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. We built Kairos to put that judgment in every rep's ear, in real time.
average tenure of the operators whose judgment Kairos captures
sales skills in the capture universe, from discovery to close
in production on real customer calls today
markets the bench comes from: enterprise IT, distribution, managed services
* As of October 2026.
The best sales judgment doesn't scale through one-on-ones.
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. One-on-ones run on a clock measured in weeks. Deals run on a clock measured in seconds. Reps face the hardest moments alone.
Kairos exists to fix that. Real-time judgment, calibrated to your team's methodology, surfaced at the moment the rep needs it. Not a debrief. 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, Business Development
20-year entrepreneur who's built and exited businesses in regulated, high-compliance industries.
Head of Technology
We're hiring
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
Makes the judgment category legible to the leaders who live it.
The judgment behind the judgment.
A bench of senior sales leaders who shape what Kairos captures, how it reasons, and which moves it surfaces. Not a logo wall. The people whose hard-won judgment becomes the product.
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
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Want to talk?
If you're a sales leader curious about real-time judgment, an investor exploring the category, or a candidate interested in joining what we're building, we'd like to hear from you.
For demo requests, the fastest path is the button in the header. For everything else, this form goes straight to us.