5 Strategies to Engage Prospects After a Free Trial or Demo

December 28, 2021
Contributor: Sara Hartanov

Use these tips and techniques to convert a higher number of free users into paying customers.

Nearly every tech provider offers some kind of “try it for free” option as a part of their marketing mix. And for good reason — calls to action (CTAs) that mention a free trial or demo are among the best-performing CTAs in attracting customers and generating marketing-qualified leads. 

Demos, free trials and freemium models give users a taste of what you offer. But they are only a part of the process. Many tech providers that jump on this bandwagon often struggle to get their prospects past that free stage. 

Without a proper free-to-paid conversion strategy outlining what happens before, during and after a trial or a demo, your free offerings can easily turn into nice-to-have conversations but without any conversion to a sale. 

The five strategies below can help you maximize the momentum generated in free trials and demos, and make sure your follow-up after the free period is a success.

1. Know what to use when: free trial or demo

Product demonstrations and free trials are the most valuable form of content for new users to understand a product’s value and “de-risk” their purchase. They provide users the first glimpse at a product and show how the solution can solve their problems.

However, both differ in terms of the time and effort they demand from buyers, and the points at which they should be deployed in a buyer’s journey.

A free trial requires a lot of work from the prospect in setup and configuration, but it introduces the product well to a buyer and gives them open access to resources they will need to make a purchase decision. 

A demo, on the other hand, is easier to conduct, takes less time and can be tailored to business needs.
Differences between demo, free trial, and freemium

Here are a few pointers to help you decide between the two: 

Use free product demos when:

  • You need to personalize the conversation.
  • Your software and workflow are more complex.
  • Your buyers are busy and not likely to take the time to set up and use a free trial.

Use free trials when:

  • Your software interface is simple and intuitive.
  • You can do frequent check-ins to ease your prospects into key features.
  • You need to free up higher-cost sales resources. (Keep reading for more info on how to set up automatic nurture tracks for trial users and therefore save sales resources.) 

The rule of thumb is when time is limited and your software is more complex to explain, you will be better served by first extending a demo customized to the buyers’ needs.

2. Engage only the most qualified leads

Registering for a demo or using a free trial don’t necessarily indicate a high-quality lead. Many prospects respond to free offerings even if they aren't actively seeking to buy a product: they could be educating themselves or preparing for the buying process in the near future.

If you are wasting your resources following unqualified leads, it’s worth asking yourself: Are those truly the best leads? To decide which are the most qualified leads for you, look for the following signs of an active buying cycle:
  • A group of users (versus a single person) have interacted multiple times with your marketing campaign. Most B2B software purchases happen in teams. So, a single B2B buyer trying out your product or content may not be a strong active buying signal.
  • The prospects have downloaded or tried “advanced” content. Consuming advanced content, such as taking an hour-long demo or joining a technical webinar, indicates a prospect actively seeking to buy.
  • The lead has made direct inquiries. Buyers who are trying out a product for self-education don’t usually request a call from sales reps or click on a “call me” button.
  • The lead is facing similar challenges as your existing customers. This indicates that the lead fits your ideal candidate profile (ICP). Track the type of content downloaded or inquiries made by the leads to determine their challenges. 

3. Create an outbound touch pattern on multiple channels

The B2B buying journey isn’t limited to a few channels anymore. Software providers must use multiple communication channels to reach out to their leads. That said, after a free trial or a demo, engaging prospects via personalized media holds more water than other channels.

Email and chatbots are low-cost methods to keep in touch with demo and free trial users. More customized support can be given via calls and chats with human representatives right before and after a demo or free trial.

Live phone support and instructor-led tutorials can be expensive. In their place, give users access to informative online content, such as short, easy-to-consume how-to videos or FAQs.

As you select your channels, create a touch pattern to manage your outreach effectively. A touch pattern gives you a visual representation of which channels you will be using, how frequently, and at what intervals you plan to send messages to your prospects. It can be divided around a few themes or CTAs best suited to the buyer’s journey.
Outbound touch pattern - example

Following a touch pattern will help you engage and track your prospects and measure the impact of your conversations more easily.

4. Align your messaging to buyers’ needs

Buyers’ attention spans are short, so it’s crucial to target them with the right messaging to stay top of mind, and most importantly, to do so when they are still listening.

Reaching out with self-centered content that lists the features and benefits of your product instead of addressing their business needs can render your time and efforts put into the free trial and demo a waste.

You can hone in on what buyers want to know after a trial or demo by conducting “discovery sessions” within your team and with the prospect. Focus on gathering their honest opinion of your product, and understand the strategic objectives and goals they plan to achieve with this purchase. 

Then, target them with content centered around the following CTAs.

CTAs that are most effective after:

A free trial or freemium

  • Learn more about customer success stories and case studies
  • Determine how the software helps your company with links to value assessment tools
  • Read customer testimonials and product reviews
  • Sign up for a monthly or yearly plan, and save X% 
  • Request a demo from a sales rep

A demo

  • Download our technical documentation
  • Sample requirements checklist
  • Download return on investment (ROI) calculators
  • Read customer success stories
  • Talk to our experts
  • Checklist to plan the purchase and implementation

You can web them in email nurture tracks (as shown below) based on leads’ behavior. Conduct A/B testing to automate the tracks that best suit your demo and trial subscribers. 
Email nurture tracks examples

5. Wait for the right time to introduce the paid plan

Heading into closing conversations too early or late can be counterproductive. It can make you seem imposing and unhelpful. Be authentic and considerate as you introduce paid product and service offers.

Prepare your prospects with a variety of conversion marketing messages before the demo or trial ends.

  • Communicate what happens next after the trial ends and explain the process for upgrading to a paid version.
  • Unlock paid features for a limited time or extend the free trial by a few weeks or months to push active users closer to an upgrade.
  • Design a customized and compelling offer with lucrative discounts for the first few months for new paid subscribers. The key is to make an offer that a demo or free trial user cannot refuse.

Pro tip: Build software usage analytics into your SaaS solution

Integrating usage analytics into your Software-as-a-Service (SaaS) in your free trial can help users get the most from a trial and help you monitor and actively remove the obstacles faced while using the product. 

It can also help you improve your communication by giving micro-level support with automated interactions. You can time your nurture track emails to certain events, which can be triggered when a free trial user reaches those junctures.  

By 2025, 80% of enterprise software providers are expected to adopt free trials or freemium products in their business models. Curating a free-to-paid conversion strategy will enable you to follow up with the right conversations in the right manner after a free trial or demo, resulting in more closed business. 
Customer Engagement Evolves

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Sara Hartanov

Sara Hartanov is a Senior Manager of Client Success at Gartner Digital Markets, where she helps software companies connect with buyers through research, reviews, and lead generation. Sara manages and trains account managers and sales leaders to deliver first-class customer service to clients, while focusing on revenue growth, account retention and product adoption. Connect with Sara on LinkedIn.
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