Lemonade (LMND 0.86%) is challenging traditional insurance companies with its digital insurance. It's powered by artificial intelligence and data learning, and more than a million customers have already signed on. In this video recording of "Deep Dive 45: Lemonade, Part 2," Motley Fool contributors Brian Withers and Jennifer Saibil talk about Lemonade's C-Suite and how it's a great fit for what the company does. This video was recorded on Motley Fool Live on Sept. 13

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Jennifer Saibil: I prepared this little slide presentation which I will share, and tell me if it's working.

Brian Withers: It's coming up, there we go.

Jennifer Saibil: Yeah? Great.

Brian Withers: Then hit it presentation mode so you get all through the screen. I just love to share. Perfect.

Jennifer Saibil: Super. We have CEO, Daniel Schreiber. The truth is, he's Co-CEO now. They made a change maybe in July. He's just sharing CEO role now with Shai Wininger, we'll go through next. He has a tech background, as you can see. He's a founder and executive in various roles. He's sharing CEO role for now with Shai Wininger, who started off as the COO. He's got really interesting personality because he's founded so many companies. A lot of them tend to become a household name, but one of them is Fiverr, which he founded with Micha Kaufman who is the CEO now, and Shai was the Chief Technology Officer. Interestingly, Brian and I were discussing yesterday how they met and I actually did find out this story. [laughs]

Brian Withers: Awesome.

Jennifer Saibil: When Shai was leaving Fiverr, before he was figuring out his the next big thing, he approached Michael Eisenberg who has a venture capital firm called Aleph. They were one of the original investors in Lemonade. Michael Eisenberg knew what he wanted to do, introduced him to Daniel Schreiber, and had the two of them figure out what it was that was going to be the next big thing that they were going to disrupt and that is what they did. They sat down and they just went through different industries, trying to figure out, what is the next big thing that we can disrupt and they came up with insurance. [laughs]

Brian Withers: Fantastic.

Jennifer Saibil: Then you have Dan Ariely. You don't really talk about very much, but he a well-known personality. I don't know why they don't [laughs] bring his name up too much. He is the Chief Behavioral Officer, whatever that means, but I think he is a Behavioral Economist. "Note," it's supposed to say, "noted" speaker. He is someone good to have in an insurance company. We have Tim Bixby, who's had a lot of experience as CFO's executive positions. Adina Eckstein who's the new COO, has a background from executive positions at the BBC and HSBC. We haven't heard her name so much but we'll see what comes up in the next quarter.

Finally, we have John S. Peters, who is the Chief Insurance Officer and he is their main underwriting guy. He's the guy that actually knows insurance. I've had a quote somewhere that Daniel Schreiber said that, "They are going to milk their ignorance for all its worth." [laughs] Daniel and Shai basically know nothing about insurance. All they knew they wanted to disrupt insurance. They're the guys that basically said like we don't want to know about insurance because we want to start from scratch, we'll do it our own way. But they did have to bring on somebody like [laughs] John Peters who actually knows what's going on.

Brian Withers: I like the John, their Chief Insurance Officer and their CFO have considerable experience in the industry, certainly the CFO has experience in tech. To me, they're the ballasts for a new company as you get new ideas and the Co-CEO is trying to innovate, you have a little bit of grounding here in the financials, as well as the underwriting to make sure everything [laughs] goes. If you screw up the underwriting and you screw up the financials, you can go bankrupt. [laughs] That would be bad [laughs] for our investment.

Jennifer Saibil: Yes, I think they really have a great mix of the innovation guys, and the people who know how to put it all together.

Brian Withers: Yeah. Now that's a great overview. Thanks, Jennifer.