Design problem: giving users flexibility and designing product onboarding

In the past week, I was trying to figure out just how much control to give users at the initial stages of a product's onboarding. The product required 3 steps to accomplish what it was designed to do and we spent a fair amount of time debating whether to allow users to access the full interface or to remain effectively stuck in the onboarding process until they complete all steps required to start getting to output.

At the end, we decided that it was best to allow users to gain full access all parts of the product interface to allow exploration and see whether it was a good fit for them and supplement that with calls to action in relevant portions of the UI to nudge them towards completing the onboarding steps for them to start getting results.

The primary factor that influenced this decision was users may not have all the pieces they need to complete all onboarding steps — they may need to do some back and forth with their respective team members to collect all the data in order to start using the product.

Which leads to the next design problem I'm working on:

  • At which phase should an onboarding heavy application prompt a user to pay for the product? Considering that post the onboarding process some manual work is required on the customer success team's side to set everything up after all the data is collected from the user.

Right now our thinking is to set up a page where they're prompted to sign up for a call and after they're sold on the product, they can submit payment and get forwarded to the 3-step onboarding process. The question is how well it would work under a full self-serve model?

For context: the current iteration of the product is aimed at e-commerce and SaaS startups (not enterprise companies)

When should customers be charged?
  1. After a call but prior to onboarding
  2. After a call and onboarding but prior to using the product
  3. After a call, onboarding, and a free trial of the product
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