How to Build a Trial Onboarding Email Flow with Stripe

Most free trials fail not because the product is wrong, but because the user never reaches the "aha" moment. A trial onboarding flow guides new trialists to activate, use the features that matter, and see real results — so that when the trial ends, upgrading is the obvious choice.

Here's how to build one in Audienceful using your Stripe trial event.

What you'll need

• A Stripe integration connected to your workspace.
• Three short emails.

How the trial onboarding flow works

When a Stripe subscription enters a trialing state, the customer enters your automation over the length of the trial:

1. A welcome that gets them set up and to first value fast.
2. A wait, then an email surfacing a high-value feature people often miss.
3. A wait, then proof — results and outcomes — with an upgrade nudge.

It's set to send on weekdays only by default, when B2B engagement is highest.

Step 1: Connect Stripe

Connect your account from the Integrations tab. The Trial started trigger then appears in the automation builder.

Step 2: Write your three emails

• Email 1 — activation. Welcome them and drive the single most important setup step. Example subject: "Welcome aboard — let's get you set up"
• Email 2 — depth of use. Highlight the feature that turns a trial into a habit. Example subject: "The feature most people miss"
• Email 3 — proof + upgrade. Show the results customers see, and make upgrading easy. Example subject: "The results our customers see"

Personalize with the {{first_name}} merge tag.

Step 3: Build the automation

In the Automations tab, click New Automation:

1. Trigger: Stripe event → Trial started.
2. Send Email 1 immediately.
3. Wait 3 days.
4. Send Email 2, the feature most people miss.
5. Wait 3 days.
6. Send Email 3, proof + upgrade.
7. Optionally add a tag like trialing.

Pick your theme and click Run.

Best practices

• Drive one action per email. Onboarding fails when it asks for too much at once. Give each email a single job.
• Sell outcomes, not features. Frame everything around the result the customer gets.
• Send on weekdays for B2B — you can control sending days from the automation's settings (the gear icon).

Start from a template

→ Trial onboarding → convert template

Browse the full automation template gallery for more Stripe flows.

Frequently asked questions

When exactly does the flow start? When Stripe reports the subscription as trialing — i.e. the moment the trial begins. From there the emails are spaced across the trial period.

What if someone upgrades mid-trial? You can add a conditional or a conversion goal so paying customers stop receiving "please upgrade" messaging once they've converted.