diff --git a/apps/web/pages/auth/sso/[provider].tsx b/apps/web/pages/auth/sso/[provider].tsx
index 5e0a96a1..f72a8304 100644
--- a/apps/web/pages/auth/sso/[provider].tsx
+++ b/apps/web/pages/auth/sso/[provider].tsx
@@ -3,6 +3,10 @@ import { signIn } from "next-auth/react";
 import { useRouter } from "next/router";
 import { useEffect } from "react";
 
+import { checkPremiumUsername } from "@calcom/ee/lib/core/checkPremiumUsername";
+import stripe from "@calcom/stripe/server";
+import { getPremiumPlanPrice } from "@calcom/stripe/utils";
+
 import { asStringOrNull } from "@lib/asStringOrNull";
 import { getSession } from "@lib/auth";
 import prisma from "@lib/prisma";
@@ -44,7 +48,7 @@ export const getServerSideProps = async (context: GetServerSidePropsContext) =>
   const providerParam = asStringOrNull(context.query.provider);
   const emailParam = asStringOrNull(context.query.email);
   const usernameParam = asStringOrNull(context.query.username);
-
+  const successDestination = "/getting-started" + (usernameParam ? `?username=${usernameParam}` : "");
   if (!providerParam) {
     throw new Error(`File is not named sso/[provider]`);
   }
@@ -55,9 +59,29 @@ export const getServerSideProps = async (context: GetServerSidePropsContext) =>
   const ssr = await ssrInit(context);
 
   if (session) {
+    // Validating if username is Premium, while this is true an email its required for stripe user confirmation
+    if (usernameParam && session.user.email) {
+      const availability = await checkPremiumUsername(usernameParam);
+      if (availability.available && availability.premium) {
+        const stripePremiumUrl = await getStripePremiumUsernameUrl({
+          userEmail: session.user.email,
+          username: usernameParam,
+          successDestination,
+        });
+        if (stripePremiumUrl) {
+          return {
+            redirect: {
+              destination: stripePremiumUrl,
+              permanent: false,
+            },
+          };
+        }
+      }
+    }
+
     return {
       redirect: {
-        destination: "/getting-started" + (usernameParam ? `?username=${usernameParam}` : ""),
+        destination: successDestination,
         permanent: false,
       },
     };
@@ -103,3 +127,41 @@ export const getServerSideProps = async (context: GetServerSidePropsContext) =>
     },
   };
 };
+
+type GetStripePremiumUsernameUrl = {
+  userEmail: string;
+  username: string;
+  successDestination: string;
+};
+
+const getStripePremiumUsernameUrl = async ({
+  userEmail,
+  username,
+  successDestination,
+}: GetStripePremiumUsernameUrl): Promise<string | null> => {
+  // @TODO: probably want to check if stripe user email already exists? or not
+  const customer = await stripe.customers.create({
+    email: userEmail,
+    metadata: {
+      email: userEmail,
+      username,
+    },
+  });
+
+  const checkoutSession = await stripe.checkout.sessions.create({
+    mode: "subscription",
+    payment_method_types: ["card"],
+    customer: customer.id,
+    line_items: [
+      {
+        price: getPremiumPlanPrice(),
+        quantity: 1,
+      },
+    ],
+    success_url: `${process.env.NEXT_PUBLIC_APP_BASE_URL}${successDestination}&session_id={CHECKOUT_SESSION_ID}`,
+    cancel_url: process.env.NEXT_PUBLIC_APP_BASE_URL || "https://app.cal.com",
+    allow_promotion_codes: true,
+  });
+
+  return checkoutSession.url;
+};
diff --git a/apps/web/pages/getting-started.tsx b/apps/web/pages/getting-started.tsx
index 6103aeda..93a60eca 100644
--- a/apps/web/pages/getting-started.tsx
+++ b/apps/web/pages/getting-started.tsx
@@ -352,25 +352,6 @@ export default function Onboarding(props: inferSSRProps<typeof getServerSideProp
           </div>
           <form className="sm:mx-auto sm:w-full">
             <section className="space-y-8">
-              {(props.usernameParam || props.user?.identityProvider !== IdentityProvider.CAL) && (
-                <fieldset>
-                  <label htmlFor="name" className="block text-sm font-medium text-gray-700">
-                    {t("username")}
-                  </label>
-                  <input
-                    ref={usernameRef}
-                    type="text"
-                    name="username"
-                    id="username"
-                    data-testid="username"
-                    placeholder={t("username")}
-                    defaultValue={props.usernameParam ? props.usernameParam : props.user?.username ?? ""}
-                    required
-                    className="mt-1 block w-full rounded-sm border border-gray-300 px-3 py-2 shadow-sm focus:border-neutral-500 focus:outline-none focus:ring-neutral-500 sm:text-sm"
-                  />
-                </fieldset>
-              )}
-
               <fieldset>
                 <label htmlFor="name" className="block text-sm font-medium text-gray-700">
                   {t("full_name")}
diff --git a/apps/web/playwright/onboarding.test.ts b/apps/web/playwright/onboarding.test.ts
index 773c59f4..cc58d499 100644
--- a/apps/web/playwright/onboarding.test.ts
+++ b/apps/web/playwright/onboarding.test.ts
@@ -11,17 +11,4 @@ test.describe("Onboarding", () => {
       },
     });
   });
-
-  const username = "calendso";
-  test(`/getting-started?username=${username} shows the first step of onboarding with username field populated`, async ({
-    page,
-  }) => {
-    await page.goto("/getting-started?username=" + username);
-
-    await page.waitForSelector("[data-testid=username]");
-
-    await expect(await page.$eval("[data-testid=username]", (el: HTMLInputElement) => el.value)).toEqual(
-      username
-    );
-  });
 });