How to Automate a Free Trial to Paid Nudge

Free trials bring people in, but they don’t guarantee revenue. In fact, most SaaS companies see the majority of trial users walk away without upgrading. But, with such a vast number of free trial users, is it even possible to even try to convert them?

The answer is yes! Using an automated, behavior-based flow that nudges trial users at the right time with the right message.

In this guide, you’ll learn how to set up a trial-to-paid conversion journey in Mailmodo, so you can engage users before they drop off and highlight your product’s value.

Why most free trial users don’t convert

A typical trial starts strong with a signup, a quick look around, but the the time the trial ends, the user has dropped off.

The main reasons:

• Key features stayed hidden

• They weren’t reminded at the right time to extend their subscription

• There was no urgency to upgrade

How to automate your free trial to paid flow

Here how you can set up your email flow to convert free trial users to paid ones:

1. Set up the tools

Creating a free trial-to-paid flow requires using a mixture of tools to act on user behavior. This includes:

• Email + Automation: Mailmodo serves as the central platform for sending emails and managing automated workflows.

• Product Events Tracking: Tools like Segment, PostHog, or Mixpanel allow you to capture important user actions, such as account creation, feature usage, or key activation milestones.

• Payments & Upgrades: Stripe can be integrated via webhooks to track when a user upgrades or completes a payment, triggering relevant follow-up emails.

You need to ensure your automation stack is properly configured so that every event in your product triggers the right message at the right time.

At a minimum, your workflow should follow a simple chain: product events → email automation tool →paid tools. This ensures that every action a user takes in your product can automatically trigger the right communication at the right stage of the trial.

2. Define the trigger

The first step to create any email flow is to set up your trigger. For a free trial to paid flow, the core trigger is when a user starts their free trial (Day 0). But depending on your product and how users engage with it, you can also track other important events like:

• Account created: Confirms the user successfully signed up.
• Key activation action completed: For example, their first project, first import, or first invite.
• Feature usage milestones: Helps you tailor emails based on what the user has tried so far.
• Trial expiration date: Essential for sending time-sensitive reminders.

3. Create email flow

Day 0: Welcome

The goal here is to set expectations & point to the “aha” moment. Here are the free things your email should contain:

• What problem you solve
• What success looks like during the trial
• One clear action to take now

Day 1–2: Activation push
This is a conditional email based on what action the user took after setting the trigger. If the user has not activated, send a step-by-step instruction email to guide them toward their first key action and help them achieve a quick win. If they have already activated, send a reinforcement email highlighting the value they’ve gained so far (“You’ve already done X”) and suggest the next steps to explore more features.

Day 4–5: Social proof or use case

The goal here is to build belief and show the user that real teams are achieving value with your product. This email should include:

• A short case study or success story, along with statements like “Teams like yours use this to…” to make it relatable.
• Tie the benefits directly to what the user has already done (or hasn’t done yet) to reinforce relevance and motivate further engagement.

Day 7: Soft upgrade nudge

This email should clearly explain “Here’s what you unlock on the paid plan,” highlighting the additional features and benefits available.

Emphasize the limits the user will hit soon on the free trial, but avoid urgency or fear-based language at this stage, keeping the message informative and encouraging rather than pushy.

2–3 days before trial ends

This email is meant to remind users before their trial expires so they aren’t caught off guard. Include the exact trial end date, highlight what they’ll miss out on if they don’t upgrade, and provide a clear, simple upgrade CTA to make it easy for them to take action.

Trial expiration day

This email is designed to give hesitant users one final opportunity to upgrade. Clearly state, “Your trial ends today,” remind them of the value they’ve already gained during the trial, and optionally offer an incentive such as a discount, bonus, or call.

Tools like Mailmodo AI can help create these email templates with a single prompt, ensuring the message is timely and effective.

4. Metrics to watch

Once your free trial-to-paid flow is live, it’s important to monitor key metrics to understand how users are engaging and where improvements are needed. Track:

• Trial → Paid conversion rate: The percentage of users who upgrade from the free trial to a paid plan.
• Activation rate by day 3: How many users complete the key activation action within the first few days of their trial.
• Email click-through rate (CTR): Especially mid-trial, to see which emails drive engagement and which may need adjustments.
• Time to upgrade: How long it takes users to move from activation to conversion

Conclusion

Automating your free trial to paid journey ensures users see your product’s value at the right time.

With Mailmodo, you can set up this automation process easily by dragging and dropping blocks to create behavior-driven email sequences that guide users toward conversion and improve your business outcomes.

Want to see it in action?
Sign up for Mailmodo and set up your first trial-to-paid journey in minutes.