How To Optimize Your Free Trial

May 17, 2023

“Do PLG.”

You might’ve heard that advice before from a well-meaning investor, CEO, or product manager. You probably started researching the topic only to be bombarded by an endless array of three-letter acronyms (PLG, PLS, PLM, PQA, PQL, oh my!) and a dizzying stream of advice about things to do.

Driving PLG improvements can feel overwhelming even for the most experienced practitioner. Today’s piece is here to help.

I collaborated with Jonathan Anderson from Candu on a nine-step PLG audit to get a pulse-check on how you’re doing and discover quick wins to move the needle on activation and conversion. Candu helps product and growth teams including Gorgias and Vidyard run more growth experiments—all without coding.

This is a guest post with Jonathan Anderson at Candu. If you <3 PLG and want to keep the conversation going, join us on the OpenView roof deck in Boston on May 18th (RSVP here).

9 steps to creating a product-led free trial experience that converts

The work to optimize a free trial is never done. As any ambitious PLG team knows, your activation and conversion rates can always be just that much higher.

But how do you know which lever to pull on? While each product experience is unique, we’ve outlined 9 user experiences you’ll want to consider while building your PLG motion. For each, we’ve highlighted a few best-in-class examples and identified the mistakes you’ll want to avoid. By the end of this post, you’ll be able to audit your PLG motion and (hopefully) identify the quick wins most likely to move the needle on activation and conversion.

The free trial experience typically consists of three stages: sign-up, activation, and conversion. Let’s take a closer look and explore best practices at each stage, starting from the beginning.

Step 1: Create a sign-up page that promotes your value proposition

The basic need of any sign-up page is to make it easy for users to sign into your product, without getting in their way. Beyond that, however, it is an opportunity to provide a clear and compelling reason why a new user should sign up for your product.

A common myth is that your sign-up page should be completely blank. Instead, consider it a moment to reinforce what your product does and what value your soon-to-be users will get.

While users enter their details to create a new account, continue to remind them about the key pain your product solves, build credibility with social proof like relevant logos or testimonials, and make the terms of your free trial clear. Snyk does a great job at including all three, without detracting from the primary getting started CTA.

Pro-tip: Think of your account creation screen and your login screen as two fundamentally different experiences. For a returning user, consider promoting new features or your upcoming user conference. Surprisingly, this is likely your product’s highest-traffic page. Don’t waste it.

Step 2: Ask better questions in your sign-up survey

The sign-up survey is among the most debated areas in any free trial experience. In one camp, we hear, “We need to learn more about our users. We need to ask more questions!” The other camp will worry, “Won’t adding more questions lead to a drop-off in this critical flow?”

Although we encourage product teams to test each question, we’ve found little evidence for a big drop-off at this phase in the user journey. We hypothesize that this is because users have already given their email, and are excited to see the product. If they believe that providing additional information will help the product better meet their needs, they’re unlikely to quit now.

The most common signup questions we see successful PLG companies implement include asking about users’ primary jobs to be done, their role, and what technologies they already use. Whether or not these companies then use that information to create a personalized onboarding experience is another question, which we’ll cover later.

Example sign-up survey questions include:

  • What are you planning to use X for?
  • Which team are you on? What is your role? What industry are you in?
  • What would you like to do first?
  • How did you hear about us?

Airtable’s onboarding wizard does a brilliant job at initially capturing basic user intent, then digging deeper to determine a targeted use case for the user to get started with.

Step 3: Goal-oriented onboarding checklist

Once a user lands in your product, they need a map of what to do first. Use the insights from your onboarding survey to surface the shortest possible pathway to value. Initial onboarding is a critical part of any user journey. Personalizing the initial steps will help users achieve their desired outcome as quickly as possible.

Shopify does an excellent job connecting its nine question signup survey with its onboarding checklist. Users tell Shopify what kind of store they want, and then are given a set of clear instructions and templates that help them build the store they want as quickly as possible.

Step 4: Personalized templates and recipes

Does your product offer many templates, workflows, integrations, etc.? If so, you should already know what are the most popular examples, and you can share these with users – so they don’t need to start from scratch or dig through a large pile of items. This helps them understand and discover common use cases proven to deliver value. Again, bonus points if you can personalize this content from the results of the signup survey!

Zapier highlights common recipes based on apps users have expressed interest in using. It’s an excellent way to show off Zapier’s range of workflows while encouraging users to set up their first Zap.


Step 5: Value-add empty states

As their name implies, empty states are often left empty (or at least underappreciated). This is a big mistake.

Instead of a blank page, a sole CTA to “Get Started”, or a “no data yet” message, consider leveraging this valuable real estate to build excitement for your feature set. In effect, an empty state is an opportunity to market to your users. Think of it as an in-product landing page. It’s important to provide clear, concise messaging so new users can know why and how to adopt a feature.

Consider each feature. Is it clear from the empty state what the feature is and why it will create value for me as the user? Is the CTA compelling? Is there any supporting content I might need to get started (e.g., a video)?

Make’s interactive empty state is a great example of how to get users to activate before they’ve set up a workflow.

Step 6: Contextual guidance

To reduce drop-off, make your help content discoverable at the point in time when users need it. Contextual help caters to users who are attempting to set up a new feature but are not motivated enough to go search Google or your help center. Instead of burying how-to links in a help center or search bar, add to the product page, and make it as discoverable as possible.

Intercom does an excellent job of integrating its help content into the product experience. Most of its feature pages have a banner that provides links to guides or triggers for videos or product tours. You don’t need to leave the page to learn more or get your questions answered – the instructions are already in the box.

Step 7: Resource hubs

If there’s a big gap between new and power users, consider adding a resource hub to your product. This is an excellent way to build users’ confidence and skill level.

Here you can centralize and showcase how-to guides, videos, tours, and courses in a single, easy-to-discover place within your product. Bite-sized content is key here, as users are more likely to engage with short, tactical resources that help them achieve their goals quickly.

Miro’s Learning Center is a central hub done right, as it provides users with easy access to helpful tutorials & all of the resources they need to be successful with Miro.

Step 8: Upgrade prompts

It may sound trivial, but make it obvious why someone should upgrade to a paid or higher tier plan. Instead of hiding premium features, consider exposing them within the navigation, within templates, etc. Then, on the product pages, encourage users to convert at that moment.

Hotjar’s ‘Funnels’ feature is a great example of an effective upgrade prompt. The value proposition is promoted, there is a learn more option, and there is a clear CTA to upgrade.

Step 9: Trial limits / paywalls

Beyond the initial onboarding steps, this is probably the most critical part of your flow to get right. Once users get to the first value, they must understand the boundary.

Consider content such as:

  • A countdown banner letting users know how long is left in their trial
  • A simple billing/pricing page that differentiates plan options and highlights any discounts or offers (e.g., annual vs. monthly pricing)
  • A blocking modal that prevents further activity until payment

Featuring one of our designs, here is a trial countdown banner built in Candu. It displays the days remaining in the trial and allows users to request more time.

The TL;DR: 19 free trial mistakes to avoid

  1. Sign-up pages: (a) providing no content whatsoever, (b) blocking or distracting from registration (e.g., using two primary CTA)
  2. Sign-up surveys: (a) too many questions per page (think 1-2), (b) phrasing questions to benefit your team vs to benefit the user, (c) not using this data to then trigger personalized experiences
  3. Onboarding checklist: (a) don’t have a goal-oriented onboarding checklist, (b) the onboarding checklist goes away too quickly
  4. Personalized templates: (a) providing too many options without recommending popular or high-quality items, (b) hiding time-saving templates, use cases, or workflows in a help center
  5. Empty states: (a) including empty dashboards or product pages, (b) providing conflicting CTAs, (c) not testing different messaging
  6. Contextual help: (a) burying support content in a help center or search, (b) out-of-date support content
  7. Resource hubs: (a) content is too long-form (e.g., hour-long course or webinar), (b) content is not tactical (too abstract or high level)
  8. Upgrade prompts: (a) you set out messaging once and forget it
  9. Trial limits / paywalls: (a) not doing enough QA – users will be quite frustrated if they cannot access something they feel they should have access to, (b) not enforcing limits your trial’s limits


Kyle Poyar

Partner at OpenView

Kyle helps OpenView’s portfolio companies accelerate top-line growth through segmentation, value proposition, packaging & pricing, customer insights, channel partner programs, new market entry and go-to-market strategy.