mga
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Gage Caligaris
Gage Caligaris is the founder and CEO of Ledgebrook, a tech-enabled managing general agent (MGA) modernizing the Excess and Surplus (E&S) specialty insurance market. A Harvard-trained applied mathematician and former Barclays commodity derivatives trader, he spent eight-plus years as an actuary at Liberty Mutual, where he became the fastest person ever to pass the Casualty Actuarial exams and later scaled a new-mobility products line from under $50M to over $450M in gross written premium. He founded Ledgebrook in 2022 to pair modern engineering with deep insurance expertise, reaching a $100M run rate in under two years and raising an oversubscribed $65M Series C in 2025. In 2026 he was named an EY Entrepreneur Of The Year New England Award winner.
Tim Attia
Tim Attia is the co-founder and CEO of Slice Labs, a New York insurtech he launched in 2015 to sell insurance the way the on-demand economy actually works - in bite-size, pay-per-use chunks bought the moment a homeshare host or rideshare driver needs it. Trained as an electrical engineer at McGill and shaped by three decades moving between consulting firms and insurance carriers, Attia built Slice into a cloud platform (Insurance Cloud Services) that lets incumbents like AXA XL, Progressive, Lenovo and Microsoft spin up digital insurance products, and more recently he has been pushing the company toward AI, machine learning and large language models to automate underwriting and claims.
Kevin Stein
Kevin Stein is the CEO and cofounder of Delos Insurance Solutions, a San Francisco insurtech MGA that writes homeowners insurance for wildfire-exposed California properties that mainstream carriers refuse. A Bay Area native and aerospace engineer who once sold satellites at SSL/Maxar, Stein co-founded Delos in 2017 with Shanna McIntyre to apply satellite imagery, geospatial AI, and wildfire science to a problem the rest of the market treats as uninsurable. Delos accepts roughly two-thirds of the homes the standard market declines, and Stein reports it has never insured a home that later burned. He moonlights as a bassist and songwriter.
Roy Mill
Roy Mill is the Co-Founder and CEO of Joshu, a no-code insurance product platform that lets carriers and MGAs launch digital distribution channels in weeks rather than years. A Stanford PhD economist who pivoted into product, he spent years at Ancestry and At-Bay before founding Joshu in 2020. The company has raised $11.7M in total funding and was named to the InsurTech100 list in 2024.