How You Can Boost Your Trial to Paid SaaS Conversion Rate

How We Were Able to Boost Trial to Paid Conversions by 4% - And How You Can Too

Every SaaS product owner wants to boost trial to paid conversion rates.

Why do some succeed while others fail?

Well, we will be terribly honest with you: there is no one-size-fits-all cure for low conversion rates.

This is not another ‘7 proven tactics’ listicle post that prescribes a universal cookie-cutter recipe for success.

Before you start working on improving your conversion rates, you need to (brace yourself for the cliche!) – start with the why.

But after you have identified why your free triallists aren’t converting – there are some proven ways to boost the trial-to-paid conversion rates for each scenario – both outside and inside your app.

Let’s dive in!

First: Determine Why Your SaaS Conversion Rates Are Low & Users are Not Converting

There are many best practices with wide applications that can boost trial to paid conversions. We’ll talk about many of them in the next two sections.

But first, it’s essential that you understand why your own users are not converting.

Why? Because the most effective solutions are tailored to the problems they solve.

Examine analytics, support tickets, and other data for friction and drop-off points

The single most helpful tool here is to have event-based analytics installed in your app.

We would recommend Heap, Mixpanel, or Amplitude as they all have ready-made integrations with Userpilot.

To boost trial to paid conversion, first work out why people are not converting


Studying in-app activities will show you the points at which users fail to complete tasks successfully or struggle to achieve value. Once you know where the workflows are breaking down, you can start to fix them.

Heavy drop-offs at the checkout page, for example, could indicate:

  1. A bug in the app
  2. The range of payment options offered is limited
  3. The price is too high!

You will need to dig deeper, but you know that this page is where to start looking!

Aggregated analytics is not the only source of information: support tickets and help center usage stats will also give you valuable information about what kinds of things users are struggling with.

If the same problems keep appearing:

Boost trial to paid conversion with concierge onboarding


Study session recordings for qualitative information

Session recording tools like Fullstory allow you to watch back in real-time how users have been interacting with your app. This will really help you boost trial to paid conversion by figuring out where people go wrong.

Combine the quantitative data you’ve seen from analytics and other sources (which tells you which problems keep cropping up) with qualitative insights from the recordings.

Fullstory also provides heatmaps (below) which can aggregate and visualize click and cursor movement data – bridging the gap between individual stories and mass behavior.

Fullstory lets you dig in to qualitative data


By studying actual cases of people failing or succeeding to use your tool, you will see:

  1. Where they get stuck
  2. When they give up
  3. What mistakes they make and why

You’ll also start to see what would solve those problems.

Talk to your users to get feedback

Sometimes there’s no substitute for just ASKING people what they expect.

These questions are taken directly from our own Userpilot user research questionnaires:

  1. What happened exactly and why did you start searching for a solution like this?
  2. Before you signed up, how did you imagine things would get better with our tool?
  3. What drove me to use or search for a product like this? What were you trying to solve?

Sometimes you’ll need to give incentives for feedback. has a great way of doing this: they offer a three-day trial extension to users who explain to them why they’re not ready to convert!

Look at price/value fit and prequalify triallists

Maybe users are telling you that your tool is too expensive?

Then adopt a value-based pricing strategy – price your product on the basis of the value provided.

Nick Kozmin of recommends pricing SaaS products so that you provide value worth ten times the price tag. If the value is overwhelming relative to price, you’ll convert more trials.

Some triallists don’t care about price. They’re just there to test out your service.

You need to identify these people and focus your efforts on users who are serious about becoming paid customers.

Asking a question about company size and readiness to start during the sign-up process can help identify users who are likely to pay. Here’s part of BAMF’s sign-up form.

Prequalify triallists


At Userpilot, we increased our MRR by 50% in a matter of months by prequalifying triallists and focusing our attention on the most likely prospects.

We defined them as a segment and tailored onboarding experiences accordingly:

Userpilot segments users after prequalification

Get a free demo of userpilot now!

Segment the audience by use cases and solutions

Users come to your tool looking for different things. “Value” is not the same thing for everyone.

If you lead to brand new users through onboarding for features they’re not interested in, you’ll lose some of them.

So use everything you know about users to sort them into segments, and then provide onboarding experiences tailored to what value means for their different use cases.

Userpilot enables you to create experiences that are triggered only by certain users, defined by profile details or activity patterns.

Userpilot enables tailored onboarding

Get a free demo of Userpilot now!

If you have a one-size-fits-all approach to your audience and their onboarding, you will certainly lose triallists who could have been converted had you given them a more relevant experience.

In-App Tactics to Boost Trial to Paid Conversion

Once you know why users are not upgrading, you can start to fix the problems.

Your particular situation will determine the best mix of tactics, but it’s sure to involve most of the following approaches.

Segment during sign-up

In the last section, we showed why it’s vital to segment. The earlier you can do this, the better. This ensures the onboarding experience is relevant from the very start.

Rather than asking for loads of personal details during sign-up, Sprout Social asks questions that help them segment by use case.

Boost trial to paid conversion by segmenting users at sign-up


But don’t bombard new users with long lists of questions. Keep it minimal and contextual by asking for small amounts of data (for example, with microsurveys) at different times, building up a picture gradually.

This is called Progressive Profiling.

Orient new users as soon as they arrive

It’s always intimidating to find yourself in a strange new environment. Imagine walking into a party and not knowing anybody. Many people would turn around and leave.

So we were surprised that 40% of SaaS products still don’t provide a welcome screen for new users.

A welcome screen:

  • Makes new users feel valued
  • Gives you a chance to convey essential information about getting started

Here’s an ideal example from Buffer, which gets new users right on the road to value.

Boost trial to paid conversion with welcome screens


Eliminate “empty state” confusion

The worst thing you can do is welcome new users with something they don’t understand. Compare these examples:

Banish empty states


Would you know what to do with the one on the left?

If your tool needs the user to do certain things before there is anything for them to interact with, make sure you explain that immediately.

This is something Trello does well, providing a sample board to help users understand what the service does.

Trello handles empty states


Provide guidance, example data, templates, and other examples of how other people are using your tool to avoid leaving new users confused by empty states.

Make onboarding interactive

One big error that’s often made is to provide a generic Product Tour:

  1. Being one-size-fits-all, they don’t acknowledge that different use cases matter to different users
  2. They’re passive
  3. They have notoriously low completion rates

Most people learn best by doing, which is why Interactive Walkthroughs are so much better.

Boost trial to paid conversion with interactive walkthroughs


By using an Interactive Walkthrough to talk you through the process of adding a messaging service – and making you do it why you learn – Rocketbots drives users directly to value.

This Interactive Walkthrough increased Rocketbots’ triallist activation rate from 15% to 30%!

Use a checklist to make it clear how much Primary Onboarding a user has done and how much is left.

You can even offer incentives to promote completion and pre-fill a number of boxes as a neat little psychological trick, as Postfity does in the example below.

Boost trial to paid conversion with progress checklists


Minimize Time to First Value

Everything we’ve talked about in this section so far is focused on reducing the time between a user signing-up and experiencing the benefit they came for.

That is, reducing Time to First Value (TTFV).

First Value is a critical step on the user journey. We usually call it Activation.

User journey


As well as the tactics we’ve already looked at, you should:

  1. Remove clutter and complexity from your User Interface
  2. Exploit familiarity: everyone recognizes an envelope as an icon that represents messaging. Forcing people to learn a new language (visual or otherwise) is a major source of friction
  3. Onboard contextually so as to drive action: native tooltips can show where features are and how to use them; checklists can remind users to complete unfinished tasks; and Userpilot’s unique Driven Actions let you build onboarding flows that require user input to move forwards
Boost trial to paid conversion with driven actions


Don’t neglect Secondary and Tertiary Onboarding

TTFV is important but it’s not the end of the journey. Once you’ve activated a user, you need to turn your attention to Secondary and Tertiary Onboarding.

User journey onboarding stages


That is, keep showing the user more features. Keep pushing them to achieve more value.

Follow the same practices as we talked about earlier for Primary Onboarding, but assuming a higher degree of knowledge and engaging with more advanced features.

Make sure Activated users are kept engaged by:

  1. Announcing new features to them
  2. Asking for and listening to feedback
  3. Sharing testimonials and case studies that will reveal new use cases and sources of value to them

Keep pushing for the upgrade

Another way to boost trial to paid conversion is to reserve premium features for paid users.

This can be done in various ways:

  • Show free and Freemium users a standard dashboard, but with premium features deactivated. Use native tooltips to ensure they understand what they have to do to get them!
Boost trial to paid conversion with upgrade reminders


The most important email we send is the email that tells users that they’ve reached their free plan limit (1,000 popup views). This email converts free users to paid users more than anything else.

  • Alternatively, provide access to the full range of features during the trial period – but then either opt for the paid service or a free, restricted version.

And don’t be shy about asking for the upgrade in-app.

Dropbox uses a variety of in-app messages to drive users from free plans to paid one, such as this slideout.

Dropbox pushes upgrades in-app


While Adobe uses modals to remind users when their free trials end and push for the upgrade.

Adobe modal


Tactics to Boost Trial to Paid SaaS Conversion Rate When Outside the App

In the product-led era, in-app is the best environment to convince triallists to convert. However, you can complement your in-app efforts through other channels as well.

And some barriers to conversion are actually better dealt with elsewhere, as we shall see.


“Preboarding” means getting new users onboarded before they even sign up for a trial.



Ahrefs does a great job of Preboarding users through content marketing. They produce loads of great blogs and videos – which get an average 1.5 million and 400,000 views per month, respectively.

These target a whole host of people interested in SEO and related topics, and explain how to serve the common Jobs To Be Done in those areas.

Surprise, surprise: the solution provided always involves Ahrefs!

As CMO Tim Soulo explains, Ahrefs creates demand AND educates future users on how to use their tools with their marketing content. They already understand the value available before they start a trial.

It’s possible to go even further and give access to some features of your tool as part of Preboarding- eg Buzzsumo lets visitors to their site try out its content analysis tools:

Buzzsumo makes features available before trial


While Hubspot lets visitors try out their website grader:

Hubspot website grader


This is a great way to build familiarity and demonstrate value, while showcasing what else paid customers get.

Re-engage with email sequences, push notifications and retargeting

If a user is engaged with your product, the best channels for driving conversion will be in-app. They’re most likely to upgrade when they are successfully using it.

But what if they’re not?

Then you need to engage them elsewhere to draw them back.

Email is the most obvious channel. Here’s a great example from Airtable:

Airtable re-engagement email


It provides:

  1. A sense of urgency – reminding the user that they will soon lose Airtable’s benefits if they don’t upgrade
  2. A quick way back into the app, with the “Start with a template” button
  3. Educational content to help readers get more out of the product

A personalized end-of-trial email is a great way to win back disengaged users. It can be used to win them back with:

  1. A trial extension to allow more evaluation time
  2. A discount on the subscription
  3. Introductions to features they have not tried, which may give them more value
  4. Offers of alternative solutions you may have

At the very least, an end-of-trial email is an opportunity to get feedback that can be used to help future users.

And you don’t have to limit these kinds of re-engagement to email:

  • Web push notifications and SMSs can be used to drive users back to the app, especially for timely events such as webinars
  • Retargeting triallists with ads on other sites can be a handy way to remind them about your app when they’ve forgotten!

Remove the perceived risks of converting from trial to paid

As John Kopelman of First Round Capital says on CXL’s blog:

Scaling from $5 to $50 million is not the toughest part of a new venture—it’s getting your users to pay you anything at all. The biggest gap in any venture is that between a service that is free and one that costs a penny.

Why? Users see a risk in paying for something they may not get value out of. We’ve already talked about getting pricing right specifically, and much of this blog has been about making sure users get value fast.

But there are other things you can to address risk-aversion:

  • Provide price anchors to help users understand your value proposition. This example from SEMRush sets the Guru package as the “standard” price level
Price anchoring


  • Don’t make it hard to cancel – minimize the financial commitment it takes to become a paid user and you’ll get more of them
  • Indeed, offer no strings refunds if you can
  • Make it easy to switch plans, both up and down
  • Allow users to keep their data if they downgrade. The fear of losing time and effort invested can be a big deterrent to getting started
  • Provide a range of convenient payment options with a friction-free checkout process

Pay individual attention to users with webinars, personalized emails and calls

One trial to paid conversion tactic that has worked really well for Userpilot has tailored webinars.

If we see a user struggling to achieve value, we invite them to a problem-solving webinar. This triggered contextual slide got 14% of everyone who saw it to sign up!

Userpilot webinar slideout

Get a free demo of Userpilot now!

Then we make the webinar valuable and personal:

  1. The demo features to show how to use them
  2. Find out more about our users and their friction points
  3. Ask for questions, so that we can personalize the content to attendees and guarantee the relevance

As a result:

  1. We convert more than 50% of webinar attendees into paying customers
  2. We’ve improved our overall trial to paid conversion rate by 4%
  3. We’ve cut churn by 2%

Closing the loop, we follow up:

  • Via personalized emails
  • Via phone calls

This kind of personalized attention is one of the reasons for our success! One-to-one attention is really the best way to understand your users, so spend as much time talking to them as you can afford.

Wrapping up on how to increase your SaaS conversion rates from trial to paid:

– To boost trial to paid conversion, you first need to work out why users are not converting.

– Once you’ve diagnosed the problem, use the tactics we’ve discussed in-app and outside to make sure they get value and to make sure they know how to get value from your app.

Want built-in, proven ways to boost your trial-to-paid conversion rates? Try our product adoption platform – which you can get a demo of for free here!

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