BKREA Co-Founder Seth Samowitz Joins WithCoverage to Tackle Rising Real Estate Insurance Costs With AI

After helping build BKREA alongside Bob Knakal, Samowitz joins the Sequoia- and Khosla-backed company to help property owners manage risk and reduce insurance costs

NEW YORK CITY, NY / ACCESS Newswire / October 7, 2026 / WithCoverage today announced that Seth Samowitz, co-founder and former COO of BKREA, has joined the company to lead its commercial real estate business. After co-founding BKREA with legendary real estate broker Bob Knakal and scaling the firm to nearly $4 billion in sales in about two and a half years, Samowitz is now combining that operating experience with his background in AI and technology to bring AI-powered risk management to real estate owners and operators.

"Insurance has become one of the largest and fastest-rising costs facing property owners," said Samowitz. "From my experience building BKREA, I saw how quickly a traditional brokerage business can evolve when you rethink the operating model around technology and AI. Commercial insurance is an enormous, fragmented market, and under the traditional commission structure, brokers can actually make more as premiums rise. That creates a massive opportunity to build something better - a model that is better aligned with owners, uses AI to make smarter decisions, and helps clients reduce costs while managing risk more proactively across their portfolios."

WithCoverage, backed by Sequoia Capital and Khosla Ventures, combines a dedicated team of insurance experts with an AI-powered digital platform to help businesses understand exposures, build tailored insurance programs, and reduce costs. Its approach puts AI in the hands of experts, with the aim of making risk management more informed and proactive throughout the year.

For commercial real estate, the opportunity starts with information. Insurance policies, property data, claims histories, and institutional knowledge are often spread across emails, spreadsheets, and separate systems. Samowitz sees AI as a way to connect that information and help experts evaluate risk and coverage in the context of an owner's broader portfolio.

The financial implications can extend beyond the insurance budget. As an illustrative example, $100,000 of recurring annual insurance savings that fully flows through to NOI would equate to approximately $1.67 million of additional implied property value at an unchanged 6% capitalization rate. Actual valuations vary based on market conditions and other property-specific factors.

"Insurance is no longer just a policy decision. It's a real estate investment decision," Samowitz said. "Owners scrutinize debt, taxes and virtually every expense that affects NOI. Insurance and risk should be approached with the same level of sophistication."

"Seth understands how owners think about NOI, asset value and operating expenses, and he has already helped build a technology-enabled real estate business from the ground up," said Max Brenner, co-founder and CEO of WithCoverage. "We think that combination can help us deliver a fundamentally better risk management experience for property owners."

WithCoverage's model pairs ongoing expert support with an AI-powered digital platform where clients can manage policies, claims, and billing in one place. Its flat-fee structure aligns incentives with clients: the company does not earn more when their insurance premiums rise.

"AI gives us the ability to rethink risk management, not just make the old insurance process faster," said JD Ross, co-founder of WithCoverage who previously co-founded Opendoor. "The goal is to scale expertise, make better decisions with more information and give customers a more proactive way to manage risk throughout the year."

At WithCoverage, Samowitz will initially focus on serving real estate owners, operators, developers, investment managers, and property managers.

About WithCoverage

WithCoverage is a modern risk management partner that helps ambitious businesses protect their operations, save money, and get time back. The company combines a dedicated team of insurance experts with an AI-powered digital platform to build tailored insurance programs and bring policies, claims, and billing into one place. Its flat-fee model aligns incentives with clients, while year-round expert support helps businesses manage risk proactively as they grow.

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SOURCE: WithCoverage