Tomer Kashi

The outsider who priced risk by the mile

Tomer Kashi likes to say the quiet part out loud. "I'm not an insurance guy," he tells interviewers. "My background is in computer science and physics." For most founders that would be a disclaimer. For Kashi it is closer to a strategy. He built VOOM Insurance on the belief that the people least burdened by how insurance has always worked are the ones best placed to change it.

His path there was not obvious. Kashi is a graduate of Talpiot, the small and famously selective program that pulls a few dozen recruits into the Israeli military each year and trains them across physics, math, and engineering. He earned a BSc in computer science and physics from the Hebrew University of Jerusalem and an MBA, magna cum laude, from Tel Aviv University. Before insurance, he led interdisciplinary technology projects inside the cyber unit of the Israeli Prime Minister's Office, work that contributed to a project awarded the Israel Defense Prize.

Then, as he puts it, he stumbled into insurance. In 2016 he and Ori Blumenthal launched SkyWatch, a digital product built to cover commercial drone pilots who fly a handful of days a year and had few good options. A year later that idea widened into VOOM: a company aimed squarely at the parts of mobility that traditional insurers find awkward to price - vehicles used irregularly, seasonally, or intensely, where the usual actuarial shortcuts break down.

The pitch Kashi returns to is comparison by analogy. "Just like Lemonade is doing home insurance or Next is doing small business insurance, VOOM is the Lemonade or Next for Mobility," he told CTech. But he is careful to draw a line between the first generation of insurtech and what he is trying to do. The early wave, he argues, mostly made buying insurance smoother - a nicer app on top of an old product. VOOM, he says, is "insurtech 2.0," changing the risk model underneath rather than the packaging around it.

That distinction shows up in the products. In 2020 VOOM launched VOOM & RIDE, which it describes as the world's first pay-per-mile motorcycle insurance. The logic is plain once stated: a motorcycle owner who rides a few thousand miles a year in fair weather is a different risk than the annual premium assumes. Measure the usage, price the usage. VOOM has since extended the same thinking to e-bikes, scooters, and gig and rideshare drivers through products like VOOM & Drive.

Building products like these is not a solo act, and Kashi is candid about the machinery required. "You need the risk people, the actuaries, and the IT," he has said, "or you have tons of tech debt." It is an engineer's answer to an insurance problem: put the disciplines in one room and make them argue early, so the product that ships is coherent rather than stitched together. VOOM co-founders Blumenthal and Ronny Ahituv came out of the same technical world, and the company runs from a base in Tel Aviv with a Palo Alto office and licensed brokers across all 50 U.S. states.

The results have been enough to attract investors who see mobility as a category, not a niche. VOOM has raised roughly $27 million in total, including a $15 million round in October 2021 co-led by JAL Ventures and UP.Partners, with participation from F2 Venture Capital, Arbor Ventures, Verizon Ventures, Kaedan Capital, and ICON Continuity Fund. Along the way SkyWatch became the top drone insurance result on American Google searches - a small but telling proof point that the underserved corners Kashi chose were real.

Kashi's framing of the opportunity is deliberately unhurried. Mobility, he notes, "is changing much faster than the insurance industry," and he treats that gap as the whole point. Electric scooters, delivery drones, rideshare fleets, and pay-as-you-go ownership are reshaping how people and goods move, and each new mode arrives without the coverage infrastructure the last one had. VOOM's bet is that whoever builds that infrastructure first, on the right data, gets to define the category. For a founder who insists he is not an insurance guy, it is a notably long-term wager on insurance.

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The road to VOOM