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Use a trial extension request as a gate in your demand generation funnel and a chance to advance the prospects further into the sales process.

If part of your inbound motion includes the offer of a free trial, there’s a strong possibility that you’ve had a prospect ask for a trial extension. So, should you allow it, and if so under what circumstances?

Before we answer that, let’s unpack why you’re getting requests for trial extensions in the first place.

TRIAL DURATION

One of the first factors to consider is whether the trial is long enough for your prospects? I’m 100% not advocating for lengthy, unlimited trials, but it’s worth understanding your buyer journey and the evaluation process that your prospects are running.

If there’s a broad buying team, then chances are a 7-14 day trial may not be enough time for them to engage with all stakeholders. Conversely, leaving a trial active for too long can see prospects lose interest, and doesn’t give your sales team the opportunity it needs to address concerns and sales objections in a timely manner.

WHY ARE PROSPECTS ASKING FOR A TRIAL EXTENSION?

Before you make any decisions, you’ll also want to understand the most common reasons for a trial extension when asked for by a prospect. In most cases, the reasons will fall into one of the following categories:

• The prospect got distracted and “didn’t get a chance” to trial your product properly.
• They need a wider group of stakeholders to try your product and haven’t had time to coordinate that yet.
• They are evaluating competitive offers and want to retain access for comparison.

Ultimately, all of these reasons are preventable (to a degree), and any kind of trial extension is simply a solution to a problem that’s occurring earlier in the process. And, more alarmingly, for every genuine prospect that does ask for extension, many more will simply let the trial lapse and move on to a competitor product.

That’s why thinking about a policy for trial extensions shouldn’t be run in a silo. Instead, it’s important to look at the root cause.

Let’s map those reasons for a trial extension to the most common root causes.

The trial isn’t built to convert easily

• Do you understand your “Trial Conversion Indicators”? These are the actions that high-intent prospects take when trialling your product. If so, can you track them and intercept with timely sales outreach?

You’re not involving all stakeholders

• Do you understand the typical buying process of your ICP? Are there multiple stakeholders involved and, if so, how are you encouraging the original trialist to pull them into the trial quickly? Look at in-app or email nurture mechanisms to make this happen.
• Understand how different stakeholders are evaluating you. There’s often a difference between the user and the buyer. Do you need to demonstrate ROI or other TCO metrics? If so, look at developing content that can be used alongside your trial experience to service this need; for example webinars or case studies.

Your trial isn’t set up to help the prospect find success

• Based on how your ICP buys, do you understand what a “good” trial looks like? What are the key features that help to differentiate your product? And how are products like yours evaluated?
• If you understand this, are you guiding prospects along that path to success? Is your email / trial messaging too vague, and not tied to the success metrics that you know work to progress trials to opportunities?

If you can fix these things, then you’ll almost certainly make a positive difference in the number of prospects requesting a trial extension.

SHOULD I ALLOW TRIAL EXTENSIONS?

Of course, no matter what you do, you will still have prospects asking for a trial extension, and I think we can all agree that it’s better to extend a trial than to lose a prospect forever. So where’s the balance? After all, simply auto-enabling an extension could just prolong non-activity and be kicking the proverbial can down the road. In short, it’s a bad idea.

Instead, use the trial extension request as a gate in your demand generation funnel and a chance to advance the prospects further into the sales process.

• If your trial has not converted (at least to a sales call), deploy a mechanism that offers the opportunity for an extension. This may be in-app, or in your trial nurture emails, and should start at least five days before the trial ends.

• Importantly, the extension is not auto-activated. It should be given on provision of the prospect booking a call with your SDR or sales team. This then gives you the opportunity to identify why they need an extension (see the reasons table above) and put a plan in place for success; effectively moving the prospect out of lead status and into an MQL, or even SAL, position in your funnel.

This gate alone will be enough to m§ove the “tyre-kickers” out of the funnel.

• In the call, you may look to define some trial success metrics and use the opportunity to identify other key stakeholders in the evaluation. Given it’s highly probable that this is the first time you will have directly engaged with the prospect, you will also have the opportunity to run some basic qualification and push your prospect into the funnel as a SAL.

• Based on ICP fit, you can even explore the possibility of moving into a managed trial scenario with guided onboarding and regular check-ins. This may be resource intensive so should be reserved for high-yield ICP prospects and those where it makes sense from a CAC perspective. However, making the investment at this stage makes sense if you consider it as a first entry point into customer onboarding.

That’s a long answer to a seemingly simple question, I know. So, in short, yes you can offer trial extensions but:

• Only when you understand why extensions are being requested – do you need to fix something in your trial experience?

• Not automatically. Don’t kick the can down the road. Talk to the prospect first to understand what success looks like.

• Only if you can use the request as a way of advancing the prospect further into the sales funnel; e.g. run it as a new stage in your funnel / qualification gate.