Chris Williams: Liz Pearce started her career in marketing. She worked for Sony on the PlayStation, worked for Google on a range of marketing initiatives, and helped Amazon launch their wedding registry. She even hung out her own shingle as a marketing consultant. But it wasn’t until she worked for a startup where she realized her true calling.
At LiquidPlanner, she rose from contract marketing assistant to the CEO. There she found her stride and is now co-founder and CEO of Seattle startup Fresh Chalk. In our conversation, Liz talks about her fun journey, the difference between working for the big guys and a startup, and what makes being a startup CEO both a challenge and a blast. And that’s what this is all about.
This is Leading Smart, the show about managing in the brainpower age. It’s a field guide to the joys and challenges of leading and working in the modern workplace.
I’m Chris Williams, your guide to the stories and ideas that I hope will inspire you to be a better leader in the world of knowledge work.
This episode is another conversation with a leader. This time it’s with a dynamic startup CEO. This is Episode 232, my conversation with Liz Pearce.
Liz Pearce started out in communications, specifically political communications with both a Bachelor’s and Master’s in the field from George Washington University. But like so many leaders we’ve talked to, a chance turn in school letter on a different path.
Liz Pearce: I grew up in Central Indiana, just north of Indianapolis, so a suburb of Indianapolis.
CW: And so how did you get to George Washington?
LP: Well, I had been born in Annapolis, Maryland. And my dad was born in Washington, DC. And I had a kind of a fascination with politics in Washington, DC, I have grown up visiting my grandparents in Annapolis and other family up and down the East Coast. And I was really, you know, had Washington in my crosshairs. And so I applied to American, George Washington, and Georgetown, and then IU as my fallback school, and ended up getting a scholarship to GW and that was it.
CW: Your BA is in political communications, you’re, you really were focused on sort of what looked to be a political communications career. But here you are…
LP: I was studying political communications. But at the same time I was my work study job was for the Student Services Division of GW doing graphic design. So I had in high school, and throughout my childhood, I did a lot of fine arts, I painted and drew and that was kind of my primary hobby, as I was growing up, and so I kind of translated that into graphic design in college. And just through my involvement in Student Services in some of the organizations on campus, I ended up receiving a leadership fellowship, called the presidential administrative fellowship for grad school.
So I got, straight from undergrad, I went straight into grad school, and GW paid for it. And they put me up in on campus housing and I, I changed my job when I started doing web design and development as a paid job in addition to my full time master’s program, and other kind of extracurriculars.
So I had two more years at GW. And that was really my first technology jobs in like a technology organization within student services. And so I started interacting with like IT people and developers for the first time. And then when I ultimately moved to the west coast and got a job at Sony, still, I was in marketing. So it wasn’t like I’m working with game developers all day, but it still was a technology company and that started to kind of become like part of my own story to myself, which is like I can I can work and be comfortable working in technology.
CW: Were you code? I mean, were you writing the websites, or were you just helping to design them?
LP: I was doing basic HTML. But I was I was partnered up with is not only the person I would later marry, who was more of a developer. And so I kind of did front end design stuff. And I also did, essentially customer support. So we built the first content portal for all the different divisions of student services. So for, you know, the international student group, and for all these different areas, we build a way for them to without any knowledge of coding, update their own piece of the website.
So we had to train them and design a site that mapped to their little department. And it was all very new at that point. But it’s, you know, it’s essentially, what people do now have all kinds of websites where they can very easily go in and update their own copy.
My coworker future husband moved to the west coast to go work on Sand Hill Road at a startup. And I had a couple months left to grad school. And then on the day, I graduated, I moved to California, and settled in the Bay Area.
CW: I see. So you go to work at Sony…
LP: I actually started as a temp. So I worked for a temp agency, they placed me as an EA, reporting to the head of PlayStations. legal department. And this is a kind of a funny story.
I did well as an EA, and I had a master’s degree, I could file and create meetings pretty well. And he ended up kind of offering to pay for me to go to law school, and come back and be an attorney. And I said, “could you get me a job in marketing or an interview in marketing.” And I ended up moving into the department as a full time employee.
CW: After a time working at Sony, hoping to market the PlayStation, Liz got a job at Google through a friend.
LP: Google was very small 500 people roughly at the time, search was new. I mean, we were all like using AOL and everything up to that point. And I saw it as a big opportunity. And so I made the move to Google.
CW: you, you must have really had an opportunity then also to, to really jumpstart in the marketing organization, because that’s right about when they were just really starting to move sort of beyond organic to outbound marketing, right?
LP: That’s right. My role was I was the marketing coordinator. And I was effectively the traffic manager for all of the marketing projects taking place across the organization. So I had roughly 200 projects per quarter, that would pass through my hands where there was a product marketing manager, who was the client, and we had internal resources, writers, designers, and then we had external resources. If you know, if we were doing an ad buy, or we were doing something printed, I would manage that whole workflow for all these different projects. And it was every line of product. It was International, it was internal corporate marketing, it was probably still the hardest I’ve ever worked in my life.
CW: The sleeping under your desk kind of thing?
LP: Yeah, every meal at Google, I had because every product organization had to be served fairly equally, I had to divide my day into these like minute increments where I’m like, okay, for these 20 minutes, I’m going to work on the most important projects for the Search Appliance group. And it was really that, you know, that tightly managed, my time and then all of these different projects to make sure they were all shipping at the same time.
CW: Did that? Did that teach you a lot about how to do that? Is that part of the reason why you think you’re pretty good at what you’re doing now?
LP: Definitely the ability to context switch, and to get a lot of plates spinning at once, get a lot of projects happening at once and leveraging resources to make all those things happen. Understanding how people are spending their time what they could squeeze in what might have to push out to fit something else in, you know, seeing that chessboard, in that role, I think has helped me because it’s very much the same set of skills I use today as CEO of a smaller company, where we’re like: Okay, here’s, here’s the players. Here’s the set of work, what’s the priority? What’s the breakdown of the work? What’s the order of execution? What’s the quality control? What’s the delivery? And yeah, I definitely think it helped me.
CW: When Liz’s husband got a job at Microsoft, they moved to Seattle where she got a job at Amazon. Here too. She was there early, just as the company was moving from books into a broader product array.
LP: My first job at Amazon was in the hard lines retail group. That’s what we called it. So Home and Garden, kitchen, automotive, all the non media effectively. And I worked as a product manager in that group, and did a lot of kind of cross merchandising on the side and different programs. I’ve worked on our first search advertising campaigns. So, yeah, very early, there are about 5000 people at Amazon at the time.
CW: After working at Amazon, including helping to start the wedding registry, Liz took a big leap and decided to become an independent marketing consultant. One of our clients was a startup called LiquidPlanner.
LP: They initially hired me, the two founders, one of them was a friend of a friend who I had known a little bit and then his business partner was a CEO. And they actually had not incorporated the company. But they were vetting some ideas, and they had me do a market sizing analysis of project management software.
And I didn’t really even know what a market sizing analysis was, I had to google it after I agreed to it. But I did a little research project to see how much you know whether there was money to be made in this industry. And I wrote a report on it and handed it over, had a baby. And a few weeks later, they’re like, we’re gonna come back and talk a little bit more of a little more about marketing.
And so that following year, I started just doing a handful of hours with them here and there, helping them, you know, with the initial concept, value proposition, messaging, and eventually, all my other clients fell away. And at one point, I said to them, I think I work for you guys. And that that was when I went on full time.
CW: Did you feel like you were sort of leaving something? Was the was the loss of independence there a problem?
LP: No, no, not at all. I was running to something. For sure. I really love being part of a team. And so the consulting was, was challenging for me, in that way, I felt more isolated than I did when I was working in a full time role. And I was like, really part of a group of people all working to build something together every day. And I really missed that.
It’s just so exciting. In the early days of a startup, when you haven’t made any mistakes, that there’s like, only opportunity, right? And there’s all of these interesting problems to solve. Like, there are just everywhere you look, there’s a problem slash opportunity.
And that was so thrilling compared to even by that point, the experiences I had had in a big company were like, they plop you down, you do your training, you do your onboarding, they put you in your lane. You know, you get into your weekly meeting routine, and you start to play the promotion game, and, you know, figure out how to advance your your own career within the framework of this big company, there was none of that at a startup, the startup was like, Can we keep this thing alive? And that just was such an interesting challenge.
CW: Is there? Is there an adrenaline rush from that?
LP: Yeah, it’s it’s kind of the, you know, it’s the David and Goliath type of fight. You know, we we started LiquidPlanner in Microsoft Project’s backyard. And right away people were, you know, we’re like, What are you thinking? challenging Microsoft Project in their own backyard? And that was just like, oh, you’re daring me?
LP: You want me to step up to this challenge? And maybe Wait, and yeah, I think that was just, it kind of triggered my competitive nature. And I really wanted to be part of a team that would prove people wrong.
CW: It was at LiquidPlanner, where Liz got her first taste of managing people.
LP: So I think that that was my first time managing people. The founders of the company were very experienced managers. And so I was able to learn a lot from from them and also from my prior experiences on, you know, how do you get what you need from people while also giving them what they need?
And that was, you know, you learn that I think pretty quickly. I you know, I learned by watching, emulating people I admire reading, using my gut instinct, I think so much of management is… yeah… just kind of like your innate way of dealing with humans that you learn from your parents, right?
CW: Or, or from bad experience. Oh, yeah. Yeah. I know, I don’t want to be that manager. Right?
LP: Exactly. Yeah. But yeah, I think, you know, just the fundamentals, like treat people with respect, be open, be direct, you know, be kind.
CW: As you worked your way up, when did you first get out of your, you know, you you had all this long experience being a marketing person, but then you got to be the COO. Oh, so you started to sort of expand outside of your core… forgive me for this, but competencies… right, your core history?
LP: Yeah. Well, it just evolved with the company. Every time the company took a step forward, I tried to keep up with it. So the thing that happened was that we had a product that people were going to use, and those people needed to be supported.
So even before I did sales, I was doing customer support, answering the phone, figuring out how to get them to tell me what happened in a way that I could take back to engineering, and all of those things that you learn in customer support and nurturing those customer relationships. And that translated, now after we decided that the product was ready to sell into sales, and then we did, we did have a week long bootcamp on sales. So I can credit my friend Brant Williams, for teaching me how to sell and he was like sitting with me, at the desk, when I picked up the phone and made my first sales call.
I’ll never forget it, it was to a… a customer named Butterball Farms. And that my point of contact said, Whatever you do, do not mention Turkey, because they make butter balls, not Turkey.
So So that was our first that was my first sales call ended up being our first deal. And I kind of got a sales bug at that point to it combined. Other loves, like my natural curiosity and love of people and my interest in persuading people. And so I got really interested in sales and ended up becoming VP of Sales at LiquidPlanner, and ultimately leading, you know, decent size sales organizations there.
CW: As you moved up in the organization, your your sphere of influence got bigger and broader. Did you find that having an impact on the on the organization from a strategic perspective was an important component of what makes you tick?
LP: Yeah, again, this is just kind of part of the nature of startups, I think, you know, less, so anything special to me, but you know, as you are building your first product, everyone’s a product person, everyone’s looking at the product, evaluating the product, weighing in, you know, trying it, testing it, see how well it works. And as you know, with my history, as a project manager, I think I had kind of a unique perspective on that and what project manager means.
And so from very early on, I felt like I was able to really be part of those product conversations and influence them, and then even more importantly, to be able to bring the voice of the customer to the product conversations. And that’s, that is really the most critical thing. So that was that was fuel for the fire, for sure.
CW: How did you end up in the big chair? How’d you end up as the CEO?
LP: Yeah, well, we got to the crossroads in the business where we really needed to either raise some capital or figure out kind of a long term bootstrapping strategy. And I was advocating for capital. And as COO at that point, and our then CEO, kind of made the call that he would, his preference would be to stay in the role of head of product, and to have me go raise money, and be CEO and be the face of the company.
And he you know, he really was the vision behind the product. And it was his brainchild. And he wanted to see that through. And he would leave the shaking hands and kissing babies and flying to Silicon Valley to me.
So we ended up making that change. And we went on that way for for several years. And he remained on the board. And I took over the CEO role. And we, you know, we I ended up leaving after five years. But I think he gets a lot of credit for kind of understanding his strengths and interests and where he could provide the most value in the business and it was great to have the opportunity to step into that leadership role and take the reins and, you know, see what we could do. And we ended up raising a $10 million Series B round growing the team quite a bit, you know, growing our revenue and now the company is still out there selling project management software today. So it’s good to see.
CW: There’s a certain level of, I hate this term, but imposter syndrome that that takes place, right? Did you look at yourself in the mirror and say, Oh, my God, I’m a CEO.
LP: You know, I think when I became, it was when I became COO, that I kind of felt like, there was something outside of me, like pushing me forward. And that maybe it was inevitable that I would be in the CEO role, not that I had really aspired to that, prior to that. You know, I had kind of dreamed of like being VP of Marketing at a big company. And then when I became CEO, and I saw that that was a possibility for me in the future. You know, it really kind of did seem like it someday it would happen. I don’t think I quite expected it to happen so quickly.
But it did. And and I think when you have that opportunity, you have to jump on it and do the best you can i describe, I’ve described it in the past a couple times, it’s like taking a pair of jeans out of the wash, and like you put them on, they’re so tight, you can’t breathe, and you’re like, oh my god. And then over time, you loosen into them, and it starts to feel more comfortable, you can breathe again. And you know, you don’t feel like an imposter as much.
CW: Is it the fact that the role is at the top of the organization and therefore has its fingers in all the different pies that makes it interesting? Is it? Is it the… being the final say, that’s interesting? Is it controlling the vision and direction? That’s interesting, is it.
LP: I mean, all of that stuff is interesting. I do love every aspect. Well, not every aspect, I do love almost every aspect of know of running a startup.
And there’s, there’s definitely the multitasking, I think there’s, it’s, it’s fun and challenging, too, look externally, to try to see the landscape and your place in it and who it makes sense to align with and who to kind of, at least internally make your demons so you can you know, it’s always it always helps, not demon, your villain always helps to have a villain.
And, you know, I think that’s really fun, I really came to enjoy the the aspect of leading people and bringing people together, getting up and talking to the team and helping everyone get on the same page about what you’re doing and why we’re doing it. And that was also something that took time.
CW: Yeah, one of the things I’ve always said is that as you move up in an organization, your, your scope changes in a bunch of different dimensions. So your scope goes from being you know, as a as an individual contributor, your scope is very narrow. And as you work up in your scope through the organization gets bigger and bigger and broader and broader. And when you finally break up into the, at least senior exec roles, and certainly the COO role, your scope suddenly becomes the world, right? It’s it’s your organization’s relationship in the world.
In addition, you also change the scope and time, right, as an individual contributor you’re worried about this week, and next week, and as you move up, it’s got, you know, this month, and next month, and longer and longer. And as you move all the way up to the CEO, you know, the scope is sort of the lifespan of the company that the scope of time is this much longer thing.
LP: That was a big lesson for me actually was, you know, you’re you’re running out two miles ahead and trying to look around the corners. And it’s very easy to forget, and a huge mistake to forget that other people are not in that same place with you.
And, you know, you need to bring people with you. And that is work. And there’s a lot of kind of repetition of themes and ideas and reasons. And that’s required because people are, you know, they’re in there working within their scope, and they’re very focused on what they’re delivering. And it’s, you know, it is hard and detailed and, you know, a lot of effort so for them to pick their head up and join you like you are responsible for helping them to see how you get from here to there.
CW: Do you feel like as the CEO… is the last arbiter of of decisions? Is that empowering? Does that make you feel nervous? Do you? Is that a is that important to you?
LP: Um… that’s an interesting question.
I don’t know. I don’t really think about it too often, I want to get to the best decision. And a lot of times I have like really bad ideas, or I’m on the verge of making a very bad decision. And I count on the people around me to pull me back from that.
So I think I’m kind of oftentimes steering the ship, but like everyone has their hands on the wheel. So I’m just looking for the best outcome for the business. And I don’t have a lot of ego wrapped up into being the decider.
Yeah, I mean, I subscribe more to the lead from behind philosophy, where you are best or when the people on the team are getting the credit, the spotlight and the growth, like that is what will ultimately make the company and, you know, and, and by affect you, if you do a good job of developing the team and creating opportunities for people and helping them make good use of those opportunities, then you’ll ultimately win.
Yeah, the other thing is, and actually the the original CEO at LiquidPlanner, used to say this, but the CEO never gets to have a bad day. And I’m not perfect in that, like I can, that I have occasionally gotten into a mood.
But you did try to have that. That perspective where like, your job is to like hold everyone up and and keep everyone positive and moving forward as much as possible. So I take that part of the role seriously.
CW: So where do you turn for, you know, everybody’s gotta vent and let it out? And whatever you do you do that on your cat? Or do you…
LP: I actually do that with other entrepreneurs. So I talked to other CEOs, I’m part of a group of a couple groups of CEOs. And that is a really safe space to let it out. Because there are some unique aspects to this particular role that sometimes it seems like only other CEOs can understand. And so that’s my outlet.
CW: After 11 years at LiquidPlanner, Liz felt it was time to move on. The company had reached a couple of important milestones, and she felt it was best for both the company and her, if she stepped aside, she did a short stint with a startup in Portland called Streem. But working remotely just didn’t work well for someone with such a team focus.
LP: With Streem I love my time is Streem, I had a great time there. I really enjoyed that team, I really enjoyed the product, it’s super cool product.
The thing that was that was rough for me was not physically being with the team in Portland, which I was unable to do, because my kids are here in Seattle. And I felt like I was missing all the good stuff. I’d be like on the Zoom call. They’re all in the room, having beers and, you know, trading information across the desk. And I felt really disconnected from the team. They did a great job trying to include me, but it was just not the startup experience that I really felt like was optimal for me or helped me really be the best for them. So I did have another opportunity come along based in Seattle, and I decided that the best thing to come back to my hometown and and work in person with a team in Seattle.
CW: So tell me about the story of Fresh Chalk. How did that get started?
LP: Fresh Chalk. So Fresh Chalk was started, you know, is the brainchild of a couple of my co founders. So I have three co founders, Adam Doppelt, Nathan Kriege, and Patrick O’Donnell. And in various combinations. They’ve done a number of startups, including Urbanspoon, which was one of the original restaurant apps for iOS, and then a company called Dwellable, which was a travel app that they ultimately sold to HomeAway, which became Expedia.
And they’re all three very talented engineers and very kind people. And they had this idea for a way to help friends share recommendations with each other for the best plumbers and the best accountants and the best pediatricians. And they approached me through a friend and we met for coffee and I wasn’t really quite sure what the meeting was about. I thought maybe it had to do with Streem. I was still at Streem at the time.
And I thought it sounded like a cool idea. But I wasn’t sure what my what my role was. And at the end of the meeting, they were like, oh, we’re recruiting you for CEO. I went through the whole meeting, not realizing that …
So that was our first meeting and we ended up banding together. And I came in as the fourth co founder and CEO, we have basically a prototype of the product at that point. And that was at the beginning of 2019. And it’s been a very fun, exciting and challenging ride since then more fun and exciting than challenging, right up until the pandemic.
But yeah, it was a fairly big leap for me, and that I had just spent so long the last 12 years up to that and B2B software, that taking on consumer marketplace, maybe isn’t the decision that other people would have made.
But I once again, was excited by the challenge. And, you know, my co founders confidence in me and my again, interest in the problem. Yeah, push it over the line.
CW: People keep telling me that in the startup world, everybody’s got an idea. There’s a million ideas, the money, you know, truly, there’s a lot of money in the world to be gotten. What really matters is the team and the ability to execute against the ideas. That you’ve got to have a team that knows how to get something done. By virtue of the fact that you came in, you had to have felt pretty strong about this team’s ability to execute, right?
LP: Oh yeah, when I was doing my back channel, reference, checking on my now co founders, I heard over and over again, that the best technical founding team in Seattle, whatever they’re doing do that.
So I was pretty excited to go tackle a business with three of them and a little intimidating, I guess, coming in as, as the outsider and non engineer and the three of them all having known each other for decades. But they have been very welcoming, and I think they appreciate the aspects of my skill set that are very different from theirs.
CW: Does.. and and so what is your You are the external face? Right? You are, are you helping to find the money?
LP: So I mean, my main charge is on go to market, so bringing the product to market. And, of course, you know, the fundraising falls to me, we raised a seed round, last fall. So just over 2 million from both VCs and angels. And that’s giving us some runway to try to build our community and ultimately expand to other other parts of the country.
CW: In your role, you said right now that there’s the four of you, then must really be your own board. Right? So that’s where you’re getting your sort of external guidance from, are you getting input or support or advice and counsel from any of your investors?
LP: For sure, I treat our investors as almost like a informal board or a loosely formed board and I, I update them frequently. And I make an effort to connect with them over the phone from time to time, and there are a handful of the investors that we have that have been particularly helpful. So they’re the people I go back to time and again,
CW: One of the things we were talking about when with respect to LiquidPlanner was your focus. You know, it’s interesting, I had a conversation with Todd Nielsen, who’s been a multi-time CEO at a bunch of different companies. And we talked about, you know, the difference, the amount of time that a CEO spends sort of inside looking versus outside looking. Has there been a difference in your, your role at LiquidPlanner? With respect to inside versus outside? Is there a difference at Fresh Chalk between the amount of time you’re spending looking inside versus looking outside?
LP: I think it’s somewhat stage dependent. You know, as as we got into the later stages at LiquidPlanner. I definitely spent a lot of time with customers. Obviously, investors, when you’re fundraising, with analysts at conferences, I probably spent…
Gosh, I’d have to thinking if I had to, like put a percentage on it, you know, around half of my time, at least, maybe more 60% externally.
And it’s less right now at Fresh Chalk. Because just where we are, you know, we’re just we’re pretty early and in the beginning, We were kind of bootstrapping our way to having recommendations on the site, I would sit with customers and do usability tests, like all day, every day, and I’m kind of out of that now, we have a team, I’m kind of helping to orchestrate the work of a number of different people on the team, and still doing some external stuff.
But, you know, admittedly less so now that we’re, you know, we used to be life was kind of dominated by events, and, you know, meetups and speaking events, all these different things, and I think that’s less true now. I’m hoping comes back.
CW: Yeah, I was just gonna ask, Do you think that’s, do you think this is a set of changes in what components of this weird world we’re living in? Do you think will stick and what components do you think are, are going to spring back as it were?
LP: Well, I, I would predict that people are going to want to be getting back together again, as soon as possible. As soon as it’s safe, maybe not in the same way in physical offices all the time, or, you know, with a lot of travel, but I think people are craving that human connection that they’ve been missing. And I think there will be a strong rebound to, in person activities, events and working.
I think we intend to, to get an office again, once schools are open and we feel confident that they’ll stay that way. Although we’ve learned know how to have a remote team that is very effective, and you know, united and and, you know, able to get as much or more done than before. So I think there will be more flexibility in work and in education, and hopefully improvements in health care, but I don’t see the end of of in person gatherings and and in person working.
CW: Liz Pearce is clearly an excellent startup CEO. Her perspectives on leadership in the high stakes and high energy world of software startup or something I think we can all learn from. I want to thank her for her time, and her insights.
Leading Smart is from me, Chris Williams. You can find out more about the show and discover other resources for leaders at my website, CLWill.com.
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That’s it for this episode. The next episode begins a series on organizational culture. We’ll begin with an exploration of what makes up the culture of an organization. It’s called “Culture Club”. I hope you’ll listen. Until then please remember that each of the several dozen decisions you make today are part of Leading Smart.