Dear SaaStr: Why Do Enterprise Customers Insist on Pilots?

I know your sales team probably hates pilots, because in a sense, it means they have to sell the deal twice.  Once for the pilot, and again to convert the pilot for a longer deal.  Having an “opt out” clause after a pilot ends helps, but still, it’s a double sale.

But the thing is, net net it might be less work.  Because so many enterprise customers won’t buy from new start-ups without a pilot.

They benefit in several ways, especially when it’s structured properly. Here’s how:

  1. Risk Mitigation: Pilots allow customers to test your product in a controlled environment before committing to a full rollout. This reduces the perceived risk of adopting a new solution, especially if they’re replacing an existing system or investing significant resources.  Risk reduction is key.  You are a new or at least a small vendor, after all.

  2. Proof of Value: A well-executed pilot demonstrates the tangible value your product delivers. It’s not just about proving functionality—it’s about showing measurable outcomes, like increased efficiency, cost savings, or improved workflows. This is critical for building trust and confidence in your solution.

  3. Customization and Fit: Pilots give clients a chance to see how your product fits into their specific workflows and processes. They can identify any gaps or customization needs early on, ensuring a smoother implementation if they decide to move forward .

  4. Internal Buy-In: For enterprise clients, a pilot can help them build internal support for your product. If key stakeholders or end-users see the value during the pilot, it’s much easier for the client to justify the investment to their leadership team.

  5. Hands-On Experience: Pilots provide clients with a hands-on experience of your product. This is especially important for solutions that require behavior or process changes. It helps them understand how your product works in practice, not just in theory.

  6. Faster Decision-Making: A successful pilot can accelerate the sales cycle. Once the client sees the value and gets buy-in from their team, they’re more likely to move forward with a full contract without prolonged deliberation.

You can fight doing paid pilots.  Or you can lean in … and get good at them.  Do the matter, at least in the earlier days, and more deals will close.  For the exact reasons above.

But it is … more work.  At least at first.  At least for some in your org.

The key to a successful pilot is setting clear success criteria upfront.

Both you and the client need to agree on what success looks like—whether it’s a specific ROI, user adoption rate, or another metric. Without that, the pilot risks becoming an endless evaluation with no clear outcome.

More here:

Dear SaaStr: Should We Charge for Pilots and How Much?

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