specialty-insurance
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Max Bruner Found Insurance’s AI Opportunity Hiding in the Inbox
After foreign policy, farm drones and pay-per-mile auto coverage, Bruner arrived at a stubborn conclusion: the most useful AI may be the kind that quietly finishes an insurance broker’s work.
Alice Phillips Topping Built a Brand for Risks That Resist the Usual Box
She began close to the risk, then learned how to explain it. At Ryan Specialty, Alice Phillips Topping has turned insurance fluency, curiosity and an agile in-house team into a durable communications system for a growing public company.
Luke Button Is Teaching Insurance to Stop Asking, ‘Any Update?’
After startups in cloud software, warehouse staffing and retail brokerage, Luke Button found his next company in the least glamorous sentence in commercial insurance: ‘Any update?’ Hedge is his attempt to make the answer arrive before the opportunity disappears.
Tyler Van Spanje Built a Career Around the Quiet Machinery of Risk
From cargo paperwork to warehouse liability, the TIMBY founder has spent three decades making obscure risks legible - then turning that expertise into a company built for brokers in a hurry.
Jonathan Levine and the Art of Making Hard-to-Place Risks Legible
For more than three decades, Jonathan Levine has worked at the point where complicated products meet busy customers. His career offers a quiet lesson in B2B marketing: clarity becomes a form of service.
Aparna Sarin Is Putting the Customer Inside the Revenue Equation
After building products for small-business owners, the former Capital One and American Express executive has taken on a broader experiment at Hiscox: joining customer insight, product, distribution and growth in one job.
Sivan Iram
Sivan Iram is the co-founder and CEO of Flow (Flow Specialty), a Mountain View-based next-generation wholesale brokerage that uses GenAI and licensed human experts to automate specialty commercial insurance placement. A former software engineer turned operator with a Harvard MBA, he spent a decade writing code and running go-to-market at Lenovo before starting Flow in 2021 to bring enterprise-grade service to the small and mid-market accounts the industry had long ignored. Flow has raised roughly $20-25M led by Lightspeed Venture Partners.
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.
William Ross
William Ross is the CEO and Co-Founder of Federato, an AI-native insurance technology company that has raised $180M including a $100M Series D led by Goldman Sachs. A Stanford-trained researcher who published wildfire modeling research at NeurIPS 2021, Ross left a career spanning IBM Watson and Venrock to build what the industry calls a 'RiskOps' platform - bringing portfolio-level intelligence to daily underwriting decisions across the $1 trillion+ P&C and specialty insurance market. Federato's revenues tripled year-over-year and the platform now powers insurers managing hundreds of millions in gross written premiums.