diff --git a/packages/web/src/components/UpgradeFreeTrial/index.ee.tsx b/packages/web/src/components/UpgradeFreeTrial/index.ee.tsx
index 4fca59a0..9a0cfa90 100644
--- a/packages/web/src/components/UpgradeFreeTrial/index.ee.tsx
+++ b/packages/web/src/components/UpgradeFreeTrial/index.ee.tsx
@@ -16,14 +16,26 @@ import Paper from '@mui/material/Paper';
 import LockIcon from '@mui/icons-material/Lock';
 
 import usePaymentPlans from 'hooks/usePaymentPlans.ee';
+import useCurrentUser from 'hooks/useCurrentUser';
+import usePaddle from 'hooks/usePaddle.ee';
 
 export default function UpgradeFreeTrial() {
   const { plans, loading } = usePaymentPlans();
+  const currentUser = useCurrentUser();
+  const { loaded: paddleLoaded } = usePaddle();
   const [selectedIndex, setSelectedIndex] = React.useState(0);
   const selectedPlan = plans?.[selectedIndex];
 
   const updateSelection = (index: number) => setSelectedIndex(index);
 
+  const handleCheckout = React.useCallback(() => {
+    window.Paddle.Checkout?.open({
+      product: selectedPlan.productId,
+      email: currentUser.email,
+      passthrough: JSON.stringify({ id: currentUser.id, email: currentUser.email })
+    })
+  }, [selectedPlan, currentUser]);
+
   if (loading || !plans.length) return null;
 
   return (
@@ -140,7 +152,13 @@ export default function UpgradeFreeTrial() {
             <Typography variant="subtitle2" sx={{ fontSize: '12px', mt: 0 }}>
               + VAT if applicable
             </Typography>
-            <Button size="small" variant="contained" sx={{ mt: 2 }}>
+            <Button
+              size="small"
+              variant="contained"
+              sx={{ mt: 2 }}
+              onClick={handleCheckout}
+              disabled={!paddleLoaded}
+            >
               <LockIcon fontSize="small" sx={{ mr: 1 }} />
               Pay securely via Paddle
             </Button>
diff --git a/packages/web/src/contexts/Paddle.ee.tsx b/packages/web/src/contexts/Paddle.ee.tsx
new file mode 100644
index 00000000..e4c0d5b7
--- /dev/null
+++ b/packages/web/src/contexts/Paddle.ee.tsx
@@ -0,0 +1,72 @@
+import * as React from 'react';
+
+import useCloud from 'hooks/useCloud';
+import usePaddleInfo from 'hooks/usePaddleInfo.ee';
+
+declare global {
+  interface Window {
+    Paddle: any;
+  }
+}
+
+export type PaddleContextParams = {
+  loaded: boolean;
+};
+
+export const PaddleContext =
+  React.createContext<PaddleContextParams>({
+    loaded: false,
+  });
+
+type PaddleProviderProps = {
+  children: React.ReactNode;
+};
+
+export const PaddleProvider = (
+  props: PaddleProviderProps
+): React.ReactElement => {
+  const { children } = props;
+  const isCloud = useCloud();
+  const { sandbox, vendorId } = usePaddleInfo();
+  const [loaded, setLoaded] = React.useState(false);
+
+  const value = React.useMemo(() => {
+    return {
+      loaded,
+    };
+  }, [loaded]);
+
+  React.useEffect(function loadPaddleScript() {
+    if (!isCloud) return;
+
+    const g = document.createElement('script')
+    const s = document.getElementsByTagName('script')[0];
+    g.src = 'https://cdn.paddle.com/paddle/paddle.js';
+    g.defer = true;
+    g.async = true;
+
+    if (s.parentNode) {
+      s.parentNode.insertBefore(g, s);
+    }
+
+    g.onload = function () {
+      setLoaded(true);
+    }
+  }, [isCloud]);
+
+  React.useEffect(function initPaddleScript() {
+    if (!loaded || !vendorId) return;
+
+    if (sandbox) {
+      window.Paddle.Environment.set('sandbox');
+    }
+
+    window.Paddle.Setup({ vendor: vendorId });
+  }, [loaded, sandbox, vendorId])
+
+  return (
+    <PaddleContext.Provider value={value}>
+      {children}
+    </PaddleContext.Provider>
+  );
+};
diff --git a/packages/web/src/graphql/queries/get-paddle-info.ee.ts b/packages/web/src/graphql/queries/get-paddle-info.ee.ts
new file mode 100644
index 00000000..4e801865
--- /dev/null
+++ b/packages/web/src/graphql/queries/get-paddle-info.ee.ts
@@ -0,0 +1,10 @@
+import { gql } from '@apollo/client';
+
+export const GET_PADDLE_INFO = gql`
+  query GetPaddleInfo {
+    getPaddleInfo {
+      sandbox
+      vendorId
+    }
+  }
+`;
diff --git a/packages/web/src/hooks/usePaddle.ee.ts b/packages/web/src/hooks/usePaddle.ee.ts
new file mode 100644
index 00000000..747f0661
--- /dev/null
+++ b/packages/web/src/hooks/usePaddle.ee.ts
@@ -0,0 +1,14 @@
+import * as React from 'react';
+import { PaddleContext } from 'contexts/Paddle.ee';
+
+type UsePaddleReturn = {
+  loaded: boolean;
+};
+
+export default function usePaddle(): UsePaddleReturn {
+  const paddleContext = React.useContext(PaddleContext);
+
+  return {
+    loaded: paddleContext.loaded,
+  };
+}
diff --git a/packages/web/src/hooks/usePaddleInfo.ee.ts b/packages/web/src/hooks/usePaddleInfo.ee.ts
new file mode 100644
index 00000000..85ff5905
--- /dev/null
+++ b/packages/web/src/hooks/usePaddleInfo.ee.ts
@@ -0,0 +1,19 @@
+import { useQuery } from '@apollo/client';
+
+import { GET_PADDLE_INFO } from 'graphql/queries/get-paddle-info.ee';
+
+type UsePaddleInfoReturn = {
+  sandbox: boolean;
+  vendorId: string;
+  loading: boolean;
+};
+
+export default function usePaddleInfo(): UsePaddleInfoReturn {
+  const { data, loading } = useQuery(GET_PADDLE_INFO);
+
+  return {
+    sandbox: data?.getPaddleInfo?.sandbox,
+    vendorId: data?.getPaddleInfo?.vendorId,
+    loading
+  };
+}
diff --git a/packages/web/src/index.tsx b/packages/web/src/index.tsx
index c2cd7099..bc657214 100644
--- a/packages/web/src/index.tsx
+++ b/packages/web/src/index.tsx
@@ -6,6 +6,7 @@ import ApolloProvider from 'components/ApolloProvider';
 import SnackbarProvider from 'components/SnackbarProvider';
 import { AuthenticationProvider } from 'contexts/Authentication';
 import { AutomatischInfoProvider } from 'contexts/AutomatischInfo';
+import { PaddleProvider } from 'contexts/Paddle.ee';
 import Router from 'components/Router';
 import LiveChat from 'components/LiveChat/index.ee';
 import routes from 'routes';
@@ -18,11 +19,13 @@ ReactDOM.render(
         <ApolloProvider>
           <AutomatischInfoProvider>
             <IntlProvider>
-              <ThemeProvider>
-                {routes}
+              <PaddleProvider>
+                <ThemeProvider>
+                  {routes}
 
-                <LiveChat />
-              </ThemeProvider>
+                  <LiveChat />
+                </ThemeProvider>
+              </PaddleProvider>
             </IntlProvider>
           </AutomatischInfoProvider>
         </ApolloProvider>