Built by operators.
Kairos is the system we wished existed when we were the ones in the room. Built by people who've carried the bag, run the deal review, missed the quota, and had to figure out why.
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 guidance, calibrated to your team's methodology, surfaced at the moment the rep needs it. Not coaching. Not training. The judgment a senior sales leader would offer if they were in the room.
Operators who came from the deal.
Matt Carey
FOUNDER AND CEO
Matt Carey is the founder and CEO of Kairos. Before Kairos, he spent over 20 years in B2B technology sales and business development, most recently as Chief Revenue Officer of Xcelocloud, a next-generation IT services platform delivering partner-branded solutions across managed services, advanced engineering, and global operations.
At Xcelocloud, Matt led the Customer Development organization spanning Sales, Customer Success, Marketing, Product, and Partner teams. He worked alongside the CEO from the company's inception to craft the go-to-market strategy and build the revenue and growth teams that scaled the business. His most notable achievement was building a white-label sales channel with global solution providers, resellers, and distributors that reduced costs and accelerated speed to market for new offerings.
Across his career, Matt has consistently led with a partner-first approach, building and scaling deep relationships with leading distributors, resellers, and global integrators. His operating principles, speed to market, flexibility, and customer obsession, drive Kairos's product philosophy.
Kairos is the system Matt wished existed when he was the one in the room.
Gavin Carpenter
PARTNER AND HEAD OF BUSINESS DEVELOPMENT
Gavin Carpenter is a Partner and Head of Business Development at Kairos. He is a seasoned entrepreneur who has built and exited several B2C businesses over a 20-year span.
Gavin is an operator himself, with deep experience navigating complex regulatory environments, building customer trust in highly regulated industries, and translating business and financial requirements into commercial outcomes.
In addition to his work at Kairos, he owns CBD Healing Resources, a Scottsdale-based wellness company, where the discipline required to operate in a regulated industry shapes his perspective on the operational rigor Kairos requires.
Want to talk?
If you're a sales leader curious about real-time guidance, 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.