Episode 13
· 23:47
Welcome to Momentum Mode. My name is Corey Ferengle, and you'll hear me alongside my cohost Mike Shannon shortly. This episode will feature an interview with Amanda Leonard, a seasoned executive and is the longtime CEO of Jellyvision, a company recognized as a great place to work for many years. Gonna cover a wide range of topics including growing the company, teams, team culture, managing boards of directors, as well as evolution of leadership in a fast growing organization. But before we jump in, we'd like to thank our sponsor Kilpatrick Townsend and Stockton, an innovative, focused law firm with 22 offices around the world, including our hometown of Chicago.
Corey:Also, to Mike's company, Improve, and Corey's company, Appearium Ventures, for their support of the pod. On with the episode. And we're joined today by Amanda Lannert, who Mike and I have both known for a long time. And for those that don't know Amanda, she's CEO of Jellyvision for thirteen, fourteen years,
Amanda:something like Oh, so adorable. It is something like that, but I've been there since 1938.
Corey:That's what I thought. And you know, you look it. Mean, just Oh my There we go. But no, you've been with Jellyvision while I've been CEO for a very long time. But you're really well known in Chicago as as an investor, adviser, board member.
Corey:You serve currently on quite a few boards. About how many?
Amanda:Six boards of directors, and then I'm an adviser to a formal adviser for three additional ones.
Corey:Okay.
Amanda:And That's how I stay fresh. That's how I learn.
Corey:Well, and I totally agree with that. I mean, number of times I walked out of a board meeting, like, I should be doing that at my company. But anyway and so you're involved in more than just one company. You see a whole lot out there. Also, two time CEO of the Year in Chicago, best place to millennial to work as well.
Corey:So you you get all the accolades. So highly decorated here.
Amanda:Our nerds, have parents in the Midwest who vote. I'm just saying. Like, I just I just wanna be clear. Like, Facebook, army of aunts and uncles of jelly vision employees come out in full force.
Corey:So you you run a great campaign is what you're saying. You know how to mobilize the vote.
Amanda:Saying that the kids have people who vote. Know? Don't let everybody help.
Corey:The kids got the people. Yeah. That's it. And I feel like every event I go to in Chicago, our speakers, featured speaker Amanda Leonard's featured speaker here. So you're obviously very frequently speaking around the city.
Corey:So we're we're wanna talk to you today about your role at CEO and really your unique perspective. And let's start out with so when you became CEO, you'd been with the company a while. What's the biggest surprise to
Amanda:you? Sadly, becoming CEO. Not the answer, expect I'm gonna tell the story really quickly. On my birthday, many, many moons ago, the founder said, hey, Let's go to lunch. And I'm already there's enough there used to be a lot of pomp and circumstance, making fun of me on my birthday that I thought it was a weird request to go mano a mano.
Amanda:And he says, hey. Let's go to the art institute, which is like a $20 cab ride away. It is not conveniently located. So we're Lunch
Mike:is okay.
Amanda:And then he says, it's a really nice September day. Before we go inside to have lunch, let's sit down on this bench. And I'm just like, okay. Final thing he says, it's weird. He goes, I have a gift for you.
Amanda:And I'm like, you're not really a gifty person. I'm a gifty person, but you're not really a reciprocal. Okay. It's gonna be a gift. And he reaches into a messenger bag and pulls out a gift bag and hands it to me.
Amanda:And it's heavy. And I say, oh no, Harry has wrapped a brick. And it's gonna be a metaphor. No, it's like a metaphor for what we're building together. Didn't think it was a joke.
Amanda:Thought it was like a symbol. Like, We're building something to And then he says, Open it. And I'm like, Oh, no. This brick is gonna have a plaque on it that I have to keep on my desk until the end of days. I'm like, Okay.
Amanda:And I go to open it. It's not a brick. It's a box of business cards that said Amanda Lanart, CEO. So I look at it and I was like, no. He's like, yeah.
Amanda:I'm like, no. He's like, yeah. I'm like, no. He said, yeah. And so it actually bothers me that I had never even consider it being CEO, let alone had aspirations or ask for it or plan for it.
Amanda:So the first thing that surprised me about being CEO was that I was a CEO. I was a kid of academics.
Corey:That's crazy.
Amanda:It's not my path. It was done in a surprise, and he's like, And everyone already knows. So it's like, I came back to an office where people had had more time with it than I did. They said, Congratulations. And I'm like, I'm sorry.
Corey:Can I call my husband?
Amanda:No. Harry left behind a CEO some really big shoes to fill. He was the founder CEO. Right. And he was still there, and we had a peaceful transition of And it's just like, always better lucky than good in the ways I've been lucky, are working with insane people.
Amanda:And he's kinda like, You're doing the work. You might as well have the title. Like, who does that?
Corey:Yeah. My And you
Mike:mentioned he was still there. What was the founder's role then
Amanda:when he
Mike:was CEO?
Amanda:So he's an inventor.
Corey:Yeah.
Amanda:He's like one of the most prolific zero to one guys. Jackbox games, he's now working on a company that's literally trying to save democracy. He's a zero to one guy, and our one finally went to two, to three, to four. And I started liking it and putting systems in place. And I'm like, Scale's awesome.
Amanda:And he's like, I don't like not knowing everyone and their business. And I don't like the same thing I like new. I'm gonna put you on this thing, and then we're gonna have people new. So it was a very different stage of the business, and I did like scale. I do like scale.
Amanda:I do like more people. I do like more customers and solvency and security and things like that. So that he stayed and was creative and I became CEO and then he left the business about five or six years ago and basically was like, okay.
Corey:And he nicely stepped back.
Amanda:He did.
Corey:I mean, that's amazing. I got fortunate. My first CEO role is I walk into the room. CEO walks into my office founder and says, I'm done.
Amanda:So talk about it. Founders, though.
Corey:Yes.
Amanda:CEO day one, or or in it day one, architect owner mindset day one. How do you think it's different if you imagine like you replace yourself? How is the mentality different?
Corey:He might have done both day one and replaced himself.
Mike:How is it different being founder from CEO or how is it different from
Amanda:like surprised about CEO being being an operating CEO versus a founding CEO?
Mike:I think my transition was similar to like any team manager, kind of going from individual contributor to manager, because we started as a group of founders, right? So we had four co founders, we were young, we didn't have a CEO title, It was all co founder. And so then to eventually define a CEO, which we got introduced to a VC in San Francisco and the VC asked me a question, who's the CEO? Oh, we haven't defined a CEO. I'm not taking the meeting.
Mike:That was actually the impetus for us to sit down and decide roles.
Amanda:Did you, like, pull names out of a hat? Did you rock paper scissors?
Mike:I just looked at what
Corey:we knew them at that point. It was clear who was CEO. They just didn't admit to us.
Mike:Well, we didn't. But so like the transition was an awkward one of like, Okay, now one of us is like the manager per se. Everybody's doing different things. So I relate it to when I've seen like an individual contributor go to a manager role because we're still only a dozen or so people. And then as the scale came, I mean, went through failure, pivot, survival mode, all that, right?
Mike:But as scale of a repeatable thing came, then it was like, who am I surrounded with of folks like you that can help me figure out my methods?
Amanda:I do think that's probably becoming CEO, and the vast majority of situations is probably a surprise. It's very rare that you're sat down two years in advance, and like, We're grooming you to take over a business that's going to continue the way it was before, only a little bit bigger. It's like, something goes wrong, something breaks. Or it's like Hunger Games, where like, five executives are like a fight to the death for the job. It's so rarely.
Mike:Well, I went through exactly what you just said before.
Corey:Yeah, actually did the transition.
Mike:With Kelsey, who you mentored.
Corey:So I don't know. We've talked every time I get a call from a recruiter, I'm like, You're not calling me because everything's going right in the business. So tell me what's happening.
Amanda:Yes. Right?
Corey:Yes. But but it is interesting that you had a founder who stepped back nicely because we don't always see that. Sometimes you see the founder isn't as, involved and proactive about the transition that you saw there. Did did you happen?
Amanda:Yeah. That I really want to call out.
Corey:Yeah.
Amanda:You're so right. You came to me a year before it happened. You're like, I have this idea. I've got this person. What do I do?
Amanda:So you not only were one of the most thoughtful people and went out and talked about it well in advance before she knew I knew, your replacement CEO. But then you did it exactly to plan. When does that occur? Does that happen? And then you did it, and then everything that was supposed to happen happened.
Amanda:I'm like,
Corey:That's never I was telling you,
Mike:Help make that happen.
Corey:Well, I told Mike this story about sharing when we were sharing about what was going on. You looked at me when he did it. He actually did it. Yeah, you did it. So but and yeah, those kind of transition that was a probably the smoothest transition I've ever been involved in by by a mile.
Corey:Did you have to make other changes when you stepped in?
Amanda:Yeah, I started doing things like putting leadership in place, and I made a of mistakes because I took the best in any function. I was like, Now you're in charge of the function, and I didn't fully understand the difference between management and leadership. You can be an amazing leader as an individual contributor, but managers, those who set goals, hold people accountable, think about how to professionally develop rather than just lead with awesomeness, and let me show you how awesome my work is so you can aspire up to it, Very, very different things. So I think my second surprise was that I felt very unqualified to lead, and yet people still were willing to follow. There's so much expectation when you get the title.
Amanda:People are like, So now what, chief? And you're like, okay. Let's start to, like, let's wrangle some chaos.
Corey:Let's Yeah.
Amanda:Let's start to put a plan together. Well, a
Corey:little bit for you, though. You're so authentic. You're not I mean, some leaders you run into, and you're like, oh, that's an act. You're not. I think that's part of what helps people wanna follow you, is just you're yourself.
Amanda:Well, and I also, I think one of the things people don't realize, which is how much CEOs care about their people or their sociopaths. And they may not act like they care about their people. They may not show it. They may have to make really grueling calls. But I guarantee CEOs think about the individuals, their happiness, their well-being, their growth, whether they're getting a good value proposition, more than any employee has ever thought about their CEO's happiness.
Amanda:It's like you're work children in a certain way, and you get maternalistic, and you care weirdly as a CEO. And I think that that's because I'm always like, But let's go, let's go, let's go. I am change obsessed. I am like, Let's try it. It breaks, so what?
Amanda:There's nothing that can't be improved at Jellyvision, so don't be precious about it. But I also understand that with scale, and when you have 1,600 customers, some of the largest employers in the nation, you can't just be messy. So I've hired a lot of people who are great at process.
Corey:Yeah, yeah.
Amanda:Perfection, protection. And so now I have, like, I'm trying to wrangle of how do I get us going while deeply valuing the polar opposite skills I put in place that are great for stability and scale. Right. Like, how do you continue to change? Like, how do you have enough chaos to, like, have the peanut butter fall on the chocolate, but not enough chaos to disappoint a customer?
Corey:Right. And and and did you have to figure out you needed people the opposite as you, or did you know that when you got the role going, I'm gonna need some of these people?
Amanda:No, I asked for feedback, and the thing was, you go too quickly,
Corey:you
Amanda:change your mind. I'm like, I got new information.
Corey:People want a little more stability.
Amanda:They would like a different pace than I would like. And frankly, when you're not just trying to find zero to one, but it's nine to 10, you really got to value the priorities and principles of nine and not just like reinvent from 10.
Corey:Yeah.
Amanda:So it's a balancing act.
Corey:Well, and I know last company I took over had exactly the issue where we had a founder who had lots of ideas and changing and it was a whiplash feeling organization. Yeah. So the
Amanda:I may have been referred to as y.
Corey:Oh, okay. Internally
Mike:or by the board or what?
Amanda:I have a chief of staff who worked for me for fifteen years, and she's like, Okay, whirling dervish. You think people understand what you're talking about and you're moving on? No one is on board yet. So she's like, You can go because you're now bored of it. Okay, here's what she meant.
Corey:This is what's going on.
Amanda:Step one is what. Step two is what. Really breaks it down. But I very quickly try to be self aware, and I try to be humble, which means nobody's perfect. So how can I create foils that get energy from things I don't?
Amanda:So I really think of business thing as a team sport.
Mike:And is that so everybody needs a balance on wherever they are on that spectrum? Is it your chief of staff that is your counterbalance to you, you know, whiplashy or whatever people have Or is it somebody else on the exec team or what?
Amanda:I have over indexed in phases of jelly vision to have too many sort of like collaborate, communicate types. Yep. And that is the death of innovation. I think we're getting to a place of having really good balance, because I just appointed a president of jellyvision, and he's like a, Let's let it He's like, Let's let it rip. I'm like, Let's?
Amanda:Yeah. But then we have Brynn, who's still here, who has deep domain knowledge, deep understanding of the people she's working with.
Mike:And Brynn, what is Brynn's role?
Amanda:Chief of Staff.
Corey:Okay, okay.
Amanda:And she's like, Step one, step two, step three, step four. Madness, Here's our method. And she's just, she's utterly listened
Corey:to It's really managing it down the funnel, the execution on the bottom end. Yeah. Right? That was the one thing that I put in place. The last company was, you're all gonna understand what the change is.
Corey:And it was one of the co founders stating it was getting really frustrated. He said, why should we do it? I said, yeah, but we got to got to bring them along. People have to come along with you. You can't just say we're going to do that tomorrow because then they're not going to listen the next day because they know it's going to change the day after that.
Corey:Right? You got to bring them all with you. As you think about what you do now, where do you spend your time?
Amanda:So kind of if you think about like a typical day, the first thing I do is I read for about an hour a day, just like on my phone, I read newsletters, articles. I go to LinkedIn. I am just consuming the thoughts, opinions, and data of the world around me to try to get better in industry, better as a leader, know what's going on in the world. I spend a lot of time meeting with people, and I recently gotten very involved in our sort of innovation division around Medicare. Our business is largely employer benefits.
Amanda:We're getting into Medicare benefits. And I run that team like a startup.
Corey:Okay.
Amanda:Where I am directly involved in looking at creative and directly involved, and it's like very, very close
Corey:to So run it like a startup with your level of involvement or the autonomy you give the team?
Amanda:No, I'm part of the team.
Corey:Okay.
Amanda:So I have two heads. I lead a leader of leaders for our core established business. I talk to, that leader,
Mike:man This is the new president?
Amanda:That new president, I talk to him multiple times a day.
Corey:Okay.
Amanda:We probably we have one calendared meeting, but it's just like, you have a minute? And I try to be I do. Yeah. What you got? What do want to talk We'll spitball stuff.
Amanda:And I recently had a really fun moment that was very self aware. I said, I want to riff with you. And I said, Here's an idea. And he said, What about I'm like, No, no, no, no.
Corey:Had an idea for And
Amanda:he said, But we're riffing. And I'm like, Okay, that's how it was gonna be?
Corey:I thought it was a really good idea. Put a lot of thought into that.
Amanda:But I work through Brian, and he is then empowered to make decisions, run the team, have the team, etcetera. Once goals are set, there's a lot of freedom there, where I am much more involved in how do we do, what do we do, when do we do it on Medicare. And I'm doing a lot of the work. It's like, in a startup, you do five jobs. Getting licensed as a broker so that I can deeply get stuff, deeply understand the details.
Amanda:I think one of the skills I have may not be financially operating at scale and learning how best to optimize for EBITDA, but I know how to create experiences. I know that our magic isn't in what we do, but the way we do it. Yep. And I know what that means. And it's the way we treat people, way we treat customers, the way we design our product.
Amanda:Like, there's a zhuzh factor that has created a lot of wealth for us as a business, a lot of success. And so I like to come in and it's like, even if I can't create the zhuzh, I can be like, it's not there yet. And this is what I So I'm very, very involved
Mike:sort
Mike:of
Amanda:Well, point
Mike:earlier of authenticity. I mean, that's so core to your personal brand of somebody who's observed and admired from afar, and it precedes the reputation of the whole company. And so, back to the becoming CEO way back in the day, did you ever feel any pressure to, like, act differently once you were CEO?
Amanda:No, because it was really such a blur. But I'll say something. Yeah, okay. Logan LaHive, who's a serial founder, I did a Lunch and Learn for his people, and he asked me the question of like, What about being a CEO? And I said, You know what?
Amanda:I have always been the CEO of whatever I'm working on, and that I probably disproportionately care, disproportionately sweat the details. When I left Leo Burnett, my first of two jobs, jellyfish has been my second job, I was like, Are you guys gonna be okay? I mean, was forgotten the second that the door started to
Corey:close, I
Amanda:was gone from memory, but I cared so much. It's gotta be like, it's just so, and you've got this stuff coming up, and don't drop the ball, and the client this. It's like there was an intensity of ownership that my parents are workers, and they put it in me and stuff. So now it's just ownership of not a project, but a company. But that caring, sweating the details, believing in potential that is greater than what is and wanting it to manifest into something great is day one.
Amanda:It almost got me fired, actually, right out of my job because I was insufferable as a 21 year old. I'm like, I don't think we should do this. This isn't worth my time.
Corey:Then when I'm sorry, who are you? Yeah, my boss is Do you have an ID badge?
Amanda:Oh, my goodness. I'm so sorry that you thought I was asking you for your opinion. You don't know anything. And then those very same skills of being ornery, of driving, of challenging are welcomed from executives. Unfortunate.
Amanda:Can make you that's why a lot of people maybe start early.
Corey:Yeah.
Amanda:Because bosses don't want to deal with what can be problematic friction that is also conducive.
Corey:How does that manifest itself with a board then? Right? Or time spent? Like, if you think about your time, you spend a lot with your board, a little with your board.
Amanda:I spend very little time
Corey:with
Amanda:my I am also deadly transparent with the board. I think about the board as a team. And I say, I don't work for you. You work for me.
Corey:Interesting.
Amanda:This is not true. They could fire me. Yeah. That's Okay. Just want to
Corey:be But as we've learned, they don't really want to.
Amanda:They don't. They don't
Corey:Nobody wants to fire me.
Amanda:Want us to be successful. They want us to be convicted. Convicted. And so I have, it's a board of four people. I am one fourth of the board.
Corey:Okay,
Amanda:we've kept it very, very small. I interviewed intensely. I did 11 backchannel references on our last investor to board and I backchanneled him because I wanted I am predictable. I try, and my promise is no surprises. And that's what I wanted from him.
Amanda:I don't like this bait and switch, different agenda. I will never surprise you. You never surprise me. And I remember I sat down with him at one point and I said, If there comes a day where you need to shoot me, shoot me in the face. I give you my word.
Amanda:I will act as a shareholder first. My ego will take a backseat until we're long done. Will You
Mike:said this
Amanda:just after a meeting or I said, as I was talking to him, expectations. No one does that with board directors. What are your expectations? How do you like to get information? Here's how I like to give it.
Amanda:And it had come up because I write prose. I write emails and long form prose, and I used to write a lot of written updates. That was when I owned the deck. And as I got more executives and they brought their own thing, like, kind of lost And
Corey:for those sort of owning the deck means who's responsible for having the end creation of
Amanda:board That's right. Like, who owns the materials? And I remember him saying, I really hate pros except for yours. And I was like, Funny that you hate pros, and I never bothered to ask you. Whereas I talk to every team member I work with, How do you learn?
Amanda:What motivates you? Do you like a long leash or short leash? Do want me to be hovering? Do you want me to be far away? You talk to your team about how they do their best work.
Amanda:It never even occurred to me to be like, Oh, Carter likes a bullet point that says, Here's what you're looking at, and then you look at it. And it's like, he's a very predictable guy, and it just never occurred to me to treat my board like a team until he said that. And so, said, Let me tell you how I wanna be treated. Yeah. I don't want executive sessions where I leave the room and you tell each other the truth.
Amanda:The single most important vessel of your honest opinion is me. And if there comes a day when I need to leave, don't do that thing where you log in and you're, like, locked out of email.
Corey:Yeah,
Amanda:right. This is my life's work. Trust me to put shareholder value ahead of my ego. I will do the right thing, but don't just, like, swipe me. Like, don't don't let's not do that.
Amanda:And he said, okay. He did not say, I'd never shoot you. He said, I'll shoot you in the face.
Corey:Yeah. Which, I mean, I'm gonna guess it's a struggle for him to act differently, and I don't know him at all, cause that's not how you act on most boards.
Amanda:We
Corey:we have those private sessions and all that good stuff.
Amanda:But my the the board I have is beautifully consistent. Nice. They do not change. They're not tigers changing their stripes. And I think if I did anything well, I picked consistent.
Mike:Yeah. So we And what is the dynamic, if we can ask, is it like there's a lead investor and then independents? Or like, who are these other people?
Amanda:There's founder, Harry's on the board, a long standing investor and a newer growth equity investor.
Corey:Okay.
Amanda:And there's not a dynamic of like, I truly think I'm here as accountability for the team. Yep. I am here as a check-in and reflection. I've done various things. Like, used to end board meetings with a by next board meeting, we will.
Corey:Yep.
Amanda:And you're like, three weeks, you're starting to think about the next boarding. You're like,
Corey:Oh, uh-oh. Quick, quick, quick, What's my schedule list?
Amanda:Get stuff done. But I say it's not valuable to me if you start to pick at our numbers in the Chicago market and are wondering why this broker did whatever. It's like, are we marching towards value? Are we marching towards building a great business? Are we following playbooks and pattern recognition that you have seen?
Amanda:That's what I want. And what they want is for us to have an opinion. Yep. I think one of the most dangerous things you can do as a CEO is get down to two options and then say, What do you think? When you acquiesce power, boards go, Oh, no, you're not the CEO anymore.
Corey:Right.
Amanda:And I just have a group where I'm like, I think this, and I've gotten a very long leash because I am very transparent about our woes. Very transparent about what I think has to be better.
Mike:You also outlining for them what B is, though? You're saying, I think A, but are you thinking B? I've looked at C.
Amanda:I I said, Not this for these reasons.
Mike:Okay.
Amanda:Or I'll say, you know, just riffing that we've talked about this, but, like, we thought about these things, or, We have to get better at this. It's not the main plan, but, like, we're really looking at the delta, for example, between gross and net revenue. Don't have the perfect plan yet, but hold us accountable to that. That's an important dynamic of the business. And they're just, okay.
Corey:Got I
Amanda:pulled up my notes next time, and oh,
Corey:you
Amanda:That's
Corey:what, yeah, we agreed.
Amanda:Just simple, basic stuff. And also, I would say, really good people. My board, they are good people. They are partnerly. They are ethical.
Amanda:They're supportive. They lead with kindness and benefit of the doubt. That's just like, that's a huge part of jelly vision, but we even have it in our board that they never say, There are corners worth cutting. They would never say And that is very motivating. It makes me want to fight really hard for them.
Corey:Well, we keep these tighter, so we're out of time. I have a feeling we could have gone on a whole lot longer. Amanda, thank you so much and thank you all for listening. Thanks.
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