Can You Sign A Deal Without A Pilot? 

(Yes, but it depends)

How self-service is your product?

The less implementation (aka project management) needed, the easier it is to sign a contract with a pilot period. 

🌐 When I was in the customer service space, we had to assign humans to post-edit customer service translations––even for pilots

(Plus sandbox testing for a native CRM integration, meh)

🎯 When I sold coaching, we had to assign the right human coaches––even for pilots

Now if you don’t have humans in the loop and no custom integrations needed––aka highly self-service––you can keep it much simpler:

You can give test access for a few days or even weeks. 

(Pro tip: align on success criteria to be make outcome tangible)

Then use those outcomes and learning to immediately go for an annual subscription, and not a paid pilot period. 

If the buyer is still a bit timid, offer them an opt-out period of 1 month (again, tied to outcome criteria). 

✅ It is MUCH easier to convert a deal that way than negotiating twice––also for the buyer’s legal team (scarce resource usually)

❌ What I will NEVER do again: 

Bundle pilot + annual subscription contract with a “gap” period of 1 month for them to reflect. 

Pilot outcomes are never what you expected, and your accounting team will struggle to book the revenue. 

How do you structure your deals?

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