diff --git a/packages/features/webhooks/lib/cron.ts b/packages/features/webhooks/lib/cron.ts
index 79dc78a6ef..667e2fd21f 100644
--- a/packages/features/webhooks/lib/cron.ts
+++ b/packages/features/webhooks/lib/cron.ts
@@ -31,20 +31,35 @@ async function handler(req: NextApiRequest, res: NextApiResponse) {
         lte: dayjs().toISOString(),
       },
     },
+    select: {
+      id: true,
+      jobName: true,
+      payload: true,
+      subscriberUrl: true,
+      webhook: {
+        select: {
+          secret: true,
+        },
+      },
+    },
   });
 
+  const fetchPromises: Promise<any>[] = [];
+
   // run jobs
   for (const job of jobsToRun) {
     // Fetch the webhook configuration so that we can get the secret.
     const [appId, subscriberId] = job.jobName.split("_");
+    let webhook = job.webhook;
 
-    let webhook;
-    try {
-      webhook = await prisma.webhook.findUniqueOrThrow({
-        where: { id: subscriberId, appId: appId !== "null" ? appId : null },
-      });
-    } catch {
-      logger.error(`Error finding webhook for subscriberId: ${subscriberId}, appId: ${appId}`);
+    if (!webhook) {
+      try {
+        webhook = await prisma.webhook.findUniqueOrThrow({
+          where: { id: subscriberId, appId: appId !== "null" ? appId : null },
+        });
+      } catch {
+        logger.error(`Error finding webhook for subscriberId: ${subscriberId}, appId: ${appId}`);
+      }
     }
 
     const headers: Record<string, string> = {
@@ -56,33 +71,15 @@ async function handler(req: NextApiRequest, res: NextApiResponse) {
       headers["X-Cal-Signature-256"] = createWebhookSignature({ secret: webhook.secret, body: job.payload });
     }
 
-    try {
-      await fetch(job.subscriberUrl, {
+    fetchPromises.push(
+      fetch(job.subscriberUrl, {
         method: "POST",
         body: job.payload,
         headers,
-      });
-    } catch (error) {
-      console.log(`Error running webhook trigger (retry count: ${job.retryCount}): ${error}`);
-
-      // if job fails, retry again for 5 times.
-      if (job.retryCount < 5) {
-        await prisma.webhookScheduledTriggers.update({
-          where: {
-            id: job.id,
-          },
-          data: {
-            retryCount: {
-              increment: 1,
-            },
-            startAfter: dayjs()
-              .add(5 * (job.retryCount + 1), "minutes")
-              .toISOString(),
-          },
-        });
-        return res.json({ ok: false });
-      }
-    }
+      }).catch((error) => {
+        console.error(`Webhook trigger for subscriber url ${job.subscriberUrl} failed with error: ${error}`);
+      })
+    );
 
     const parsedJobPayload = JSON.parse(job.payload) as {
       id: number; // booking id
@@ -122,6 +119,8 @@ async function handler(req: NextApiRequest, res: NextApiResponse) {
     });
   }
 
+  Promise.allSettled(fetchPromises);
+
   res.json({ ok: true });
 }
 
diff --git a/packages/features/webhooks/lib/scheduleTrigger.ts b/packages/features/webhooks/lib/scheduleTrigger.ts
index 9048be3c65..6664f9d31c 100644
--- a/packages/features/webhooks/lib/scheduleTrigger.ts
+++ b/packages/features/webhooks/lib/scheduleTrigger.ts
@@ -297,6 +297,11 @@ export async function scheduleTrigger(
         payload,
         startAfter: triggerEvent === WebhookTriggerEvents.MEETING_ENDED ? booking.endTime : booking.startTime,
         subscriberUrl,
+        webhook: {
+          connect: {
+            id: subscriber.id,
+          },
+        },
       },
     });
 
diff --git a/packages/prisma/migrations/20240322152654_add_webhook_to_scheduled_webhook_triggers/migration.sql b/packages/prisma/migrations/20240322152654_add_webhook_to_scheduled_webhook_triggers/migration.sql
new file mode 100644
index 0000000000..65b79c4ebb
--- /dev/null
+++ b/packages/prisma/migrations/20240322152654_add_webhook_to_scheduled_webhook_triggers/migration.sql
@@ -0,0 +1,5 @@
+-- AlterTable
+ALTER TABLE "WebhookScheduledTriggers" ADD COLUMN     "webhookId" TEXT;
+
+-- AddForeignKey
+ALTER TABLE "WebhookScheduledTriggers" ADD CONSTRAINT "WebhookScheduledTriggers_webhookId_fkey" FOREIGN KEY ("webhookId") REFERENCES "Webhook"("id") ON DELETE CASCADE ON UPDATE CASCADE;
diff --git a/packages/prisma/schema.prisma b/packages/prisma/schema.prisma
index 7b961a62d3..fd6e8f8cb9 100644
--- a/packages/prisma/schema.prisma
+++ b/packages/prisma/schema.prisma
@@ -691,23 +691,24 @@ enum WebhookTriggerEvents {
 }
 
 model Webhook {
-  id              String                 @id @unique
-  userId          Int?
-  teamId          Int?
-  eventTypeId     Int?
+  id                String                     @id @unique
+  userId            Int?
+  teamId            Int?
+  eventTypeId       Int?
   /// @zod.url()
-  subscriberUrl   String
-  payloadTemplate String?
-  createdAt       DateTime               @default(now())
-  active          Boolean                @default(true)
-  eventTriggers   WebhookTriggerEvents[]
-  user            User?                  @relation(fields: [userId], references: [id], onDelete: Cascade)
-  team            Team?                  @relation(fields: [teamId], references: [id], onDelete: Cascade)
-  eventType       EventType?             @relation(fields: [eventTypeId], references: [id], onDelete: Cascade)
-  app             App?                   @relation(fields: [appId], references: [slug], onDelete: Cascade)
-  appId           String?
-  secret          String?
-  platform        Boolean                @default(false)
+  subscriberUrl     String
+  payloadTemplate   String?
+  createdAt         DateTime                   @default(now())
+  active            Boolean                    @default(true)
+  eventTriggers     WebhookTriggerEvents[]
+  user              User?                      @relation(fields: [userId], references: [id], onDelete: Cascade)
+  team              Team?                      @relation(fields: [teamId], references: [id], onDelete: Cascade)
+  eventType         EventType?                 @relation(fields: [eventTypeId], references: [id], onDelete: Cascade)
+  app               App?                       @relation(fields: [appId], references: [slug], onDelete: Cascade)
+  appId             String?
+  secret            String?
+  platform          Boolean                    @default(false)
+  scheduledTriggers WebhookScheduledTriggers[]
 
   @@unique([userId, subscriberUrl], name: "courseIdentifier")
 }
@@ -989,6 +990,8 @@ model WebhookScheduledTriggers {
   startAfter    DateTime
   retryCount    Int       @default(0)
   createdAt     DateTime? @default(now())
+  webhookId     String?
+  webhook       Webhook?  @relation(fields: [webhookId], references: [id], onDelete: Cascade)
 }
 
 enum WorkflowTemplates {
diff --git a/packages/prisma/zod/webhook.ts b/packages/prisma/zod/webhook.ts
index 5ba7998b37..6f5f2c0203 100755
--- a/packages/prisma/zod/webhook.ts
+++ b/packages/prisma/zod/webhook.ts
@@ -1,7 +1,7 @@
 import * as z from "zod"
 import * as imports from "../zod-utils"
 import { WebhookTriggerEvents } from "@prisma/client"
-import { CompleteUser, UserModel, CompleteTeam, TeamModel, CompleteEventType, EventTypeModel, CompleteApp, AppModel } from "./index"
+import { CompleteUser, UserModel, CompleteTeam, TeamModel, CompleteEventType, EventTypeModel, CompleteApp, AppModel, CompleteWebhookScheduledTriggers, WebhookScheduledTriggersModel } from "./index"
 
 export const _WebhookModel = z.object({
   id: z.string(),
@@ -23,6 +23,7 @@ export interface CompleteWebhook extends z.infer<typeof _WebhookModel> {
   team?: CompleteTeam | null
   eventType?: CompleteEventType | null
   app?: CompleteApp | null
+  scheduledTriggers: CompleteWebhookScheduledTriggers[]
 }
 
 /**
@@ -35,4 +36,5 @@ export const WebhookModel: z.ZodSchema<CompleteWebhook> = z.lazy(() => _WebhookM
   team: TeamModel.nullish(),
   eventType: EventTypeModel.nullish(),
   app: AppModel.nullish(),
+  scheduledTriggers: WebhookScheduledTriggersModel.array(),
 }))