Startup Sales — How to Get Pilot Customers to Pay

Getting a customer to pilot your product is an exciting moment, but it’s only one step toward a more important milestone: getting a customer to pay. Here are the most effective ways to get a pilot customer to pay:

Paid Pilots

A common way to convert a customer from pilot to paying is to simply charge them upfront. This is always worth a shot to test demand, even if it does not work every time.


  • Money Back Guarantee. The customer pays the normal price upfront but if they decide to cancel within a certain time period, they receive a full refund. E.g. Usual monthly price is $5k, customer pays $60k for the year upfront with a full refund if they cancel within 60 days.

Pilot Limitations

Offer the initial pilot for free with clear limits to ensure the customer converts to paying. This is useful if your customer will not agree to pay upfront.


  • Time Limit. Allow the customer to pilot the product for free, then charge the normal price after a short time. E.g. your product is free for the first 30 days, then $5k/month thereafter.

Contract Conversions

When and how you ask a customer to pay can influence their decision to convert. Details such as pricing, contract length and start date should be discussed at the best time for you and your product.


  • Automatic Conversion. Before the pilot begins, agree to both a price and a payment start date. Then charge the customer on that date, unless they cancel. E.g. Netflix requires a credit card for its 30 day trial and automatically charges you when the trial ends.

If you do not convert your pilots into paying customers, your startup will struggle. Test the various approaches to push customers to pay and see what works for best for your team.

Thanks to Kaego Rust and David Smooke for their help on this article.

Photo by Sharon McCutcheon

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