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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.

on October 6, 2025
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    Great question - the handoff between sales and success is always messy. For us, the biggest slowdown is gathering all the customer's info (SSO details, user lists, org chart) because it's never in one place. We've automated kickoff scheduling via Calendly and compliance docs via DocuSign, but the data collection part is still mostly manual back-and-forth. Would love to see a single intake form that adapts based on package tier.