Proactively cancel inactive trials 3 days before end (#4553)

* Proactively cancel inactive trials 3 days before end

* ✂️

* ✨

* Send email when canceling trial proactively

* ✂️

* Log in Slack

front/lib/email.ts

@@ -189,3 +189,29 @@ export async function sendAdminDataDeletionEmail({
   };
   return sendEmail(email, msg);
 }
+
+export async function sendProactiveTrialCancelledEmail(
+  email: string
+): Promise<void> {
+  const message = {
+    from: {
+      name: "Gabriel Hubert",
+      email: "[email protected]",
+    },
+    subject: "[Dust] Your Pro plan trial has been cancelled early",
+    html: `<p>Hi,</p>
+
+    <p>I'm Gabriel, a cofounder of Dust. Thanks for trying us out with a free trial of the Pro Plan.</p>
+
+    <p>You've not used core features of the product (adding data sources, creating custom assistants) and you haven't used assistant conversations in the past 7 days.
+    As a result, to avoid keeping your payment method on file while you may not intend to convert to our paid plan, we've cancelled your trial ahead of time and won't be charging you.</p>
+
+    <p>If you did intend to continue on Dust, you can subscribe again. If you'd like to extend further, feel free to just email me.</p>
+
+    <p>Thanks again for trying Dust out. If you have a second, please let me know if you have any thoughts about what we could do to improve Dust for your needs!</p>
+
+    Gabriel`,
+  };
+
+  return sendEmail(email, message);
+}

front/lib/plans/subscription.ts

@@ -1,7 +1,10 @@
-import type { WorkspaceType } from "@dust-tt/types";
 import type { PlanType, SubscriptionType } from "@dust-tt/types";
+import type { WorkspaceType } from "@dust-tt/types";
+import { sendUserOperationMessage } from "@dust-tt/types";
+import type Stripe from "stripe";
 
 import type { Authenticator } from "@app/lib/auth";
+import { sendProactiveTrialCancelledEmail } from "@app/lib/email";
 import { Plan, Subscription, Workspace } from "@app/lib/models";
 import type { PlanAttributes } from "@app/lib/plans/free_plans";
 import { FREE_NO_PLAN_DATA } from "@app/lib/plans/free_plans";
@@ -20,6 +23,8 @@ import {
 import { redisClient } from "@app/lib/redis";
 import { frontSequelize } from "@app/lib/resources/storage";
 import { generateModelSId } from "@app/lib/utils";
+import { getWorkspaceFirstAdmin } from "@app/lib/workspace";
+import { checkWorkspaceActivity } from "@app/lib/workspace_usage";
 import logger from "@app/logger/logger";
 
 // Helper function to render PlanType from PlanAttributes
@@ -463,3 +468,52 @@ export const updateWorkspacePerMonthlyActiveUsersSubscriptionUsage = async ({
     }
   }
 };
+
+/**
+ * Proactively cancel inactive trials.
+ */
+export async function maybeCancelInactiveTrials(
+  stripeSubscription: Stripe.Subscription
+) {
+  const { id: stripeSubscriptionId } = stripeSubscription;
+
+  const subscription = await Subscription.findOne({
+    where: { stripeSubscriptionId },
+    include: [Workspace],
+  });
+
+  if (!subscription || !subscription.trialing) {
+    return;
+  }
+
+  const { workspace } = subscription;
+  const isWorkspaceActive = await checkWorkspaceActivity(workspace);
+
+  if (!isWorkspaceActive) {
+    logger.info(
+      { action: "cancelling-trial", workspaceId: workspace.sId },
+      "Cancelling inactive trial."
+    );
+
+    await cancelSubscriptionImmediately({
+      stripeSubscriptionId,
+    });
+
+    const firstAdmin = await getWorkspaceFirstAdmin(workspace);
+    if (!firstAdmin) {
+      logger.info(
+        { action: "cancelling-trial", workspaceId: workspace.sId },
+        "No first adming found -- skipping email."
+      );
+
+      return;
+    } else {
+      await sendProactiveTrialCancelledEmail(firstAdmin.email);
+    }
+
+    await sendUserOperationMessage({
+      logger,
+      message: `Trial for workspace ${workspace.sId} cancelled proactively!`,
+    });
+  }
+}

front/lib/workspace.ts

@@ -5,6 +5,8 @@ import type {
 } from "@dust-tt/types";
 
 import type { Workspace } from "@app/lib/models";
+import { User } from "@app/lib/models";
+import { MembershipModel } from "@app/lib/resources/storage/models/membership";
 
 export function renderLightWorkspaceType({
   workspace,
@@ -21,3 +23,20 @@ export function renderLightWorkspaceType({
     role,
   };
 }
+
+// TODO: This belong to the WorkspaceResource.
+export async function getWorkspaceFirstAdmin(workspace: Workspace) {
+  return User.findOne({
+    include: [
+      {
+        model: MembershipModel,
+        where: {
+          role: "admin",
+          workspaceId: workspace.id,
+        },
+        required: true,
+      },
+    ],
+    order: [["createdAt", "ASC"]],
+  });
+}

front/lib/workspace_usage.ts

@@ -1,5 +1,8 @@
 import { format } from "date-fns/format";
-import { QueryTypes } from "sequelize";
+import { Op, QueryTypes } from "sequelize";
+
+import type { Workspace } from "@app/lib/models";
+import { AgentConfiguration, Conversation, DataSource } from "@app/lib/models";
 
 import { frontSequelize } from "./resources/storage";
 
@@ -94,3 +97,28 @@ export async function unsafeGetUsageData(
 
   return csvHeader + csvContent;
 }
+
+/**
+ * Check if a workspace is active during a trial based on the following conditions:
+ *   - Existence of a connected data source
+ *   - Existence of a custom assistant
+ *   - A conversation occurred within the past 7 days
+ */
+export async function checkWorkspaceActivity(workspace: Workspace) {
+  const sevenDaysAgo = new Date();
+  sevenDaysAgo.setDate(sevenDaysAgo.getDate() - 7);
+
+  const hasDataSource = await DataSource.findOne({
+    where: { workspaceId: workspace.id },
+  });
+
+  const hasCreatedAssistant = await AgentConfiguration.findOne({
+    where: { workspaceId: workspace.id },
+  });
+
+  const hasRecentConversation = await Conversation.findOne({
+    where: { workspaceId: workspace.id, updatedAt: { [Op.gte]: sevenDaysAgo } },
+  });
+
+  return hasDataSource || hasCreatedAssistant || hasRecentConversation;
+}

front/pages/api/stripe/webhook.ts

@@ -15,6 +15,7 @@ import {
 } from "@app/lib/email";
 import { Plan, Subscription, Workspace } from "@app/lib/models";
 import { createCustomerPortalSession } from "@app/lib/plans/stripe";
+import { maybeCancelInactiveTrials } from "@app/lib/plans/subscription";
 import { countActiveSeatsInWorkspace } from "@app/lib/plans/workspace_usage";
 import { frontSequelize } from "@app/lib/resources/storage";
 import { generateModelSId } from "@app/lib/utils";
@@ -562,6 +563,14 @@ async function handler(
           }
 
           break;
+
+        case "customer.subscription.trial_will_end":
+          stripeSubscription = event.data.object as Stripe.Subscription;
+
+          await maybeCancelInactiveTrials(stripeSubscription);
+
+          break;
+
         default:
         // Unhandled event type
       }