ba-b88fffd2d24d" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_MinorityInterest"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterest_d4789433-8971-4602-8ccf-5dfcb789bf9f" xlink:to="loc_us-gaap_MinorityInterest_b45f680c-22e9-42b3-95ba-b88fffd2d24d" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.gooseheadinsurance.com/role/CondensedConsolidatedStatementsofCashFlowsUnaudited" xlink:type="simple" xlink:href="gshd-20250630.xsd#CondensedConsolidatedStatementsofCashFlowsUnaudited"/>
  <link:calculationLink xlink:role="http://www.gooseheadinsurance.com/role/CondensedConsolidatedStatementsofCashFlowsUnaudited" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_963840b2-e326-4cd9-a19a-545a3aa2ff34" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_52d3114e-ec9c-492e-86ba-683b579468c2" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_NetCashProvidedByUsedInOperatingActivities"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_963840b2-e326-4cd9-a19a-545a3aa2ff34" xlink:to="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_52d3114e-ec9c-492e-86ba-683b579468c2" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_329668a8-4e8e-4a09-a419-b157d2ea7a20" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_NetCashProvidedByUsedInInvestingActivities"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_963840b2-e326-4cd9-a19a-545a3aa2ff34" xlink:to="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_329668a8-4e8e-4a09-a419-b157d2ea7a20" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_67b516e6-bef6-44c9-ae91-796cf1398de0" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_NetCashProvidedByUsedInFinancingActivities"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_963840b2-e326-4cd9-a19a-545a3aa2ff34" xlink:to="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_67b516e6-bef6-44c9-ae91-796cf1398de0" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_4b491197-281b-4783-a85a-f811c4457443" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_NetCashProvidedByUsedInOperatingActivities"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProfitLoss_0e160144-c773-4ccc-be20-fc0e377fa340" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ProfitLoss"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_4b491197-281b-4783-a85a-f811c4457443" xlink:to="loc_us-gaap_ProfitLoss_0e160144-c773-4ccc-be20-fc0e377fa340" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DepreciationDepletionAndAmortization_91ab7fcc-1792-42b9-85dc-5e7d5229898a" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DepreciationDepletionAndAmortization"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_4b491197-281b-4783-a85a-f811c4457443" xlink:to="loc_us-gaap_DepreciationDepletionAndAmortization_91ab7fcc-1792-42b9-85dc-5e7d5229898a" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetImpairmentCharges_b295d806-7e45-46b1-9195-42120414ec36" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AssetImpairmentCharges"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_4b491197-281b-4783-a85a-f811c4457443" xlink:to="loc_us-gaap_AssetImpairmentCharges_b295d806-7e45-46b1-9195-42120414ec36" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProvisionForDoubtfulAccounts_981579d1-c1d7-4982-ad7f-106948726ef5" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ProvisionForDoubtfulAccounts"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_4b491197-281b-4783-a85a-f811c4457443" xlink:to="loc_us-gaap_ProvisionForDoubtfulAccounts_981579d1-c1d7-4982-ad7f-106948726ef5" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensation_b47ad563-639a-44bd-b2d9-24ac16d7e41a" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ShareBasedCompensation"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_4b491197-281b-4783-a85a-f811c4457443" xlink:to="loc_us-gaap_ShareBasedCompensation_b47ad563-639a-44bd-b2d9-24ac16d7e41a" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInDueToRelatedParties_56968945-96b5-4604-871c-8715db8aeda1" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncreaseDecreaseInDueToRelatedParties"/>
    <link:calculationArc order="6" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_4b491197-281b-4783-a85a-f811c4457443" xlink:to="loc_us-gaap_IncreaseDecreaseInDueToRelatedParties_56968945-96b5-4604-871c-8715db8aeda1" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredIncomeTaxExpenseBenefit_42cf472b-f2bb-42a0-9900-4c131669f686" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DeferredIncomeTaxExpenseBenefit"/>
    <link:calculationArc order="7" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_4b491197-281b-4783-a85a-f811c4457443" xlink:to="loc_us-gaap_DeferredIncomeTaxExpenseBenefit_42cf472b-f2bb-42a0-9900-4c131669f686" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_gshd_NoncashLeaseExpense_cac66571-32e1-4b26-b13a-74af08021f73" xlink:href="gshd-20250630.xsd#gshd_NoncashLeaseExpense"/>
    <link:calculationArc order="8" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_4b491197-281b-4783-a85a-f811c4457443" xlink:to="loc_gshd_NoncashLeaseExpense_cac66571-32e1-4b26-b13a-74af08021f73" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_gshd_IncreaseDecreaseInAccountsReceivableFranchiseReceivable_bc458d6b-3046-4fb2-9fda-832d72afc493" xlink:href="gshd-20250630.xsd#gshd_IncreaseDecreaseInAccountsReceivableFranchiseReceivable"/>
    <link:calculationArc order="9" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_4b491197-281b-4783-a85a-f811c4457443" xlink:to="loc_gshd_IncreaseDecreaseInAccountsReceivableFranchiseReceivable_bc458d6b-3046-4fb2-9fda-832d72afc493" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_gshd_IncreaseDecreaseInAccountsReceivableCommissionsAndAgencyFeesReceivable_3e36c5a4-243b-4f82-b48b-0a67e664f502" xlink:href="gshd-20250630.xsd#gshd_IncreaseDecreaseInAccountsReceivableCommissionsAndAgencyFeesReceivable"/>
    <link:calculationArc order="10" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_4b491197-281b-4783-a85a-f811c4457443" xlink:to="loc_gshd_IncreaseDecreaseInAccountsReceivableCommissionsAndAgencyFeesReceivable_3e36c5a4-243b-4f82-b48b-0a67e664f502" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInPrepaidExpense_7fdc43df-867c-4d87-af5d-4e7b3a5607e4" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncreaseDecreaseInPrepaidExpense"/>
    <link:calculationArc order="11" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_4b491197-281b-4783-a85a-f811c4457443" xlink:to="loc_us-gaap_IncreaseDecreaseInPrepaidExpense_7fdc43df-867c-4d87-af5d-4e7b3a5607e4" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInOtherOperatingAssets_9e1a92ce-c2c7-471b-8667-c76fdca8d13e" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncreaseDecreaseInOtherOperatingAssets"/>
    <link:calculationArc order="12" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_4b491197-281b-4783-a85a-f811c4457443" xlink:to="loc_us-gaap_IncreaseDecreaseInOtherOperatingAssets_9e1a92ce-c2c7-471b-8667-c76fdca8d13e" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities_83ebf031-cf37-4475-a9ba-29674f74014c" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities"/>
    <link:calculationArc order="13" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_4b491197-281b-4783-a85a-f811c4457443" xlink:to="loc_us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities_83ebf031-cf37-4475-a9ba-29674f74014c" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInContractWithCustomerLiability_2fe1df64-82c5-46e4-ae89-9a58497573a4" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_IncreaseDecreaseInContractWithCustomerLiability"/>
    <link:calculationArc order="14" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_4b491197-281b-4783-a85a-f811c4457443" xlink:to="loc_us-gaap_IncreaseDecreaseInContractWithCustomerLiability_2fe1df64-82c5-46e4-ae89-9a58497573a4" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_gshd_PaymentsForCloudComputingArrangements_f2e2bd6f-6405-42fd-896a-c550035ac3f7" xlink:href="gshd-20250630.xsd#gshd_PaymentsForCloudComputingArrangements"/>
    <link:calculationArc order="15" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_4b491197-281b-4783-a85a-f811c4457443" xlink:to="loc_gshd_PaymentsForCloudComputingArrangements_f2e2bd6f-6405-42fd-896a-c550035ac3f7" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GainsLossesOnExtinguishmentOfDebt_2bc34770-36d0-4d98-af91-e95a2f2c5f62" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_GainsLossesOnExtinguishmentOfDebt"/>
    <link:calculationArc order="16" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_4b491197-281b-4783-a85a-f811c4457443" xlink:to="loc_us-gaap_GainsLossesOnExtinguishmentOfDebt_2bc34770-36d0-4d98-af91-e95a2f2c5f62" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GainLossOnDispositionOfAssets_a8b13592-9c58-4e9c-818e-30eceae27962" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_GainLossOnDispositionOfAssets"/>
    <link:calculationArc order="17" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_4b491197-281b-4783-a85a-f811c4457443" xlink:to="loc_us-gaap_GainLossOnDispositionOfAssets_a8b13592-9c58-4e9c-818e-30eceae27962" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_ef2edead-4d07-4e28-b0d9-d4d47e2bd3fc" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_NetCashProvidedByUsedInFinancingActivities"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromIssuanceInitialPublicOffering_791c000e-9cd1-4642-bb6e-fedb66ae7c92" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ProceedsFromIssuanceInitialPublicOffering"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_ef2edead-4d07-4e28-b0d9-d4d47e2bd3fc" xlink:to="loc_us-gaap_ProceedsFromIssuanceInitialPublicOffering_791c000e-9cd1-4642-bb6e-fedb66ae7c92" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_gshd_PaymentForPartnershipDistributionsAndDividends_c476840e-ee1e-4f90-add8-fcc07f3aa40e" xlink:href="gshd-20250630.xsd#gshd_PaymentForPartnershipDistributionsAndDividends"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_ef2edead-4d07-4e28-b0d9-d4d47e2bd3fc" xlink:to="loc_gshd_PaymentForPartnershipDistributionsAndDividends_c476840e-ee1e-4f90-add8-fcc07f3aa40e" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_gshd_IncreaseDecreaseInCustomerPremiums_802e82e9-c955-468f-aa90-da7dad1e9303" xlink:href="gshd-20250630.xsd#gshd_IncreaseDecreaseInCustomerPremiums"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_ef2edead-4d07-4e28-b0d9-d4d47e2bd3fc" xlink:to="loc_gshd_IncreaseDecreaseInCustomerPremiums_802e82e9-c955-468f-aa90-da7dad1e9303" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RepaymentsOfSecuredDebt_b8fd8c83-cc7c-4bcb-89ef-2857522f11b5" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_RepaymentsOfSecuredDebt"/>
    <link:calculationArc order="4" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_ef2edead-4d07-4e28-b0d9-d4d47e2bd3fc" xlink:to="loc_us-gaap_RepaymentsOfSecuredDebt_b8fd8c83-cc7c-4bcb-89ef-2857522f11b5" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromIssuanceOfSecuredDebt_c838cc18-1bf5-432c-a330-088332bc14f5" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ProceedsFromIssuanceOfSecuredDebt"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_ef2edead-4d07-4e28-b0d9-d4d47e2bd3fc" xlink:to="loc_us-gaap_ProceedsFromIssuanceOfSecuredDebt_c838cc18-1bf5-432c-a330-088332bc14f5" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsOfDebtIssuanceCosts_3b94788b-9037-4121-9d26-b85bc25b0be0" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PaymentsOfDebtIssuanceCosts"/>
    <link:calculationArc order="6" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_ef2edead-4d07-4e28-b0d9-d4d47e2bd3fc" xlink:to="loc_us-gaap_PaymentsOfDebtIssuanceCosts_3b94788b-9037-4121-9d26-b85bc25b0be0" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsForRepurchaseOfCommonStock_6e755427-0064-4f8a-87a8-6cf942c05902" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PaymentsForRepurchaseOfCommonStock"/>
    <link:calculationArc order="7" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_ef2edead-4d07-4e28-b0d9-d4d47e2bd3fc" xlink:to="loc_us-gaap_PaymentsForRepurchaseOfCommonStock_6e755427-0064-4f8a-87a8-6cf942c05902" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_62fd077c-f4e5-4ea2-a5d1-66bf3477e42b" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_NetCashProvidedByUsedInInvestingActivities"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireNotesReceivable_3eb64737-4fc8-427f-aa96-52c86104dc25" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PaymentsToAcquireNotesReceivable"/>
    <link:calculationArc order="1" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_62fd077c-f4e5-4ea2-a5d1-66bf3477e42b" xlink:to="loc_us-gaap_PaymentsToAcquireNotesReceivable_3eb64737-4fc8-427f-aa96-52c86104dc25" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsForSoftware_dc0736a0-3af1-45ab-8c91-df940724858d" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PaymentsForSoftware"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_62fd077c-f4e5-4ea2-a5d1-66bf3477e42b" xlink:to="loc_us-gaap_PaymentsForSoftware_dc0736a0-3af1-45ab-8c91-df940724858d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment_fceb2be4-5da0-4dc4-aaaf-207b3a246087" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PaymentsToAcquirePropertyPlantAndEquipment"/>
    <link:calculationArc order="3" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_62fd077c-f4e5-4ea2-a5d1-66bf3477e42b" xlink:to="loc_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment_fceb2be4-5da0-4dc4-aaaf-207b3a246087" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromSaleAndCollectionOfNotesReceivable_7d4bb9a9-e694-43d9-94b8-936a4df6331f" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ProceedsFromSaleAndCollectionOfNotesReceivable"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_62fd077c-f4e5-4ea2-a5d1-66bf3477e42b" xlink:to="loc_us-gaap_ProceedsFromSaleAndCollectionOfNotesReceivable_7d4bb9a9-e694-43d9-94b8-936a4df6331f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetAcquisitionConsiderationTransferred_fd176d93-e77c-4b72-a1fc-ce9c20a6d008" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AssetAcquisitionConsiderationTransferred"/>
    <link:calculationArc order="5" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_62fd077c-f4e5-4ea2-a5d1-66bf3477e42b" xlink:to="loc_us-gaap_AssetAcquisitionConsiderationTransferred_fd176d93-e77c-4b72-a1fc-ce9c20a6d008" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.gooseheadinsurance.com/role/SummaryofSignificantAccountingPoliciesScheduleofRestrictedCashDetails" xlink:type="simple" xlink:href="gshd-20250630.xsd#SummaryofSignificantAccountingPoliciesScheduleofRestrictedCashDetails"/>
  <link:calculationLink xlink:role="http://www.gooseheadinsurance.com/role/SummaryofSignificantAccountingPoliciesScheduleofRestrictedCashDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_79f44bf3-6f41-4137-9050-038afb2dc788" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashAndCashEquivalentsAtCarryingValue_3f781d49-0323-4c17-9174-418e1981ee76" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_CashAndCashEquivalentsAtCarryingValue"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_79f44bf3-6f41-4137-9050-038afb2dc788" xlink:to="loc_us-gaap_CashAndCashEquivalentsAtCarryingValue_3f781d49-0323-4c17-9174-418e1981ee76" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestrictedCashAndCashEquivalentsAtCarryingValue_31181be4-de63-4f2c-9712-941a7d4b89eb" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_RestrictedCashAndCashEquivalentsAtCarryingValue"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_79f44bf3-6f41-4137-9050-038afb2dc788" xlink:to="loc_us-gaap_RestrictedCashAndCashEquivalentsAtCarryingValue_31181be4-de63-4f2c-9712-941a7d4b89eb" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.gooseheadinsurance.com/role/FranchiseFeesReceivableScheduleofFranchiseFeesReceivableDetails" xlink:type="simple" xlink:href="gshd-20250630.xsd#FranchiseFeesReceivableScheduleofFranchiseFeesReceivableDetails"/>
  <link:calculationLink xlink:role="http://www.gooseheadinsurance.com/role/FranchiseFeesReceivableScheduleofFranchiseFeesReceivableDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NotesReceivableNet_847ecf4c-0eab-4311-82e4-aa40c909b18e" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_NotesReceivableNet"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NotesReceivableGross_f15fa987-670e-41d1-a23f-cc530b816f0c" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_NotesReceivableGross"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NotesReceivableNet_847ecf4c-0eab-4311-82e4-aa40c909b18e" xlink:to="loc_us-gaap_NotesReceivableGross_f15fa987-670e-41d1-a23f-cc530b816f0c" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReceivableWithImputedInterestDiscount_ec30a2c4-dd88-41df-8e07-8bbbb41801cf" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_ReceivableWithImputedInterestDiscount"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NotesReceivableNet_847ecf4c-0eab-4311-82e4-aa40c909b18e" xlink:to="loc_us-gaap_ReceivableWithImputedInterestDiscount_ec30a2c4-dd88-41df-8e07-8bbbb41801cf" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancingReceivableAllowanceForCreditLosses_09c67484-3a78-4469-9931-6c47be610777" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FinancingReceivableAllowanceForCreditLosses"/>
    <link:calculationArc order="3" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NotesReceivableNet_847ecf4c-0eab-4311-82e4-aa40c909b18e" xlink:to="loc_us-gaap_FinancingReceivableAllowanceForCreditLosses_09c67484-3a78-4469-9931-6c47be610777" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.gooseheadinsurance.com/role/PropertyandequipmentDetails" xlink:type="simple" xlink:href="gshd-20250630.xsd#PropertyandequipmentDetails"/>
  <link:calculationLink xlink:role="http://www.gooseheadinsurance.com/role/PropertyandequipmentDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentNet_ff42e097-3d74-42c6-9274-cfb2fd0ce317" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PropertyPlantAndEquipmentNet"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentGross_6cbb0a31-38d8-4934-a63a-31fb1f421d80" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_PropertyPlantAndEquipmentGross"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentNet_ff42e097-3d74-42c6-9274-cfb2fd0ce317" xlink:to="loc_us-gaap_PropertyPlantAndEquipmentGross_6cbb0a31-38d8-4934-a63a-31fb1f421d80" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccumulatedDepreciationDepletionAndAmortizationPropertyPlantAndEquipment_ae002bd8-5a10-48b9-9250-1f3124e454ec" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_AccumulatedDepreciationDepletionAndAmortizationPropertyPlantAndEquipment"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentNet_ff42e097-3d74-42c6-9274-cfb2fd0ce317" xlink:to="loc_us-gaap_AccumulatedDepreciationDepletionAndAmortizationPropertyPlantAndEquipment_ae002bd8-5a10-48b9-9250-1f3124e454ec" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.gooseheadinsurance.com/role/IntangibleassetsDetails" xlink:type="simple" xlink:href="gshd-20250630.xsd#IntangibleassetsDetails"/>
  <link:calculationLink xlink:role="http://www.gooseheadinsurance.com/role/IntangibleassetsDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsNet_e6475d27-cd0f-4010-be6c-e44b6c7312f8" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FiniteLivedIntangibleAssetsNet"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization_94b5a9b3-c8e2-4d63-8671-23c98ec9c90d" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization"/>
    <link:calculationArc order="1" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsNet_e6475d27-cd0f-4010-be6c-e44b6c7312f8" xlink:to="loc_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization_94b5a9b3-c8e2-4d63-8671-23c98ec9c90d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsGross_c96326f2-6087-4c99-b1c6-4f763d2a480b" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_FiniteLivedIntangibleAssetsGross"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsNet_e6475d27-cd0f-4010-be6c-e44b6c7312f8" xlink:to="loc_us-gaap_FiniteLivedIntangibleAssetsGross_c96326f2-6087-4c99-b1c6-4f763d2a480b" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.gooseheadinsurance.com/role/DebtScheduleofMaturitiesofNotePayableDetails" xlink:type="simple" xlink:href="gshd-20250630.xsd#DebtScheduleofMaturitiesofNotePayableDetails"/>
  <link:calculationLink xlink:role="http://www.gooseheadinsurance.com/role/DebtScheduleofMaturitiesofNotePayableDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentCarryingAmount_32938e0a-dd65-4ebd-809f-10de909f766b" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_DebtInstrumentCarryingAmount"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalRemainderOfFiscalYear_148bd262-c893-43b0-979d-b491ab9f2354" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalRemainderOfFiscalYear"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_DebtInstrumentCarryingAmount_32938e0a-dd65-4ebd-809f-10de909f766b" xlink:to="loc_us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalRemainderOfFiscalYear_148bd262-c893-43b0-979d-b491ab9f2354" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInNextTwelveMonths_21b24a32-116d-489e-b848-a4917dbc9da7" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInNextTwelveMonths"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_DebtInstrumentCarryingAmount_32938e0a-dd65-4ebd-809f-10de909f766b" xlink:to="loc_us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInNextTwelveMonths_21b24a32-116d-489e-b848-a4917dbc9da7" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInYearTwo_6c9ba2f8-c370-4b39-b472-318bb5ff72bf" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInYearTwo"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_DebtInstrumentCarryingAmount_32938e0a-dd65-4ebd-809f-10de909f766b" xlink:to="loc_us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInYearTwo_6c9ba2f8-c370-4b39-b472-318bb5ff72bf" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInYearThree_cca90e45-d616-4870-a3c9-c8e564730830" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInYearThree"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_DebtInstrumentCarryingAmount_32938e0a-dd65-4ebd-809f-10de909f766b" xlink:to="loc_us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInYearThree_cca90e45-d616-4870-a3c9-c8e564730830" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInYearFour_c18eee46-c8fc-4695-a9c1-419a844b4288" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInYearFour"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_DebtInstrumentCarryingAmount_32938e0a-dd65-4ebd-809f-10de909f766b" xlink:to="loc_us-gaap_LongTermDebtMaturitiesRepaymentsOfPrincipalInYearFour_c18eee46-c8fc-4695-a9c1-419a844b4288" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://www.gooseheadinsurance.com/role/StockholdersEquityScheduleofEarningsPerShareBasicandDilutedDetails" xlink:type="simple" xlink:href="gshd-20250630.xsd#StockholdersEquityScheduleofEarningsPerShareBasicandDilutedDetails"/>
  <link:calculationLink xlink:role="http://www.gooseheadinsurance.com/role/StockholdersEquityScheduleofEarningsPerShareBasicandDilutedDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted_0d03fe84-3414-49b6-a981-49f09ef74a8d" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted"/>
    <link:loc xlink:type="locator" xlink:label="loc_gshd_IncomeTaxEffectOnIncomeAttributableToNonControllingInterests_1b79acc6-a522-4843-8eef-9f5e08f9db0e" xlink:href="gshd-20250630.xsd#gshd_IncomeTaxEffectOnIncomeAttributableToNonControllingInterests"/>
    <link:calculationArc order="1" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted_0d03fe84-3414-49b6-a981-49f09ef74a8d" xlink:to="loc_gshd_IncomeTaxEffectOnIncomeAttributableToNonControllingInterests_1b79acc6-a522-4843-8eef-9f5e08f9db0e" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic_96393149-0979-42f0-b11c-c85b59e3257f" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted_0d03fe84-3414-49b6-a981-49f09ef74a8d" xlink:to="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic_96393149-0979-42f0-b11c-c85b59e3257f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_gshd_IncomeLossBeforeIncomeTaxesAttributableToNoncontrollingInterest_6fab3a77-2ec9-440d-896e-25abc8bc01cf" xlink:href="gshd-20250630.xsd#gshd_IncomeLossBeforeIncomeTaxesAttributableToNoncontrollingInterest"/>
    <link:calculationArc order="3" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted_0d03fe84-3414-49b6-a981-49f09ef74a8d" xlink:to="loc_gshd_IncomeLossBeforeIncomeTaxesAttributableToNoncontrollingInterest_6fab3a77-2ec9-440d-896e-25abc8bc01cf" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_0251e3e0-d542-4e4c-95a5-aa17e79a3caa" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic_1334d880-311b-4538-aa5b-32d8df846819" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_WeightedAverageNumberOfSharesOutstandingBasic"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_0251e3e0-d542-4e4c-95a5-aa17e79a3caa" xlink:to="loc_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic_1334d880-311b-4538-aa5b-32d8df846819" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustment_fbb7a551-a808-44a7-a3b9-fe9ff6907d63" xlink:href="https://xbrl.fasb.org/us-gaap/2025/elts/us-gaap-2025.xsd#us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustment"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_0251e3e0-d542-4e4c-95a5-aa17e79a3caa" xlink:to="loc_us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustment_fbb7a551-a808-44a7-a3b9-fe9ff6907d63" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_gshd_WeightedAverageNumberOfSharesOutstandingDilutedDilutiveConvertibleSecurities_af89eaa8-13ac-4201-87ca-714edeb66615" xlink:href="gshd-20250630.xsd#gshd_WeightedAverageNumberOfSharesOutstandingDilutedDilutiveConvertibleSecurities"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_0251e3e0-d542-4e4c-95a5-aa17e79a3caa" xlink:to="loc_gshd_WeightedAverageNumberOfSharesOutstandingDilutedDilutiveConvertibleSecurities_af89eaa8-13ac-4201-87ca-714edeb66615" xlink:type="arc"/>
  </link:calculationLink>
</link:linkbase>
