How to scale your career alongside your startup: Lessons after 10 years at Greenhouse

 Mike, thank you so much for joining us today.

 Um, so one place I thought we could start, uh, you're one of the few non founder CTOs that has made it a decade at one, you know, startup through the transition to, to sort of a very large business. Um, and, and I'm curious, why do you think that's been the case for you?

 It's a good question. Um, I don't, I don't know that I have the complete answer, but I do get asked this question sometimes and, and I think I have some perspective. Um, so, you know, number one, I think, uh, actually aligning with like the right founders in the first place probably plays an outsized role. Like, are you going to be the right type of person that they wanna partner with long term?

Um, so I think that's a thing. Maybe is, you know, a combination of luck and, and good intuitions at the beginning. Um, a lot of the other stuff, I, I think there's maybe two different lenses I'll apply. Um, one of which is, uh, the lens of, you know, what kept me there so long because I think, you know, when, when you, uh, end up building a successful business, you have more and more options over time.

So, you know, what, what caused you to stick around and continue investing there versus putting your energy towards something else? And the other one was maybe like the survival lens, which is, you know, every single role in Greenhouse, um, has had at least a couple of other folks go through the executive team over time.

And so, um, you know, frankly, you know, I, I fully expected at the beginning, um, that, you know, I would be replaced by, by the right person at the right time. And I kind of had that in my mind the entire time. It was like, you know, the best thing for the business is to hire the right person for the job. And the only thing that's really within my control is whether or not I.

Am the right person for the job at the right time. And so maybe I'll actually start there, which is, um, I think at the very beginning I felt like, all right, there's, you know, this business that I can go join with these two founders who have actually done stuff before and I can learn from them. And that's kind of my worst case.

My worst case is I show up, I've taken a salary, cut and done all of that, you know, stuff that you have to do in the early days of startups. Um, you're working for a company, no one's ever heard of. Uh, and then, uh, I thought, I'm in it for the learning experience and in a year or two I'm gonna go off and I'm gonna found my own business.

Well, it turns out like 10 months later, after writing the first line of code, we made our first sale and actually had our first customer. if you flash forward about six months from that moment, we had built a business that looked like it was gonna take off.

 I think we had, um, Airbnb, Pinterest, Uber, and Snapchat. We're four of our first 20 customers. And so sort of some of the fastest growing biggest, uh, you know, uh, potential most interesting startups had placed a bet on us. And so I started changing my own perception of what the reality could be with this business and what role I wanted to play.

 And so I started getting into my head, um, you know, the things that I didn't love about other workplaces, I could actually change here, we're building it from scratch. I could make this the workplace that I actually want to be at every day. And so when I saw that opportunity, I felt like, well, I can create my own environment.

 You don't get to do that when you go join a thousand person company or you join an already established culture. that was, um, you know, kind of a motivating factor and that kept me grounded in like, okay, I need to Build out, you know, uh, fairness and respect and, you know, growth and, you know, the ability to make changes and all of those things, um, into the culture 

 And then I needed to always look maybe a year and a half out and say, okay, well what is it in 18 months? Cuz I always say that, you know, maybe an executive is, is bound to survive 18 to 24 months in a startup. What is it in 18 or 24 months that will be expected from my role? And what can I do to make sure that I'm actually ready for those things?

And I think one of the big readiness things that people often forget is you have to stop doing the previous job. , this is like a key survival thing, if you're kind of the first level engineering manager, and then what's really required is that you build a recruiting brand and level up the technical stack and make sure that the site gets stable.

Those are maybe some early responsibilities of, the sort of head of engineering role. Um, you have to stop doing a lot of those things and hand it off to someone else and then focus on the next job. So maybe the next job is something more like, you know, the VP job where, um, you have to operationalize processes across a growing group.

You have to, um, you know, make it function autonomously. Um, you have to keep employee engagement high and do all these things at scale. You have to communicate at scale, and so you have to shift a lot of how you. You have to hire the right people and make sure that they're doing the right things and you have the right sort of processes and meta processes for iterating on your processes, um, you know, baked into the team's culture.

And when you have all those things, you can step into this next role, which is kind of an open space. And so, um, I always felt like I did that over and over again every year and a half or two years and occupied the different job. And so now we're 10 years in, And a lot of my job now is like corporate strategy and product strategy and m and a stuff, and, you know, being an internal figurehead and, you know, an external, um, you know, voice to, to customers and to the market.

Um, and so that job is obviously totally different from right the first lines of code. Set basic sort of infrastructural requirements about how to, how to keep things up and how to build out processes for a team. And so I always saw like, what is that next job and what do I need to learn? And around that point, when I saw what was coming, that's when I would really start focusing my learning.

And so I'm doing whatever the job is that needs to be done today, but I'm making a plan for who I need to hire. Um, I'm reading books, so like when I knew the strategy thing was coming, like, oh, I gotta know what I'm talking about here and actually have some good opinions on it. I read like three or four strategy books, , for example.

 that helped give me a grounding and like, what is the language that needs to be used? When I realized I was gonna be part of an exec team for the first time, I read two books on every other person's area of the business. So I read like two marketing books and two sales books and, uh, took like a finance course.

 I just tried to make sure I understood how the whole thing kind of worked together. Um, and I think that was transformative. And then I relied a ton on, you know, Intros from maybe people like you, uh, , you know, to, you know, venture capitalists or other board members or people I knew in the community who had already been there and done that.

And, you know, you don't have to experience every pain from scratch. You can learn from other people. And so I found, um, you know, a lot of the things that, um, I needed to tackle other people had done before and even failed that and had some good insights and wisdom that I could take with me. that's a good framing. Lots to dig in on there. I guess one piece that you left out is, is I, I like the idea that for someone to be successful in a role, they need two things. They need to be competent at the thing, and they need motivation to do the thing. 

 what did you figure out about motivation? Um, and did you want to be doing that thing 18 months later versus what you were doing 18 months previous?

 I think my motivation changed over time, to be perfectly honest. at the very beginning, um, I think my motivation was I need to learn how to build a company. , if I go, you know, way back to when I was like 18 or 19 years old I had been programming like in my room and trying to dream up products and, and make things for a while.

 And I went out after high school and actually started two companies, both of which, um, didn't particularly go well. 

And at that point I had actually hit kind of like a low in my life where I, you know, maxed out all of my credit cards. And thankfully they only give you like $7,000 worth of credit limits when you're like 18 or 19 and have no real, um, income of any sort. And so I'd, you know, run out of money.

It was 2001. I was, you know, nine 11 happened. I was, you know, unable to raise more money and I kind of fell into like a little bit of a funk around it. And I think the funk was, Interesting when I pick it apart. And this does relate, you know, back to your question, which is that part of it was this feeling like, maybe you can't do this.

You know, like maybe you are not someone who can make, you know, your dream happen. You're not someone who can make all these things, um, real. And so, you know, I, I kind of like decrease the scope of my ambitions for a little while. And I like, you know, uh, did my undergrad and I ran my consulting business and you know, just kind of focused on plotting through there, assuming like, I'm going to, you know, need this degree,

Um, that was not quite the, the, you know, fantasy that I had as a kid and I started writing off, um, you know, the idea of building something as a little bit of a fantasy. Um, and I think I had this realization while I was, um, you know, traveling a bit in, uh, in my mid twenties where it was like, you know what, maybe that fear I have about not knowing what to do is rational.

And, and that was, that was kind of a moment. It was like, okay, well, if it's rational that I, I, you know, I know I don't know how to build, uh, like a billion dollar business from scratch. What can I do in order to close that gap and, you know, actually learn what it takes in order to succeed? And I started thinking about like an orchestral, you know, performance, right?

It's like if you've never seen an orchestra play something before, it's like you've, well, maybe you don't know about the crescendo. Maybe you don't know about how songs end, or how songs begin, or what needs to change over time, and all of those things I felt like were analogous to company building that I didn't really know, um, enough to be able to improvise successfully all the way through from beginning to end.

Um, and that motivated me to want to join, um, greenhouse and, and, uh, you know, join two founders that already knew what they're doing. So, at the very beginning, you know, to get back to your earlier question, it was really about learning. Like, I, I felt like I want to learn from people who really know what they're doing.

What it takes to build a company. And I still feel 10 years in that I'm learning about how to build a company. Um, and they're improvising at this point as well. You know, this, uh, we're almost a thousand person company. It's the biggest company that, um, any of us have ever been a part of building.

Um, but, you know, I think I learned a ton about what the early movements look like. I learned about, um, you know, the struggles and, and how to reason about the next stage and how to make it successful, um, along the way. And, and I think that's actually been, you know, one of the core motivators. Now. There was also this big identity shift I had to go through, maybe even several times in a couple of different phases through my time at Greenhouse, where towards the beginning it was like, okay, I'm gonna come in, I'm gonna learn, and then I'm gonna leave as soon as possible so I can go start my own.

and that lens, I started challenging a little bit, so I was about four years in greenhouse, had raised its series C I think it was maybe valued at 250 million or something at that point. And so I put a ton into it and I started talking with the founders and I was like, you know, I want to stay like, this is exciting. I have this other dream, I've kind of been focused on.

And so, you know, I basically, you know, gave them the, the challenge on some level of like, what do we need to do in order for this to be my best? And that, I think involved a bunch of different things. It involved, um, you know, the level of autonomy I had, I was sort of treated like a peer I think in many ways.

Um, you know, throughout that time. Um, and engaged in all aspects of, of running the business. So I got to sort of have something that was more like a co-founder experience, even though I was not a co-founder, um, than, uh, a functional area leader experience as the company was growing. of course there's like, how do I participate in the upside of this thing that's going really well? Um, so, you know, that's just of course an implementation detail, sort of like necessary, but, uh, but not sufficient on its own. Um, and then, uh, and, and I think I went through a, you know, a few different waves with it about, you know, when, when you hit your lows, like when Covid happened and we had to do a layoff of, you know, a bunch of people and you see, you know, a quarter of your friends, uh, and, and colleagues, um, yeah, sort of, uh, disappear in an instant.

Those types of lows. I think a lot of people are like, am I doing the right thing with. Right now is, is this, is this, uh, you know, is this going to, to scratch all my itches? Um, and, and so I think I had a few different moments where I sort of reassessed, um, you know, does the identity I want to have in the future line up with the future I'm expecting to have here?

Um, and as I inspected those questions, the answer just kind of kept being yes. And so here I am, you know, 10 years later, um, having, uh, both survived and, and not been, um, you know, topped by someone more qualified yet. Although I fully expect that to be the case at some point whenever I'm no longer the right person for the job.

Um, and, uh, you know, I'm still feeling sort of intrinsically motivated to, um, to build this thing. And, you know, maybe the last note on that is I know that I am not a co-founder of the company. I wasn't in the, you know, room sitting there. Uh, you know, when, when the idea for, um, structured hiring and how to layer it into the recruiting market was formed at the same time, um, I think the shift in identity from this is somebody else's company to, this is my company.

Actually really helped because it, it, it changed the relationship I had to the work, um, in a way that allowed me to feel like, you know, I am building my own business.

 I think it happened in a few different phases. Like I definitely felt that way with the engineering culture at the beginning.

Like, this is my team, I can build it how I want. When I, I think maybe this is an interesting, um, you know, topic and I don't know how shared this is, but I think it's, it's often true that in these early stage startups, cuz you have less product than market demand for it, you end up with the engineering organization being one of the first larger organizations.

And of course eventually you get really big and like engineering shouldn't be the biggest organization anymore and in most companies. Um, but I got to be sort of the first one with no HR person to go create like the people pay practices and you know, what cadence we, you know, um, set up for growth conversations and all these different things.

And I think a lot of that imprinting of like what we did in engineering got. Brought into the rest of the company, um, made me feel like, oh, this is, this is a company I shaped. I helped make, you know, all the culture and processes and all of this stuff. Like, it's lots of people all working together, but I could see my imprint on it.

And I think that was significant. And then again, I think, you know, that moment sort of after the Covid layoffs when I was thinking about, you know, um, is, is the trajectory still gonna be good? Like, what's happening in the world? Like, I think all of us kind of had some level of existential crisis around that time period.

 Um, but you know, as, as I thought about it more and more, it was like, you know, you don't have, I don't know, you don't, you don't abandon your kid kind of thing is almost what it felt like.

 It was like, no, this is, this is, uh, this is my company. I helped feel that I need to, um, you know, steward it through, uh, through the rough times and, you know, to the degree that I'm still the right person for the job. Um, it's, you know, both my responsibility and my desire to, to be there and show up.

 You touched on on sort of the conditions that the founding team created to enable this 10 year career that you've had at Greenhouse, but I'd be interested if other founders wanna create the conditions such that there are more career trajectories that look like. what would the advice that you have for them, maybe outside of the generic that everyone talks about, which is, you know, give people opportunities, support them. What are the, the sort of levers that come to mind if other founders wanna create an environment such that there are more people that, that look like you?

 maybe I'll break it down into Innate Plus environment, cuz I think the intersection of those is probably where the answer lies. maybe these are personality traits that I believe are central to my identity and were only reinforced by my, my experience at Greenhouse, probably number one was adaptable.

 I don't just say like growth mindset, I mean like adaptable, like I could actually fundamentally change even how I'm processing and thinking about the world a bit depending on the conditions. And so, you know, startups being incredibly dynamic environments, I think usually the failure mode is that people don't end up changing fast enough at the right moments.

So I think I was always proactive in adjusting myself and that. Difficult thing to interview for, but that might actually be a good thing if you were hiring early employees.

 Usually I think it's just like, will someone please join my brandless moneyless venture? That is my idea. Um, as the first employee and, and help me make it real, um, I think in that desperate situation, there's often not a ton of, um, you know, scrutiny on adaptability, nor is there an expectation that whoever they end up hiring is actually going to be the person who would continue scaling.

Um, and so there's maybe low emphasis there. So that might be an area for high emphasis if you actually wanna hire someone. It's kind of more, more like hiring your co-founder maybe, right? Is this, is this somebody who, um, you know, has sort of unlimited potential to scale? Is it someone who can participate in the creative and strategic process and are they going to be able to change over time in the ways that the, the company is going to demand?

 And then in terms of environmental conditions, um, I think I. Well, let's, let's get into, I, I'll probably get, uh, get killed for this, but one of the co-founders of Greenhouse, is my direct manager, John STRs, um, is really a product guy and, you know, he's helped build some, um, pretty great products.

 Obviously Greenhouse included over time. He was also, uh, you know, I think first product manager@babycenter.com and, you know, if anyone who's had kids, um, you know, you, you, uh, you've, you've probably used that at some point. He's done call center performance management stuff, all of these things. And the way that he manages, because he kind of hates management as a, as a, like an activity.

Like let's sit down and do a performance review and all of those types of things. Not that anyone, you know, particularly loves having, having those types of conversations, he tended to almost automatically like manage by. . And by that I mean he would just sort of express something he was worried about. He would be like, I'm really worried about, you know, whether XYZ thing is going to succeed or happen, or whatever it was.

Um, and I think that allowed me to be really autonomous in solving big important problems that the founders saw without ever being assigned a task. And I think he would almost like broadcast some of these anxieties. He would, you know, go chat with all of his, his direct reports, other people in the company and just kind of say, I'm anxious about xyz.

Um, and so, you know, if it was appropriate for me to pick up, if I was the right person to go drive some sort of change, um, I would just say, okay, let me, let me go look into that and, and, you know, go try to work on it. Um, and I think that that allowed me to both work on the right stuff and feel deep down that I.

Um, you know, discovering and finding, um, and solving for all the right things in the business as it went. So the autonomy was a big part of the environment. Another one that maybe they, they didn't do specifically with me, but I think probably would be helpful, and it's something that I definitely do with, with my direct reports, is try to help them envision the future.

 the thing I do with my direct reports is I'll, you know, draw out like, True of, of our future plans. what does the business look like in five years? If we sustain growth, how many people are in the company? How big is our team? Like, what shape might it take? What are the things that it's going to, you know, need to be able to do that it can't do today?

What's gonna take a long time? What's gonna take a short time in order to realize? And so just kind of talking through some of the long term planning stuff and how that, um, future of the company intersects. The demands on the org helps you kind of break it down almost like stepwise refinements, like how do I refine my way to the specific next thing that I need to do?

 Well, if you can see in two years what we're going to actually need is multiple VPs and we're going to need to sort of restructure some of the teams and do this or that, that helps provide a clear picture for, you know, both direct reports.

And I think people who are in a position like me, whereas you know, sort of head of engineering, um, to imagine that future if they haven't done it proactively on their own, um, or didn't have enough information to even do so on their own. Um, and then collaborate with them to try to figure out like what it would take for them to get there at the right time.

It's like, okay, well you know, what if in 18 months you need to be doing this strategic role? you need to understand finance well, you need to understand how the whole business works better. Uh, you need to understand our partner ecosystem. You need to have enough free time to be able to focus on those things and not do all the sort of day to day operational stuff, which means, you know, the person reporting to you needs to be able to do that really well, or they're not the right person for the job.

 for the environmental stuff, I, I think, um, helping them see the future and helping them figure out what the specific plan is so that they can be ready for the future as it comes, um, is probably the, the most helpful thing I can say.

 So another thing that you shared a little bit about was the other part of the equation, which is how did you approach, um, your own growth in each chapter of the company's life? Um, you talked about reading other books on functional areas, um, developing new muscles like strategy through reading, leveraging members of your extended community.

But I was wondering if you could, you, you could share more about that, maybe share some stories or your approach that allowed and enabled your success in all of these different roles over the last decade.

 one area in particular, um, that I think is important for anyone who's trying to grow and adapt, um, I have this specific theory around one's identity and like what you should absorb and what you should deflect and what you.

 Uh, you know, sort of work on proactively. And so by that I mean, um, there are probably core parts of who you are that you don't wanna change and are positive attributes. And they might very well be two-sided coins in certain cases. many personality attributes are.

But same time you want to have that identity. And so, for example, you know, part of my positive identity attributes are, um, you know, one that I talked about already. Like, I'm adaptable. You know, whatever situation I'm in, I'm pretty sure that I will be able to learn what I need to learn and change at the right pace in order to be able to do the thing well.

 Another one is that, um, you know, uh, I try to be kind to everyone.

 Um, now is that always true? Am I always kind a hundred percent of the time? No, but it's, it's like a personality attribute that I want to have, and I think strengthens who I am and how I show up in the world but I try to take any of those sort of positive things that I think are, are really, you know, fundamental to who I am and absorb them and take them in and accept them as an identity.

Now on the other side, there's all the negative stuff. There's the times when you screw up. There's the times when you don't meet your own or other people's expectations. There's the times when somebody has an opinion about you. Um, you know, that that is, uh, you know, potentially labeling you as one thing or another, you know, you're incompetent.

You don't, uh, you know, these are not necessarily things that people are saying of me, but, uh, you know, you're, you're incompetent. You, you don't, you're unreliable. You don't complete things on time. Um, you know, you are a real jerk in that meeting, whatever it is. All of those types of things. I very much intentionally will absorb the behavior and deflect the identity.

And so the behavior might be that I didn't show up as well as I could have, or somebody asked me to do something and I didn't get it done until three weeks later and, you know, that created some harm. All of those things are sort of like observational data to me. It's like I can. Um, how I'm behaving. And then I need to sort of devise some way in order to take those negative labels, turn them into behaviors that I can observe as actions, and then turn those negative behaviors into behaviors that are no longer part of how I'm operating day to day.

And so I think that requires a fair amount of, um, sort of self-reflection and and depth. So sometimes I'll literally sit down and take something I've screwed up and kind of do my own retrospective. So it's not like literally sitting up there with like a whiteboard with, you know, happy mass, sad or, or something along those lines.

But it's like sitting there and writing with myself and, and it's, you know, a reflection exercise of, um, you know, how did I feel like, how did I make this other person feel? What was the context What other things were going on for me that caused me to, um, you know, uh, behave in that way? What is it that I believe to be true that caused me to make the assumptions I made that caused that interaction to go badly?

Just kind of like tearing all those things apart and trying to surface them so my conscious mind, um, can process them. And so that it doesn't all just happen to me subconsciously, I think, I think there's like this, uh, default of. Uh, victimhood almost of like, you're a victim of the worst attributes of yourself.

And it does feel that way sometimes, cuz you're like, well, the version of myself that I identify with would never have behaved in that way. But there it is. You did, 

And so sitting down and reflecting on it and, um, you know, coming up with a plan for how to make it better, I think, um, is, is actually a key, learning approach that's allowed me to go through some of these cycles and iterate on myself over time.

I think that's a good foundation. Can you go into a little bit more detail in terms of techniques, tactics, things that you did that sort of sat on top of that, that enabled it? You know, you talked about some of the reading that you've done and how that influenced you. Maybe things like when you leveraged other CTOs or other people that were maybe farther along, did you engage with them in a certain way to sort of maximize your own learning?

 Yeah, I mean, I think, I think one thing I've actually done with my peers is even asked them for feedback. And so like, I'm in, you know, a few different little CTO pods where, you know, people meet up once a month and, um, you know, some of them I've, I've met with for a really long time and they've gotten to know me and so usually you bring up some topic and everyone kind of discusses it over breakfast And so periodically I'd bring up instead of a topic, the question of, um, you know, what is it that you. see about the way that I'm thinking, the way I approach problems, um, whatever it is that I can learn from. And so I've gotten some interesting feedback that's usually very specific and specific to that moment that I can act on really quickly from peers who are sometimes a step ahead.

So, you know, just to, um, I guess name drop a, you know, a friend of mine who, um, gave me a specific piece of feedback at sort of just the right moment It was, uh, Yi Fang who's, uh, co-founder and and CTO of, of Peloton.

Um, you know, and helped build, build that company up. And it was a few years ago and I think. You know, he was going through like super, super hyper growth. You know, the first time I met him, I think he was, uh, he was still building the first prototype of the bike and we were at some like 2013, you know, CTO conference.

And I was like, oh, that sounds really cool. And we stayed friends over time and, and the wisdom he gave me was, I think you're trying to control things a little bit too much, you know, and that was, that was a key learning moment just to reflect on, which was, um, in years, let's say five through eight, Where I think I transformed into big team leader where you have to, you know, lead teams of, you know, 60, 80, a hundred, you know, a hundred plus people, and you start transitioning into broadcast mode and you start, um, really focusing on process as opposed to like specific decisions, right?

You're trying to figure out how do I create the framework for decisions. Um, I was actually so productive in creating process probably in that first year and a half, um, that I kind of got into this default mode where I just kept adding more and more. Process. And I kind of thought that was my job. And I, I think the company wasn't quite ready for me to paradigm shift at that moment either into, uh, you know, sort of more of the, the strategy role stuff.

So I kind of felt like I was wedged into, uh, you know, the, the sort of VP of engineering type job of create process. And I was going too far. And I think what I didn't realize was, um, that that structure, part of which was very much intended to create empowerment, created a level of disempowerment where people felt like, um, you know, because I was so engaged in every process detail, that processes needed to be run by being.

or that they needed to do it in the way that I was prescribing and not, not necessarily change it. Um, and I think that was, that was the right wisdom at the right time, um, for me to absorb. Um, other times, you know, I, I got, uh, you know, I would be talking about some operational details. This was maybe the same era of like, how did I transition from, you know, doing the VP of engineering type job to doing the, you know, sort of bigger company CTO type job.

Um, you know, someone was like, you know, I, I haven't heard you take huge swings. You always make measured decisions, you know, and, and so like little moments like that where I kind of have to interrogate myself and say like, is that true? Like, does that, does that jive with who I think I am? Does that jive with like, the behaviors I, I have?

Um, and a lot of times like, you know, I get, get that feedback from someone who's, who's, uh, you know, been there and done that. It rings true. And that helps me realize at the right moment, um, that I need to get better at. or identify a void that needs to be filled in, um, you know, in, in the growing business.

 So I wanna loop back to, to strategy and some of the things you figured out there. But, but before we move on to sort of this growth thread, a couple other things sort of came to mind for me. one is that you seem to, to be quite self-aware that you're able to sort of understand yourself and kind of how you fit into the broader company strengths and weaknesses, et cetera.

Is that just a way that you were wired or is part of the journey developing your own self-awareness?

 I think it's probably both. I think I'm in some ways wired for it, but I, I do remember when I was really young, this might sound slightly unrelated, but I think it's actually deeply related. Um, every time my parents screwed something up, they would almost always admit it and then say if there was anything that you think should have been different about how we handled that.

Cuz we don't really, you know, always know what we're doing. Um, you can do that differently with your kids. And so I think that kind of put in my. That you're not a fixed person, in terms of other like, you know, ways of reflecting on myself and where I fit in the broader context. I don't even know if I'm thinking about myself on honestly all that much.

I think it's more there's this like dynamic system of a business in a way, and it has a bunch of inputs and outputs and needs that are met and not met. And, um, you know, and I think I usually wedge myself into a place where, I have the ability to express creative energy, and I think it's because I can get really interested in something that seems important to me.

And so I think the task is like, identify something that feels important to me, get really interested and kind of like hyper focus on that thing. And I think that lets me leverage my superpowers. And so I think when I feel bored or I feel like I don't have anything that I can uniquely make a difference in doing, um, that's sort of like stagnation sets in in a way that feels bad and I wanna go find something that makes me sort of feel good, which is like the next interesting problem to go solve that I'm uniquely suited to solve.

Photo of Mike Boufford sitting down on a bench in front of trees

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Mike Boufford wrote Greenhouse’s first line of code back in 2012 — and he’s still CTO today. His advice for scaling as a leader and getting more strategic.

Scaling your career alongside your startup (without getting layered)

Mike Boufford wrote Greenhouse’s first line of code in 2012—and is still CTO today. His advice on scaling as a leader.

How to scale your career alongside your startup: Lessons after 10 years at Greenhouse

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