Built by operators.
Kairos is the system we wished existed when we were the ones in the room. We've carried the bag, run the deal review, missed the quota, and had to figure out why. We've also been the senior leader the whole team leaned on — the one who knew the question that turns a stalled call, who could read a prospect's silence. We built Kairos to put that judgment in every rep's ear, in real time.
The best sales judgment can't scale through 1:1 coaching.
Most enterprise B2B sales organizations have one or two senior leaders whose judgment compounds across deals. They know the question that turns a stalled call. They read the prospect's silence. They feel the moment a competitor mention is going to land before it does.
That judgment is the most valuable asset on the team. And it does not scale. The 1:1 coaching model runs on a clock measured in weeks. Deals run on a clock measured in seconds. Reps face the hardest moments alone, and the senior leaders can't be in every room.
Kairos exists to fix that. Real-time judgment, calibrated to your team's methodology, surfaced at the moment the rep needs it. Not coaching. Not training. The move a senior sales leader would make if they were in the room.
Operators who came from the deal.
Matt Carey
Founder and CEO
Two decades in B2B revenue leadership; the system he wished existed when he was the one in the room.
Gavin Carpenter
Partner and Head of Business Development
20-year entrepreneur who's built and exited businesses in regulated, high-compliance industries.
Head of Technology
We're hiring
The person who turns real-time sales judgment into shipped, reliable product.
Head of Finance
We're hiring
The discipline that turns a category bet into a durable, fundable company.
Head of Marketing
We're hiring
The voice that makes the judgment category legible to the leaders who live it.
The judgment behind the judgment.
Kairos is only as good as the judgment inside it. That's why we're building a bench of senior sales leaders — CROs, VPs, and revenue operators — who shape what Kairos captures, how it reasons, and which moves it surfaces. They're not a logo wall. They're the people whose hard-won judgment becomes the product. This is a growing group, and we're adding to it deliberately.
Greg Klausa
VP, Digital Architecture
Brian Donath
President and CEO
Blake Anderson
AI Solution Engineering
Jim Hilbert
Global CRO
Greg Degleffetti
Global CRO
Bill Thrash
VP Customer Success
Sam Bowley
Revenue Operations Leader
Joining soon
Joining soon
Joining soon
Want to talk?
If you're a sales leader curious about real-time judgment, an investor exploring the AI sales category, or a candidate interested in joining what we're building, we'd like to hear from you.
For pilot and demo requests, the fastest path is the request demo button on the homepage or pricing page. For everything else, this form goes straight to us.
30 days. Your team. Your deals.
Pilot Kairos on real calls with real reps. Decide for yourself.