diff --git a/.env.example b/.env.example
index fe36f11116..003c195a22 100644
--- a/.env.example
+++ b/.env.example
@@ -19,6 +19,11 @@
 # instructions. This environment variable is deprecated although still supported for backward compatibility.
 # @see https://console.cal.com
 CALCOM_LICENSE_KEY=
+# Signature token for the Cal.com License API (used for self-hosted integrations)
+# We will give you a token when we provide you with a license key this ensure you and only you can communicate with the Cal.com License API for your license key
+CAL_SIGNATURE_TOKEN=
+# The route to the Cal.com License API
+CALCOM_PRIVATE_API_ROUTE=
 # ***********************************************************************************************************
 
 # - DATABASE ************************************************************************************************
diff --git a/apps/web/lib/settings/license-keys/new/getServerSideProps.tsx b/apps/web/lib/settings/license-keys/new/getServerSideProps.tsx
new file mode 100644
index 0000000000..600c2ece01
--- /dev/null
+++ b/apps/web/lib/settings/license-keys/new/getServerSideProps.tsx
@@ -0,0 +1,22 @@
+import type { GetServerSidePropsContext } from "next";
+
+import { getServerSession } from "@calcom/feature-auth/lib/getServerSession";
+import { AUTH_OPTIONS } from "@calcom/feature-auth/lib/next-auth-options";
+
+export const getServerSideProps = async (context: GetServerSidePropsContext) => {
+  const session = await getServerSession({
+    req: context.req,
+    res: context.res,
+    authOptions: AUTH_OPTIONS,
+  });
+  // Disable this check if we ever make this self serve.
+  if (session?.user.role !== "ADMIN") {
+    return {
+      notFound: true,
+    } as const;
+  }
+
+  return {
+    props: {},
+  };
+};
diff --git a/apps/web/pages/settings/license-key/new/index.tsx b/apps/web/pages/settings/license-key/new/index.tsx
new file mode 100644
index 0000000000..f217036ee2
--- /dev/null
+++ b/apps/web/pages/settings/license-key/new/index.tsx
@@ -0,0 +1,33 @@
+"use client";
+
+import LicenseRequired from "@calcom/features/ee/common/components/LicenseRequired";
+import { CreateANewLicenseKeyForm } from "@calcom/features/ee/deployment/licensekey/CreateLicenseKeyForm";
+import { useLocale } from "@calcom/lib/hooks/useLocale";
+import { WizardLayout, Meta } from "@calcom/ui";
+
+import { getServerSideProps } from "@lib/settings/license-keys/new/getServerSideProps";
+
+import PageWrapper from "@components/PageWrapper";
+
+const CreateNewLicenseKeyPage = () => {
+  const { t } = useLocale();
+  return (
+    <LicenseRequired>
+      <Meta title={t("set_up_your_organization")} description={t("organizations_description")} />
+      <CreateANewLicenseKeyForm />
+    </LicenseRequired>
+  );
+};
+const LayoutWrapper = (page: React.ReactElement) => {
+  return (
+    <WizardLayout currentStep={1} maxSteps={2}>
+      {page}
+    </WizardLayout>
+  );
+};
+
+CreateNewLicenseKeyPage.getLayout = LayoutWrapper;
+CreateNewLicenseKeyPage.PageWrapper = PageWrapper;
+
+export default CreateNewLicenseKeyPage;
+export { getServerSideProps };
diff --git a/packages/features/ee/deployment/licensekey/CreateLicenseKeyForm.tsx b/packages/features/ee/deployment/licensekey/CreateLicenseKeyForm.tsx
new file mode 100644
index 0000000000..18cd5e0330
--- /dev/null
+++ b/packages/features/ee/deployment/licensekey/CreateLicenseKeyForm.tsx
@@ -0,0 +1,270 @@
+import type { SessionContextValue } from "next-auth/react";
+import { useSession } from "next-auth/react";
+import { useState } from "react";
+import { Controller, useForm } from "react-hook-form";
+
+import { useLocale } from "@calcom/lib/hooks/useLocale";
+import { trpc } from "@calcom/trpc";
+import type { Ensure } from "@calcom/types/utils";
+import { showToast } from "@calcom/ui";
+import { Alert, Button, Form, Label, TextField, ToggleGroup } from "@calcom/ui";
+
+import { UserPermissionRole } from "../../../../prisma/enums";
+
+export const CreateANewLicenseKeyForm = () => {
+  const session = useSession();
+  if (session.data?.user.role !== "ADMIN") {
+    return null;
+  }
+  // @ts-expect-error session can't be null due to the early return
+  return <CreateANewLicenseKeyFormChild session={session} />;
+};
+
+enum BillingType {
+  PER_BOOKING = "PER_BOOKING",
+  PER_USER = "PER_USER",
+}
+
+enum BillingPeriod {
+  MONTHLY = "MONTHLY",
+  ANNUALLY = "ANNUALLY",
+}
+
+interface FormValues {
+  billingType: BillingType;
+  entityCount: number;
+  entityPrice: number;
+  billingPeriod: BillingPeriod;
+  overages: number;
+  billingEmail: string;
+}
+
+const CreateANewLicenseKeyFormChild = ({ session }: { session: Ensure<SessionContextValue, "data"> }) => {
+  const { t } = useLocale();
+  const [serverErrorMessage, setServerErrorMessage] = useState<string | null>(null);
+  const [stripeCheckoutUrl, setStripeCheckoutUrl] = useState<string | null>(null);
+  const isAdmin = session.data.user.role === UserPermissionRole.ADMIN;
+  const newLicenseKeyFormMethods = useForm<FormValues>({
+    defaultValues: {
+      billingType: BillingType.PER_BOOKING,
+      billingPeriod: BillingPeriod.MONTHLY,
+      entityCount: 500,
+      overages: 99, // $0.99
+      entityPrice: 50, // $0.5
+      billingEmail: undefined,
+    },
+  });
+
+  const mutation = trpc.viewer.admin.createSelfHostedLicense.useMutation({
+    onSuccess: async (values) => {
+      showToast(`Success: We have created a stripe payment URL for this billing email`, "success");
+      setStripeCheckoutUrl(values.stripeCheckoutUrl);
+    },
+    onError: async (err) => {
+      setServerErrorMessage(err.message);
+    },
+  });
+
+  const watchedBillingPeriod = newLicenseKeyFormMethods.watch("billingPeriod");
+  const watchedEntityCount = newLicenseKeyFormMethods.watch("entityCount");
+  const watchedEntityPrice = newLicenseKeyFormMethods.watch("entityPrice");
+
+  function calculateMonthlyPrice() {
+    const occurrence = watchedBillingPeriod === "MONTHLY" ? 1 : 12;
+
+    const sum = watchedEntityCount * watchedEntityPrice * occurrence;
+    return `$ ${sum / 100} / ${occurrence} months`;
+  }
+
+  return (
+    <>
+      {!stripeCheckoutUrl ? (
+        <Form
+          form={newLicenseKeyFormMethods}
+          className="space-y-5"
+          id="createOrg"
+          handleSubmit={(values) => {
+            mutation.mutate(values);
+          }}>
+          <div>
+            {serverErrorMessage && (
+              <div className="mb-5">
+                <Alert severity="error" message={serverErrorMessage} />
+              </div>
+            )}
+
+            <div className="mb-5">
+              <Controller
+                name="billingPeriod"
+                control={newLicenseKeyFormMethods.control}
+                render={({ field: { value, onChange } }) => (
+                  <>
+                    <Label htmlFor="billingPeriod">Billing Period</Label>
+                    <ToggleGroup
+                      isFullWidth
+                      id="billingPeriod"
+                      defaultValue={value}
+                      onValueChange={(e) => onChange(e)}
+                      options={[
+                        {
+                          value: "MONTHLY",
+                          label: "Monthly",
+                        },
+                        {
+                          value: "ANNUALLY",
+                          label: "Annually",
+                        },
+                      ]}
+                    />
+                  </>
+                )}
+              />
+            </div>
+
+            <Controller
+              name="billingEmail"
+              control={newLicenseKeyFormMethods.control}
+              rules={{
+                required: t("must_enter_billing_email"),
+              }}
+              render={({ field: { value, onChange } }) => (
+                <div className="flex">
+                  <TextField
+                    containerClassName="w-full"
+                    placeholder="john@acme.com"
+                    name="billingEmail"
+                    disabled={!isAdmin}
+                    label="Billing Email for Customer"
+                    defaultValue={value}
+                    onChange={onChange}
+                    autoComplete="off"
+                  />
+                </div>
+              )}
+            />
+          </div>
+          <div>
+            <Controller
+              name="billingType"
+              control={newLicenseKeyFormMethods.control}
+              render={({ field: { value, onChange } }) => (
+                <>
+                  <Label htmlFor="bookingType">Booking Type</Label>
+                  <ToggleGroup
+                    isFullWidth
+                    id="bookingType"
+                    defaultValue={value}
+                    onValueChange={(e) => onChange(e)}
+                    options={[
+                      {
+                        value: "PER_BOOKING",
+                        label: "Per Booking",
+                        tooltip: "Configure pricing on a per booking basis",
+                      },
+                      {
+                        value: "PER_USER",
+                        label: "Per User",
+                        tooltip: "Configure pricing on a per user basis",
+                      },
+                    ]}
+                  />
+                </>
+              )}
+            />
+          </div>
+
+          <div className="flex flex-wrap gap-2 [&>*]:flex-1">
+            <Controller
+              name="entityCount"
+              control={newLicenseKeyFormMethods.control}
+              rules={{
+                required: "Must enter a total of billable users",
+              }}
+              render={({ field: { value, onChange } }) => (
+                <TextField
+                  className="mt-2"
+                  name="entityCount"
+                  label="Total entities included"
+                  placeholder="100"
+                  defaultValue={value}
+                  onChange={(event) => onChange(+event.target.value)}
+                />
+              )}
+            />
+            <Controller
+              name="entityPrice"
+              control={newLicenseKeyFormMethods.control}
+              rules={{
+                required: "Must enter fixed price per user",
+              }}
+              render={({ field: { value, onChange } }) => (
+                <TextField
+                  className="mt-2"
+                  name="entityPrice"
+                  label="Fixed price per entity"
+                  addOnSuffix="$"
+                  defaultValue={value / 100}
+                  onChange={(event) => onChange(+event.target.value * 100)}
+                />
+              )}
+            />
+          </div>
+
+          <div>
+            <Controller
+              name="overages"
+              control={newLicenseKeyFormMethods.control}
+              rules={{
+                required: "Must enter overages",
+              }}
+              render={({ field: { value, onChange } }) => (
+                <>
+                  <TextField
+                    className="mt-2"
+                    placeholder="Acme"
+                    name="overages"
+                    addOnSuffix="$"
+                    label="Overages"
+                    disabled={!isAdmin}
+                    defaultValue={value / 100}
+                    onChange={(event) => onChange(+event.target.value * 100)}
+                    autoComplete="off"
+                  />
+                </>
+              )}
+            />
+          </div>
+
+          <div className="flex space-x-2 rtl:space-x-reverse">
+            <Button
+              disabled={newLicenseKeyFormMethods.formState.isSubmitting}
+              color="primary"
+              type="submit"
+              form="createOrg"
+              loading={mutation.isPending}
+              className="w-full justify-center">
+              {t("continue")} - {calculateMonthlyPrice()}
+            </Button>
+          </div>
+        </Form>
+      ) : (
+        <div className="w-full">
+          <div className="">
+            <TextField className="flex-1" disabled value={stripeCheckoutUrl} />
+          </div>
+
+          <div className="mt-4 flex gap-2 [&>*]:flex-1 [&>*]:justify-center">
+            <Button
+              color="secondary"
+              onClick={() => {
+                newLicenseKeyFormMethods.reset();
+                setStripeCheckoutUrl(null);
+              }}>
+              Back
+            </Button>
+          </div>
+        </div>
+      )}
+    </>
+  );
+};
diff --git a/packages/lib/telemetry.ts b/packages/lib/telemetry.ts
index 757ab05161..8816bfd489 100644
--- a/packages/lib/telemetry.ts
+++ b/packages/lib/telemetry.ts
@@ -22,6 +22,7 @@ export const telemetryEventTypes = {
   team_created: "team_created",
   slugReplacementAction: "slug_replacement_action",
   org_created: "org_created",
+  license_key_created: "license_key_created",
 };
 
 export function collectPageParameters(
diff --git a/packages/trpc/server/routers/viewer/admin/_router.ts b/packages/trpc/server/routers/viewer/admin/_router.ts
index c81693b56f..a99df03afb 100644
--- a/packages/trpc/server/routers/viewer/admin/_router.ts
+++ b/packages/trpc/server/routers/viewer/admin/_router.ts
@@ -2,6 +2,7 @@ import { z } from "zod";
 
 import { authedAdminProcedure } from "../../../procedures/authedProcedure";
 import { router, importHandler } from "../../../trpc";
+import { ZCreateSelfHostedLicenseSchema } from "./createSelfHostedLicenseKey.schema";
 import { ZListMembersSchema } from "./listPaginated.schema";
 import { ZAdminLockUserAccountSchema } from "./lockUserAccount.schema";
 import { ZAdminRemoveTwoFactor } from "./removeTwoFactor.schema";
@@ -62,4 +63,13 @@ export const adminRouter = router({
     );
     return handler(opts);
   }),
+  createSelfHostedLicense: authedAdminProcedure
+    .input(ZCreateSelfHostedLicenseSchema)
+    .mutation(async (opts) => {
+      const handler = await importHandler(
+        namespaced("createSelfHostedLicense"),
+        () => import("./createSelfHostedLicenseKey.handler")
+      );
+      return handler(opts);
+    }),
 });
diff --git a/packages/trpc/server/routers/viewer/admin/createSelfHostedLicenseKey.handler.ts b/packages/trpc/server/routers/viewer/admin/createSelfHostedLicenseKey.handler.ts
new file mode 100644
index 0000000000..f69d7d388c
--- /dev/null
+++ b/packages/trpc/server/routers/viewer/admin/createSelfHostedLicenseKey.handler.ts
@@ -0,0 +1,77 @@
+import * as crypto from "crypto";
+import { z } from "zod";
+
+import type { TrpcSessionUser } from "../../../trpc";
+import type { TCreateSelfHostedLicenseSchema } from "./createSelfHostedLicenseKey.schema";
+
+type GetOptions = {
+  ctx: {
+    user: NonNullable<TrpcSessionUser>;
+  };
+  input: TCreateSelfHostedLicenseSchema;
+};
+
+const generateNonce = (): string => {
+  return crypto.randomBytes(16).toString("hex");
+};
+
+// Utility function to create a signature
+const createSignature = (body: Record<string, unknown>, nonce: string, secretKey: string): string => {
+  return crypto
+    .createHmac("sha256", secretKey)
+    .update(JSON.stringify(body) + nonce)
+    .digest("hex");
+};
+
+// Fetch wrapper function
+const fetchWithSignature = async (
+  url: string,
+  body: Record<string, unknown>,
+  secretKey: string,
+  options: RequestInit = {}
+): Promise<Response> => {
+  const nonce = generateNonce();
+  const signature = createSignature(body, nonce, secretKey);
+
+  const headers = {
+    ...options.headers,
+    "Content-Type": "application/json",
+    nonce: nonce,
+    signature: signature,
+  };
+
+  return await fetch(url, {
+    ...options,
+    method: "POST",
+    headers: headers,
+    body: JSON.stringify(body),
+  });
+};
+
+const createSelfHostedInstance = async ({ input, ctx }: GetOptions) => {
+  const privateApiUrl = process.env.CALCOM_PRIVATE_API_ROUTE;
+  const signatureToken = process.env.CAL_SIGNATURE_TOKEN;
+
+  if (!privateApiUrl || !signatureToken) {
+    throw new Error("Private Api route does not exist in .env");
+  }
+
+  // Ensure admin
+  if (ctx.user.role !== "ADMIN") {
+    console.warn(`${ctx.user.username} just tried to create a license key without permission`);
+    throw new Error("You do not have permission to do this.");
+  }
+
+  const request = await fetchWithSignature(`${privateApiUrl}/v1/license`, input, signatureToken, {
+    method: "POST",
+  });
+
+  const data = await request.json();
+  const schema = z.object({
+    stripeCheckoutUrl: z.string(),
+  });
+
+  return schema.parse(data);
+};
+
+export default createSelfHostedInstance;
diff --git a/packages/trpc/server/routers/viewer/admin/createSelfHostedLicenseKey.schema.ts b/packages/trpc/server/routers/viewer/admin/createSelfHostedLicenseKey.schema.ts
new file mode 100644
index 0000000000..64189e28f5
--- /dev/null
+++ b/packages/trpc/server/routers/viewer/admin/createSelfHostedLicenseKey.schema.ts
@@ -0,0 +1,15 @@
+import { z } from "zod";
+
+const BillingType = z.enum(["PER_BOOKING", "PER_USER"]);
+const BillingPeriod = z.enum(["MONTHLY", "ANNUALLY"]);
+
+export const ZCreateSelfHostedLicenseSchema = z.object({
+  billingType: BillingType,
+  entityCount: z.number().int().nonnegative(),
+  entityPrice: z.number().nonnegative(),
+  billingPeriod: BillingPeriod,
+  overages: z.number().nonnegative(),
+  billingEmail: z.string().email(),
+});
+
+export type TCreateSelfHostedLicenseSchema = z.infer<typeof ZCreateSelfHostedLicenseSchema>;
diff --git a/turbo.json b/turbo.json
index 4354d7bcc2..4ab67328d7 100644
--- a/turbo.json
+++ b/turbo.json
@@ -236,6 +236,8 @@
     "BLACKLISTED_GUEST_EMAILS",
     "AUTH_BEARER_TOKEN_VERCEL",
     "BUILD_ID",
+    "CAL_SIGNATURE_TOKEN",
+    "CALCOM_PRIVATE_API_ROUTE",
     "CALCOM_APP_CREDENTIAL_ENCRYPTION_KEY",
     "CALCOM_CREDENTIAL_SYNC_ENDPOINT",
     "CALCOM_CREDENTIAL_SYNC_SECRET",