Trial Ending Signal Playbook

Playbook Overview
When should you run this playbook?
Your product offers a free tria.
ACV is high enough to support using sales resources to improve conversion from free to paid customer.
You’ve noticed individual users or teams from enterprise-fit accounts sign up for trials.
Who to target?
Active product users who align with your ICP and are nearing the end of their trial.
Playbook goal?
Convert free users to paid customers.
Responsible team(s)?
Marketing to support
  • Trial users are some of your warmest lead opportunities, as they’ve built the habit of product usage and are already seeing value. Reaching out when a free trial is ending helps ensure you don’t leave any revenue on the table by assuming users will upgrade on their own without prompting.
  • Trial leads can be divided between marketing and sales, with marketing automating outreach to lower-value prospects and sales manually connecting with enterprise users.
  • Outreach messaging should remind users their trial is ending, highlight the value they’ve already experienced, and warn them about the features they’ll lose access to once the trial ends

What is the key signal?

An account’s free trial period coming to an end can be a great indicator that they’re open to conversations around upgrading to a paid account. Because this signal is consistently time-bound due to a standard free trial length, you can choose a consistent point towards the end of the trial period to run this playbook.

What is this playbook? 

Free trials can be an effective way to build pipeline, allowing users a no-risk self-serve product experience. The users’ engagement and success during the free trial can help build a compelling case to transition into a paid plan tier. Conversions from free to paid users can be driven through automated marketing outreach for individuals and via personal outreach from sales for those that fit your enterprise ICP.

When should you run this playbook? 

It’s important to time outreach far enough into the trial period that a user has experienced at least one aha moment and can see the ROI potential, but early enough that users have time to consider the purchase. Automated outreach can be timed to just a few days before the trial ending, but sales outreach to potential enterprise customers will need to account for purchasing and procurement. One thing to consider is extending an enterprise user’s free trial through the contract process.

Try This Playbook

Step 1

Track the product usage of free trial users. Specifically, identify which free users are nearing the end of their trial, engaging regularly with the product, and have experienced at least one aha moment. Don’t reach out to every trial user. Look at your existing closed/won accounts to identify key characteristics of an ideal customer (customer size, specific actions like invites sent, or number of team members in the workspace). 

Step 2

Route free trial leads to sales. This step will likely take experimentation and partnership between sales and marketing. First, decide how leads will be routed between sales and marketing. Sales should likely own any free users with high-value potential, for example, enterprise accounts that match your ICP and have multiple free users. Marketing should take the lead on any individual free users or those that have not yet reached their aha moment. Marketing or scaled outbound to these users can help nurture them. 

Step 3

Connect with your leads and drive home product value. When reaching out to leads make sure to remind them their trial is ending, highlight the value they’ve found, and cover the features they’ll lose access to when their trial is over. This message will be slightly different when trying to convert enterprise-level users versus individuals.

Sample Sales Outreach

Hi [first name],

I hope you're doing well! I wanted to reach out because I noticed that [number] people on your team are near the end of their free trial period with [product]. It seems like your team is getting great value out of the product, including:

[usage proof points, like number of projects or documents created, hours saved, etc]

Let's ensure this momentum continues. Our enterprise solution is tailored to meet the needs of teams like yours, offering [key enterprise features].

I'd love to chat about how we can seamlessly transition your team to our enterprise package. When's a good time for a quick call to discuss further?

Looking forward to it!

Sample Marketing Outreach

Time flies when you're exploring awesome tools, doesn't it? Your free trial of [product] is nearing its end, but the adventure doesn't have to stop there!

Upgrade now to unlock the full potential of [product] and keep the momentum going. With our paid version, you'll enjoy exclusive features, priority support, and uninterrupted access to all the perks you've been loving.

Don't miss out! Upgrade today and take your experience to the next level.

Upgrade Now

Got questions or need assistance? We're here to help. Just hit reply, and we'll get back to you ASAP.

Enable this playbook in Pocus

  1. Connect your relevant data sources.
  2. Select your goal (in this case, Conversion).
  3. Build your playbook based on the signal (trigger) and actions outlined above.
  4. Run the playbook by rolling it out to the relevant members of your team.
  5. Iterate over time based on reporting and results. You may find ways to improve this playbook’s effectiveness beyond what we’ve outlined here!

About the author
Alexa Grabell
Co-Founder & CEO at Pocus

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