Head of Content and Communications, Lemonade
Ep217: Yael Wissner-Levy | VP Communications at Lemonade
Yael Wissner-Levy is the Vice President, Communications at Lemonade ($LMND) a digital insurance company powered by artificial intelligence and behavioral economics and driven by social good. Previously, Yael was a speechwriter and communications consultant for political and business leaders, having written for heads of state, CEOs of multibillion-dollar corporations, and non-governmental organizations. Prior to that, she worked as a journalist at various media outlets, including Ha'aretz and Israel's Channel 10 News, serving also as the channel's correspondent to the UK. Yael also worked with...
About Yael Wissner-levy
Yael Wissner-Levy, Vice President of Communications at Lemonade, discussed her career trajectory and approach to storytelling in a 2021 podcast interview. She noted that after working as a speechwriter and communications consultant for political and business leaders, she concluded that "technology and Silicon Valley was where maybe policy was even trumping a lot of things that are in government." Wissner-Levy described Lemonade as "a B Corporation" and "a for-profit business but we have social good embedded in our business model." She emphasized that when crafting a narrative, she considers the audience and what she wants them to feel, citing the challenge of limited attention spans. Wissner-Levy, who previously worked as a journalist for Ha'aretz and Israel's Channel 10 News, said her goal was originally to become a diplomat but that she found a common thread of storytelling across her various roles. When asked to describe herself, she declined to self-describe but identified resilience, integrity, and compassion as qualities she admires in a person and a leader, noting their importance "especially in 2020."
Transcript (34 segments)
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Yael Wissner-Levy0:00
My goal was always to be in the UN. I thought I was going to be a diplomat. I threw that in the trash, but the storytelling aspect of it all, I think, does actually run deep, and there is a real common denominator between the things that I've done.
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Michael0:46
Yael, lovely, thank you so much for being on my show. I'm so incredibly excited to have you here.
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Yael Wissner-Levy0:50
I am too, thanks for having me, Michael.
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Michael0:53
I've been waiting for this for a long time. You're one of the most wanted, you know, high-tech entrepreneurs, communications writers, whatever you want to call it in the world. The work that you've been doing with Lemonade, being Vice President of Communications there in a company that is revolutionizing the way content is being delivered in the world of insurance. I'm now in the insurance space with Hippo Insurance, so I get to appreciate this art of communications and content there. It's remarkable. But I actually know you back from your speechwriting days and previously as a news anchor, so you have a breadth of experience in the world of communication. Take me back to the good old days, you're back with Channel 10 News and then i24 News. Why journalism? Why communications?
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Yael Wissner-Levy1:45
I will take you definitely back, but I have to comment on those crazy, crazy compliments you gave earlier. I can't take any of the credit. I work with an incredible team, and I know Hippo also has a really outstanding team. But here at Lemonade, I've been fortunate enough to work with really the best entrepreneurs, I think, on the planet, and learning from them. Just kind of being here for five years, I'm actually celebrating my five-year anniversary here at Lemonade. It has been an unbelievable journey on a personal level as well, but also on a professional level, really working side by side with the top of the best, like really, really top talent. But we'll get to that.
As you mentioned, I had an unorthodox way of jumping into the tech scene, but I like to say that if you look back and try to connect the dots, it's actually very clear. It just wasn't clear at the time when I was in my 20s and I was going through, as you said, journalism to politics, back to journalism, back to politics. It looked like I was hopping around, whereas I feel like I was just diving deeper and deeper into this world of storytelling. Storytelling is actually the elements of it are pretty basic, and you put it in journalism, or you put it in politics, or you put it in tech, and the very kind of elements and the fundamentals of storytelling are the same.
I started my storytelling experience, if you will, right after the army here in Israel. Actually, even before, I grew up in a home that was very much of a storyteller's home. Books and stories, and my mother's a teacher, as you know, were part of the everyday life. And I always liked to write and kind of delve into that. After the army, I worked in the US Congress for a Democrat from New York, and that's where I was exposed for the first time to storytelling kind of as a profession that was beyond just what I've known before as authors and so forth.
Suddenly I saw all these members of Congress that would come into the Senate or the House, and they wouldn't say a word without having their speechwriter write it for them. And it wasn't because they were incompetent; they were actually extremely competent individuals. I was lucky enough to work with Representative Steve Israel from New York, but they understood the power of the word and the power of everything that they were saying. They had the opportunity to change hearts and minds, they had the opportunity to get bills passed, they had the opportunity to get votes for their legislation. Whatever it was, they understood that there was an opportunity here, and there's an opportunity that could not be missed. And if you have that opportunity to have that time, you have the attention of someone in front of you, how do you use it to optimize what you're saying so that people want to hear you and activate or go out and implement what you just said?
That fascinated me, that kind of very idea. It's really human behavior of how we internalize something and we decide to go do something because we read it or we saw it or we're actually looking at someone as a role model and trying to replicate or emulate them. And Representative Israel, Congressman Israel, he saw this in me, and I was itching to write. It was the year after the Second Lebanese War, and he was putting through a lot of legislation in Congress around the end of the war. I asked to write some of his speeches. I also input a lot of what he would be saying on the floor of the House.
That's where it kind of started. From there, I went into Haaretz and was an editor on the website for three years, and then went to Channel 10 here in Israel, which is now Channel 13, and i24 News. And then I studied in London. My goal was always to be in the UN. I thought I was going to be a diplomat. I threw that in the trash, but the storytelling aspect of it all, I think, does actually run deep, and there is a real common denominator between the things that I've done. So if I can even say anything that I learned from that, is everything will make sense in the end. If you follow your passion and continue doing things that you like, you don't need to create your resume in advance. You actually look back and you'll say, 'Wow, that actually really does make sense.'
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Michael6:27
The very first thing that you said was storytelling. It's pretty basic in its roots, but I have to tell you, I took a class very recently at Stanford with David Demarest. He was a senior staffer for the White House for George Bush Senior, and we had dinner a few times. The stories that he told me about the responsibility—he wrote most of the speeches for George Bush Senior—and the responsibility and the burden of being the storyteller with the nuances. You wrote speeches for heads of state, presidents, CEOs, right? And so it's not just taking the content and putting it in a nice way, but it's actually the art of delivering it and convincing others in your message. And I can only imagine the responsibility and the anxiousness of watching them deliver the speech and seeing the reactions. Because we can see, especially in 2020 with the elections on all sides, how every speech, every debate is so fundamentally crucial to the position of the candidates. I can only imagine the skills that you have to build. And what's remarkable, I think, about your journey that I'm getting a lot of inspiration from is I see a trend today that people are moving very, very quickly between domains as if it's a checkbox. And while you've moved quite a bit from different domains, you've really dug deep into them. You've spent five to seven years in editing and journalism, and then in speechwriting, and now in high tech, five years spending in a hyper-growth startup. That's incredible. So while you did change, you really dug deep into all of those subjects. Do you feel that way?
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Yael Wissner-Levy7:59
Yes, and I think I do in retrospect. I don't claim to have known all of this ahead of time. I didn't go out and say, 'I'm going to spend five years here.' I mean, had you asked me six years ago if I thought I'd be working in an insurance company, I would have thought you were absolutely crazy. That wasn't on my grand scheme of things. But I can say that one thing I have learned, and this is only in retrospect—so everything, we're all so smart in retrospect—is that the focus, and when you focus on one or two skills that you want to hone on and understand and get really good at, you have to. There's only focus. You can't spread yourself too thin. You have to know what you're good at and what you want to get better at. And I think I'm a true believer in getting better at stuff that you're not great at. But I also think that when you focus on something and you don't try to win it all, you get to interesting results.
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Michael8:55
So what are you really good at? What is your focus?
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Yael Wissner-Levy8:59
So I think I'm trying to understand the flexibility and the dynamics of storytelling to its core. As I said, when I was just starting out, I was absolutely sure I was going to be a journalist forever. And then that kind of turned into, well, journalism is great, and I think I can give a lot and learn a lot, but I don't think it's actually going to change policy. And then I wanted very much to go into the foreign service and be a diplomat. I went to school in London thinking that would be the next stop before the UN or something like that.
And I think understanding in London, my understanding there was, sure, you can go into the foreign service, but actually, as you said, the person really helping some of the leaders formulate their policy are these ghostwriters or speechwriters or whatever you'd like to call them. And so that fascinated me. I said, you know, it's not only about the words, it's about who you're working with. And I was fortunate enough to work with really top leaders here in Israel, writing their speeches in English. And then that relationship also really fascinated me because I said, wow, if you take that relationship, you put it to business, to public companies, and you work with CEOs of a public company on formulating their message, how are they going to speak when they have earnings calls and stuff like that? That really fascinated me as well. And I was fortunate to work with the CEO of Teva Pharmaceuticals for a while, and I started adding on clients in business, not only in politics, and understanding that in terms of the storytelling, if I go back to what I started with, this is fascinating. This is something that you keep on learning and learning. And if I can focus on that and get better and kind of expand my knowledge in the storytelling realm by working with different leaders, I really will expand my knowledge base in general.
And then it was pretty clear to me after a few years doing that that technology and Silicon Valley was where maybe policy was even trumping a lot of things that are in government. And no pun intended, that didn't sound very good. But I did kind of feel like I wanted to join something that was bigger than what I could do by myself.
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Michael11:27
We're going to dive into it, but I have to ask before that because I need you to take us into the mind of this storyteller for a second. Because the majority of the people listening to this, including myself, are young, scrappy, hungry entrepreneurs. We tell ourselves stories and we think of the world and we keep trying to reinvent things that are happening around us. Yet I'd love to learn a little bit from you. When you approach a story, whether it's writing it, helping write a speech for a president or for a CEO or for a limited, what are some of the thought process that goes into building this narrative that at the end others want to follow? And I'm generally asking this because I'm curious to what constitutes a good story, a good narrative.
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Yael Wissner-Levy12:09
So I think one of the first things that you have to think about when you're writing anything is who you're writing for. Who are the audience, and what do you want them to feel? What do you want them to take away from it? Because everyone has, especially now, zero attention span. People are on the go, they're getting their information in 10 different ways that you didn't even optimize for. So when you're trying to write something, you really need to narrow down. It goes back to the focus. Focus on who exactly you want to be reading this and what they want to be feeling, or what you want them to be feeling. And when you have that in mind, you can kind of create that story in a way that makes sense. Not for you. A lot of times we're writing and we think, 'This is my story.' Sure, it may be your story, but if you want people to go and execute on that story, or buy your product, or believe in you, and vote for you, or whatever it is that you want them to do, you really have to think about them and what they're feeling, and kind of create that story for them and not for you. And I think that's a lot, you know, it's kind of counter-intuitive because you open up your Google Docs and you start typing and you feel like you're sharing who you are, but it's actually not really about you. It's about your end customer, whether that be your constituent or your customer, or your parents, whatever it is. Who is this audience?
And then the second thing that I would say is that because we have such a short attention span, you need content. You need stories or data points or whatever it is that you're constructing that sticky content, they call it. Something that people will walk away, if they can remember one thing from what you just wrote or what you just said, or the graph or the infographic that you made, what will that be? And sometimes you need to shock them, sometimes it needs to be something that is actually inspiring and not just fluffy content, which a lot of people like to, you know, 'Oh, I read a nice quote somewhere, let me put it in,' but nobody really remembers it. Like, what is a sticky part of your content that you're going to be leaving the audience with? I guess that would be my two.
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Michael14:06
How do you know that? So when I'm sitting down and I'm preparing a talk or I'm preparing a letter, how do I know if something is going to stick? Do you test it out before? Do you get feedback from others? And how do you run all those experiments? Because that sounds complicated.
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Yael Wissner-Levy14:22
It is. It's a lot of trial and error, and it's a lot of getting to know your audience. So sometimes you'll write something and it'll fall flat. Sometimes people will like that, they'll say, 'Okay, I wrote something, people read it, but it didn't do anything.' And sometimes that's comforting because, okay, it didn't move the needle, but at least it didn't get anyone angry. On the other hand, if you take more risks and you go out on a limb and you say, 'I'm not going to speak to everyone, I'm going to speak to two percent of my audience because I know that those two percent are the most engaged and they will follow me and they'll come after me if I ask them to,' you see that a lot in politics. It's not only—I was just about to say, I mean, we're watching it unfold live, these different tactics. And so you don't want to—you can't win everyone, and you can't win the hearts and minds of everyone. But if you go and you say something that will make someone's ears perk up, and another person, and another person's, you're probably going to get a more engaged audience than if you say kind of the cliche that everyone's used to. And so you have to be a risk-taker. It's a lot of risk, and be prepared to kind of own what you're saying.
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Michael15:31
So when you sit down and listen to a speech, when you watch the news, or when you're listening to somebody talk, do you cringe sometimes? Like, do you have wheels and motions saying, 'Oh, this is the tactic that they're using, they're alluding to something bigger, they're trying to get me to feel these emotions'? Do you have that process?
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Yael Wissner-Levy15:49
Yeah, sometimes. I try to take it off because you don't want to become too cynical. You want to believe that there's—cynicism will at the end really make us not optimistic. So I want to keep the hope alive. I want to think that there are people that are speaking genuinely and they're not trying to artificially implant all kinds of speaking tactics and rhetoric and stuff like that. And I do believe that there are people out there that are speaking from their heart and their brain and not just trying to rouse up the crowds. But yes, you can't ignore it. Once you see it, it's like you can't unsee it.
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Michael16:28
I love it. So, Vice President of Communications at Lemonade, hyper-growth startup, you're joining from the early days, and that's a fascinating thing because you're coming in from the political world right into high tech. What is that experience like, and what was the journey like reinventing the messaging behind insurance?
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Yael Wissner-Levy16:46
So as I said from the start, I really am privileged to be able to work with two of the finest entrepreneurs that I can think of today, Daniel Schreiber and Shai Wininger. They were tech veterans and they had been around the tech scene, so to speak. And when they stopped at insurance, they found an opportunity that really was this huge opportunity because it was so unchanged. It had gone through decades, if not centuries, of stagnation. It was so unloved. You know, when I heard about insurance for the first time through Lemonade, I said, 'That sounds like—I don't know, it can't be something compelling.' But the fact that it was unchanged and unloved was a huge market opportunity and a huge storytelling opportunity. Because suddenly you can change the perception of something that is really such a fundamental part of society, right? When something goes wrong, you want to make sure that you have something to cover you. And why did it lose its way? What happened to that story of insurance that started really as communities coming together and really lost its way through the kind of evolution of society? It kind of really ignored every other revolution that went through. Insurance stayed the same.
And I think that part of the story of taking on an industry that was so vast but also so unloved is a storyteller's dream. It's an entrepreneur's dream. It's a product dream, right? You can see it through any lens that you'd like. But really understanding the opportunity here, both to work with Daniel and Shai and the rest of the team, and also understanding the opportunity at hand for the world. Lemonade is also a B Corporation, so understanding that we're a for-profit business but we have social good embedded in our business model was something that I wanted to be part of that story. I wanted to tell that story. And as I said, joining something that is bigger than the sum of yourself is really gratifying in the end, if it works. And even if it doesn't work, it's great.
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Michael18:56
It's almost like the ultimate challenge for a storyteller because you're literally trying to change the perception of what it means to be insurance. Because just like yourself, I think the majority of the people, they think of insurance until today and they think of, 'Okay, this is the enemy, they're trying to take my money, and maybe if I have an accident I can finally get the money back from them.' It's almost like a win in front of your insurance company. And also in here, you're trying to work on a startup that is trying to create a social contract with insurance. What was the biggest challenge there with sort of trying to reinvent that messaging?
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Yael Wissner-Levy19:31
So it's everything that you said. How do we make insurance interesting for people that never really either liked insurance, or in our case especially, people that never had insurance before? A lot of our customers are first-time insurance buyers, meaning they never ever had insurance. And what will make them want to come to Lemonade? We talk about Lemonade in general, and insurance—I think Hippo does also similar messaging—is understanding that insurance can be lovable. It can be spoken about in a way that nobody ever dared to speak about it before. And when we launched in New York in September 2016, we started seeing people tweet about their Lemonade experience being delightful and amused, and 'Is it weird that I love my insurance company?' And it started ringing back to us saying, you know, we're on to something. And if we make an experience that is absolutely delightful from start to finish, that is seamless and fun and brings smiles to people's faces, and they can choose a charity that they'd like to support, then we're really kind of changing the entire fundamentals of insurance, not just the financials, but really how people interact with it. And that's kind of the ultimate story.
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Michael20:46
No, and obviously, I think from the start, I've been following the journey for a long time. There's so many different facets that you've employed in order to change that narrative, starting from the transparency of being fully transparent from day zero. And when you think of insurance, you think of this big monster that's like getting all the cash, and all of a sudden you're being transparent about the financials and about the intentions. And I think that I gained a lot of inspiration, and I'm delighted to be now with Hippo and seeing how, you know, the different companies—somehow all of them are Israelis—but also Next Insurance, they're coming in, and all of a sudden such a big field is changing so dramatically. And at the end, it's for the benefit of a lot of people, it's for the benefit of millions of people. But unfortunately, I can't believe 20 minutes are almost up. I have about 100 different questions that I wanted to ask here.
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Yael Wissner-Levy21:34
Yeah.
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Michael21:35
I want to thank you so much for being on the show, and I really appreciate it. Back from when you very generously donated your time to come to one of my debate programs, our debate clubs at school, to teach us about storytelling. That was one of the most inspiring sessions that we had, and I was in that club for about five years. So thank you going all the way back there. And before we leave, I have to ask you for three words that you would use to describe yourself.
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Yael Wissner-Levy22:01
Oh, you ask tough questions. The hardest one, yeah. I don't want to self-describe, but I can tell you the three things that I kind of really admire and I hope that I use when I'm with my team. And they know this, and so I'm happy to kind of spread it around. But the three things that I really admire in a person and a leader are resilience, integrity, and compassion. And I think the three of them together really kind of touch upon different aspects of leadership, but also of human behavior that is crucial, especially in 2020.
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Michael22:46
Especially. Thank you so much. I can't wait to share this with the world, and best of luck with everything that you're doing.
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Yael Wissner-Levy22:52
Thank you.