Daniel Schreiber, Lemonade CEO

For Lemonade, 2019 was a banner year.

The InsurTech, which launched in New York in 2016, attracted a $300 million financing round, bringing its total cash haul to nearly half a billion dollars. The company began an expansion in Europe and a focus on expanding its products beyond home and rental insurance. To that end, it began doing business in Germany, offering contents and liability insurance anytime and from any device.

Speculation increased that Lemonade was gearing up for an initial public offering in late 2019, but that didn’t happen. Via email, Carrier Management Editor Mark Hollmer asked Lemonade Cofounder and CEO Daniel Schreiber about IPO plans. The 48-year-old entrepreneur responded with a “no comment” to the IPO question but answered a number of other questions about Lemonade’s 2020 growth plans, his leadership approach and how he maintains a healthy lifestyle. (Hint: a hammock is involved.) See below for Schreiber’s responses.


Q: Could you rate the year that Lemonade just had?

Schreiber: This was our third full year in market, and in a nutshell, Lemonade saw 500 percent growth, 10 percent market share, and we were ranked No. 1 by consumers in a number of comparison platforms and review sites. It’s been a rewarding year, with a bunch of lessons learned as well. I review 2019 in this Transparency Chronicle where I reveal all the latest numbers and behind-the-scenes stories, including our growth strategy.

Q: What went well over the past year in Lemonade’s development? What actions would you have done differently?

Schreiber: We’re big believers and students of testing everything and make decisions based on data and analysis. So, when it occurred to us that our success at becoming so well known for renters insurance came at the expense of homeowners insurance, we decided to right this wrong. We’ve been selling homeowners insurance since we launched and think of ourselves as a multiline business, but all too often we are thought of by others only as a “renters insurance company.” Being pigeonholed so narrowly always irked us, but it was a problem of our own making. In truth, it was more than irksome; it was a significant failure on our part, and it threatened our continued growth.

FYI: Renters insurance is less than 10 percent of the broader “homeowners” market, and achieving 10 percent share of renters insurance so early was at once cause for celebration and a warning of an impending glass ceiling.

So, after conducting user testing and other A/B tests, we started to give homeowners the love and focus they deserve. It’s been rewarding work: in the past 12 months we’ve seen over 500 percent year-on-year growth in sales of homeowners policies, even as our cost to acquire them dropped 70 percent. Back in August 2018, 5 percent of our sales came from homeowners; now it’s about 35 percent and growing.

Q: How would you describe your approach as CEO?

Schreiber: As CEO, I really have three jobs. The first is to provide true north to the team. The second is to hire amazing people who know how to do their job far better than I. The third is to remove barriers from their way so they can do what they know how to do.

Q: What was your first paying job? What did you learn from that job?

Schreiber: I started my career as a corporate commercial attorney. I learned a ton but didn’t last a year before handing in my notice and starting my first startup. I still consider myself a recovering attorney — though I’ve been clean for 20 years!

Q: There were news reports that Lemonade had planned an IPO in 2019 and then pulled back because of the market climate. Can you comment on this? Is an IPO planned in 2020?

Schreiber: No comment.

Q: How many hours a week do you work?

Schreiber: While I work many hours a week and travel non-stop between NY and Tel Aviv, I prioritize a good night’s sleep and exercise. And no matter what, I stop everything on Friday eve for the Jewish day of rest (Shabbat) until Saturday eve. I’m blessed with a fabulous wife, an amazing marriage and three kids I adore. I couldn’t work as hard as I do at Lemonade without their encouragement and support.

Q: How do you unwind?

Schreiber: Lying in a hammock on Shabbat is when I unplug everything and completely “undigitize.” That’s when I can truly clear my mind and think through ideas. I also enjoy reading — always non-fiction — and photography when time permits.

Q: What inspires you?

Schreiber: Independent thinkers.

Q: How long do you plan to be at Lemonade?

Schreiber: As long as they will have me.

Q: Is there another Lemonade in you? (i.e., are you itching to launch another company?)

Schreiber: Never say never. But no 🙂

Q: What are your plans for Lemonade in 2020?

Schreiber: We’d like to continue our geographical expansion in Europe, look into more insurance products for our Lemonade customers, and continue to grow by attracting new consumers and grow with our renters who are becoming homeowners, making our AI smarter and providing an ever surprisingly delightful experience for our community.

Topics Leadership Homeowners