How to Convert Free Trial Users to Paying Customers

You have prospects signing up for your free trial — but the conversion rates aren’t where you want them to be. While there’s no ‘standard’ conversion rate for your B2B SaaS, you know you need better — you’re just not sure what to do about it.

Here’s the thing: your trial email sequence is the primary driver of conversion. It’s the onboarding, and the period when you show your user they can’t live without your app (reaching the ‘AHA’ moment)… and when you can do that, convincing users to part with their money becomes so much easier.

This guide breaks down the need-to-know strategies your free-to-paid trial sequence needs to get your users to the ‘AHA’ moment, improve your conversions, where to focus, and the resources to help you take action on each piece:

There’s Two Parts of Your Free Trial: Onboarding and Sales

Think of your free trial in two parts: onboarding and sales (or closing).

The first battle is getting users on board with a new way of working. There’s a commitment to starting with your software AND you have to pull them away from their old way of doing things.

What most companies forget is that it’s highly unlikely that your prospect has a brand new problem with no way of currently solving it. Yes, their current solution might be time-consuming, laggy, or inefficient—but there’s something about it that’s not totally fulfilling their needs, which is why they’re coming to YOU.

Still, they’re technically already solving the problem, and you’ve got to fight against them just going back and defaulting to their old ways. That’s the battle in the first part (onboarding).

The second battle is getting them to part with their money. But if you do your job right in the first part, the battle in this sales phase becomes so much easier.

Most companies spend all their time onboarding, then expect the in-app experience and a few “your trial is expiring” emails to sell the subscription. This doesn’t usually end up working out as expected (and is often the reason you’re seeing lower-than-desired conversion rates).

Before You Change Anything In Your Free-to-Paid Trial Flow

You need to understand what “trial conversion” actually means for your B2B SaaS—and make sure you’re optimizing for the right metric.

Your trial-to-paid conversion rate measures how many users upgrade from your free trial to a paid plan. But if users aren’t activating during their trial—meaning they’re not actually engaging with your software—they’re definitely not converting to paid.

Trial activation is when your users engage with your software—they log in and take key actions that move them toward discovering your product’s value.

Trial activation is a necessary step in trial conversion.

→ While knowing the difference is important, it’s also important to audit your sequence to see why (and where) your users aren’t converting. Watch this to see where to get started:

What to Know About Onboarding—Getting Users to Adopt Your Tool

When you onboarding your users, you need to do it properly. You’re merging all the things you want them to do in your tool—from first login all the way through every single action you want them to take—with the strategies that actually get users into the tool and taking those actions.

-> This is what gets them to adopt the new way, using YOUR tool, and not go back to the old, comfortable, way of doing things.

Your trial email sequence needs to nail four things for onboarding:

Specificity → Using your onboarding questionnaire (if you have one) to make their onboarding journey feel specific to THEM.
Voice of Customer (VOC) → Using your customers’ exact words and phrases in your copy to create immediate recognition and trust.
Jobs-to-Be-Done (JTBD) → Understanding WHY users are hiring your software and the job it’s doing for them—whether that’s functional, social, or emotional.
Premium Feature Adoption → Getting your users to use and fall in love with premium features they can’t access on the free tier.

Want to learn more about how to optimize your free trial to paid flow? Read this.

Where it All Begins: Your Day 0 Experience

If you’re wondering where to start when working to improve your free-to-paid trial conversion rates, your Day 0 experience is one of the best places to start.

The first emails your trial users receive can make or break their experience with your software. Get these right and users engage with your software, experience value, and move toward conversion. Get them wrong and your software gets ghosted.

For your Day 0 emails, you’ll use the same strategies and free trial onboarding best practices (and then some) mentioned above, but, you’ll:

Give your users ONE clear action to take (ditch the laundry list of features)
Send multiple emails
Personalize them based on sign-up information (remember, specificity converts!)
Match what you tell users in email to what they see in your app (what your emails tell them to do and your software shows should be the SAME)

If you want to see these in action, along with works—and what doesn’t—when it comes to Day 0 onboarding emails, we analyzed real emails from successful B2B SaaS companies and how they work to get users to the “AHA” moment here.

What About Sales? Your Free-to-Paid Flow and Getting Users to Part With Their Money

This is one area where a lot of companies fall flat—they spend a whole lot of time on the beginning of their trial onboarding users, and then expect the experience inside the tool and a few “your trial is expiring” emails to sell the subscription.

But, if you’re waiting until the “your trial is ending in 3 days” email to start selling, you’re waiting too long.

I wish there was a hard and fast rule for when you should transition from onboarding to selling emails (like if a trial is 14 days, you spend 7 onboarding and 7 selling), but it’s just not how it works. However, I can say this: you should start selling while you’re still onboarding.

You can use the space in the PS area, or underneath the signature, to start promoting the idea of a paid subscription part-way through the trial. You’ll start to ease into it and plant those seeds into the minds of your trial users.

But, when you DO move into dedicated sales emails, make sure you’re STILL using the same best practices—just in a different way.

I break it down more in this video:

Other Email Sequences That Impact Conversion (That Most B2B SaaS Companies Neglect)

Your onboarding and sales emails are the main two steps in creating conversions, but they’re not the only email sequences involved in a user’s decision to stick with your software.

For example, abandoned cart sequences help recover users who got all the way to your checkout page, but didn’t complete the upgrade. Another is personalized report emails proving your software’s value using their OWN usage data.

Even a customer review campaign is useful for generating social proof that your future trial users will see when they’re evaluating whether to sign up or keep scrolling.

The experience doesn’t stop in the free trial, either, there are other sequences (and emails) that are necessary for maintaining paid user’s trust and keeping users engaged throughout their lifecycle—for example, price increase emails, software updates, product adoption emails for features they’re not currently using but would love.

Can Other Factors Impact Conversions? What if it’s Not Your Emails?

Yes, there are other factors that can impact whether a user converts from their free trial to a paid subscription outside of your onboarding and sales emails (although you should always be working to improve your emails… unless you’re at 100% conversion).

For instance, your conversions can be impacted by:

Your landing page and sign-up experience, they set expectations before users enter the trial and if your pre-trial messaging is vague or misleading, your emails will fight against those wrong expectations (leading to fewer conversions).
Your in-app experience and how well it delivers on what your emails promise. If your emails guide users to take a specific action, but your software is confusing when they try, the disconnect kills the momentum.
Your free vs. paid feature positioning matters if you offer a free tier. Users need to experience the value of premium features during the trial and understand what they’ll lose if they don’t upgrade.

These elements support your email strategy. Fix major problems in these areas, but don’t let perfectionism delay optimizing your email sequence. Your emails will have the biggest impact.

Ready to Improve Your Trial Conversions?

Start with your trial email sequence—specifically, your onboarding emails.

Get users activating. Get them experiencing value. Get them to adopt your tool instead of going back to their old way of doing things. Once that’s working, optimize how you transition from onboarding to sales emails. THEN improve your abandoned cart sequence. THEN layer in the other funnels.

Don’t try to fix everything at once. Pick the highest-impact area, make it better, measure the results, and move to the next thing.

If you do these things, and you do them well, you will start to convert more trial users into paying customers during and immediately after their trial.

Want my team and me to take over your free trial onboarding sequence, strategize and write a sequence that grabs your users’ attention, onboards them properly, and then sells them into a paid plan so you can increase conversions on your free trial? Book a discovery call and let’s do it!