Convert Free Trials to Paying Customers (2021)


Attracting an engaged user base is an essential part of building a successful app. A product that doesn’t have enough active users will simply die. The average app loses the majority of its users after the first use. Apps that offer a free trial are faced with an even bigger challenge: 80 percent of trial users never sign up to a paid plan, according to Totango’s 2016 SaaS metrics report, and conversion rates can be wildly different, depending on whether or not you require a credit card to initiate a free trial or if you follow a freemium model. 

Over the last few years, the practice of app onboarding has become increasingly important to product developers. The term “onboarding” originates from the human resources industry, and in user experience (UX) design it refers to the process of getting users familiar with a new interface, highlighting key benefits and features.

“How do you retain users past the trial period and, critically, get them to upgrade to a paid plan? Your app onboarding is the key.”

Making a good first impression is crucial, but effective app onboarding goes beyond the first experience and is designed with longevity in mind, encouraging users to keep using a product. So, how do you retain users past the trial period and, critically, get them to upgrade to a paid plan? Your app onboarding is the key.

To find out what makes a stellar app onboarding experience, we talked to 10 experts from the worlds of content strategy, interaction and UX design, UX writing, product design and development, and growth marketing. In this article, we share their top recommendations to help you optimize your trial-to-paid conversions.

1. Set out clear user expectations

Julia Tsoi, a design strategist at EY wavespace, has found the best way to convert free trial users to paying customers is to plan in advance. She recommends that when you start your business, spend time strategizing how to sustain your company in the long run after it runs out of initial funding. 

“Set the first year as the experimental period,” Tsoi says. “Starting from the second year, you would then be charging a freemium, premium, or subscription fee to users. Be transparent. Put it on your website. Display the message on the onboarding page. It’s crucial to let people know what to expect next.”

Tsoi also advises getting people to pay before they enjoy the fully-featured service. A good example would be meditation app Headspace: users receive a free trial on one module, then need to pay for the subscription model to get full access to the themed course.

“You have to take cautious steps to transform your free users into the geese who lay the golden eggs,” Tsoi emphasizes. “Have a roadmap in your head, and get a clear picture of how you could achieve that in the future. Put your users at the heart of every step in designing the conversion process.”

Put your users at the heart of every step in designing the conversion process.

Julia Tsoi, Design Strategist at EY wavespace
App onboarding: Screenshot of the Headspace app onboarding process, prompting users to try the service for free for two weeks before upgrading to an annual or monthly paid subscription.
Headspace’s onboarding flow guides new users to choose a session that’s customized to their schedules, goals, and experience levels.

2. Get inspired by established software-as-a-service best practices

Nick Disabato of Shopify Plus consultancy Draft came to ecommerce from software-as-a-service (SaaS), where onboarding is a robust practice with lots of literature and clear metrics. 

One of the best resources is Samuel Hulick’s User Onboarding, which features humorous, detailed, and actionable teardowns of dozens of popular apps, as well as important design patterns that you can “steal” for your own app.

“Onboarding reduces churn,” Disabato points out. “People are more likely to use your app when they get value from it. Yet it may take some effort to show them how. If you don’t put in that work, people will churn.”

People are more likely to use your app when they get value from it. Yet it may take some effort to show them how. If you don’t put in that work, people will churn.

Nick Disabato, Draft

In Disabato’s experience, the onboarding bar is low for Shopify apps. 

“Good onboarding should introduce your app,” he advises. “It should get people through Shopify’s required auth process, walk code-averse store owners through any embedding of code, address data migration, and allow you to double-check whether you installed everything properly. 

“This sounds like a lot, but it’s table stakes for most software businesses—and it can be a significant competitive leverage if you play your cards right.”

For a best practice example Disabato points to JSON-LD for SEO by Little Stream Software, which has a solid onboarding sequence that walks you through the process of setting up rich snippets, showing you what steps are missing along the way. And In Cart Upsell lets you integrate upsell dialogs with no code needed, showing you how they’re placed in real-world contexts.

“If you’re maintaining a Shopify app and you want to increase engagement, reduce churn, and generate more revenue for yourself, use SaaS’s sophisticated playbook and create an onboarding sequence that delights your customers,” Disabato recommends. 

app onboarding: Screenshot of In Cart Upsell's checkout upsell pop-up, offering a discounted t-shirt to the customer to add to cart.
In Cart Upsell’s onboarding is clear, requires no code, and shows you exactly where the upsell will be placed in context.

3. Be transparent about pricing and billing 

Set clear payment expectations up front. In app stores, products often obscure what exactly users get for free and which services sit behind a paywall. And users can feel frustrated after picking an app, downloading it, signing up, and completing onboarding only to find the service requires payment, cautions Elaine Short, UX Writer at personal finances app Dreams.

“They might feel hoodwinked and lose trust,” she says. “Unfortunately, companies often don’t set payment expectations properly for the simple reason that different people are responsible for different content.”

To avoid unintentionally losing the trust of potential customers, Short recommends getting together with the people responsible for communications across the conversion experience and map out all first-time user stories. 

“Get together with the people responsible for communications across the conversion experience and map out all first-time user stories.”

“Explore the communication touch points that lead to the premium conversion funnel, including outside of the app,” she advises. “You might find there are multiple starting points for potential users: the app store, a referral link sent by a friend, your marketing site, and more. Clearly state payment expectations at least once in each possible route to premium conversion. Sure, not every user is there to upgrade—but you won’t lose potential premium users for lack of trust.”

Ryan Bigge, former Senior Content Strategist at Shopify and part of the team behind the Polaris guide on designing onboarding flows, agrees:

“Be transparent about pricing and billing. The trust you’ve built can be damaged or lost very quickly if customers feel like they’ve been tricked or misled about the cost of an app.”

app onboarding: Side-by-side screenshots of Noom and Spotify's premium costs for in-app purchases.
Some apps—like Noom and Spotify—do a good job of comprehensively, although not predominantly, listing their premium costs.

4. Offer flexibility in free trial experiences

Krystal Higgins, onboarding specialist and creator of the First Run UX catalog, believes that free trials let a wide range of new users build a personal connection to a product’s value proposition, which may lead to a better chance of conversion. 

Higgins says it’s important to offer options at the start and end of a free trial to maximize its success for the diversity of users it might be serving. 

This means offering options like:

  • Letting folks sign up with social login, a phone number, or an email to ensure almost everyone has a means to join.
  • Allowing someone to start a free trial without providing payment information up front to encourage new users who might otherwise worry about being unknowingly charged. 
  • Supporting a wide range of payment methods to ensure people ready to convert won’t be blocked by an unsupported payment type.
  • Offering flexible cancellation options and sharing them at point of payment to reassure new users they have control.
  • Providing options for deleting or exporting personal content and data if the user decides to end their trial early. This leaves them with a positive impression of your product, which encourages referrals. For example, if a trial user of a music app curated a list of favorite songs, you could let them download a list of those songs. 

“When you offer new users more than one path through a free trial, you’re ensuring it’s as successful as possible for as many users as possible,” Higgins says.

When you offer new users more than one path through a free trial, you’re ensuring it’s as successful as possible for as many users as possible.

Krystal Higgins, Creator of First Run UX

You might also like: How to Market an App: 11 Expert Tips.

5. Deliver value first and show your app’s future benefits 

When designing an onboarding experience, we tend to focus on educating users through tutorials to get them up to speed. UX designer Zoltan Kollin, Senior Design Manager at IBM Watson Media, says your ultimate goal should be to deliver value for your users as soon as possible while minimizing the effort and the cognitive load.

To achieve that, show, don’t tell. “Instead of crafting tutorials, you should get users to leverage the product immediately,” Kollin suggests. 

“Get back to your user journey map and seek opportunities to deliver value as early as possible,” he says. “How might a user benefit from your app in only three minutes after signing up? How about in one minute? In 10 seconds? How might we achieve this without asking for too much user input or overwhelming them with options?”

“Think about onboarding as the first step in your funnel.”

Think about onboarding as the first step in your funnel, Kollin adds. If you keep your users engaged and provide an effortless way to discover and leverage your offering step by step, you won’t need to worry about churn.

Demonstrating a service’s value can be difficult for apps that require time, engagement, or premium conversion to actually deliver value, so UX writer Short also recommends highlighting the value users will receive in the future. 

“To encourage and inspire early users, I suggest bundling a success moment with a teaser of what the user can achieve through the service in the future,” Short says. 

Do the research to understand the benefits your app delivers in a person’s real day-to-day life, and then show them what that benefit will look like after conversion.

Elaine Short, UX Writer at Dreams

“Take a simple personal savings app, for example. It can take time for a user to save enough money to feel like the app is working for them. If a user saves money for the first time, you can both congratulate them and tell them the sum they will have if they repeatedly save that amount again, say, once a week for one year. Do the research to understand the benefits your app delivers in a person’s real day-to-day life, and then show them what that benefit will look like after conversion.”

“Clearly communicate the value of your app,” Bigge agrees. “As the teardowns on useronboard.com demonstrate, many products struggle to focus on their core benefit during onboarding. Knowing exactly how your app solves a real pain point will allow you to tell a clear, compelling, and transparent story across onboarding.”

A clear focus on value also makes it easier to teach users how to use your app and unlock the core benefit you promised them. Bigge stresses that delivering on what you promised builds trust with your customers and will help you nudge people into paying for your app. 

“Once customers have experienced firsthand how your app solves a pain point, it’s easier to imagine how paid features will enhance the experience.”

App onboarding: Screenshot of Codecademy's learn to code process, displaying side by sides of regular text, code, and HTML output
Instead of overexplaining things, Codecademy gets users to write code right away, providing a sense of accomplishment in just a few seconds.

6. Include social proof in the onboarding flow 

Social proof is one of the keys to successful user onboarding, according to Ramli John, Managing Director at ProductLed and author of Product-Led Onboarding, a book on how to onboard new users.

“Social proof does so much at the same time,” he explains. “It sets expectations, gives leads a comparison party to weigh themselves against, reinforces your messaging, and substantiates your claims.”

In John’s experience, most products only include social proof on their landing pages, but he recommends going beyond that:

  • Use social proof as supporting copy near a call-to-action (CTA) or at a point of friction.
  • Use social proof to counter objections. What are the reasons someone might not convert?
  • Use social proof to support the value of a product.
  • Use social proof to humanize your marketing. A one-line testimonial from John Smith is meaningless. Put names to faces, list companies, link to their Twitter pages. Don’t leave out social media.
  • Use social proof in your in-app content and onboarding emails.

As an example, Shopify uses a testimonial from Fred, Luca, and Danni in an onboarding email to show how easy it is to start an ecommerce business: “Shopify lets us build an ecommerce platform without having prior knowledge or allocating significant resources.”

app onboarding: screenshot of a testimonial from Shopify merchant Luca and Danni during merchant onboarding.

7. Segmentation is “conversion steroids” for onboarding

“Imagine if Disneyland cast members, aka their employees, forced visitors to follow a predetermined, one-size-fits-all schedule and route through the park,” John points out. “They’ve created it based on where the majority of the ‘average’ guests go. The goal is to give visitors the full Disneyland experience as efficiently as possible.” 

App onboarding: A map of Disneyland showing the theoretical best route through the park.
A map of Disneyland showing the theoretical best route through the park.

“If this were the case, it would be pretty upsetting! The priorities of a couple on their honeymoon are different from a family with three kids. It doesn’t make sense to force everyone to undergo the same schedule and route. This scenario sounds absurd.”

John explains that for most companies, their user onboarding is precisely this—a one-size-fits-all, linear experience for everyone. They’ve built their user onboarding for the “average” new user. However, a product might accomplish different customer jobs for separate market segments. So instead of a one-size-fits-all experience, John recommends tailoring the user onboarding for each customer job. 

“Instead of a one-size-fits-all experience, tailor the user onboarding for each customer job.”

“With this approach, you can highlight the right features at the right time, giving users the tools to execute each specific job,” he advises. “You can also better position the product as the solution to their needs. For example, one of Canva’s onboarding questions is, ‘What will you be using Canva for?’ Based on this response, Canva suggests relevant designs and templates based on your needs that you saw in the previous example.”

App onboarding: A screenshot of Canva's onboarding, showing a pop-up box asking how the user will be using Canva.
Canva’s onboarding includes a segmentation feature to determine what onboarding experience best suits the individual user.

8. Personalization makes the user feel like they own the product

Personalization is essential for a great experience.

“Personalization is essential for a great experience.”

Dan Benoni and Louis-Xavier Lavallee, co-founders of growth.design, spent years reverse-engineering popular apps and SaaS products. They compiled those growth tactics and user onboarding flows in an ever-growing list of 25+ UX case studies and discovered that one of the most misused (yet powerful) onboarding opportunities was personalization.

“Persona-based onboarding is when user inputs allow you to understand their most common needs and customize the experience accordingly,” Benoni explains.

For an example, check out growth.design’s Trello onboarding case study. Right after the signup, users have to indicate why they are interested in using Trello:

App onboarding: Three screenshots showing how Trello asks users to indicate what they are interested in using Trello for.
Trello asks new users to indicate why they’re interested in Trello.

Based on that answer, Trello can then personalize the onboarding experience of the following steps.

For instance, default text fields are all related to the “Marketing” use case:

App onboarding: Two screenshots of Trello, showing that if you indicate that you are interested in Trello for marketing, the default text that Trello uses is marketing related. Cards are labelled,
Trello’s default text fields are determined by what the user inputs as their interest during onboarding.

This makes it easier for new users to understand the value that Trello can bring them. It also minimizes the cognitive load that’s typically required to understand a brand new product.

Trello’s growth team reported a lift of more than 36 percent in their onboarding through a mix of personalization experiments (including the one above).

“Small investments like these get users to gradually customize their own experience, making them feel like the product is theirs,” Lavallee points out. 

Later in the onboarding, Trello uses that concept by prompting users to customize the appearance of their board in one simple click:

App onboarding: A screenshot from Benoni and Lavallee's case study showing a prompt from Trello asking the user to personalize their Trello board with a background image.
In this screenshot from Benoni and Lavallee’s case study, the user is prompted to personalize their Trello board.

This concept of “stored value” can lead to the Endowment Effect, which states that people are more likely to keep something if they feel like they own it (this applies to physical and digital products).

So if you want more users to experience a memorable first-time experience:

  • Understand why most of them come to you in the first place
  • Identify their specific end goal (see Headspace Jobs-to-be-done case study)
  • Reverse-engineer a personalized path for them

Here are five simple dos and don’ts, compiled by Benoni and Lavallee, to keep in mind while including personalization in your onboarding:

1. User empathy

  • Don’t use a one-size-fits-all approach and try to guess user needs.
  • Do leverage user research to better understand their most common needs. Learn to identify the psychological principles that affect their behavior (this list of cognitive biases has 101 principles with concrete product examples).

2. Personalization criteria 

  • Don’t just rely on demographics to segment people. 
  • Do focus on user intent to personalize their experience.

3. Simplify

  • Don’t overwhelm users with too many personalization options. 
  • Do focus on the most common cases and leverage Hick’s Law.

4. Educate

  • Don’t just throw more information at your new users.
  • Do use personalization choices that educate users about your product’s value.

5. Reciprocity

  • Don’t ask your users complicated questions too early.
  • Do make the complexity of your questions proportional to the value you’ve delivered so far.

You might also like: 22 Basic UX Laws That Every Designer Should Know

9. Consider offboarding experiences 

It’s important to plan for a positive final impression by building offboarding into the experience, since developers may deprecate app support or merchants might decide to uninstall an app.

No business wants to waste time making a good customer ending, but good consumer offboarding can actually deliver many opportunities, according to Joe Macleod, founder of andEnd (a business that helps companies end their customer relationships) and author of Ends.

“There are some overlooked physiological quirks around consumer endings,” Macleod explains. “Daniel Kahneman ⁠found that humans encode memories at two points of an experience—the peak and the end. Businesses assume success will come from delivering repeated peaks of positive experience and overlook the impact of a bad ending—despite the risk that a bad ending will undo good work elsewhere in the consumer experience.”

Companies that implement better consumer offboarding have higher satisfaction rates. Macleod points out that US cable companies hate people ending an account, so they put in place punitive contracts to punish leavers. 

Netflix, however, is proud of their easy account cancellation and returning customer experiences. This easygoing policy helped Netflix achieve a customer satisfaction rate of 79 percent in 2019, which dwarfs traditional Pay-TV at 62 percent, according to the American Customer Satisfaction Index.

Macleod suggests aiming for a consumer offboarding experience that is:

  • Consciously connected to the rest of the experience
  • Emotionally triggered—similar to those created in advertising
  • Measurable and actionable by the user—this helps to engage people
  • Timely—users shouldn’t have to linger
  • Keeping waste inside the consumer lifecycle and bonding the consumer and provider together in mutual responsibility

Just to further expand on that last point: When people put a plastic bottle in the trash, for example, it breaks out of the consumer lifecycle and becomes society’s problem. Mixing with other consumer items, it then becomes impossible to process and recycle. A successful method to avoid this is the PANT scheme operated in many Northern European countries. Working with producers and supermarkets, the scheme guides the consumer, with incentives to bring back the item to the supermarket and place it in special deposit machines. Sweden now captures 90 percent of its plastic bottles.

App Onboarding: A screenshot from a fictional app showing alternatives to canceling when a user attempts to delete the app. Users can choose to fully delete, or pause their subscription instead.
The Polaris onboarding guidelines state that good offboarding experiences give alternatives to canceling, such as the option to downgrade a plan or pause the subscription, like in this fictional app.

Better endings for free trials 

Macleod cautions that moving from freemium to premium can be a challenge and points out there are three types of endings popular with freemium models:

  • Time Out: Ends after an agreed duration
  • Credit Out: Ends after a value of credits has been exhausted
  • Proximity: Beyond a certain proximity, features are unavailable

“These types of endings are fairly predictable to the consumer, who can manage and predict when freemium ends,” Macleod explains. “For a business, the ideal ending is one that requires increased engagement, creating opportunities for the provider to communicate benefits and convert the sale. A potentially improved freemium system would create instability at the end.”

A “Time Out” version, for example, could give customers two weeks of full access and then go down to every second day. A Credit Out Ending could be in place for up to 10 uses. A Proximity type ending could reduce features daily until the end.

App onboarding: A graph showing different freemium model options for apps.
Macleod suggests ambiguous ends for free trials. A short stable period of using the product is followed by an unpredictable “withdrawal” type of ending.

Build for continuous engagement

To boost your free-trial conversion rate, it’s important to design an efficient onboarding flow that gradually introduces your users to the features of your app, clearly demonstrating its value from the start and being transparent at every step. 

Tailor your onboarding approach to your own app and personalize the experience. Offer options to cater for a wide range of users with different needs and preferences, but keep things simple and don’t overwhelm users. Make use of social proof to establish trust, which is what good app onboarding is all about. And consider offboarding, too, for example letting users know what information they might lose if they cancel or downgrade.

A free trial is a great way to get new users to find out what your app can do for them. A carefully planned app onboarding flow then motivates users not only to sign up but also to keep using—and paying for—your app in the long run. 





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