Forbes April 16, 2021
Eliza Haverstock

There’s no reason why paying for a root canal should be more complicated than paying for a steak dinner. That’s how it looked, at least, to Paul Aaron, one the first 20 employees at digital payments giant Square and later a product manager at Oscar Health, the direct-to-consumer health insurance upstart founded in 2012. Connecting the dots between these two jobs inspired him in 2018 to build Level, a New York startup hoping to sell employers on more efficient and affordable insurance benefits for their employees.

“The big insight behind Level was this idea that insurance is just a way to pay for things,” says CEO Aaron, speaking at 6:30 a.m. over a zoom call from Hawaii (he’s keeping...

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