diff --git a/.env.example b/.env.example
index 971dc8a620..cef10a0cf0 100644
--- a/.env.example
+++ b/.env.example
@@ -209,11 +209,13 @@ NEXT_PUBLIC_STRIPE_PREMIUM_PLAN_PRICE=
 NEXT_PUBLIC_IS_PREMIUM_NEW_PLAN=0
 NEXT_PUBLIC_STRIPE_PREMIUM_NEW_PLAN_PRICE=
 STRIPE_TEAM_MONTHLY_PRICE_ID=
+STRIPE_TEAM_ANNUAL_PRICE_ID=
 NEXT_PUBLIC_STRIPE_CREDITS_PRICE_ID=
 ORG_MONTHLY_CREDITS=
 STRIPE_TEAM_PRODUCT_ID=
 # It is a price ID in the product with id STRIPE_ORG_PRODUCT_ID
 STRIPE_ORG_MONTHLY_PRICE_ID=
+STRIPE_ORG_ANNUAL_PRICE_ID=
 STRIPE_ORG_PRODUCT_ID=
 # Used to pass trial days for orgs during the Stripe checkout session
 STRIPE_ORG_TRIAL_DAYS=
diff --git a/packages/features/ee/organizations/lib/OrganizationPaymentService.test.ts b/packages/features/ee/organizations/lib/OrganizationPaymentService.test.ts
index 77e801c687..09ca77a8d7 100644
--- a/packages/features/ee/organizations/lib/OrganizationPaymentService.test.ts
+++ b/packages/features/ee/organizations/lib/OrganizationPaymentService.test.ts
@@ -8,6 +8,7 @@ import type { IOrganizationPermissionService } from "./OrganizationPermissionSer
 
 vi.stubEnv("STRIPE_ORG_PRODUCT_ID", "STRIPE_ORG_PRODUCT_ID");
 vi.stubEnv("STRIPE_ORG_MONTHLY_PRICE_ID", "STRIPE_ORG_MONTHLY_PRICE_ID");
+vi.stubEnv("STRIPE_ORG_ANNUAL_PRICE_ID", "STRIPE_ORG_ANNUAL_PRICE_ID");
 const defaultOrgOnboarding = {
   id: "onboard-id-1",
   name: "Test Org",
@@ -209,6 +210,50 @@ describe("OrganizationPaymentService", () => {
       });
     });
 
+    it("should use annual fixed price when billingPeriod is ANNUALLY and no custom price", async () => {
+      vi.mocked(prisma.membership.findMany).mockResolvedValue([]);
+
+      await service.createPaymentIntent(
+        {
+          bio: "BIO",
+          logo: "LOGO",
+          teams: [],
+        },
+        {
+          ...defaultOrgOnboarding,
+          billingPeriod: "ANNUALLY",
+        }
+      );
+
+      expect(mockBillingService.createSubscriptionCheckout).toHaveBeenCalledWith(
+        expect.objectContaining({
+          priceId: "STRIPE_ORG_ANNUAL_PRICE_ID",
+        })
+      );
+    });
+
+    it("should use monthly fixed price when billingPeriod is MONTHLY and no custom price", async () => {
+      vi.mocked(prisma.membership.findMany).mockResolvedValue([]);
+
+      await service.createPaymentIntent(
+        {
+          bio: "BIO",
+          logo: "LOGO",
+          teams: [],
+        },
+        {
+          ...defaultOrgOnboarding,
+          billingPeriod: "MONTHLY",
+        }
+      );
+
+      expect(mockBillingService.createSubscriptionCheckout).toHaveBeenCalledWith(
+        expect.objectContaining({
+          priceId: "STRIPE_ORG_MONTHLY_PRICE_ID",
+        })
+      );
+    });
+
     describe("admin overrides", () => {
       beforeEach(() => {
         mockPermissionService.hasPermissionToModifyDefaultPayment.mockReturnValue(true);
diff --git a/packages/features/ee/organizations/lib/OrganizationPaymentService.ts b/packages/features/ee/organizations/lib/OrganizationPaymentService.ts
index 5a10aadcd3..96fc631bf4 100644
--- a/packages/features/ee/organizations/lib/OrganizationPaymentService.ts
+++ b/packages/features/ee/organizations/lib/OrganizationPaymentService.ts
@@ -219,11 +219,21 @@ export class OrganizationPaymentService {
       })
     );
 
-    if (!process.env.STRIPE_ORG_PRODUCT_ID || !process.env.STRIPE_ORG_MONTHLY_PRICE_ID) {
-      throw new Error("STRIPE_ORG_PRODUCT_ID or STRIPE_ORG_MONTHLY_PRICE_ID is not set");
+    if (!process.env.STRIPE_ORG_PRODUCT_ID) {
+      throw new Error("STRIPE_ORG_PRODUCT_ID is not set");
+    }
+
+    const fixedPriceId =
+      config.billingPeriod === "ANNUALLY"
+        ? process.env.STRIPE_ORG_ANNUAL_PRICE_ID
+        : process.env.STRIPE_ORG_MONTHLY_PRICE_ID;
+
+    if (!fixedPriceId) {
+      const envVar =
+        config.billingPeriod === "ANNUALLY" ? "STRIPE_ORG_ANNUAL_PRICE_ID" : "STRIPE_ORG_MONTHLY_PRICE_ID";
+      throw new Error(`${envVar} is not set`);
     }
 
-    const fixedPriceId = process.env.STRIPE_ORG_MONTHLY_PRICE_ID;
     if (!shouldCreateCustomPrice) {
       return {
         priceId: fixedPriceId,
diff --git a/packages/features/ee/teams/lib/payments.test.ts b/packages/features/ee/teams/lib/payments.test.ts
index b98990ae5b..4b4d0af7ab 100644
--- a/packages/features/ee/teams/lib/payments.test.ts
+++ b/packages/features/ee/teams/lib/payments.test.ts
@@ -6,6 +6,7 @@ import stripe from "@calcom/features/ee/payments/server/stripe";
 import { BillingPeriod } from "@calcom/prisma/zod-utils";
 
 import {
+  generateTeamCheckoutSession,
   getTeamWithPaymentMetadata,
   purchaseTeamOrOrgSubscription,
   updateQuantitySubscriptionFromStripe,
@@ -13,7 +14,9 @@ import {
 
 beforeEach(async () => {
   vi.stubEnv("STRIPE_ORG_MONTHLY_PRICE_ID", "STRIPE_ORG_MONTHLY_PRICE_ID");
+  vi.stubEnv("STRIPE_ORG_ANNUAL_PRICE_ID", "STRIPE_ORG_ANNUAL_PRICE_ID");
   vi.stubEnv("STRIPE_TEAM_MONTHLY_PRICE_ID", "STRIPE_TEAM_MONTHLY_PRICE_ID");
+  vi.stubEnv("STRIPE_TEAM_ANNUAL_PRICE_ID", "STRIPE_TEAM_ANNUAL_PRICE_ID");
   vi.resetAllMocks();
   // eslint-disable-next-line @typescript-eslint/ban-ts-comment
   // @ts-ignore
@@ -36,6 +39,12 @@ vi.mock("@calcom/app-store/stripepayment/lib/customer", () => {
   };
 });
 
+vi.mock("@calcom/features/auth/lib/dub", () => {
+  return {
+    getDubCustomer: vi.fn().mockResolvedValue(null),
+  };
+});
+
 vi.mock("@calcom/features/ee/payments/server/stripe", () => {
   return {
     default: {
@@ -58,6 +67,74 @@ vi.mock("@calcom/features/ee/payments/server/stripe", () => {
   };
 });
 
+describe("generateTeamCheckoutSession", () => {
+  it("should use monthly price by default", async () => {
+    const checkoutSessionsCreate = mockStripeCheckoutSessionsCreate({
+      url: "SESSION_URL",
+    });
+
+    await generateTeamCheckoutSession({
+      teamName: "Test Team",
+      teamSlug: "test-team",
+      userId: 1,
+    });
+
+    expect(checkoutSessionsCreate).toHaveBeenCalledWith(
+      expect.objectContaining({
+        line_items: [
+          expect.objectContaining({
+            price: "STRIPE_TEAM_MONTHLY_PRICE_ID",
+          }),
+        ],
+      })
+    );
+  });
+
+  it("should use annual price when billingPeriod is ANNUALLY", async () => {
+    const checkoutSessionsCreate = mockStripeCheckoutSessionsCreate({
+      url: "SESSION_URL",
+    });
+
+    await generateTeamCheckoutSession({
+      teamName: "Test Team",
+      teamSlug: "test-team",
+      userId: 1,
+      billingPeriod: BillingPeriod.ANNUALLY,
+    });
+
+    expect(checkoutSessionsCreate).toHaveBeenCalledWith(
+      expect.objectContaining({
+        line_items: [
+          expect.objectContaining({
+            price: "STRIPE_TEAM_ANNUAL_PRICE_ID",
+          }),
+        ],
+      })
+    );
+  });
+
+  it("should store billingPeriod in checkout session metadata", async () => {
+    const checkoutSessionsCreate = mockStripeCheckoutSessionsCreate({
+      url: "SESSION_URL",
+    });
+
+    await generateTeamCheckoutSession({
+      teamName: "Test Team",
+      teamSlug: "test-team",
+      userId: 1,
+      billingPeriod: BillingPeriod.ANNUALLY,
+    });
+
+    expect(checkoutSessionsCreate).toHaveBeenCalledWith(
+      expect.objectContaining({
+        metadata: expect.objectContaining({
+          billingPeriod: "ANNUALLY",
+        }),
+      })
+    );
+  });
+});
+
 describe("purchaseTeamOrOrgSubscription", () => {
   it("should use `seatsToChargeFor` to create price", async () => {
     const FAKE_PAYMENT_ID = "FAKE_PAYMENT_ID";
@@ -268,6 +345,116 @@ describe("purchaseTeamOrOrgSubscription", () => {
     );
   });
 
+  it("should use annual fixed price when billingPeriod is ANNUALLY and no custom price", async () => {
+    const FAKE_PAYMENT_ID = "FAKE_PAYMENT_ID";
+    const user = await prismock.user.create({
+      data: {
+        name: "test",
+        email: "test@email.com",
+      },
+    });
+
+    const checkoutSessionsCreate = mockStripeCheckoutSessionsCreate({
+      url: "SESSION_URL",
+    });
+
+    mockStripeCheckoutSessionRetrieve(
+      {
+        currency: "USD",
+        product: {
+          id: "PRODUCT_ID",
+        },
+      },
+      [FAKE_PAYMENT_ID]
+    );
+
+    const team = await prismock.team.create({
+      data: {
+        name: "test",
+        metadata: {
+          paymentId: FAKE_PAYMENT_ID,
+        },
+      },
+    });
+
+    expect(
+      await purchaseTeamOrOrgSubscription({
+        teamId: team.id,
+        seatsUsed: 10,
+        userId: user.id,
+        isOrg: false,
+        pricePerSeat: null,
+        billingPeriod: BillingPeriod.ANNUALLY,
+      })
+    ).toEqual({ url: "SESSION_URL" });
+
+    expect(checkoutSessionsCreate).toHaveBeenCalledWith(
+      expect.objectContaining({
+        line_items: [
+          {
+            price: "STRIPE_TEAM_ANNUAL_PRICE_ID",
+            quantity: 10,
+          },
+        ],
+      })
+    );
+  });
+
+  it("should use annual fixed price for org when billingPeriod is ANNUALLY and no custom price", async () => {
+    const FAKE_PAYMENT_ID = "FAKE_PAYMENT_ID";
+    const user = await prismock.user.create({
+      data: {
+        name: "test",
+        email: "test@email.com",
+      },
+    });
+
+    const checkoutSessionsCreate = mockStripeCheckoutSessionsCreate({
+      url: "SESSION_URL",
+    });
+
+    mockStripeCheckoutSessionRetrieve(
+      {
+        currency: "USD",
+        product: {
+          id: "PRODUCT_ID",
+        },
+      },
+      [FAKE_PAYMENT_ID]
+    );
+
+    const team = await prismock.team.create({
+      data: {
+        name: "test",
+        metadata: {
+          paymentId: FAKE_PAYMENT_ID,
+        },
+      },
+    });
+
+    expect(
+      await purchaseTeamOrOrgSubscription({
+        teamId: team.id,
+        seatsUsed: 5,
+        userId: user.id,
+        isOrg: true,
+        pricePerSeat: null,
+        billingPeriod: BillingPeriod.ANNUALLY,
+      })
+    ).toEqual({ url: "SESSION_URL" });
+
+    expect(checkoutSessionsCreate).toHaveBeenCalledWith(
+      expect.objectContaining({
+        line_items: [
+          {
+            price: "STRIPE_ORG_ANNUAL_PRICE_ID",
+            quantity: 5,
+          },
+        ],
+      })
+    );
+  });
+
   it("It should not create a custom price if price_per_seat is not set", async () => {
     const FAKE_PAYMENT_ID = "FAKE_PAYMENT_ID";
     const user = await prismock.user.create({
diff --git a/packages/features/ee/teams/lib/payments.ts b/packages/features/ee/teams/lib/payments.ts
index 4d59578ecc..ab31e48fab 100644
--- a/packages/features/ee/teams/lib/payments.ts
+++ b/packages/features/ee/teams/lib/payments.ts
@@ -43,6 +43,21 @@ export const checkIfTeamPaymentRequired = async ({ teamId = -1 }) => {
   return { url: `${WEBAPP_URL}/api/teams/${teamId}/upgrade?session_id=${metadata.paymentId}` };
 };
 
+function getTeamPriceId(billingPeriod: BillingPeriod): string {
+  const priceId =
+    billingPeriod === "ANNUALLY"
+      ? process.env.STRIPE_TEAM_ANNUAL_PRICE_ID
+      : process.env.STRIPE_TEAM_MONTHLY_PRICE_ID;
+
+  if (!priceId) {
+    throw new Error(
+      `Missing env var: ${billingPeriod === "ANNUALLY" ? "STRIPE_TEAM_ANNUAL_PRICE_ID" : "STRIPE_TEAM_MONTHLY_PRICE_ID"}`
+    );
+  }
+
+  return priceId;
+}
+
 /**
  * Used to generate a checkout session when trying to create a team
  */
@@ -51,18 +66,21 @@ export const generateTeamCheckoutSession = async ({
   teamSlug,
   userId,
   isOnboarding,
+  billingPeriod = BillingPeriod.MONTHLY,
   tracking,
 }: {
   teamName: string;
   teamSlug: string;
   userId: number;
   isOnboarding?: boolean;
+  billingPeriod?: BillingPeriod;
   tracking?: TrackingData;
 }) => {
   const [customer, dubCustomer] = await Promise.all([
     getStripeCustomerIdFromUserId(userId),
     getDubCustomer(userId.toString()),
   ]);
+  const priceId = getTeamPriceId(billingPeriod);
   const session = await stripe.checkout.sessions.create({
     customer,
     mode: "subscription",
@@ -83,7 +101,7 @@ export const generateTeamCheckoutSession = async ({
     line_items: [
       {
         /** We only need to set the base price and we can upsell it directly on Stripe's checkout  */
-        price: process.env.STRIPE_TEAM_MONTHLY_PRICE_ID,
+        price: priceId,
         /**Initially it will be just the team owner */
         quantity: 1,
       },
@@ -106,6 +124,7 @@ export const generateTeamCheckoutSession = async ({
       teamName,
       teamSlug,
       userId,
+      billingPeriod,
       dubCustomerId: userId, // pass the userId during checkout creation for sales conversion tracking: https://d.to/conversions/stripe
       ...(isOnboarding !== undefined && { isOnboarding: isOnboarding.toString() }),
       ...(tracking?.googleAds?.gclid && {
@@ -269,17 +288,27 @@ export const purchaseTeamOrOrgSubscription = async (input: {
    * If the organization has a custom price per seat, it will create a new price in stripe and return its ID.
    */
   async function getFixedPrice() {
+    const isAnnual = billingPeriod === "ANNUALLY";
     const fixedPriceId = isOrg
-      ? process.env.STRIPE_ORG_MONTHLY_PRICE_ID
-      : process.env.STRIPE_TEAM_MONTHLY_PRICE_ID;
+      ? isAnnual
+        ? process.env.STRIPE_ORG_ANNUAL_PRICE_ID
+        : process.env.STRIPE_ORG_MONTHLY_PRICE_ID
+      : isAnnual
+        ? process.env.STRIPE_TEAM_ANNUAL_PRICE_ID
+        : process.env.STRIPE_TEAM_MONTHLY_PRICE_ID;
 
     if (!fixedPriceId) {
-      throw new Error(
-        "You need to have STRIPE_ORG_MONTHLY_PRICE_ID and STRIPE_TEAM_MONTHLY_PRICE_ID env variables set"
-      );
+      const envVar = isOrg
+        ? isAnnual
+          ? "STRIPE_ORG_ANNUAL_PRICE_ID"
+          : "STRIPE_ORG_MONTHLY_PRICE_ID"
+        : isAnnual
+          ? "STRIPE_TEAM_ANNUAL_PRICE_ID"
+          : "STRIPE_TEAM_MONTHLY_PRICE_ID";
+      throw new Error(`Missing env var: ${envVar}`);
     }
 
-    log.debug("Getting price ID", safeStringify({ fixedPriceId, isOrg, teamId, pricePerSeat }));
+    log.debug("Getting price ID", safeStringify({ fixedPriceId, isOrg, teamId, pricePerSeat, billingPeriod }));
 
     return fixedPriceId;
   }
diff --git a/packages/trpc/server/routers/viewer/organizations/createWithPaymentIntent.handler.test.ts b/packages/trpc/server/routers/viewer/organizations/createWithPaymentIntent.handler.test.ts
index 7927f8fca8..909dcc7e2e 100644
--- a/packages/trpc/server/routers/viewer/organizations/createWithPaymentIntent.handler.test.ts
+++ b/packages/trpc/server/routers/viewer/organizations/createWithPaymentIntent.handler.test.ts
@@ -13,6 +13,7 @@ import { createHandler } from "./createWithPaymentIntent.handler";
 
 vi.stubEnv("STRIPE_PRIVATE_KEY", "test-stripe-private-key");
 vi.stubEnv("STRIPE_ORG_MONTHLY_PRICE_ID", "test-stripe-org-monthly-price-id");
+vi.stubEnv("STRIPE_ORG_ANNUAL_PRICE_ID", "test-stripe-org-annual-price-id");
 vi.stubEnv("STRIPE_ORG_PRODUCT_ID", "test-stripe-org-product-id");
 vi.stubEnv("NEXT_PUBLIC_ORGANIZATIONS_SELF_SERVE_PRICE_NEW", "37");
 
diff --git a/packages/trpc/server/routers/viewer/teams/create.handler.ts b/packages/trpc/server/routers/viewer/teams/create.handler.ts
index df2150a1e1..79fb2be812 100644
--- a/packages/trpc/server/routers/viewer/teams/create.handler.ts
+++ b/packages/trpc/server/routers/viewer/teams/create.handler.ts
@@ -9,6 +9,7 @@ import { getTrackingFromCookies } from "@calcom/lib/tracking";
 import type { TrackingData } from "@calcom/lib/tracking";
 import { prisma } from "@calcom/prisma";
 import { MembershipRole } from "@calcom/prisma/enums";
+import type { BillingPeriod as BillingPeriodEnum } from "@calcom/prisma/zod-utils";
 
 import { TRPCError } from "@trpc/server";
 
@@ -28,12 +29,14 @@ const generateCheckoutSession = async ({
   teamName,
   userId,
   isOnboarding,
+  billingPeriod,
   tracking,
 }: {
   teamSlug: string;
   teamName: string;
   userId: number;
   isOnboarding?: boolean;
+  billingPeriod?: "MONTHLY" | "ANNUALLY";
   tracking?: TrackingData;
 }) => {
   if (!IS_TEAM_BILLING_ENABLED) {
@@ -46,6 +49,7 @@ const generateCheckoutSession = async ({
     teamName,
     userId,
     isOnboarding,
+    billingPeriod: billingPeriod as BillingPeriodEnum | undefined,
     tracking,
   });
 
@@ -59,7 +63,7 @@ const generateCheckoutSession = async ({
 
 export const createHandler = async ({ ctx, input }: CreateOptions) => {
   const { user } = ctx;
-  const { slug, name, bio, isOnboarding } = input;
+  const { slug, name, bio, isOnboarding, billingPeriod } = input;
   const isOrgChildTeam = !!user.profile?.organizationId;
 
   // For orgs we want to create teams under the org
@@ -94,6 +98,7 @@ export const createHandler = async ({ ctx, input }: CreateOptions) => {
       teamName: name,
       userId: user.id,
       isOnboarding,
+      billingPeriod,
       tracking,
     });
 
diff --git a/packages/trpc/server/routers/viewer/teams/create.schema.ts b/packages/trpc/server/routers/viewer/teams/create.schema.ts
index 7dd088e0a2..41e4fc8011 100644
--- a/packages/trpc/server/routers/viewer/teams/create.schema.ts
+++ b/packages/trpc/server/routers/viewer/teams/create.schema.ts
@@ -1,6 +1,7 @@
 import { z } from "zod";
 
 import slugify from "@calcom/lib/slugify";
+import type { BillingPeriod } from "@calcom/prisma/enums";
 
 export type TCreateInputSchema = {
   name: string;
@@ -8,6 +9,7 @@ export type TCreateInputSchema = {
   logo?: string | null;
   bio?: string;
   isOnboarding?: boolean;
+  billingPeriod?: BillingPeriod;
 };
 
 export const ZCreateInputSchema: z.ZodType<TCreateInputSchema> = z.object({
@@ -20,4 +22,5 @@ export const ZCreateInputSchema: z.ZodType<TCreateInputSchema> = z.object({
     .transform((v) => v || null),
   bio: z.string().optional(),
   isOnboarding: z.boolean().optional(),
+  billingPeriod: z.enum(["MONTHLY", "ANNUALLY"]).optional(),
 });
diff --git a/turbo.json b/turbo.json
index bdf2a80aa1..7a7c2ddb56 100644
--- a/turbo.json
+++ b/turbo.json
@@ -175,8 +175,10 @@
     "STRIPE_WEBHOOK_SECRET_APPS",
     "STRIPE_WEBHOOK_SECRET_BILLING",
     "STRIPE_TEAM_MONTHLY_PRICE_ID",
+    "STRIPE_TEAM_ANNUAL_PRICE_ID",
     "STRIPE_TEAM_PRODUCT_ID",
     "STRIPE_ORG_MONTHLY_PRICE_ID",
+    "STRIPE_ORG_ANNUAL_PRICE_ID",
     "STRIPE_ORG_PRODUCT_ID",
     "STRIPE_ORG_TRIAL_DAYS",
     "TANDEM_BASE_URL",
@@ -372,10 +374,12 @@
         "SENTRY_REPLAYS_ON_ERROR_SAMPLE_RATE",
         "STRIPE_PREMIUM_PLAN_PRODUCT_ID",
         "STRIPE_TEAM_MONTHLY_PRICE_ID",
+        "STRIPE_TEAM_ANNUAL_PRICE_ID",
         "NEXT_PUBLIC_STRIPE_CREDITS_PRICE_ID",
         "STRIPE_TEAM_PRODUCT_ID",
         "ORG_MONTHLY_CREDITS",
         "STRIPE_ORG_MONTHLY_PRICE_ID",
+        "STRIPE_ORG_ANNUAL_PRICE_ID",
         "STRIPE_ORG_PRODUCT_ID",
         "STRIPE_ORG_TRIAL_DAYS",
         "NEXT_PUBLIC_API_V2_URL",