In this talk, Maya Prosser, founding team member and Head of Partnerships at Lemonade, explores the experience of imposter syndrome—particularly among women—by weaving together research findings, a vivid childhood anecdote, and pivotal career moments. She notes that research shows the syndrome is not linked to talent; in fact, the more successful a person becomes, the more likely they are to feel it, and that it develops later in life rather than being innate. She recounts a seven‑year‑old audition for an American movie, illustrating a time when she acted with total confidence and no self‑doubt. Later, as a young professional, she faced insecurity when vying for a strategic pilot account with Starbucks. Despite initial rejection, she accepted a demanding three‑month relocation to Boston, led the pilot to success, and secured the largest deal in her company's history. This achievement led her boss to invite her to join Lemonade as a founding team member. Maya concludes with a concise formula: acknowledge the imposter feeling, push through discomfort, and actively pursue opportunities, because asking for more yields more.
Chapters
Hi everyone, my name is Maya Prosser and I am— thank you, it's just my name— and I'm a founding team member and the head of partnerships for a company called Lemonade, which is one of the fastest growing— yay, good— so it's one of the fastest growing tech companies and insurance companies in the US today. And so I thought a lot about what I was gonna talk when I came here, and actually I think there are a lot of kind of connecting webs or similar lines in between our talks. Also, I'm the last one, so I hope this is good. And I guess what I thought about a lot, something that was kind of troubling me in the past few months, and it's kind of self-doubt, or in its more sophisticated way, the imposter syndrome. And that's kind of the feeling that I guess a lot of us get to have, some of us more, some of us less. If you're a woman, a little bit more. And it's a feeling that you get that you feel like maybe you don't deserve everything that you have, you don't deserve the position that you're in, and you feel like that in any given moment, you know, you might be exposed. And so, kind of thinking about, you know, that feeling that you get and thinking about about that fear that sometimes women have to get exposed. And meeting so many successful, talented women who, when I talk to them, really credit a lot of their success to, "I just got lucky." Right? And I don't know if you've had or met women who say that, but really, the really interesting thing that I found is that research shows that there's almost no connection between how talented you are or how skillful you are to you actually experiencing the this syndrome, actually the opposite is true. The more successful you get, you tend to feel that a little bit more. But the second thing that research showed that is actually interesting is that we're not born with it. So as kids, if we all go back and remember kind of our childhood, we were pretty secure. We feel we're kind of the greatest in almost everything we do, and we have kind of great dreams of what we want to become. And we have that tendency until someone tells us otherwise that we're kind of the best thing that ever happened to the world. And my childhood was— I grew up in Israel in a small town near Jerusalem. And when I was 7, I came back home and I ate my lunch and spilled some ketchup on my shirt. It's kind of any, like, a really regular day for me. And then the phone rang. And I pick up the phone and it's a casting director for this American movie called "Desperate Rescue," which was starring Muriel Hemingway. And she got my phone number from my, you know, my principal at school. You know, there was almost obviously no data sharing information or laws in Israel at that time. And so they were looking for blonde girls to play the role of the daughter of the main actress. And she said, "Listen, if you want to audition, you'll need to get in like the next hour, 10 minutes away to studio. By the way, also, we talked to your best friend, she's coming." I'm like, "This is great." I was like, "Sure, sure, no problem." Got this down. I hang up the phone, and then I called my best friend. I said, "Can you come and pick me up when you're going?" She says, "Sure." And then I remember I'm 7. So I need to get approval for this, right? So I go, OK, who's babysitting me? OK, my brother. So I go to him, and I'm like, listen, everything's set. Someone's picking me up. I'm going to audition. All good. And he says, sure. And so I go. I get to the audition. I pass the audition. This is great. Next stop, we need to get to Tel Aviv, Hilton Tel Aviv Final Edition. My best friend doesn't pass, so next logical thing, I attach myself to another mom that's there with her kid. They're going, "I'm with you." I remember, you need to do the responsible thing. I call up my brother again. It's like, "Listen, I passed, I rock, right? Good for me. I need to get to Tel Aviv. Someone's taking me. Don't worry about it. You don't need to do anything." And he's like, "Sure." And so I get to Tel Aviv. The first thing that I remember, I walk in, I see this sea of blonde girls all dressed up in beautiful dresses, all accompanied by their moms or dads. And this is me with my ketchup stain. And I couldn't be happier. I was having the best time of my life. And as I was having the best time of my life, the same time, different part of Israel, my mom walks home. And she walks home, she goes up to my brother, she's like, "Hey, where's Yotam?" My other brother, "And Maya?" And he's just like, "Your time's at a friend's. Maya's auditioning for a movie in Tel Aviv." Not the answer she was expecting. So my mom being my mom, she's a rock star mom, she just finds out the telephone, gets a waiter in the hotel to basically track me down, look for a girl that has no one. And so he tracks me down, he finds me, gets me to the phone, I talk to her, I'm like, "Eh, this is amazing." I'm like, "This is great." And she's like, "OK, never mind." She lets me play along with it. The production actually takes me back home when it's all done, and I get the part, which is really awesome. So I get to be on a movie set for a few weeks, and my brother's punishment for letting me go was to babysit me on the set for the entire time. So that was not as fun for him. So thinking about this crazy story— it is crazy— but one of the things I kind of try to tap into was I was so scared. I was so sure of myself. I had zero blocks, I was just going for it. I had complete belief in myself and in my abilities to really do this, and I was 7. Which is, ignorance is bliss, but also I think that it's kind of beautiful in many ways. And then I kind of started thinking about, okay, I'm a different person today, and I do have that insecurity, right? I do have that feeling sometimes that I can't do everything that I want to do, or that maybe I can do. And I started thinking about these points in life where people start telling you, telling us, right, that you can't do certain things because not only because of who you are, but because of what you are, right? Maybe you're not rich enough, maybe you're not strong enough, maybe you're not man enough, something along those lines. And so I started thinking, okay, why did that happen? And you carry that insecurity with you to the workspace. And so, a few years later or many years later, in my previous job, not this one, we had this huge strategic account that came in and we had to pilot with. And I was preparing to pitch to my boss that I need to manage this. This needs to be my account. And I was prepping for it and it made 100% sense that I should manage it. I managed a lot of similar accounts before that was kind of prepping me for it. But that insecurity kind of crept in. And I said, maybe I'm young and I'm not too mature. Maybe I'm younger. Maybe I'm not representable enough. Maybe I'm not going to do a good job. As women, we tend to look at a job description, and if it doesn't fit 100% of exactly what we can do, we often have like, OK, so I can't do it. But I put all that aside, and I forced myself to stand and at least look secure. And I told him, you know, I think I can do this, and this is why. And he looked at me the same serious and said, this is not happening. And I was crushed. It was tough. But a few months later, things were not going so well with the account. We were 3 weeks before launch and piloting this huge pilot with Starbucks, which is a pretty big company. I'm from Israel, so I didn't know. And so things were not going well. No one is really owning the account. And they needed someone to move to Boston in the winter for 3 months. So obviously, I became the best choice for the job. And so I took it on. I didn't ask too many questions, and I took it on. And I moved myself, and I made it work. I hired amazing people. I made sure everything is met. The account is super happy. We're meeting all of our goals. And I just really, really— crushed it to the point where we signed the biggest agreement that we ever had in our company's history. And it really changed the future and what we were doing as a company. So later on, that same boss called me up a few years later, asked me to be a founding team member at Lemonade. Is it the right one? Oh, not yet. Not Oscar. At Lemonade. And I was kind of his first pick, his first hire that he asked to join the company. He's now a mentor to me and someone I consider one of my good friends. And so I guess just to kind of go back and circle, if you look at that chain of events, it all started with me being super insecure, not wanting to put myself there, but kind of putting that aside and really replacing insecurity with action. And I think that's something we need to kind of think about, that that small action actually started the chain of events that led me to where I'm at today. And so when we think about, as women, each person can call it a different thing. I call it the imposter syndrome. Call it whatever you want. Just acknowledge it, that this is a baggage that you're taking with you, and then put it aside. And just really force yourself to feel uncomfortable, feel insecure, but go after things that you feel like that— that you can do, that you feel like that you deserve. And when we ask for more, we get more. That's just a simple equation. So thank you very much.
