“You really don’t want to do this….Really, you don’t!”
Those were the words I heard Zooming at me from Daniel, Lemonade’s CEO, as we talked about me potentially becoming part of the team, in the Chief Claims Officer role. Incidentally, they’re also the same words my oldest daughter, Hailey, used as I considered getting my first tattoo just last month.
I could understand the words from Hailey. It makes perfect sense that a daughter would wonder why, at age 50, her father felt it was time for something as permanent as a tattoo.
“Dad, is this some kind of mid-life crisis that you will regret in a few years… or a few days?”
I’ve built my career over three decades in the insurance industry, working for an astounding 27 years with the same company, USAA.
So jumping over to Lemonade, a relative upstart—albeit one that’s publicly traded on the NYSE— could seem like a risky or confusing prospect from the outside. It wouldn’t be the first time insurance execs having a “midlife career crisis” joined Lemonade to build an insurance company for today, and the future.
But the company, which recently celebrated five years in-market, has captivated me since its launch. I’ve been intrigued by Lemonade’s approach to innovating in a centuries-old industry.
The exponential growth has been admirable: scaling from one product to five different insurance products in record time (there’s at least one Lemonade product in every US state); expanding to new geographies, including Europe; acquiring one million customers faster than the giants of the industry; building social good into their DNA; acquiring a peer in the insurtech sphere; and creating a culture where people truly matter, among many other things.
So, when the opportunity came to explore what it might look like to work for this brand I’d admired for years, I was a little shocked by the response. Why did it seem like Daniel was trying to talk me out of the role?
Admittedly, it had been a long time since I’d been on an external job interview. But I had conducted hundreds over the years, and this was a… slightly different approach.
“Why would you ever want to leave after such a long career with such an admirable company?,” Daniel asked. “Why move from a Fortune 100 company with all the perks that it comes with and go to a startup? You probably wouldn’t like scheduling your own meetings; we don’t use PowerPoint; we communicate overwhelmingly on Slack…” The reasons not to join went on and on.
However, the craziest thing happened. As I talked to leader after leader at Lemonade I found myself grinning from ear to ear. Everyone was so transparent, down to earth, and innovative. They loved insurance and were working to make every bit of it lovable—not a word usually used to describe the industry I personally love so much. But I was hooked—and I’m pretty sure I subconsciously started wearing more pink, too.
I fell in love with what Lemonade stands for: customer-centricity, social responsibility, and moving faster than anyone else in the industry (launching car insurance from scratch in 10 months, are you kidding me?).
Add to that the company’s unbelievable growth, with even more potential for the future, and a knack for handling many claims in mere seconds—the list goes on. And beyond the visionary tech leadership, I’d be following a line of veteran insurance execs who have jumped ship into the 21st-century waters of Lemonade.
The industry is at a true pivot point, where the ability to rapidly scale both products and services in a digitally native world will determine winners and losers. Getting a policy and settling a claim—things that used to take days, weeks, and even months—must be done in seconds now. Customers demand it, and deserve it.
I have been in the industry a long time. It’s finally embarking on transformational changes (think: telematics) that I’m not sure all legacy carriers are ready for. Lemonade is in the perfect position to leapfrog many long-standing carriers, and the company has already proven they know how.
At the end of the day I didn’t listen to Daniel or Hailey telling me “not to do it.” I accepted the offer to join Lemonade (and yes, I got my first tattoo).
I promise to work on my listening skills going forward, but sometimes it pays to just go with your gut.
I am honored that the Lemonade team invited me to join them. I am humbled by all the success this team has earned in just five years in the market, and unbelievably excited about what the future will bring. Let’s do this!
