Oct. 21, 2025, 9 a.m.

How do you research customers for a subscription software business?

Draft's Letters

As we’ve repositioned, our research practice has shifted. Think about how research typically works:

  • You observe existing behavior
  • You call some customers
  • Do some synthesis
  • Prioritize, experiment, profit

A lot of this breaks down when you’re dealing with a relatively small customer base that happens to be on subscription:

  • There are more upfront objections about the sale
  • Fewer people are signing up every month, making recruitment more challenging
  • You have to deal with ongoing relationship management – and churn

And so:

  • You have to be deeply intentional about how you recruit, with more specific criteria than you usually establish
  • You need to get a much higher interview rate than you’re typically used to, providing direct entreaties with larger incentives
  • You should recruit multiple times in a customer’s lifecycle, pinging new customers as well as those who have been around for a year or more
  • Once you have someone’s attention, you can’t stay on the surface: you have to ask more, deeper questions, possibly in a longer session

I’m sure we’re missing something, so I’m curious how other software businesses do it. Hit reply and let me know what’s worked for you!

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