Vivek Shah

Vivek Shah runs SimplyInsured, a San Francisco company with a deceptively simple pitch: a small business should be able to compare and buy employee health insurance entirely online, in the time it takes to book a flight. No broker who only answers the phone between calls. No fax cover sheet. No fear.

That last word is not marketing. Shah founded the company in 2012 after trying to buy coverage for himself on the open market and finding the experience genuinely upsetting. The thing meant to reduce his anxiety about getting sick had managed to make him more anxious. An engineer's instinct kicked in: if the process is broken, fix the process.

Today SimplyInsured operates what Shah describes as the only 50-state online quoting engine built for small and medium businesses. The company has served roughly 25,000 customers and saved them, by its own accounting, north of $50 million in premiums. It is backed by Y Combinator, Bessemer Venture Partners and Polaris - the kind of investor roster that signals this is not a side project.

What makes Shah interesting is not that he spotted a slow industry. Plenty of people have complained about insurance. He counted it. There are, by his reckoning, 400,000 brokers in the United States selling the same product the same way. He looked at that number and saw a trillion-dollar market still operating like it was 1955, and decided the gap between how insurance is sold and how everything else now gets sold was the whole opportunity.

Shah arrived at the problem from an unusual direction. He studied electrical engineering, computer science and management science at MIT, graduating in 2007. Out of college he went to McKinsey & Company as a healthcare analyst, where the assignment was, more or less, to make insurance companies run more efficiently. He spent his early career studying the machinery of the industry he would later try to route around.

Then came the startup detour. He joined Cardpool, a Y Combinator company in the gift-card resale business, as Director of Retail Sales, and stayed through its acquisition. It was a crash course in a different discipline: selling, scaling, the texture of an early company that has to grow or die. Somewhere in there he also did a stint as an associate at Globespan Capital Partners, seeing the same story from the investor's chair.

So by the time the insurance frustration hit, Shah had assembled an oddly complete kit. He understood the industry from the consulting side, knew how to build software from the engineering side, had sold things from the operating side, and had watched companies get funded from the venture side. Health insurance, sold badly, was the rare problem that needed all four.

He did not build it alone. His co-founder, Bob Aspell, had been his housemate at MIT, where they both studied electrical engineering and computer science. Two engineers who had already lived together decided to take on an industry that had resisted engineers for decades.