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Episode 48: Interview with Edward Kim, Co-Founder and Head of Engineering at Gusto

As Co-Founder and Head of engineering at Gusto, Edward Kim talks about transitioning from a developer to a leader and the difficulty he had doing so, how founders see your company versus how early employees see your company, and failing as a learning opportunity.

Every few weeks as part of The Heartbeat, I ask one question to a founder, CEO, or business owner I respect about their biggest leadership lesson learned. This week, I interview Edward Kim, Co-Founder and Head of engineering at Gusto.

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CLAIRE: Hi, everyone. I’m Claire Lew and I’m the CEO of Know Your Team, software that helps you become a better leader and avoid becoming a bad boss. I am extremely excited today to have someone who is pretty much an expert on this topic in the latter case of avoiding becoming a bad boss. Someone who’s managed to do this over the years. Really proud to have Edward Kim on the show who is the Co-founder and Head of Engineering for Gusto, an all-in-one platform for HR, payroll, benefits. We actually use it in Know Your Team. I think every single person who I’ve talked to — by the way, Edward, I don’t know if you know, I mean, you probably know this, that uses your product and your company, they rave about just like how easy it is, how seamless it is. So, it’s been fun.

EDWARD: It’s an honor to serve all these companies. It’s great to hear that.

CLAIRE: Yeah. You and I, we originally met here in San Francisco. We spoke on the same panel. And I remember when I was interviewing Edward, just being really impressed with how much growth the company has undergone and for you yourself as a leader, how much growth you’ve undergone. And so, excited to ask you this one question about leadership today.

EDWARD: Cool. Excited to be here. Thanks for inviting me.

CLAIRE: Yeah, you bet. All right, so here’s the question, Edward. It’s what’s one thing, or it could be several things, that you wish you would’ve learned earlier as a leader.

EDWARD: Definitely have learned a great many things in my journey in becoming a leader. I would say one of the earliest lessons that I learned was as a technical co-founder, there is a transition period that you have to go through where you’re primarily developing a software as an individual contributor. And eventually as your team grows, you kind of need to stop doing that actually in order to properly lead your team. And for me, I think a big lesson that I learned was actually making that transition sooner. I think I held on to being a developer and contributing to the code for, I would say maybe about a year and a half longer than I should have.

CLAIRE: Wow, okay.

EDWARD: And I think that was, in hindsight, a pretty turbulent time in Gusto’s engineering team because I was trying to do two very, very important roles at the same time, probably not doing a stellar job in either. And so, it wasn’t really until I almost forced myself to fully commit to being a people leader and giving up coding myself that I was really able to embrace my growth as a leader. And I think that’s when I started just accelerating my own development because I was able to like fully focus my time there, in my opinion. And I talked to a lot of early technical leaders about this. It resonates with them so much.

CLAIRE: I’m like smiling and nodding my head. I’m like, “Yeah, yeah.”

EDWARD: It’s so obvious in hindsight, and oftentimes said but very poorly practiced in real scenarios. And there’s a lot of good reasons for that. But yeah, I think that’s one of the biggest lessons that I learned. I wish I learned it a little bit earlier.

CLAIRE: Yeah, you are hitting on one that I could not have heard enough times, like you were saying, from fellow founders and leaders that transition being so hard. I have so many questions to ask around the situation. But I guess first is just to give our listeners and viewers a little bit of context about like what this moment in time really looks like for you and what was happening. Tell me a little bit about how many employees were you out, what was going on in the company and what did that year and a half where you waited too long, like what did it actually look like? How did you know that things were maybe, I mean, were they burning down or were there no fires actually, and it was like maybe a mentor or like a coworker or something that pulls you aside and was like, “Hey…” Was it your team that’s — tell me a little, let’s zoom in a little bit on like, what was that year and a half of you’re like, “Oh, I wish I would have made that change sooner.”

EDWARD: Yeah, sure. To paint a little bit of context. I think our engineering team, and at that stage of the company, most of the head count is in engineering. So our engineering team was probably around 10 to 12 engineers, or so. And I was spending a lot of my time building features, fixing bugs, fixing bugs are things that I had written in the first two or three years of the company.

CLAIRE: I love it. Yup.

EDWARD: And I was, again, just trying to do two different roles at once. And every day, I would kind of wake up and I would have some coding work to do, building features, fixing bugs. And I also have what we now call like people empowerment. At Gusto, we use the word PE, People Empowerment, instead of people management. And I had the other bucket of work which is around people empowerment. At that stage, you have engineers that are starting to ask questions like, “Hey, what does my salary look like a couple of years from now? Not something I’m thinking about immediately because we know we’re on this journey together. But at the same time, looking to buy a house and, and I want to stay committed to this company long term. What can I expect in terms of my progression in terms of salary? What can I expect in terms of the mentorship that I’m going to get and the coaching I’ll get? Do we have titles or not?” These are all questions that you don’t really have to answer when you’re just a few engineers in a room, just trying to like spill the first feature together. But when you get to around, I think, 12 to 15 or so engineers, and there’s also time element, like when you’re maybe about a year and a half into the company, these are questions that very naturally and in a very healthy way start coming up.

And so that second bucket of work that I had to do when I wake up in the morning was answering some of those questions. It’s coming up with our compensation bands. At the time we started coming up with engineering titles. How do people get mentorship and growth? What are programs around that? Do we get budgets for people to go to conferences? All these things that you don’t really have to think about when you’re small. And so, I would wake up every day and I have these two buckets of work. And me, just loving to develop. I love coding. I love building things. I naturally gravitate towards the first bucket of work, which is building things and fixing bugs and building features. And I say to myself, “Okay, this other stuff is really important. I’ll get to it at the end of the day. But what ends up happening is you just get sucked in. When I’m coding, I just lose all sense of time. And it always feels like I’m so close to getting a breakthrough. And I’m sure a lot of developers experienced the same thing. Like you miss meals because you just get so into it. So much fun. And so, it feels very benign at first but you like reschedule like a one-on-one saying, “Okay look, can we meet maybe tomorrow because I’m like really in the zone here.” And then the end of the day comes and you don’t really get to thinking about salary progression or titles or things like that. And then you’re too tired to do it. And if you do do it, you kind of like rush through it because you’re at the end of the day.

So that was kind of like what it looked like for a while. I would say for about three to six months. I wouldn’t say things were like [inaudible] fire at any point, but I did feel like things started to get a little shaky. When your team comes up to you and they’re asking the same question three or four times, “Do you have any updates for me on this?” Everyone’s really polite and Gusto’s culture is really, really nice, but that’s a good sign that people are a little bit nudging you to get a little bit more progress on these really important things. And I think from my perspective, I didn’t see it as big of a deal as other side.

CLAIRE: That’s what I was going to ask. What was the rationalization during this time? Like you’re noticing and observing. Hindsight’s always 20/20, right? You’re observing that some people are coming to you saying some things. Tell me a little bit more. It sounds like you were about to share that, by the way. I didn’t mean to cut you off in there.

EDWARD: That’s a great question. Nobody’s actually asked me that directly, but I think that’s a really great question. I think there is a difference in how founders see the company and how even early employees see the company. When you’re a founder in the company, you actually don’t care about any of that stuff and you never will. You don’t really care about your salary, you don’t care about your title. That’s kind of what it means to be a founder. And as a founder, I think I project that thinking to the early employees. It’s like, “Oh, they’re asking about it, but it’s not that important because we’re all in this together.” And we are all in this together. The early engineers at Gusto, and even as today, were also bought into the mission of the company. That’s one of the real strengths of Gusto, I think. But I think there is a difference in the mindset of founders and in the mindset of even early employees. And as founders, I think it is easy to not take that as seriously because you yourself, it’s not as important to you. I think it’s a little bit of projection.

CLAIRE: I’m also hearing in that, too, a difference in motivation. And this is something I think a lot about, even internally with Know Your Team, is like what we are all individually motivated by is so strong. And so, it’s so easy to project that. And the thought that it might actually be different for other people, it’s like hard to wrap your head around. And I think about this question a lot with Know Your Team is like how do you figure out, also then like what are other people’s motivations? To what extent does that matter? How do you actually unpack that? It comes down to that as what you’re motivated by in building the thing and seeing it in a certain way, and what success for the company looks like is likely different naturally than the people who are coming after you and are not founders.

EDWARD: Totally.

CLAIRE: Which is fine. But it’s different.

EDWARD: It’s very normal. It’s very healthy.

CLAIRE: Exactly.

EDWARD: But everyone is, we’re all in this together. They care about the mission. And just because you care about these other things doesn’t necessarily mean you care about the mission that we’re on together any less. I guess that’s another big learning of mine because not everyone thinks like you.

CLAIRE: It’s like newsflash, seemingly so obvious. But when you’re in it, it’s hard to get your head out of it for sure.

EDWARD: Yeah. And I remember this one specific moment where it did take my co-founder, Josh, the CEO, a really tough conversation with me to tell me that, “Hey, you need to focus on this second bucket of work more. And in fact, you need to stop coding immediately.”



CLAIRE: How did you take that at the time?

EDWARD: Not good.

CLAIRE: I appreciate the honesty, man.

EDWARD: On the outside, I was obviously fine and taking the feedback well. But inside, like feedback, especially if it’s critical feedback, it’s hard to listen to. It’s good to listen to, but it’s always hard. In my head, it’s like, “You don’t understand. There’s all these bugs. All these customers are having issues. You don’t see all the stuff that’s going on in the code base and can’t just like tell me to stop coding. I need to be in there and fixing things. Otherwise, this company is going to fall apart.” That’s like kind of what’s going on in my head. And then kind of some weird things happen, like you start to hide a little bit when you’re coding because you know you shouldn’t be doing it but you still need to do it.

CLAIRE: Covert coding.

EDWARD: Yeah. I don’t know if that’s just me, but a little bit of that happened. Sometimes, you need to take a step back from it, let it sink in for a few days. You start thinking about it and you’re like, “You know what? There is some truth to this.” And feedback even if not delivered well, always has a good — my philosophy is that there’s always something beneficial that you can extract, that you can learn from that. And a great part of growth mindset is like, even if you don’t agree with every single thing, there’s something in there that’s of value to do to you. And your job is just focus on that part and nothing else. That’s the only way you’re going to really accelerate your growth personally.

CLAIRE: I love that. It’s just information. You can filter it in any way, but it’s information. It’s a data point.

EDWARD: And you can reject feedback too. You don’t have to agree with all of it, but I always try to look for some truth in it. It’s coming from somewhere. So yeah, I think after a couple of days I was like, “You know what? There is actually a lot of truth to this.” When I think maybe a year or two ahead, that is probably where this goes anyway. And so, I’m going to do an experiment for myself. I’m actually going to just stop cold turkey.

CLAIRE: Interesting.

EDWARD: And immerse myself in people empowerment and people development and leading technical teams. And so at that point, what I decided to do was a bit extreme. I actually just bought a plane ticket to New York for a week. And this is during the weekday. This is like just for Monday through Sunday.

CLAIRE: And you’re based in San Francisco at the time?

EDWARD: Yeah, I’m based in San Francisco. So, I flew to New York. I always liked New York, so I was like, “Okay, I’m going to just hang out there. I don’t have any plans, I’m going by myself. And I’m going to just pull myself up in a hotel room and read all of these books that I took with me.

CLAIRE: You’re kidding?

EDWARD: I literally took a suitcase full of management books.

CLAIRE: Okay. We’ve got to pause here. What was in the suitcase? Like what books? And how did you figure out which books to get? Were you literally just like, “Amazon business category top seller, top 20.” Or were there recommendations?

EDWARD: I did have some mentors that I’ve been talking to, people like Steve Herrod who’s the CTO of VMware and a DTO, who was the Head of Engineering at the time for Dropbox. And I would ask them questions like, “If I were to take some books, what do you recommend I read?” And so, I kind of like cobbled together through people I know or threads that I’ve read what books to get. I took it to New York. And basically, my intent was to actually go and read them all, and learn as much as I could. I utterly failed doing that.

CLAIRE: I was going to ask, “What happened?”

EDWARD: It actually ended up being a time where I actually just coded nonstop.

CLAIRE: You’re kidding me. Oh, my God.

EDWARD: There was this one feature that I was working on and I got sucked in again. I basically hold up and built relatively like big feature [ask] and just came back having not really read much and spending most of the time doing exactly what I was trying to avoid. And so, I came back somewhat proud that I had finished this feature, but also somewhat embarrassed that I had actually utterly failed into somewhat expensive investment that I had made in myself. So actually, I had another false start there.

CLAIRE: And just to pause on that moment just for a second, was it sort of a moment of like — at the time, it sounds like you did have almost like a self acknowledging guilt almost of, “Man, this is like…” It’s almost like — I’m trying to think of what a good analogy is.

EDWARD: It’s like when you’re trying to go on a diet and then you just go binge eat all the stuff.

CLAIRE: And you go to Whole Foods and you get the grocery cart with all the expensive organic fruits and vegetables and then you go home and you eat the Ben and Jerry’s like Cherry Garcia in the freezer or something like that.

EDWARD: Sour Patch Kids, my snack of choice.

CLAIRE: Okay, sure. There we go. Like mine is definitely ice cream. But the visual of that too, and like the narrative is…I’m smiling because it’s just so relatable. We’re so fallible as humans, every time we do try to make a big behavior change.


CLAIRE: So relatable.

EDWARD: Yeah. So, I came back a complete failure. But one quote I really like is you either win or you either learn. So if you lose, if you fail, it’s a learning opportunity. And that was just kind of a really painful lesson I think, and just kind of like true natural inclination and that’s how hard it’s going to be for me. And so after that, there wasn’t any glorious attempt again. I just kind of took that learning and I was like, “Okay, I actually really need to focus on my own personal development as a leader for this engineering team.” And yeah, slowly but surely. I wish there was a more exciting climax to the story, but just reading books and getting really into it and meeting as many people as I could, getting connected to people who would become my mentors later. We had raised some money, so also was fortunate enough to get connected with some executive coaches as well.

CLAIRE: Awesome.

EDWARD: And I think just through all of that really kind of embraced this new type of challenge that I was facing and how to become a better leader. And then, just knowing my inclination with coding where I tend to get like sucked in, I just had to quit cold turkey essentially.

CLAIRE: You described it almost like a drug, by the way.

EDWARD: Yeah, I think so.

CLAIRE: It’s so funny in a good way. We all have that, like the thing we’re addicted to, right?

EDWARD: Exactly.

CLAIRE: The thing that is probably the reason we got into the industry or it’s part of the work that we do. It gives us kind of that.

EDWARD: Oh, yeah. That’s why I studied engineering. It’s play for me. It’s fun. And time flies just like you’re hanging out with friends having a good time. It’s the same thing for me, too. It’s just time flies. It’s just what I naturally love doing. Yeah. So, really immersed myself. And then, as you kind of learn more and you start to get better at it, you start to like it more too as well. And you get more involved in it.

CLAIRE: I’m curious about that. It’s actually one of the things I wanted to ask you about because in some ways, you’re sort of taking one for the team and that like you’re giving up something that you actually intrinsically love to do and that you’re good at. And I mean, you think about sort of where you get that sense of flow. You don’t really get the sense of flow from management, I’m sorry. One-on-ones with people is like, thinking about compensation structures, et cetera. So I’m wondering, how did you essentially, and I don’t want to overstate it, learn to love leading people?

EDWARD: I think the big breakthrough for me is that I think it is a flow but it’s a different type of flow that happens over a bunch of longer period of time. And you can’t look at it in shorter time frames. Because if you look at it in shorter time frames, like I’m in meetings all day and a lot of them are like hearing about issues and problems and not all of them are fun. I don’t think that’s true. I don’t think everyone as a manager wants every single meeting that they’re in…


EDWARD: But those meetings turn into working with your teams to find solutions. And those solutions are oftentimes not like engineering solutions where you fix the bug, where you get the test to pass, and then all of a sudden it’s not an issue. They’re much more complex issues and they take a variety of different angles to solve. But over a period of months, you look back on that problem that you were dealing with and you see the change that you’ve helped steer over a period of months. And when you look back, that sense of satisfaction for me is incredible. I derive a lot of happiness from the change that I’m able to do over the longer period of time. And I’ve seen it happen enough now that whenever I am in a tricky situation or a difficult situation, I look forward now to see, “Okay, six months from now when we’ve kind of put together a plan and slowly but surely start to solve the problem, I’m going to look back on this moment and see how much better we are six months from now than we are today.” Because this happened so many times looking back. Now, I think I’m able to look forward and get a lot of enjoyment from what I’m doing day to day. So that’s kind of almost a mindset shift on you have to look at it over a much longer period of time. And I would say I get the same amount of satisfaction in doing this. And the same amount of addiction, I think, as I was on coding.

CLAIRE: I think those are such encouraging words for so many of the founders and leaders who started their career in an individual contributor role, got addicted to the thrill of that and now have to find a way to love something. Maybe they might not have inherently learn to love leadership, in this case. I so appreciate, Edward, the advice about changing the time scale of impact and of progress. It’s not a, “Oh, we ship the feature in a month,” and then you see revenue numbers go up, or engagement numbers go up. It’s a six-month timescale. And it’s a different kind of problem maybe that isn’t as objective of what is good or bad. Or it’s a year long timescale. So, I think that’s such a helpful advice of we should adjust our relative frame of expectation around when we expect to see something different, see something change. And then I think the other thing that you touched on, and I may be projecting here and so would be curious to sort of hear your thoughts back is the impact is also different, right? So, it’s like with the kinds of problems that you’re solving, are problems that enable other people to then do their work versus the work itself when there’s a problem in the work itself and in the code itself or in the design itself. And it’s a different kind of impact.

EDWARD: Absolutely. And I’ve seen people during their time at Gusto grow so much and some of them leave to go start their own companies and go do amazing things. Of course, everyone is kind of responsible and accountable to their own success and failures, but part of me also knows that I played a small part in helping this person get there. And it’s a totally different type of satisfaction you get, but I loved it. I love seeing that kind of stuff and an organizational growth as well.

CLAIRE: Oh, absolutely. And what I infer to from that is something we think a lot about at Know Your Team is the fact that organizational growth and success is tied directly to individual growth and success. You actually can’t have a team be successful if each individual doesn’t feel like they’re making progress against their own dreams and goals and aspirations. And so, if we think a lot about, well yeah, we need to talk about company mission. We need to talk about our team goals and values. We actually just finished off. We did a retreat last week. And one of the things I asked each team member to do was to write out essentially like a personal vision statement. I’m like, “Don’t take longer than an hour to write it. It could be a drawing. It can be a paragraph. It could be a manifesto. Whatever you want it to be, I don’t really care.” But the idea is like, 10 years from now, what do you want to be true for yourself? Because that individual person’s dreams, aspirations, idea of what a success, we have to find a way as leaders to connect that to the bigger picture or else, it just wouldn’t matter to them.

EDWARD: Totally, absolutely. I think the best alignment that you can get is if people are doing the things that are aligned with their personal goals, that’s also like really aligned with the company goals. And there are also stuff that they’re really good at. And if you can, as a leader, map the work that needs to get done to the people that you have and find that alignment, everything just like falls into place so nicely. And people will do the best work in their lives and make a huge impact in the company and they get a lot of personal growth from it. It’s really awesome to see that. So, I try to spend my time thinking about how do I grow? The alignment isn’t always there because we don’t live in a perfect world, but it’s a puzzle, right? You need to kind of figure out how to optimize for that for everybody and for the company.

CLAIRE: Absolutely. It’s actually something that I wanted to ask you. How do you create that alignment? How do you think about that? You were saying it’s kind of like a puzzle. Do you block off specific time? Is it conversations in one-on-ones? Do you spend time during retreats? One, how do you do it? And then second question being, what happens when it doesn’t line up?

EDWARD: I think it starts with hiring. You can find that alignment with the company by just being selective on who you invite into the company. And so we have interviews that test for values alignment with Gusto values. And that just kind of like makes a higher probability that the people that you are working with, there’s already that alignment. And then also skills. We’re always looking for people who have the skills that the company needs to continue to be successful. So, that’s another part of the interview process. And so, just by the interview process, you are already trying to create that alignment, the values alignment between the individual and the company, but also skills alignment of what this individual has and what the company needs. And so, you’re already in a good starting point if you spend a lot of time upfront investing there in the interview process. And then once they’re in the company, I think what I do tactically is I actually, for all of my reports, have one-on-ones that are tactical one-on-ones, which I have either every week or once every two weeks depending on the individual. And those are just more like problem solving, what’s going on, how can I help you type conversations. And then once a quarter — and everyone has a different cadence. Some do it once every two months or so. But I do it once every three months. I do like a pretty deep career personal discussion where we don’t talk about any of the tactical stuff. And I have a list of questions that I’ll ask them and have them think about before the meeting, and just have a conversation around what they’re looking for in that longer term time frame for themselves personally. What’s your personal vision statement? What are the opportunities in the company that you think could align with where you want to go personally? And the goal is not to have, like I said, like action items. You’re going to go to this team tomorrow from the conversation, but to really understand what is it that motivates that person and what they’re looking for in the long term. And again, going back to what we talked about earlier, is that it’s just very different for every person. And so, I think it’s important to have that conversation. So I think just dedicating time, a separate time.

CLAIRE: Exactly. The dedicated, the isolated time. For our own team, even thinking about how. We recently hired an operations manager who expressed she has a background in writing, degree in creative writing and expressed a desire to sort of flex those skills more. And we started having her write some things for our online leadership community, The Watercooler. Her name’s Mandy and she’s been like killing it. They’re like extremely well written and the engagement’s really great. It was just this beautiful surprise of, “Wow!” Had I not asked that question during a one on one meeting about what areas do you want to grow in? What skills do you want to further develop? She wouldn’t be contributing that and that’s like furthering the company. It not just this like, “Oh, personal thing,” where you want to improve your personal — I know that’s important. But it’s actually really helping the company. And it boggles my mind that that just one small question sort of totally furled to this bigger project. Like you said, when you get that alignment, it’s crazy. Just like what happens in that case.

EDWARD: Absolutely.

CLAIRE: So then the second part of that question was unfortunately the flip. What happens…

EDWARD: When the alignment is not there…

CLAIRE: Yeah. And you’re like, you tried to hire for it and like maybe — or here’s the other thing, it changes sometimes for people. Your motivations change.

EDWARD: Yeah. People change. Personal situations.

CLAIRE: Exactly.

EDWARD: A really tactical one is people need to move sometimes for personal reasons. And the team that they’re on is not in that location. And so all of a sudden, a very tactical reason has caused things to get misaligned. Honestly, I think it is being okay with non perfect alignment, than a good alignment. So, I think it’s very idealistic to think that during someone’s time in a company, at every single point in time, that alignment is going to exist 100%. It just not. And so I think it’s again, just optimizing for that alignment as much as you can and being okay on both sides if it’s not 100% there. Sometimes you’ll have someone work on something that’s better aligned with what they want to do, but maybe about 70% there for what the company needs. May not have been the first, the number one thing on your list, but maybe it’s like two or three and actually, I can live with that. That’s okay. And then also the opposite as well too. Sometimes, we really need someone to be working on the number one thing for the company and that the individual, maybe it’s not the perfect thing that they want to be working on personally and being okay with that too. I think on both sides, we’re on this mission together. And so, there’s like kind of a mutual understanding that there will be times where there’ll be more aligned. Sometimes they won’t be aligned and sometimes it won’t be aligned at all. And we just ask people sometimes saying, “This is kind of the most important thing for the company. When push comes to shove, we have to prioritize the company over ourselves. It won’t be like this forever because I don’t think this is sustainable, but we just need people to help out with this thing.” And I think that’s okay. I think people are very open minded about it. It goes back to the values alignment. That is one of the things we hire for is that humility and also ownership mentality that we’re all going to contribute in ways that may not be the best way that I feel like I want to contribute, but we’re all going to contribute and help out. I mean, just setting expectations with people that it will be aligned 100% of the time. And sometimes, it’s okay for a period of time where it’s not aligned.

CLAIRE: Absolutely. I think it’s a refreshing perspective. I mean, you’re kind of the living example of that Edward. You literally are doing your role today because you’re like, “Well, it’s what the company needs. And maybe in an ideal world, I would be in a hotel room coding by myself.” And learning to love it over time.

EDWARD: Exactly. And that’s something that I think I’ve found happens a lot. I think people are just really flexible in what they like to do or things that they didn’t think they like to do, they find that they love doing it. I found that having to me pressing so many times. I didn’t even want to be an engineer when I went to college. I had no idea what computer science is. They didn’t have any of that stuff at my school.

CLAIRE: Our CTO is actually very similar. He actually hated coding.

EDWARD: Oh, really?


EDWARD: Actually, the first time I coded, I loved it. I just didn’t know…

CLAIRE: Okay, you like that?

EDWARD: Yeah. I actually wanted to be a film director, believe it or not.

CLAIRE: How funny.

EDWARD: My intention was when I was applying for schools and everything and it just so happened that my roommate was taking a computer science class CS 106A and it was almost out of peer pressure. He just wanted me to go to class with him and do homework together. I was like, “Okay, I’ll try that.” And I took it in and I was like, “This is awesome. I love this stuff so much.” And so, I’ve seen countless times how things that you may not think are aligned actually turn out to be aligned. People get challenged in ways that they didn’t want to be challenged and they’re like, “Actually, I’m really liking this stuff. I want to keep doing it.” And so, kind of alignment sometimes presents itself as well.

CLAIRE: I agree. I can think about my own personal journey and the things of like the initial inclination, like where that comes from is often very random and externally influenced. And then what you end up liking ends up surprising yourself along the way. We have such capacity for growth and flexibility just as humans. And then I think the other thing that I, I’m reading between the lines here is the connection so much to the mission and the meaning of what you’re doing. Like this bigger picture, and that that’s what everyone is centered around and that gives people a reason to try to learn and challenge themselves. I think without that, not alignment doesn’t work.

EDWARD: Totally. You always need that common thread of why people are here.

CLAIRE: Even variants in alignment doesn’t work. If you have a team that’s working together and people don’t really care about the ultimate vision, and then you ask people, “Hey, can you work on this thing,” even though it’s not really personally what you want, that’s not going to fly.

EDWARD: Yeah. You just got a bunch of mercenaries in the company, instead of missionaries, which is what you want.

CLAIRE: Right. And then I think Gusto is such a living proof of, like you said, you optimize highly for values, you hire around it. It sounds like you’re extremely intentional around that. And so, it’s because of that, that you’re able to even have the conversation of like, “Hey, we really need you right now and it’s temporary. You might not like it in the beginning, that’s okay, but can you hang in there for us?”

EDWARD: People rise to the occasion all the time. I think it’s really cool because there’s kind of a recursive nature to this because Gusto is a people company, right? We are building the people platform for small businesses. We have over a hundred thousand companies that are using us for, not just payroll, but all the kind of benefits and employee life cycle aspects of things. And so, that’s something that we see and we want to also impart in the companies that we serve, as well. These are not just thoughts or conversations that people in tech have. I think there are actually things that small business owners, whether it’s a coffee shop or a church or professional services office, they all care about this stuff too. And they also have these insights about their people, as well.

CLAIRE: Oh, completely. And here’s the thing, you and I, we both work in tech. It’s not just tech companies that have a meaningful mission and a meaningful vision. It’s like every single company has a picture of a better place, a future for their customers that they want to create. It can be a construction company. It can be a law firm, whatever it is. And it’s interesting because I talked to so many founders and leaders who will tell me like, “Yeah, Claire, we’re an ad agency. So, vision isn’t really a thing. We don’t think of it. Yeah, we’ve like tried to spend some time thinking about vision.” And I get really bullish on it and I push back and I say, “Hey, here’s the thing. This is the one thing you have to commit to and talk to your team about co-creating it because if you don’t have that, then the moments when push comes to shove, when things are 70% aligned one way or another, that’s not going to work. People are going to leave, or the work’s not going to be very good.” And so, this is just such a wonderful reminder to me of very practically how much vision comes into play and values and purpose in an organization.

EDWARD: Yeah. And I think for smaller companies, a lot of times I’ve found when I talk to them and talk to our customers, it’s around the community that they’re in and how they’re contributing to the people around them, the neighborhood. And I think that’s also just as beautiful of a thing too for their mission as well.

CLAIRE: My God, it’s critical. It’s so critical. I’m loving just the encouragement and nudge here for all of us as leaders to be thinking more intentionally about it and how important that is for alignment overall.


CLAIRE: Hey Edward, thank you, my goodness, for all your insights, for sharing your story too so candidly and in such detail.

EDWARD: Thank you for having me on here. It was great to share.

CLAIRE: You bet.

EDWARD: Yeah, I really, really enjoyed the conversation.

CLAIRE: Thank you so much again. And hey, for everyone who’s listening, be sure to definitely reach out to Edward and check out Gusto. And if you’ve been enjoying this interview, to leave us a review on our Heartbeat podcast on Apple, as well. So, thank you so much everyone. And thank you to you, Edward.

EDWARD: Awesome.

Written by Claire Lew

CEO of Canopy. My mission in life is to help people become happier at work. Say hi to me on Twitter at @clairejlew.