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September 10, 2019

Lead(H)er: Maya Prosor, Vice President of Business Development at Lemonade

Insurance isn’t necessarily the most exciting industry⁠—just ask anyone actually working in it. 

“It’s the best conversation killer,” joked Maya Prosor, Vice President of Business Development at Lemonade, which provides homeowner’s and renter’s insurance. “When people at parties ask what I do and I tell them I’m an insurance agent, they back away very slowly.” 

Prosor began her career in tech, as an account manager and later senior director and associate vice president at Powermat, before joining Lemonade. While the company has a strong tech focus, it was the leadership of its co-founders that convinced her to join. 

When former Powermat president Daniel Schreiber left that company to found Lemonade, Prosor was intrigued by the idea. She knew that she and Schreiber worked well together, and when he brought on his cofounder Shai Wininger, the cofounder of Fiverr, Prosor knew the company would soon be doing big things. 

“There wasn’t a lot to go on when I joined,” said Prosor. “It was about putting my belief in Daniel and Shai, and recognizing how their ideas solidified my belief that we were going to be building something really big eventually.” 

In the early days, Prosor checked in with herself every so often to ask whether she felt she was in the right place. Thanks to the daily challenges of building partnerships with coworkers and customers, being surrounded by colleagues from diverse industries and backgrounds, and the knowledge that Lemonade truly could make the world a better place, the answer was a resounding “yes.” 

Prosor’s faith has since been rewarded, and in the four years since she joined, Lemonade has raised a total of $480 million in funding and sold more than 425,000 policies as of the end of 2018. The company can credit its explosive growth to its radical take on the insurance industry, in which customers and insurance agents are, for once, on the same team. 

Existing business insurance models rely on denying claims to make money. Lemonade, however, earns a flat fee for each insurance policy, eliminating the incentive to deny payouts and nearly instantly improving customer satisfaction. Any unclaimed money⁠—totaling $631,540 in 2019 alone⁠—is donated to charities selected by Lemonade’s customers. 

“We’re a truly double bottom line organization,” Prosor said. “You feel good about your success because you know that it’s moving Lemonade forward and hopefully bringing more good to the world at the same time.” 

Lemonade is also bringing more good to its customers by simplifying insurance for them. First-time homebuyers and renters are often startled and overwhelmed by unexpected insurance requirements baked into leases and mortgage contracts. Lemonade integrates with disruptors in the mortgage space to provide customized, easily-understood insurance policies that meet lenders’ requirements. Buyers can, in one click, receive an affordable and comprehensive insurance policy that allows them to move forward with their applications. 

Prosor and her team look for “golden moments” like these, during which insurance⁠—usually not a major priority⁠—suddenly becomes top-of-mind. They’re also focused on opening additional distribution channels within the U.S. and abroad for Lemonade, which is currently in hyper-growth mode. 

“Every four months, it feels like you’re working at a different company,” Prosor said. “If you’re at a company at this stage, you can never just stand in place⁠—standing in place means you’re going backwards. You have to stretch yourself to grow with the company.” 

Lemonade Team


Quick Q(uestions) and A(dvice) 

What do you enjoy doing in your free time? 

I have two young kids who are totally adorable, so most of my free time is spent with them. We also love to travel and try to do at least two main trips a year and go to places that we haven’t been yet. Our last trip was to Patagonia, and hopefully this year we’re going to Japan. We try to absorb other cultures as much as we can. 

How do you manage stress? 

I try to not be too hard on myself. I try to be present in whatever I’m doing, whether it’s a meeting or hanging out with my kids, and be the best at what I’m currently doing instead of thinking about everything else I have to do. 

How many cups of coffee do you have in a day? 

It depends on the day⁠—I would say two or sometimes three. I’m not a big coffee drinker ; )

What’s one of your favorite places in the New York area? 

I’m from Israel, and living in New York was always my dream. Just being here, surrounded with the energy of the city and the amount of people and their diversity is my favorite part. I love exploring the city. You can spend all your weekends here and always find something new that you haven’t seen yet. 

What do you consider one of your proudest accomplishments so far? 

When the Me Too movement exploded, two other coworkers and I felt like we had some sort of responsibility as women who have advanced through tech and reached a certain level of seniority to do something to help. We started a project called Leaky Pipeline, because when we were younger in the tech industry, we all wished we’d had more women to talk to. I had wonderful mentors who were men, but sometimes you do feel like you need a woman’s perspective. So we opened our schedules and gave our time, because it was the least we could do. It’s been quite overwhelming. We’ve spoken to hundreds of women so far, from Israel to New York and the UK, about issues like work life balance and sexual harassment at work and how to ask for a raise. It gives me so much hope to see these talented and powerful women coming up through the tech industry now. Thirty to 40 years ago, seeing women at the top was more of a rarity, so I’m hopeful just seeing the ambitious women who are coming up the ladder. 

How does where you are now compare to where you saw yourself 10 years ago? 

I wanted to be in a place where my voice is being heard, to be part of something making an impact, and to be working with talented people. I didn’t have a specific plan, other than wanting to live in New York, but I always asked myself if I was comfortable, or if I was being challenged. I never wanted to be comfortable, because then it meant I wasn’t growing. So I’m happy to be where I ended up. 

What’s your advice for recent college graduates? 

One thing I find with talented people is that they’re so talented that they can do a lot of things, which can become overwhelming and confusing. I tell them to do two things. One is that when they meet with people and ask for help, try to be as specific as possible about the request. It’s much easier to help someone if the request was very specific. 

The other thing I would say is to meet with as many people as possible when deciding a career path. Once you meet someone who has a job you want to be doing, meet with people doing the same thing and find commonalities in their career path. That should give you a pretty good idea of the type of experience you need today to get there in the next five years or more.


Samantha Costanzo Carleton is a Contributor to VentureFizz. You can follow her on Twitter @smcstnz.