When I told a friend and former colleague from the New York State Department of Financial Services that I was joining Lemonade, she wasn’t surprised. 

“I always knew that you’d end up there!”      

“Really? Why?” I responded, a bit surprised.

“I just felt that there was some connection,” she explained.

Indeed, my relationship with the company went back a ways.  From the start of my tenure leading DFS’s Insurance Division, Lemonade was on the agenda. Walking into that role, Lemonade’s application for a license was one of the first things I found on my desk. 

It’s safe to say that the licensing process is challenging under the best circumstances— and Lemonade’s circumstances were complex. Daniel, Shai, and the team had a vision of what insurance ought to be, how it should change, and how Lemonade was going to remake the industry. 

DFS’s response was, essentially: “Well, thanks Mr. Schreiber and Mr. Wininger, but insurance has been around for a millennium, I think we’ve got a handle on it…”     

One thing that gives me fits is anyone who thinks that because it’s always been done one way, it always has to be done that way.  Sure, sometimes the old way is indeed the best way—very often it is. But if you can’t explain why, then it’s time to rethink things.  Lemonade wanted to show that the old way wasn’t necessarily best— at least not in all respects—and the company was intent on challenging the received wisdom.

After leaving DFS, I moved across the table, so to speak.  I joined “big law” and helped those that I formerly regulated navigate their way through the challenging landscape that is the state-based insurance regulatory system. (This even included working with Lemonade as its outside counsel on occasion.)

While life at “big law” has been good, I found myself day dreaming about what other opportunities might there be out there. The insurance industry is simultaneously huge and small. There are lots of players in the market, most all of them doing the same thing. No disrespect to any of those companies, but did I want to do more of the same?

Yes and no. To be honest, I like familiar surroundings. Who doesn’t feel comforted revisiting a favorite restaurant, or returning to the same beloved vacation spot year after year? At the same time, I crave a challenge. I love rock climbing. I spent my birthday learning how to drive a race car. I’m not an adrenaline junkie, by any means, but I do love getting out of my comfort zone. 

Enter Lemonade, and this next phase of my professional career.  

Lemonade hasn’t followed an obvious path, nor have they relied solely on what’s been done before. Without being too cliché here, the company is charting a new course— for itself, and for the insurance industry more broadly.  It’s a marriage of next- generation tech and old-school insurance that I haven’t frequently seen.  

From the start, when I was at DFS and first sat across the table from Daniel, it was clear that Lemonade understood the scope and challenges of what it wanted to achieve.  The team proved to me that it was dedicated to finding a way for a “go-fast-and-break-things” insurtech attitude to exist, and succeed, in a “wait-and-see,” old-school industry. 

Lemonade appreciates that the old ways can inform the new, yet is always on the lookout for the innumerable opportunities to improve upon what’s come before.  Many of Lemonade’s competitors—again, no disrespect—have seemed far less able to strike that balance.

As my friend intuited from the start, Lemonade simply feels like the right fit. I’ve said before that insurance might not be sexy, but it’s at least always interesting—and I’m excited to see how interesting it can get in this new role.

Want to hear more from Scott Fischer? Check out this episode of Lemonade’s podcast series, Benevolent Bots, recorded shortly before we announced that he was joining the team.

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