18 months ago a contractor built an onboarding flow that apparently didn't work out. Your account is secondhand — Sarah Chen was there and can give you the full picture. Understanding what went wrong will directly shape the solution approach.
The Intercom recommendation came from a peer, not a technical evaluation. Mike Torres (CTO) needs to confirm it's compatible with your stack before you build a plan around it.
You're assuming Sarah's team can dedicate 50% capacity. That needs to be confirmed with her and with leadership, especially given the migration trade-off involved.
Sarah can fill in two major gaps — the prior onboarding attempt and her team's real availability. I've prepared targeted questions based on what's missing.
1. Walk me through what happened with the contractor-built onboarding flow. What specifically didn't work?
2. Realistically, how much of your team's time can we count on for this? What else are they committed to?
3. If we go with Intercom, does that create any issues with the tools your team already uses?
Mike is the technical decision-maker. He needs to weigh in on whether Intercom is viable before you commit to a solution direction.
1. Have you evaluated Intercom before? Any concerns about integrating it with our current stack?
2. Are there technical constraints or dependencies I should know about before we scope this?
Acme is your biggest incoming partner and the reason for the July 1 deadline. Understanding their expectations for the onboarding experience will strengthen your brief.
1. What does your team expect the onboarding experience to look like when you come on board?
2. How many users will you be onboarding initially, and over what timeframe?