diff --git a/apps/api/src/services/organization.ts b/apps/api/src/services/organization.ts
index 2fbaee3e..24ff6051 100644
--- a/apps/api/src/services/organization.ts
+++ b/apps/api/src/services/organization.ts
@@ -15,6 +15,9 @@ import {
   getOrganizationAudienceMember,
   getOrganizationById,
   getOrganizationBySiteName,
+  getOrganizationMemberByIdAndOrg,
+  getOrganizationMemberIdByOrgAndProfile,
+  getOrganizationPlanBySubscriptionId,
   getOrganizationTeam,
   getOrganizations,
   revokeActiveOrganizationInvitesByEmails,
@@ -41,7 +44,7 @@ import { PLAN } from '@cio/utils/plans';
 import { ROLE } from '@cio/utils/constants';
 import { createOrganizationWithOwner } from '@api/services/onboarding';
 import { deriveAudienceMemberStatus } from '@api/utils/audience-member-status';
-import { getProfileById } from '@cio/db/queries/auth';
+import { getProfileById, getProfileByEmail } from '@cio/db/queries/auth';
 import { inviteTeamMembers as inviteTeamMembersSecure } from './organization/invite';
 import { trustCustomDomainHostname, untrustCustomDomainHostname } from '@cio/db/utils';
 
@@ -520,6 +523,45 @@ export async function getOrgSetupData(siteName: string) {
   }
 }
 
+async function resolveOrgPlanTriggeredBy(params: {
+  checkoutOrgId: string;
+  targetOrgId: string;
+  triggeredBy: number;
+  payload: Record<string, unknown> | null | undefined;
+}): Promise<number> {
+  const { checkoutOrgId, targetOrgId, triggeredBy, payload } = params;
+  const checkoutMember = await getOrganizationMemberByIdAndOrg(triggeredBy, checkoutOrgId);
+
+  if (checkoutMember?.profileId) {
+    if (targetOrgId === checkoutOrgId) {
+      return triggeredBy;
+    }
+
+    const primaryMemberId = await getOrganizationMemberIdByOrgAndProfile(targetOrgId, checkoutMember.profileId);
+
+    if (primaryMemberId) {
+      return primaryMemberId;
+    }
+  }
+
+  const customer = payload?.customer;
+
+  if (customer && typeof customer === 'object' && 'email' in customer && typeof customer.email === 'string') {
+    const profile = await getProfileByEmail(customer.email);
+    const memberId = profile ? await getOrganizationMemberIdByOrgAndProfile(targetOrgId, profile.id) : null;
+
+    if (memberId) {
+      return memberId;
+    }
+  }
+
+  throw new AppError(
+    'Could not resolve organization member for plan',
+    ErrorCodes.ORG_PLAN_CREATE_FAILED,
+    400
+  );
+}
+
 /**
  * Creates a new organization plan
  * @param data - Organization plan creation data
@@ -527,22 +569,42 @@ export async function getOrgSetupData(siteName: string) {
  */
 export async function createOrgPlan(data: TNewOrganizationPlan) {
   try {
+    if (!data.orgId || data.triggeredBy == null || !data.subscriptionId) {
+      throw new AppError('Missing organization plan fields', ErrorCodes.ORG_PLAN_CREATE_FAILED, 400);
+    }
+
+    const existingPlan = await getOrganizationPlanBySubscriptionId(data.subscriptionId);
+
+    if (existingPlan) {
+      return existingPlan;
+    }
+
     // Subscriptions always attach to the primary workspace, even if a
     // secondary org id was supplied at checkout.
-    const primary = data.orgId ? await getAccountPrimary(data.orgId) : null;
+    const primary = await getAccountPrimary(data.orgId);
     const targetOrgId = primary?.id ?? data.orgId;
+    const triggeredBy = await resolveOrgPlanTriggeredBy({
+      checkoutOrgId: data.orgId,
+      targetOrgId,
+      triggeredBy: data.triggeredBy,
+      payload: data.payload as Record<string, unknown> | null | undefined
+    });
 
     const plan = await createOrganizationPlan({
       orgId: targetOrgId,
       planName: data.planName,
       subscriptionId: data.subscriptionId,
-      triggeredBy: data.triggeredBy,
+      triggeredBy,
       payload: data.payload,
       isActive: true,
       provider: 'polar'
     });
     return plan;
   } catch (error) {
+    if (error instanceof AppError) {
+      throw error;
+    }
+
     throw new AppError(
       error instanceof Error ? error.message : 'Failed to create organization plan',
       ErrorCodes.ORG_PLAN_CREATE_FAILED,
diff --git a/apps/dashboard/src/lib/features/ui/upgrade-modal.svelte b/apps/dashboard/src/lib/features/ui/upgrade-modal.svelte
index 060f5418..0ceaea32 100644
--- a/apps/dashboard/src/lib/features/ui/upgrade-modal.svelte
+++ b/apps/dashboard/src/lib/features/ui/upgrade-modal.svelte
@@ -32,7 +32,7 @@
   });
 
   async function handleClick(plan, planName: string) {
-    if (plan.CTA.IS_DISABLED || !$profile.id || !$profile.email) {
+    if (plan.CTA.IS_DISABLED || !$profile.id || !$profile.email || !$currentOrg.memberId) {
       return;
     }
 
@@ -52,7 +52,7 @@
       checkoutURL.searchParams.set(
         'metadata',
         JSON.stringify({
-          triggeredBy: $currentOrg.roleId,
+          triggeredBy: $currentOrg.memberId,
           orgId: $currentOrg.id,
           orgSlug: $currentOrg.siteName
         })
diff --git a/apps/dashboard/src/lib/utils/store/org.ts b/apps/dashboard/src/lib/utils/store/org.ts
index 39eec5ed..2c5f758d 100644
--- a/apps/dashboard/src/lib/utils/store/org.ts
+++ b/apps/dashboard/src/lib/utils/store/org.ts
@@ -48,6 +48,7 @@ export const currentOrg: Writable<AccountOrg> = writable({
   parentOrganizationId: null,
   plans: [],
   readOnlyUntil: null,
+  memberId: 0,
   roleId: 0,
   settings: {},
   siteName: '',
diff --git a/packages/db/src/queries/organization/organization.ts b/packages/db/src/queries/organization/organization.ts
index 5753af69..55add7f0 100644
--- a/packages/db/src/queries/organization/organization.ts
+++ b/packages/db/src/queries/organization/organization.ts
@@ -42,6 +42,7 @@ export const getOrganizationByProfileId = async (profileId: string): Promise<Org
   const result = await db
     .select({
       organization: schema.organization,
+      memberId: schema.organizationmember.id,
       roleId: schema.organizationmember.roleId,
       plan: {
         planName: schema.organizationPlan.planName,
@@ -61,6 +62,7 @@ export const getOrganizationByProfileId = async (profileId: string): Promise<Org
     string,
     {
       organization: typeof schema.organization.$inferSelect;
+      memberId: number | undefined;
       roleId: number | undefined;
       plans: Array<OrganizationPlan>;
     }
@@ -72,6 +74,7 @@ export const getOrganizationByProfileId = async (profileId: string): Promise<Org
     if (!organizationMap.has(orgId)) {
       organizationMap.set(orgId, {
         organization: row.organization,
+        memberId: row.memberId ?? undefined,
         roleId: row.roleId ?? undefined,
         plans: []
       });
@@ -115,6 +118,32 @@ export const createOrganizationMember = async (data: TNewOrganizationmember, dbC
   return member;
 };
 
+export async function getOrganizationMemberByIdAndOrg(
+  memberId: number,
+  organizationId: string,
+  dbClient: DbOrTxClient = db
+): Promise<{ id: number; profileId: string | null } | null> {
+  try {
+    const [row] = await dbClient
+      .select({
+        id: schema.organizationmember.id,
+        profileId: schema.organizationmember.profileId
+      })
+      .from(schema.organizationmember)
+      .where(
+        and(eq(schema.organizationmember.id, memberId), eq(schema.organizationmember.organizationId, organizationId))
+      )
+      .limit(1);
+
+    return row ?? null;
+  } catch (error) {
+    console.error('getOrganizationMemberByIdAndOrg error:', error);
+    throw new Error(
+      `Failed to resolve organization membership: ${error instanceof Error ? error.message : 'Unknown error'}`
+    );
+  }
+}
+
 export async function getOrganizationMemberIdByOrgAndProfile(
   organizationId: string,
   profileId: string,
@@ -870,6 +899,26 @@ export const getOrganizationCount = async (): Promise<number> => {
  * @param dbClient Optional DB or transaction client for use within transactions
  * @returns Created organization plan record
  */
+export const getOrganizationPlanBySubscriptionId = async (
+  subscriptionId: string,
+  dbClient: DbOrTxClient = db
+): Promise<TOrganizationPlan | null> => {
+  try {
+    const [plan] = await dbClient
+      .select()
+      .from(schema.organizationPlan)
+      .where(eq(schema.organizationPlan.subscriptionId, subscriptionId))
+      .limit(1);
+
+    return plan ?? null;
+  } catch (error) {
+    console.error('getOrganizationPlanBySubscriptionId error:', error);
+    throw new Error(
+      `Failed to fetch organization plan: ${error instanceof Error ? error.message : 'Unknown error'}`
+    );
+  }
+};
+
 export const createOrganizationPlan = async (
   data: TNewOrganizationPlan,
   dbClient: DbOrTxClient = db
diff --git a/packages/db/src/queries/organization/types.ts b/packages/db/src/queries/organization/types.ts
index 5f60a1b4..ae85743e 100644
--- a/packages/db/src/queries/organization/types.ts
+++ b/packages/db/src/queries/organization/types.ts
@@ -5,6 +5,7 @@ export type OrganizationPlan = Pick<TOrganizationPlan, 'planName' | 'isActive' |
 };
 
 export type OrganizationWithMemberAndPlans = TOrganization & {
+  memberId?: number;
   roleId?: number;
   plans: OrganizationPlan[];
 };