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Founders — what’s your biggest onboarding headache after closing a new deal?

I’ve been talking to a few teams recently and there’s a funny pattern:
We work so hard to close a deal… and then the onboarding process is chaos.

The customer’s ready to go, but internally everyone’s figuring out next steps — emails, folders, compliance forms, kickoff scheduling, etc.

I’m trying to understand how startups are handling this stage today.

So I’m curious:

  • What’s the step that always slows you down or gets forgotten after the sale?

  • Do you automate any of it, or is it still manual?

  • And if you could automate one part of onboarding tomorrow, what would it be?

Not selling anything — just trying to learn what good onboarding actually looks like for early-stage teams.

posted to Icon for group Startups
Startups
on October 6, 2025
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