Kalepa Appoints Former Affirm Engineering Leader Garrett Schlesinger as CTO

Kalepa has appointed Garrett Schlesinger as Chief Technology Officer to lead its applied AI, research, and engineering efforts as the firm scales its global operations. For insurance carriers and MGAs, the move signals a transition from experimental AI to industrial-scale deployment, leveraging Schlesinger’s experience in building real-time underwriting systems for high-volume financial transactions.

What was announced

Garrett Schlesinger joins Kalepa as CTO to oversee the technology, data, and infrastructure behind the company’s AI platform. Schlesinger arrives from Affirm, where he served as Vice President of Software Engineering. During a 12-year tenure at Affirm, he helped scale the business from its seed round to a public company, specifically focusing on the real-time underwriting systems that form the core of the business. His work included the strategic re-architecture of core systems to support a business that now processes more than $50 billion in annual transaction volume, as well as the launch of the Affirm Card.

At Kalepa, Schlesinger will lead the development of AI agents designed to perform and orchestrate work across underwriting, pricing, portfolio management, and general insurance operations. These agents are built to carry connected workflows through to completion, adapting to changing conditions while providing the traceability and reliability required for consequential insurance decisions. The appointment comes during a period of significant commercial momentum for Kalepa; the company has tripled its revenue and client count over the past year, while the number of workflows executed on its platform has nearly quadrupled. Despite this rapid growth, the company has remained cash flow positive for more than two years. Schlesinger joins a leadership team that has recently added David Meister as Chief Revenue Officer, Audrey Howell as Head of Product, and Tim Khoo-Jones as Head of Talent.

"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,"

Paul Monasterio, CEO and Co-Founder of Kalepa.

The companies involved

Kalepa is a technology provider specializing in what it terms "Professional Grade AI" for the insurance industry. The company’s primary focus is on the commercial insurance sector, where its platform is used by major carriers and MGAs including W.R. Berkley, Bowhead, and Paragon. By providing AI agents that assist in underwriting and portfolio management, Kalepa aims to improve the precision and efficiency of risk assessment. The company has maintained a distinct financial profile in the insurtech space by remaining cash flow positive during its expansion phase. Its platform is designed to offer the control and auditability necessary for insurers to move AI out of the laboratory and into production environments. This focus on "traceable" AI is intended to address the specific regulatory and operational requirements of the insurance value chain, where every automated decision must be verifiable.

What FF News has reported before

FF News has closely followed Kalepa’s expansion and its increasing adoption among major insurance players. In September 2026, the publication reported that Church Mutual Selects Kalepa AI to Streamline CM Vantage Underwriting Operations, highlighting the platform's role in improving operational efficiency. Earlier that year, in April, FF News covered the strengthening of the company’s leadership when Kalepa Appoints Audrey Howell as Head of Product. The company’s reach into the London market was also noted in February 2026, when Bishop Street Underwriters Expands Partnership with Kalepa to Support London-Based MGAs Avid and Landmark. Additionally, the platform’s selection by another major carrier was documented in the report James River Selects Kalepa’s AI Underwriting Platform.

What this means from an insurtech perspective

This appointment marks a shift in the insurtech vendor landscape from generalist AI experimentation to hardened, high-volume production. By hiring a CTO who scaled real-time underwriting at a major financial institution, Kalepa is signaling to incumbent carriers that AI is ready to handle the core "consequential decisions" of the underwriting process. This puts pressure on legacy core-system providers who have struggled to integrate advanced AI agents into existing workflows. For reinsurers and MGAs, the focus on traceability and reliability addresses the primary hurdle to AI adoption: the "black box" problem. The industry is moving toward a model where AI agents are not just assistants but orchestrators of the entire underwriting and pricing value chain, directly impacting loss ratios and customer trust through more precise risk selection.