You've invested in the tools. Hired good people. Built the methodology.

And yet the forecast still feels like guesswork, AI isn't paying off, and coaching is still based on gut feel.

The problem isn't the market or the tools. It's that nobody knows what their reps are actually doing. And without that, nothing else works.

In this candid, free live session, Chad O'Connor, CRO at People.ai and Nick Keesler, AVP, Revenue Operations & Enablement, Aidoc, will be direct about what's actually changed in the CRO role, why most AI investments are underdelivering, and what the revenue leaders who are winning have figured out that others haven't.

Key takeaways:

  • The one root cause behind most AI underdelivery that revenue leaders aren't talking about
  • What "good" actually looks like when your team has accurate, complete activity data in the forecast, the pipeline review, and the coaching conversation
  • The diagnostic questions every CRO should be asking their RevOps team right now
  • How the CRO's relationship with data has shifted and what that means for how you hire, coach, and hold teams accountable
  • A practical framework for figuring out whether your current data foundation is ready for AI to do anything meaningful

What you'll learn:

  • Why your AI tools are underdelivering and what to do about it. It's not a methodology problem. It's a data problem.
  • What trustworthy CRM data actually looks like. CRM hygiene has always been a headache. AI makes it a dealbreaker.
  • How to tell which deals are real and which ones are just hope. When rep activity isn't captured automatically, pipeline reviews become negotiation sessions.
  • How to get ahead of the role the CRO job has quietly become. Data architect wasn't in the job description. This is a candid conversation about what that means in practice and how to stay ahead of it.

Meet the experts

Chad O'Connor - Chief Revenue Officer, People.ai

Chad O'Connor leads revenue at People AI, where he's responsible for the same problem he's spent his career trying to solve: knowing what's actually happening in the pipeline.

He's been on the wrong end of stale CRM data and gut-feel forecasts and has a direct point of view on what it actually takes for AI to do anything useful in a sales organization. He doesn't sugarcoat it.

Nick Keesler - AVP, Revenue Operations & Enablement, Aidoc

Nick Keeslar is a revenue operations leader with 10+ years in enterprise SaaS. He’s currently AVP of Revenue Operations at Aidoc, where he focuses on building a scalable commercial engine while helping commercial teams operate with a bit more clarity (and a bit less chaos).

He works across sales, customer success, and implementation to turn strategy into something that actually shows up in the numbers. Lately, a lot of that work sits at the intersection of AI and GTM, figuring out how tools, data, and automation can make teams more effective without making the job more complex.