Kalepa Appoints Garrett Schlesinger as CTO After 12 Years Helping Build Affirm from Seed Round Startup to Public Company
Garrett Schlesinger joins Kalepa's leadership team after a year of tripled revenue and expansion into new products and geographies
NEW YORK, October 22, 2026--Kalepa, the leader in Professional Grade AI for insurance, today announced the appointment of Garrett Schlesinger as Chief Technology Officer (CTO). Schlesinger will lead applied AI, research, engineering, data, and infrastructure as Kalepa expands its work with insurers across the globe.
Schlesinger has spent his career at the intersection of data, AI, and financial risk. Most recently, he was Vice President of Software Engineering at Affirm, where he spent 12 years. There, he helped build and scale the real-time underwriting systems at the heart of the business and led engineering teams through every stage of hypergrowth, from seed round to public company. He oversaw several major product launches, including the Affirm Card, and led the strategic re-architecture of core Affirm systems to support the business's continued scale and reliability, which now processes over $50 billion in annual transaction volume.
"Garrett is an exceptional leader with a deep understanding of what it takes to deliver massive value from AI in production, at scale, and how to grow the teams behind it," said Paul Monasterio, co-founder and CEO of Kalepa. "He brings a rare combination of technical depth, operating experience, and a proven record of scaling systems through hypergrowth. He's the right person to help define the future of insurance technology and lead Kalepa's engineering into its next chapter."
Kalepa's AI agents perform and orchestrate work across insurance operations, underwriting, pricing, and portfolio management. Its insurance-specific AI harness and agents carry connected workflows through to completion, adapting as conditions change and verifying results along the way. Insurers use the platform in production with the control, traceability, and reliability that consequential decisions require. As CTO, Schlesinger will lead the technology and data behind the platform and extend it into new areas of insurance.
"Kalepa is at the stage every company hopes to reach, with technology proven in production and a market ready for it," said Schlesinger. "Helping grow a 12-person startup into a public company valued at more than $20 billion taught me that a great company is built over years, by teams that take on bigger challenges as the business grows. Kalepa has designed its business for the long run, and I'm looking forward to helping it scale."