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How to Convert Free Trial Users to Paying Customers


January 12, 2023


January 12, 2023

Most SaaS companies use some form of a free trial program to familiarize potential customers with their product and (hopefully) convert them to paid users. That’s because free trial offers can be an effective incentive to drive interest in your product and increase the volume of marketing responses. But many marketing strategies stop at the offer and fail to execute the follow through needed to convert those free trial users into paying customers. Let’s explore how to create an effective free trial lifecycle marketing program that will help you drive those conversions.

Track Your Trial Funnel Metrics 

Before you can begin building your new trial program, you must first determine your measures of success. For many trial programs, the bulk of the focus begins (and ends) with a signup, but for most, that should only be the first step in a process that follows your users throughout the trial. If you stop paying attention after they sign up, you’re missing valuable opportunities to convert them. 

You should be looking at next steps, as well as the actions a person takes while in your trial that can serve as the “aha!” moments. For example, if you’re a data analysis company, a user might only see real value after they upload their own data to visualize. If you’re a digital graphics company, you might find that users who upload their own logo to the design are more likely to convert. 

Based on real-life experience, we’ve identified four major steps a user takes while in trial:

  1. Sign up: When a user inputs their information 
  2. Creates their first project: When a user actually starts taking advantage of the product 
  3. The "aha!" moment: When a user realizes value
  4. Conversion: When a user subscribes or inputs their credit card information 
The four major steps a user takes in a free trial are sign up, creating the first project, the "aha!" moment, and conversion

Once you’ve outlined those milestones, you should analyze benchmark conversion rates for each and monitor them on a weekly basis. 

Note: Determining the “aha!” moments at this stage will also come in handy when you start developing content for your onboarding experience later. Whichever stages you decide to monitor, ensure you’re able to track and measure whether your trial users are hitting those thresholds. 

Connect to Your Technology Source for Personalized Onboarding

Now that you’ve determined your funnel metrics, you’ll want to connect your product with your marketing technology stack to enable a personalized onboarding experience for trial users. Having product data will be crucial to segment and nurture trial leads throughout the funnel, plus it enables your sales team to craft more personalized outreach messages. Connecting product data to your martech stack can be quite an undertaking, so you’ll want to ensure cross-functional teams are aligned. There are a number of tools out there that can help, including Zapier, Mulsoft, Segment.io, and others

Next, determine which data points to push to your martech stack. They should be the ones you’ll monitor to ensure users are moving smoothly through their free trials, meaning they’ll likely align with the funnel metrics you identified above. A few examples you might consider are sign-up date and time, trial period length, trial end date, real-time product behavior (i.e. your “aha!” moments). This data will help you segment users and determine the best content to serve them. 

Tip: When selecting which data points to push, consider not only your marketing efforts, but your sales efforts as well. Think about what data will be helpful for the sales team to have that they can then use for outreach.

Create a Robust Email Nurture Program to Convert

Now that your data is available within your martech systems, you can use it to build out nurture streams that align to your funnel metrics. Segment your audience based on actions taken within the product. For example, your company might develop eight unique paths a user can follow within their product journey, based on what actions the user takes, along with their product interest. Every unique path should also account for the length of the trial period to ensure users receive appropriate communications upon signup, throughout their journey, and when their trial period expires. 

Whether you have one path or eight, make sure your users are served up the right content at the right time to help them self-serve or get in touch with someone who can help. A few things a user might be searching for includes information about their account, how to navigate the product user interface, or getting answers to their onboarding questions. We often see the highest engagement rates on emails that include training videos, how-to guides, and links to relevant documentation. 

Another way to keep users on the path to conversion is to show progress throughout the trial journey. This can be especially helpful for highly technical products where a user can easily get stumped or frustrated. In each email you send, make it very clear what the user’s next step is in the onboarding process and ensure the content you present in that email helps them reach the next goal. 

For a deeper look at creating an email nurture program for trial users, check out How to Improve Your Onboarding and Activation Strategy

Offer a Central Hub for Resources

Trial users are generally practitioners, developers, and/or specialists who want to get hands on with the product. They are highly likely to bypass sales altogether in favor of testing out the product themselves. While your product should be intuitive and easy for your target audience to use, there’s still going to be a learning curve for new users. That’s why it’s crucial to offer up the right content at the right time to help users onboard quickly. Housing all of your ‘getting started’ resources, step-by-step guides, how-to videos, and technical documentation in one centralized, easy-to-access spot means trial users can swiftly find all of the information they need to be successful with your product. It’s also a great place to outline your ideal customer journey by showing users what steps they need to take (and in what order) to have a successful, efficient onboarding experience. 

This hub should be tightly focused on resources to get started with additional materials that offer the ability to dig deeper. Highlight how users can achieve quick wins, but also provide links to explore more specific use cases or functions. Again, these users are probably going to self-serve anyways, so equipping them with the resources to do so will set you apart from the competition. 

Explore Other Channels to Support Trial Users

As a marketing team, building out your email nurture program and resource center should be your first priority. Once you have those foundational pieces set up, it’s time to explore other channels for outreach and personalization. For example, you can align with your product development team to have in-product features like in-app messages, guided set-up tours, and a ‘getting started’ resource center. We’ve also found success with in-app chatbots that allow trial users to immediately connect with an onboarding specialist.

If you’re restricted with what you’re able to do within the product from an onboarding perspective, you can also look at leveraging your website for additional features and support. For example, you can use a cookie to determine if a user is in a trial or not. And then for trial users, you can present a personalized website experience which includes unique calls to action, ‘getting started’ content on the homepage, and a chatbot that helps users find what they need quickly. 

Get Your Sales Team Involved 

Finally, it’s important to equip and enable your cross-functional team to be successful. Creating shared goals will help align your team to your funnel metrics. Whether you sit in product, marketing, sales, or customer success, everyone should have the same measures of success. These metrics should be the same as the funnel metrics you established early on (see first paragraph) and might include something similar to a sign up, a user’s first project, a user’s ah-ha moment, and conversion.

In addition to aligning on KPIs, you’ll want to ensure that your sales team has the right information, messaging, and content. Your sales motion can differ quite a bit depending on the types of leads that come through your trial, so you’ll want to establish top notch enablement materials to help sales and the rest of your cross-functional team better understand the trial user audience. And finally, implementing feedback loops across teams will help surface insights that can inform and shape marketing content, sales messaging, and product enhancements. 

A Full-Circle Approach to Free Trials

Free trials are an effective way to connect with potential customers and create demand for your product, but the effort shouldn’t just stop at the signup. Creating an effective and relevant lifecycle marketing program is essential to seeing higher conversion rates, more subscriptions, and lower churn. 

Do you want to increase conversions from your free trial program? Contact the experts at Right Side Up to turn potential customers into paid users. Give us a shout at growth@rightsideup.co.

A highly motivated, critical thinker, Maysen is a young professional with energy and passion for simplifying technology. With her undergraduate degree in Marketing and a Master of Business Administration, she's held countless roles in marketing and sales within the technology industry. Maysen is a gifted communicator and storyteller that is dedicated to educating, equipping and empowering go-to-market teams through campaign management, content management, demand generation strategy and sales enablement. She recently led marketing strategy for the Cloud SaaS sector at Elastic where she developed, managed, and executed on the cloud trial program. Since then, she's taken her expertise in SaaS to expand her role to campaign management leading several product-led growth initiatives.

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Let's talk growth

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Let's talk growth

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