Stop over-relying on free trials as your primary sales strategy. While free trials have their place in certain contexts, they can be a dangerous crutch that undermines your sales process and wastes valuable time, especially in the enterprise space.
The misunderstood purpose of free trials
Free trials exist so prospects can verify your product does what you claim it can do. They want to kick the tyres, test the interface, and get a feel for the user experience.
Free trials can be effective in specific scenarios, particularly when you’re selling more transactional products like certain CRMs or tools where comparing one product to another is straightforward. In these cases, prospects mainly need to check the look and feel of your solution and gauge potential adoption within their teams.
But here’s where many founders go wrong: Free trials for enterprise SaaS almost never make sense and are typically a waste of time.
Why enterprise free trials fall flat
The main challenge with enterprise technology adoption isn’t about whether your product works, it’s about changing established workflows. Think about it: when a large company implements new technology, they’re asking employees to change how they work on a day-to-day basis.
When you offer a two-week free trial to an enterprise prospect, you’re essentially asking them to change their workflow for something temporary. The practical realities make this nearly impossible:
- They won’t fully migrate their data into your system
- They can’t realistically get colleagues onboard to test it properly
- Nobody receives adequate training
- They haven’t conducted internal workshops to explain how this new tool will benefit the business
The result? They simply won’t use it.
And this creates a dangerous backfire effect on your sales process. After two weeks, you’ll likely hear: “Thanks for giving us a free trial, but we didn’t use it at all. It’s not a priority right now, but we’ll get back to you if things change.”
Now you’re back to square one, except worse because you’ve given them an easy out.
The psychology behind trial requests
Understanding why prospects request free trials is critical. Most of the time, they’re not actually planning to conduct a thorough evaluation. Instead, they see it as a negotiation tactic.
Everyone likes getting something for free. It makes prospects feel like they’ve extracted value from the conversation. They can go back to their colleagues and say, “Great news! I got this free thing for two weeks.” It feels like a win for them.
But the harsh reality is that enterprise buyers rarely derive real value from these trials. The product sits unused, and you’ve wasted precious time that could have been spent on qualified opportunities.
The power of friction in enterprise sales
Successful enterprise sales follows a different playbook. One that embraces friction rather than trying to eliminate it.
When a buyer goes through a proper sales process, several important things happen:
- They review the market and do their due diligence
- Their IT team gets involved in the technical evaluation
- Their legal team reviews contracts and terms
- Multiple stakeholders across the organisation become aware of both the problem and your solution
- Most importantly, they put actual money on the table and commit for at least 12 months
This creates an entirely different internal dynamic. Now when they have their kickoff meeting, they’re saying: “Hey team, we’ve just bought this solution for 50 grand. We’ve signed a 12-month contract. This is why we’re using it. We’re going to have an internal kickoff. The customer success team from this company is coming in to do a go-live session with us. They’re going to map out our workflow and configure the product for us.”
That scenario creates stickiness.
That’s how people actually end up adopting new technology, because they’ve gone through necessary friction, put money on the table, and are fully invested in making your product successful.
Alternatives to free trials
What should you do when a prospect asks for a free trial? I always recommend founders consider these alternatives:
1. Slow down your sales process
When you hear “Can I get a free trial?” it often signals you’re dealing with an inexperienced buyer. It’s unlikely that a CFO or CEO at a large company would ask for this because they understand there’s no real value in it.
This request is a red flag that you need to:
- Slow down your sales process
- Involve more stakeholders
- Sell more value upfront
The “free trial” request often means you haven’t communicated enough value yet. This is your opportunity to take a step back and reinforce why your solution matters.
2. Consider a paid trial
If you’ve gone through an extensive sales process and they’re saying “We love your product, we just want to try it for a month,” consider a paid trial approach.
Structure this as a 30-day engagement with proper onboarding and light-touch customer success support. The key difference is they still go through procurement, sign a contract, and put some money on the table. This ensures both sides have skin in the game.
3. Implement a proof of concept that rolls into a longer engagement
I’ve found this approach particularly effective for enterprise SaaS sales. Create a proof of concept that automatically transitions into a longer-term engagement.
For example, structure a 13-month agreement where the first month is a paid POC. At the end of that month, it automatically renews into a 12-month agreement (though they have an exit option after the first month).
The advantage here is that the company has already completed the legal and procurement process and secured budget approval for the entire term. This makes it worth your time to invest heavily in that first month to ensure they have an effective POC experience.
When is the right time to walk away?
One of the biggest challenges for founders is learning when to disqualify opportunities. Sometimes, a free trial request is just false hope. It’s time you could be spending with prospects more likely to convert.
But I can’t emphasise enough that you should look in the mirror when you hear these words because more often than not it means your sales process isn’t robust enough.
The free trial request is often the prospect’s easy way of getting you off the phone: “Give me a free trial, and I’ll just tell them in two weeks we didn’t use it.”
Building a more effective sales strategy
As founders, you need to decide which levers you’re willing to pull and which ones you aren’t. In my experience, if you’re selling enterprise SaaS and hear the words “We’re looking for a free trial,” you have two choices:
- Take it as an opportunity for reflection on how you can improve your sales approach
- Potentially disqualify the opportunity because they may be wasting your time
Neither option is easy, but both are better than falling into the free trial trap.
What to do next
Free trials create an illusion of progress in your sales pipeline.
They make it seem like prospects are moving forward when they’re actually finding a polite way to exit the conversation. Enterprise sales success comes from creating real value, involving the right stakeholders, and ensuring your customers are fully committed to implementation. That commitment almost always requires financial investment.
So, the next time a prospect asks for a free trial, resist the temptation to say yes without thinking. Instead, view it as valuable feedback about your sales process and an opportunity to create a more meaningful engagement that actually leads to long-term success for both you and your customer.
