Best Practices for B2B Software Trial Conversions

Best Practices for B2B Software Trial Conversions

Free trial users can make or break the success of your B2B SaaS product– the key is in the conversions. But how do you get from signups to loyal, paying customers? It starts with meticulous planning, tracking, enablement and teamwork across departments from sales to marketing, customer success, and product.

We’ll dive into different techniques to maximize free trial conversion rates, from paying attention to how you're bringing in free trial users to providing an experience compelling enough to convert. It’s not enough to have data; you need to know which free trial period data to focus on and how to make it actionable for the right teams. Data like KPI tracking, usage optimization, customer engagement sequencing, and content that converts need to be wrapped in a personal approach from sales.

Give your teams the skills they need to convert free trial users into happy, long-term customers.

Understanding the SaaS Free Trial Process 

There are a million different ways to design a trial; there is no one “standard” approach with “standard” results. There are opt-in free trials, opt-out free trials, and a variety of other free trial models.

Free trial conversion rates vary across B2B companies, trailing behind B2C companies. The most important thing is to benchmark your measurements from the start so you can measure success against yourself.  

The first step is understanding broadly how most B2B companies approach setting up their trials can help you establish or refine your current system to get more paid customers.

B2B software trials vs. proof of concept (POC) vs. a pilot 

Deciding if your organization should focus the sales process on a trial, proof of concept (POC), pilot, or customized mix of the three depends on your specific offerings and the resources you have to work with across your teams. 

Free trials come in a variety of different forms:

  • Opt-in free trials: only require an email address to sign up with a credit card required to buy at the end.
  • Opt-out free trials: require credit card details to start the trial
  • Limited free trial: puts limits on the features available to the trial user or period of access
  • Unlimited free trial: no limits on feature access and/or period for access

POCs can be deployed either as a first step to show specific customers what is possible with your product or service before they undertake a longer trial or as a follow-up on specific features post-trial.

Pilots are typically even more customized and reserved for premium prospects who have signaled a strong interest in what you have to offer. These involve a lot more work for your team, customizing and embedding your product or service into their organization so it can be tested. 

The pros of a pilot are that they aim to address specific pain points of a target customer and prove your value beyond a doubt. The con is that most customers do not want unknown software systems interacting with their established data and systems prior to purchase. 

That makes it necessary for some aspects of B2B trials- when there is no working or real data in place- to need demoing through dummy data or videos to establish their value in a prospect’s mind. 

Managing Free Trials Effectively

It always comes down to resources: time and budget. Sales reps need to reach out to prospects involved in a trial period at just the right cadence. Too little outreach and interaction with the product might drop, leading to less interest and a failure to convert at the end of the trial. Too much outreach and the prospect might become annoyed and decide to go with a competitor who has a lighter touch approach. 

Free trials need to be customized enough to prove the value of your product without taking up an unsustainable amount of your customer-facing teams’ resources. Figuring out the right balance of customization and outreach will be an iterative process to increase free trial conversion rates.

Common Challenges in Running Free Trials, POCs, or Pilots 

While there’s a lot of overlap in the pitfalls teams can face while running trials, POCs, or pilots, each also has its unique challenges. Lack of clear objectives, unrealistic expectations, and lack of support throughout the process can hamper any of these approaches. 

Trials specifically tend to face more issues with low levels of user engagement, inadequate training, and limited feedback from free trial users. POC’s tend to run into the issue of balancing customization with technical complexities and a lack of alignment, particularly among stakeholders. 

While pilots often also face these same challenges, they also run into scaling issues, trouble with integrations (particularly with existing tech stacks), user resistance, and resource constraints. A major challenge for sales reps is getting free trial users excited enough about the capabilities offered to them to overcome any initial user resistance. The emphasis needs to be on how much the new technology will save in terms of time and energy in the long run, especially if there’s an upfront cost in setup, integration, and training. 

Understanding Your Free Trial Users

Designing a trial with the highest potential for conversions means deeply understanding your prospects. That starts with the standard process of researching personas and differentiating between the everyday users of your product and those who make budget decisions. Sometimes that will be the same person, depending on the size of the organizations in your ideal customer profile (ICP). If you’re targeting startups, for example, practitioner and budget wielder are more likely to be the same person than at enterprise companies where budget decisions typically have to be run up a chain of command. 

That means understanding the motivations, potential objections, and decision criteria each layer of person interacting with your product will have. An enthusiastic user might need help convincing their CFO that it’s worth the purchase price, so be sure your sales team is equipped to help with that conversation.

Tracking behaviors through analytics to optimize trials

The best way to optimize a trial is to track the behavior of users over time, from the beginning of the trial through to either converting or not. Understanding which behaviors are key to keeping users engaged– that might be introducing a feature at a certain time– means you’re more likely to convert more users later on. 

Start by tracking how users come to your trial. How many are finding it on their own and signing up vs. being brought in by sales or marketing? Is there a difference in the conversion rate of those who discover the trial on their own vs. those who are brought in? 

If there’s no difference in free trial conversion rates based on how users are brought in, focus on the steps taken during the trial. Crucially, this data needs to be shared with the sales team at the right time, enabling them to engage with the prospect to provide a more informed experience. Sales needs to know when to introduce prospects to key features to showcase their value for that prospect’s particular use case. Users need to be trained on how the product solves their specific pain points in a way that’s accessible and not overwhelming. 

Getting users to test key features and see their value at the right time leads to higher free trial conversion rates. Simply hoping prospects wander in, sign up for a trial, and convert a week later into paying customers isn’t a sustainable strategy. 

Failures and Learnings in B2B Saas Free Trials

Before we look at best practices that drive success, let’s work to understand what has failed. According to Userpilot, while there isn’t a single average conversion rate for B2B SaaS free trials, “15% is considered a good rate- 25% is the B2B industry average you should aim for, and a 30% conversion rate and above is excellent”. 

When B2B SaaS free trials fail to convert, it’s because the relationship manager has no insight into what’s happening. The product team might be meticulously tracking product usage data throughout the trial period, but if that data lives in a silo where it isn’t accessible to the sales team, they can’t use it. Even if it is accessible, it needs to be clear and actionable for individual sales team members to be able to effectively use it to enhance the experience of prospects. 

Don't overlook exit interviews either. While they're not always easy to get, keeping expectations clear and incentivizing participants goes a long way. Let them know the interview won’t take longer than ten minutes and they’ll get a gift card for a cup of coffee or whatever else might make more sense coming from your brand. 

The goal should be to understand if there is a clear point where user interest wanes in the trial process. Are they not aware that certain features exist, or are they not aware of how to use them? Are they overwhelmed by features? Or did they simply realize the product is more than they need right now? 

These questions can get your team to understand how you can better tailor the experience to boost free trial conversions and which key data points need to be shared with the sales team at what times to maximize it. 

Best practices to drive conversions with your trials 

Once the main failure points of B2B free trial conversion rates are understood, it’s easier to build on established best practices. Here’s how to maximize sign-ups and optimize the full trial experience for a higher conversion rate. 

Maximizing Trial Sign-Ups

Don’t just have a single page on your website that promotes your trial; promote it across channels including paid, earned, and owned. Make the entire experience as tailored as possible with the resources available. It’s not always realistic to have a completely personalized experience for every prospect, but just crafting persuasive copy triggered by different user actions can make a difference.

For example, if a prospect signs up for a trial and is immediately active, it triggers an email saying: “Thanks for signing up! We notice you’ve been enjoying X feature. Do you have any questions about Y?” 

If a prospect signs up for a trial but they are not immediately active, it triggers an email saying: “Thanks for signing up! We notice you haven’t logged in– here’s a link to the page that shows you how to do that. Got more questions? Reach out here.” The email can then direct prospects to your help center, or sales or customer support team, depending on how your organization is structured. 

Don’t be afraid to offer incentives here either, like special pricing. Let trial participants know they can get an early adopter offer if they sign up before the trial ends, or a big discount in exchange for serving on a customer board and giving regular feedback on the product and features. 

Finally, make it a priority to reduce friction in the sign-up flow as much as possible. Ask only for information that’s completely necessary to move the process along and be sure the user experience is as intuitive as possible. 

Optimizing the Trial Experience

Start with a personalized welcome screen. This should include a few basic questions to help tailor a new user’s experience: what their role is, how they plan to use your product, and why they are using it. You want to help them clarify what the job is they are trying to get done using your product or service. (The bonus is that this information will help you further refine your ICP and how you market your free trial!)

Once a user is welcomed into the trial, be sure there’s a smooth onboarding process that guides users through. In-app messaging and prompts should point out the most important areas they need to understand and access without overwhelming them. Design a dashboard that’s clean and accessible. 

Many products find success using a series of overlays that take users through a quick walkthrough of the main features and their value. Make this an opt-in process so anyone familiar with how your product and features work isn’t forced to go through it every time to gain access. 

If your product integrates with other products in users' tech stacks, be sure that the process is as seamless as possible. Prioritize fixing any bugs related to integrations so trial users have a smooth experience. Enhance this further by providing excellent support both inside your product and across channels.

Leveraging Usage Data

A key moment in trial conversions is the “wow” moment when a user realizes the value of a product or feature and how it can help solve the pain points they deal with daily. If prospects aren’t using the “wow” features, your team should reach out to point them out and train prospects on how to use them to win the deal. 

It’s equally important for your team to track any drop-off points in usage. Are there specific features that seem to confuse or overwhelm users? Do these need to be clarified in onboarding, or additional training offered to reach the “wow” moments? 

Again, be sure all of this product usage data isn’t just tracked but is also relayed to the sales team in an actionable way. If a feature gets identified as a drop-off point for trial users because they’re confused about its value, the sales team can use this information to reach out at a critical time to let them know proactively about it. 

That gives sales team members a reason to stay in touch with prospects and gives prospects a feeling of tailored service. Engagement throughout the process should be customized based on user behavior. 

Driving Adoption with Content /Training

A seamless onboarding process should start by gathering the right information upfront to set trial users up for success. Depending on your product or service, you could have several different onboarding “tracks” available. Create feature tutorials and getting started guides that are focused on the features with specific value for each of these tracks. The sales team should make recommendations for trial users based not only on the goals they state up front but also on product usage data throughout the process. 

A prospect might start a trial thinking they’re going to use your product or service one way but discover another use case that has more value for them midway. If the sales team can see this, they can pivot and tailor their approach to support this new approach. This can also help them anticipate different use cases for future prospects, encouraging active feature usage that leads to higher conversion rates. 

Sequencing Post-Trial Outreach

The baseline trial experience should include a regular schedule of sales team outreach for specific milestones: signing up, using key features, or never engaging at all.

Outreach should be tailored to help trial participants feel supported but not overwhelmed or surveilled. Objections should be anticipated and addressed as much as possible, to communicate the value you provide. Be sure to highlight what your organization can do that your competitors cannot. 

Emphasize incentives for early conversion too– a discount for signing up before the trial ends, or extended access to a key premium feature. If a prospect fails to convert, follow up a few weeks or months later asking if they want to come back and offering a discount if they do. 

Measuring and Improving KPIs

Measuring everything is just as useless as measuring nothing. Your team needs to be measuring key metrics that indicate trial health and sharing that information with the sales team at the right time. That will help continuously improve the trial experience and your team’s KPIs over time. 

Key metrics for trial health

Calculating your conversion rate is fairly simple: divide trial conversions by the overall number of signups. Time-to-conversion is also a key metric to determine trial health. A high conversion rate that takes six months might be sustainable for a complicated product with a highly personalized, extended onboarding at an enterprise level but it’s less likely a startup will be able to sustain the same pace. 

A/B testing trial variance for continuous improvement

Once you have enough trial data to work with, deploy two different types of messaging for trial participants to see which is more successful. You can also use this approach with onboarding flows, the cadence of outreach from sales, or anything else that has two different variables you want to test. 

Just be sure to deploy one A/B test at a time or it will be difficult to isolate which factors are influencing trial conversions on their own. 


A smooth, tailored trial experience is the ultimate goal. It gives you the highest chance at a high conversion rate– one that will put the variable B2B SaaS baseline to shame.

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