ai-underwriting
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David Fontain
David Fontain is the co-founder and CEO of Foresight, a San Francisco insurtech that pairs workers' compensation coverage with its own safety technology, Safesite. An Australian who grew up on the Gold Coast and started out in investment banking, he built Foresight after a childhood friend died in a preventable workplace accident. The company underwrites for hard-to-place middle-market businesses in industries like construction and manufacturing, using an 'engage and save' model that rewards safer companies with faster premium relief. Foresight has raised tens of millions from investors including OMERS Ventures, and its technology is credited with cutting workplace incident frequency by double digits.
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.
Jan-Felix Schneider
Jan-Felix Schneider is the co-founder and CEO of Arlo, a New York health insurance company rebuilding coverage for small and mid-sized businesses from the ground up. A former Palantir deployment strategist and McKinsey consultant who grew up in Germany, he pairs a Columbia data science background with a plain conviction that people should not go broke while insured. Under his lead, Arlo underwrites its own level-funded plans, supports members directly, and builds its own technology - scaling to tens of thousands of covered lives and hundreds of employer groups, reaching profitability, and raising a $4M seed in 2025.
Sachin Latawa
Sachin Latawa is the founder and CEO of Tirios, an Austin-based proptech platform that lets everyday people invest in single-family rental homes for as little as $100. Before building Tirios, he ran real estate for Carl Icahn's empire as CFO of Real Estate at Icahn Enterprises, where he managed more than $1.1 billion in assets across homebuilding, distressed assets, resorts, offices and industrial property. He now pairs that institutional pedigree with AI-driven underwriting and blockchain tokenization to crack open a $10 trillion asset class that, by his own count, only about 5% of people can actually reach.
Jeannie Tarkenton
Jeannie Tarkenton is the founder and CEO of Funding U (Funding University), an Atlanta-based fintech lender that makes no-cosigner student loans to high-achieving, low-income undergraduates based on grades, grit and trajectory rather than a parent's credit score. A Princeton English major who spent a decade in Atlanta education nonprofits, she built an AI underwriting model that reads transcripts and internships instead of FICO and balance sheets. Since 2018 the company has deployed well over $125 million to thousands of mostly first-generation students, and counts Goldman Sachs and her former college roommate MacKenzie Scott among its backers.
Michael Konialian
Michael Konialian is the founder and CEO of Modern Life, an AI-powered life insurance brokerage built for financial advisors. After a winding path from aerospace structures at NASA to nuclear diplomacy at the U.S. State Department to scaling CoverWallet's advisor business into an Aon acquisition, he was floored by how confusing, invasive, and outdated it was to buy life insurance for his own family. Modern Life is his answer: a single dashboard that lets advisors pull instant quotes from 30-plus carriers and compress a process that once took six months into minutes. In November 2025 the company raised a $20M Series A led by Thrive Capital, bringing total funding to $35M.
Michael Topol
Michael Topol is the Co-Founder and Co-CEO of MGT Insurance, a San Francisco-based company he runs with his brother Graham and describes as the world's first vertically AI-native neo-insurer for commercial property and casualty risk. After helping scale the insurtech Collective Health from 30 to more than 500 employees and a stint in investment banking at Morgan Stanley, he set out to rebuild a commercial insurance carrier from the ground up on a modern AI stack. Two years in, MGT has reached profitability, signed roughly 30,000 customers, posted about $3 million of recurring revenue per employee, and closed an oversubscribed $21.6M Series B led by Mubadala Capital in October 2025.
Michael Ulin
Michael Ulin is a three-time AI founder and engineer who builds machine-learning companies in heavily regulated industries. He was the founding AI engineer and VP of AI at ZestyAI, whose property-risk models help underwrite trillions in U.S. insured assets, then co-founded and served as CTO of Paxton AI, a generative-AI legal research tool used by thousands of attorneys that raised a $6M seed round in 2023. He now builds from Bend, Oregon, where his current work centers on Trarian, applying AI to patent underwriting, alongside ventures spanning AI forecasting and probabilistic reasoning. He also writes the Substack 'And Yet It Moves' on entrepreneurship and the case for building startups outside Silicon Valley.
Itzik Cohen
Itzik Cohen is the Co-Founder and CEO of PayZen, a San Francisco-based healthcare fintech that has raised $452M to eliminate financial barriers to medical care. A former professional basketball player for Maccabi Tel Aviv, Israeli Air Force veteran, and three-time founding CEO, Cohen channeled two decades of fintech expertise from WebEx, Prosper Marketplace, and Beyond Finance into building an AI-powered platform that gives patients interest-free payment plans while boosting hospital collection rates by 30-35%. PayZen's $232M Series B in 2024, led by NEA, validated his conviction that the fastest-growing category of American consumer debt - medical bills - is also the most solvable.