My point of view was that HR software needed to move beyond HR. At Zenefits, we had been making early tentative forays into things like app provisioning and some of the early kind of IT stuff that we ended up really doubling down on at Rippling. I felt that if I wanted this thing to exist, I needed to build it.
I had a skiing accident that opened my eyes to how fundamentally broken our healthcare system is and became obsessed with improving the industry. I realized that something was happening in consumer healthcare; the market was growing exponentially, and I was getting an itch to start something myself.
When you work in the Bay Area, there are generally two modes of operating: join a startup or a big, big company — or you start a company. At a certain point, I was like, Why can’t I work on something that is so exciting and have the opportunity to influence and touch billions of people in ways that are impactful.