Emuye Reynolds - How to build and scale your engineering teams in startups!
21 Feb 2024 · 53 min
In this episode of the Undefeated Underdogs Podcast, host 5Harath interviews engineering leader Imue Reynolds about the challenges and strategies of building and scaling engineering teams in startups. Imue shares when to form an engineering team, emphasizing product‑centric decisions and the trade‑offs between outsourcing and in‑house development. She discusses the importance of chemistry with founders, aligning on values, and the upsides and downsides of being a founding team member. Drawing on her experiences at Apple, Superhuman, and other early‑stage ventures, Imue explains how small, senior teams can achieve outsized impact, how to design intentional hiring and interview processes, and why interviews should be a two‑way conversation. She offers tactical advice on researching interview frameworks, iterating hiring criteria, and evaluating candidates for cultural fit. Imue also reflects on transitioning from a large corporation to startups, the shift from proprietary tools to open‑source resources, and the value of networking. Finally, she introduces her new venture, Udo, aimed at helping product teams make data‑driven prioritization decisions, and shares lessons on decision‑making as companies grow, including the need for pattern recognition, avoiding attachment to early‑stage decisions, and bringing in experienced advisors.
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I think it's important for the early team to be pretty involved on the hiring side and to be careful and sort of craft that team. I also think setting values early on and using that as part of the criteria for how— they don't necessarily have to— it doesn't have to be a formal process, but being intentional about it is important to then be able to select for those values. And if you don't do that, I think one of the things that can come through is sort of you end up with these accidental values, things that the company is sort of either intrinsic to the people at the company or the company's accidentally selecting for in its existing hires. And so I think that's something that's really worth being intentional about. And crafting that early team is unbelievably important.
Welcome to the Undefeated Underdogs Podcast, where I unpack and narrate stories of ambitious people who turn obstacles into opportunities. My goal for this podcast is to create a platform to narrate underdog stories and maybe play a small, teeny tiny role in inspiring you. I intend to highlight the underdog mentality and make authentic conversations with people who play the long game, take action with a chip on their shoulder, and convert obstacles into opportunities. Buckle up as I'll be bringing some authentic founders, VCs, community builders, and content creators who got underestimated their whole lives, and yet they beat all the odds to become insanely successful. Now today I want to tell you a little bit about our awesome sponsor acquire.com. Selling a business is as tough as building a business. As someone who went through this process once, selling my own startup, I know the pain it takes to get to the end zone. This is where our sponsor shines. Imagine this: you're a founder who's built a solid SaaS product, acquired customers, and generating consistent monthly revenue. The problem is you're not growing forever for whatever reason— lack of focus, lack of skill, or just plain lack of interest— and you feel stuck. What should you do? The story I'd like to hear is You buckle down, somehow reignited the fire, get past yourself and the clichés, and start working on your business rather than just in the business. You start building an audience, move out of your comfort zone to do sales and marketing, and in 6 months you triple your revenue. The reality isn't as simple. Situations may be different from every founder facing these crossroads, but too many times The story ends up being one of inaction and stagnation until the become business, the business becomes less valuable or worse, worthless. If you find yourself here or your story is likely headed down a similar road, I offer you a third option. Consider selling your business on acquire.com. Capitalizing on the value of your time is a smart move. Acquire.com is free to list and they've helped hundreds of founders already. Go to try.acquire.com/sharath and see for yourself if this is the right option for you. Now let's get into today's episode. All right. So folks who are listening, appreciate you for joining. So far I've been invited, like so many leaders, product leaders, marketing leaders, founders, bootstrappers, VCs. I can go on and on, but I've never done this before where I invited a leader in engineering in something that we want to— it's very essential for any startup to focus on. It's one of the essential key pillars. And my next guest is a master at it. Like, she built, scaled engineering teams at scale. She worked at companies like Superhuman. Her first job is at Apple, which is amazing. I can go on and on about her, but without further ado, I would love to welcome Imue Reynolds. Welcome to the show. How are you, Imue? How is your day going?
My day is going very well. Thanks. I'm happy to be here. Thanks for having me on.
Absolutely. Like I said, I think I've talked to many people on both sales, marketing, bootstrapping side, VC side, and kind of like never dived into this topic of Where should engineering start? You know, it's generally founders tend to be the engineers. They develop the product, right? Or if I'm founders like me, outsource the product or use no-code tools and like something, they'll make it happen. So I think the first question I have for you is what is like, where do founders, you know, in, in what phase do you think an engineering team should be established? Like, at what phase? There's early-stage startup to, like, you know, fast-growing pace and all whatnot. So in your opinion, in your experience, where should founders, you know, should take a decision about, like, building an engineering team?
Um, I think it varies a little bit depending on the nature of the product. Um, I mean, I imagine the ideal scenario is that you have, there is an engineering team, it grows and, you know, with the company. I think there are situations where it makes sense to outsource it. It makes sense to have it not be embedded within the company, especially if, even for a tech company, if the technical challenges aren't critical to the overall product, right? There are some tech companies where where the go-to-market strategy or some aspect about the product is the pillar and it's not, these are very hard technical challenges or we need a world-class standout user experience. You know, in those situations, I think you can get away with building it a little bit later. You know, that hasn't, you know, as an engineer, that hasn't been my experience. I'm sort of in the boat you described where I have, you know, I'm a founder now. I've been on many, many founding teams. And I actually have done something a little bit interesting, which is I've joined non-technical founders a couple years in. I've been sort of the first 5 or 6 people in a company many, many times. I think I've done that like 5 times. And those are companies that, you know, sometimes they've had, there's technical debt and we're transitioning to Um, now that the company knows what they're building or is near product-market fit, it's sort of like the let's build it for real phase. I think that's a time— I think that's a fine path for companies.
And, uh, I think you've, you know, like you said, you've, you've been like a founding employee at, you know, so many startups. So let's dive into that a little bit because I think that's very interesting for our listeners as well who are like, you know, figuring out their first roles, whether it can be like a first job or You know, I'm in that path right now. Should I join like very early or should I join an established startup? So what is something that you looked for when you joined in these early stage startups as founding member? And what is like the 2 things? One is what is the reward that you've got? You know, I kind of do know the answer for it. At the same time, what is like the downside for it? Like the upsides and the downside.
Yeah. So one of the things I look for that's maybe a little bit nontraditional is chemistry with the founders. You know, you're gonna spend so much time with those people. And I think the relationship between co-founders, there's a lot that's talked about how important that is. It's, I think it's probably equally true with your founding team, or at least very, you know, very, it's a very close second. So I wanna make sure I gel with those people. I want to make sure there's room for me and where I want to grow. Those are some of the things that I look for. You know, what are the upsides and what are the downsides of being on a founding team? I mean, impact is of course one of the upsides. And for me, it's really important to wear many hats. I like when the job is different each day and I like when I'm in the critical path for lots of different aspects of the company. And you get that as, you know, you get that as founder, you get that being on a founding team. The downsides, it's interesting because I think I'm the kind of, you know, founding team member that treats it like my life. You know, I'm as committed And dedicated to the thing I'm working on, I think, is anyone else in the company. And it can be hard to be in that situation. And there is a difference between a founder and a founding team member. There is a— in some ways, it's like the commitment that the company has to you is a little bit different. There are co-founder breakups, but it's, I think, less common for an established company to have co-founder breakups than it is to have people in that founding team cycle through. So you wanna make sure it's the right fit and you're going to put everything into it. So you wanna make sure the company is going to be somewhat loyal to you as well. That can be a downside is that your position is a little bit more tumultuous than it might be if you were a founder. But I think for anyone in that early team, You know, you have to be able to collaborate. You have to be able to— you're not going to make every decision regardless of what your position is. And so that feels very similar. I love it. I love being really early stage. You get to build, you get to wear different hats. And I think, you know, the other, I guess, downside I would say is that early stage companies are chaotic. They just are. Yeah, that's very cool.
I think it's for people who embrace chaos and uncertainty. And so I've heard this, I was talking to a founder and kind of like similar topic I was discussing with him. And he said, I look for founders who want to join us founding, you know, part of the founding team. It's like mostly they're like, like probably like 1, 2 steps away from becoming a founder. Because they— it's literally like the founding team is everything, you know, that they do as founders, right? So that's probably like, you know, an upside, which is you'll eventually kind of learn to be a founder in being part of the chaos.
Yeah, I probably have a different perspective on that than most people who are early to companies and who want to be founders. I, that was, being a founder was never important to me, honestly. And I've actually—
Oh, interesting.
Yeah, it wasn't an anti-goal, but it just wasn't a goal of mine. Like, there are so many interesting things to work on. You know, there's so many interesting people to work with. I have, you know, I've been fortunate enough to work on some really cool stuff. It was never like, oh, this, I didn't start this. So I did become a founder more recently, but that was, You know, this is probably something like my 7th startup where I, in all the ones previously, I wasn't a founder. So I don't know. We had a lot of discussions like this at Superhuman in past companies where it's like, okay, we're going to bring someone in. We want to make sure they have that founder mentality. I think people can be motivated in many different ways. I've been all in, but I don't know that I would say that's because I aspired to be a founder. I do think you're right that seeing an early stage company is some preparation for starting a company, of course. Right. It's like, I mean, I'm a sports fan, so it's kind of like seeing the ball go through the basket. Right. Yes. But I actually think seeing the large company, my experience at Apple set me up for success in a similar way. Right. Because that's truly like you're a part of a machine, a company that knows how to build successful products. that knows how to get it right. So yeah, I would say working at a startup, to use our sports analogy, being on a founding team is like shooting the ball, and working at Apple or a big company is like seeing the ball go through the basket. And those 2 combined, I think, is a really good experience to start something.
Do you think, uh, wannabe founders or operators— let's talk about operators— do you think they should have those 2 lens, which is what you described, a lens where they actually shoot a lot of shots continuously, being in early stage. And the other lens is probably someone like Steph Curry who's already hit so many shots and now he's mastered at putting the ball through the basket. So do you think it's a requirement or is it like, what's your take on having those 2 lenses? part of being an operator or even like wanna be founder?
I don't, I won't, I won't say it's a requirement. I think it is very helpful for that to be within, that exists in a company, right? You wanna have kind of the DNA on both sides. You know, I think it's a healthy balance. Like if you can, of course, an amazing candidate for a role at a startup is somebody who's been at a startup, you know, many, many times before. If that person has also worked at a really established company that, actually, you sort of like knows what they're doing. I think that's a benefit. And certainly you wanna make sure someone in the company has done that, right? I think companies are probably gonna be more successful at some point if you start to bring in sort of people who've experienced before and seen and can pattern match with an established company.
I think pattern recognition is, I think, the key skill that you develop once you, you know, work for an established company because everything is like kind of like signals. You pick a signal, At an early stage, it's all about experiments without picking up signals. The signal signaling tracking comes later. Let's— I really want to talk about Apple. Like, of course, you know, you, you, that's, I think that's your first job if I'm not wrong. And you worked at— so the first curious question I have is, is it really true that Apple at that size operates even as a startup? Like it's famously Steve Jobs said in one of the, I think, uh, DxO keynotes or whatever it is, he says that Apple is like a, like a bunch of mini startups working together on one mission, right? So is that true? At what length is it true? And what, what's— what was your experience like working at Apple?
Yeah, um, I think that is very much true. So it certainly operates like a bunch of companies. And the team I was on honestly still feels like the most startup-like experience I've ever experienced. Wow. We, you know, and there are both positives and negatives to that, but we were entering, so I worked on Apple TV and we were entering a new market. You know, when I started, Apple TV didn't even exist. Like they, I remember when they, just to put context around like what era this was, When I joined Apple, their most popular product was the iPod. And it was a product I'd only touched like 2 iPods in my life when I started. Like it just wasn't, you know, it was a very different world than the world now. Apple was a tech company and I think it certainly transitioned at some point in that era to being sort of the tech company. Mm-hmm. But yeah, so when I started, they described this product, Apple TV, and I was like, what does it have a— I didn't get it. I was like, Does it have a DVD player? You know, it just was a good thing. How do you know? It was a completely different, different world.
Right.
But entering that new market, the— we were in like perpetual crunch mode. Like I worked more there than I have in any startup I've ever worked at. And that, I guess that was in some ways like the negative side of it. 'Cause it was extreme, I would say, for some of those years. But we, Apple sort of operated in that era and I think it can be different on different teams. There were very established teams at Apple that I'm sure were not operating like a startup that were larger, all those kinds of things. My team was between 5 and 10 engineers for the 5 and a half years that I was there. It was really small. Wow.
That's it.
Mm-hmm. Yeah. And that's it. And at that time, I think it, again, this has changed somewhat. Like I left Apple in 2011. So it's been a while, but at the time, Apple had very small teams. And even some of the more established teams were small, but it was especially true for the emerging teams. But one of the things that was still fascinating to me about how Apple operated is it sort of felt like at every level of leadership, even individuals who are sort of leading themselves, It was like the company, every level was building for one person. It's like, you know, I was sort of building for me and sort of my director was like, sort of almost like a dictator of, you know, his own kind of world. It was this very bizarre structure, but it meant that you operated like you only needed to have like a very straight shot in terms of direction. We were like a very sharp-pointed arrow because sort of everyone was making decisions almost as— it seems weird, but almost as an individual as opposed to with a whole structure behind it. And in some ways, that reminds me a lot of when you're at a startup, right? It's like you do what needs to be done and you are an owner. Everyone is an owner at every level of leadership, even, you know, people who are leading themselves. Yeah, I often say that my time at Apple was my most quintessential startup experience.
And it's so interesting what you said about being very small, even it's such a big project, right? Apple TV is one of the key revenue streams right now. Of course, it's not like It took some time to like people to adapt to it, but it is fascinating to hear that 5 to 10 engineers over the 5 years of time, you built such a big ecosystem together. So I think there is a lesson there, probably like founders can even— I'm learning it to make it small and concise. So you have, like you said, like unidirection, like going one direction rigorously, ridiculously focused. I have to ask about a couple of questions for sure. Sure. I think around 2011, Steve was there on and off. What was it like part of under his leadership? What is something that did he really impact it? to a level that, you know, to you versus like, you know, was he interacting with only key stakeholders? What was it like, you know, being his aura around Apple campus?
Yeah, so he, when I left in 2011, it was shortly after he passed away actually. And, but, well, so he was there for a lot of my time and I worked in, I actually worked in the building he worked at. They had this campus back then called Infinite Loop. which was like these 6 buildings in a circle. And I worked in aisle 1, um, and he worked in aisle 1. He worked a floor above me. So you saw him around quite a bit, actually.
Wow.
Just in general, like anyone in that building would see him. You know, he would be in, you know, at lunch in the cafeteria, and we would always joke. It's like, please don't wait in this line. Like, go, go ahead of us, right? Like, I don't think your time is, is, is well served waiting behind me in this line. Um, But, and he was kind of funny. He would always sort of walk around like looking. Once the iPhone came out, he would like just be looking at his phone, like walking around campus, like literally like glued, eyes glued to his phone. But yeah, so he was around. Apple TV was, you know, I think he said at some point that it was sort of like a pet project or something like that. And in the, I remember there was quite a bit of press around that. And even some of the team felt, had sort of a negative sentiment, feeling like we're on this kind of pet project. I was kind of like, if you're on Steve Jobs' pet project, I'm okay with that, right? Yeah. So he had a lot of influence. There were some parts of the product that he sketched on a napkin. We had this sort of trailers— we had an app actually, part of Apple TV back then called the— it was like the Trailers app. And the actual UI, he sort of drew on a napkin at some point. We had, you know, we had a little demo room where we sort of like soundproofed. So just for context also, flat-screen TVs were like brand new. Like it was the era of like plasma TVs. And so it wasn't common for people to have a home setup, like home theater setups like they are today. So we had one that we could sort of, you know, experience Apple TV at Apple. And, you know, he would sort of be in there at different times. I didn't interact with him a lot, but he was around, you know, he'd come to the floor, people would demo things for him, that kind of thing.
Wow. It looks like you're, you're like inches away, you know,
to
work with someone and to create like an impact, you know, you're part of the legacy, right? You know, and That was fascinating. I think looking back, like you said, it's like, what, 12, you know, 13 years now. Uh, yeah, it is probably like one of your most, like you said, in your words, like, you know, most proudest moment, I would say, is to basically go back. It's fine to like be on a, on a pet project of Steve Jobs, right?
Absolutely.
What was it like, what was it like, you know, looking back, if you were to like do a quick retrospect, is to create like, you know, you, you have, I think Apple TV is one of my favorite products because it's so intuitive that I'm not going back to using any of the native, you know, TV OSs, right? It's so intuitive. So I can operate it through my phone. So you have left your thumbprints, fingerprints on things that I use. I'm interacting with you for the first time. So the impact is so true. What was it like? What was it like? What was the mindset after, even like before? Like, what was like, what was it like working, you know, on something that's truly like stayed forever?
Yeah, I mean, we didn't know at the time, right? And like you mentioned earlier, Apple TV sort of took some time to really land in the market. It was interesting because right when it came out, it had some of the highest user satisfaction of any product Apple had ever released, but it didn't have the traction or the buzz around it. As I think Apple TV was announced in the same, like, whatever, I don't know if it was WWDC or I forget whatever, that they used to have these kind of main press releases. And I think it was announced and the phone, the iPhone was like the one more thing in that announcement. Right. So it sort of was always overshadowed by the phone.
Yeah.
So in it, you know, we didn't know exactly what the business was going to look like. You know, the first, a lot of people forget the first version of Apple TV was not, it's not like the little black puck-like device. It was actually gray. And it had a hard drive. It didn't stream. And it had component cable hookups. Like that's how you hooked it up to the TV. It was like basically like an iPod kind of UI. There was, at the time the Apple TV first version came out, there was no movie or TV store. Like Apple didn't do movies, didn't do TV. So the content—
Right.
Had to come from, you know, it was like your own ripped DVDs or like things. It just was a very different era. So now I can sort of say, and I saw some of this when I was there too, I can look at it and be like, oh, it's really cool to have worked on this thing that impacted so many people. But I didn't know that that was going to be the case. I remember the first time I walked into an Apple Store and saw an Apple TV and people were using it. It was such a cool experience. You've got the Apple TV— sorry, the Apple workers come over and they're like, hey, can I help you? And you're like, I got it. I know what I'm doing with this one.
I've been there. Yeah, yeah.
Which is pretty fun though.
And is it true that at Apple generally it's like they think, plan, strategize 5, 10 years ahead of time? Is that true? Even for Apple TV, like, okay, we started somewhere with the hard drive and everything, but do you saw the vision or people around it building it? Hey, this is just how we enter. But I think that's something that's fascinating about Apple, right? They just let other people enter to the market so fast and they observe, observe, observe, and they just launch something ridiculously good. Even the Vision Pro is like, people are going bonkers about it, right?
Right, right.
I'm at a terrible FOMO right now. Do I have to get it or no? So is that true? To what extent is that like something that, you know, that's true? And what do you— what's something that you learned from it?
Yeah, I imagine there are some people in the company who are executing on a strategy. It didn't feel like that. And I'm honestly not sure. I think companies like Apple are in a position where they can take a lot of shots. They can try a lot of different things, right? Like Apple had a lot of products that weren't successful. Like, I could, you know, you remember the little like boombox like that, the Hi-Fi, you know? Mm-hmm. Mm-hmm. Or the round, the mouse that was like a puck. It was literally just a circle, so you couldn't tell which way it was up. You know, for, you don't know when you're working on it whether it's going to be, you know, whether I, we didn't know if Apple TV was gonna be the Hi-Fi or if it was gonna be, you know, I'd say the iPhone, but the iPhone hadn't, even come out yet. So you don't know when you're in that era. I imagine, like I said, there are some people, but I think it's more the position of the company that lets them try it and move forward with it. Like Apple TV's been on a, you know, it's been a decade of iteration. Yeah. The product itself hasn't changed that much, but its position in the market, its position in our households has changed. I don't know if someone knew that was gonna happen. I think people thought there's a chance, But they can afford to get that wrong and they do. I think I remember some of the things we used to talk about back then. Google had, I think it was called Google TV, but it had this remote that had a full keyboard on it and it was just completely bizarre. This was the era of the Zune, Microsoft's iPod. There are all these products these companies tried And those didn't necessarily stick. Apple got a few that stuck, but they got plenty that didn't
stick. I think one, uh, after like listening to you, it reassures what Steve said so many times is that we're a, you know, we're a company where we build products for ourselves and our friends.
Yeah.
And where we can share and be proud of saying that, hey, we built this, you might like it. Right. Like, I think that is like the core essence of what you said. Absolutely. It's like, try, try, try different things and, you know, I think the product is not the point. The positioning is through the product in the market is like the point, right? I love it so much. Appreciate you for sharing like, you know, some of the inside stories.
Yeah.
And let's talk about like Superhuman, you know, you again, early 2014 is when it got founded. You were, I think around 2016, you know, so Why, why Superhuman? Why did you enter like, you know, such an early— after like working at Apple, what was it? You know, you did some, a bunch of things in between as well, but I'm just curious about understanding why did you kind of, uh, didn't go back to build your own thing, which is what you're doing now. Instead of, you were like, you were a technical architect, you were again like a software engineer, you know. Mm-hmm. You were the head of technology and like you did so many other things. So I'm just curious about the big corporation to going into like a startup. Like, is that like because of the burnout, the, the number of hours you put in?
Um, I left Apple because, uh, I looked around and Apple was one of those places where a lot of people spent their entire career there. And, um, And or or had returned many many times, and I was sort of looking around the pace I was learning had declined. Like I wasn't learning at the same rate that I once was, and I kind of I was like if I want to leave now because I think you can get to a point where it's very difficult to leave a company if it's all you know. So that's that's kind of what what what made me start looking around. I didn't know anything about startups. I mean it sounds funny to say this now, but like I didn't even know what a startup was or. Like, I just had no exposure to it. When I actually, it's when I, when I was an intern, when I was in college, like the summer after my sophomore year, I interned at Microsoft and I worked on the Word team. And I thought I wanted to find the opposite experience, which is sort of what led me to Apple. In my mind, the opposite of Microsoft was Apple, right? Like, I mean, of course, they obviously have a lot more in common than many, many other companies.
Right.
So yeah, I sort of entered that startup world and I just got hooked. And a lot of the reason I got hooked was my first team. Mm-hmm. We just had great chemistry. Still to this day, a lot of the people I work with are my close friends. It was a really great ride. So I kind of got lucky with these 2 very different early experiences. Then I bounced around a little bit because I'd never learned how to vet. I didn't know how to vet a company because I got— went to Apple and then I went to another startup. I went to a startup for several years, which was great. Mm-hmm. So I was bouncing around a little bit trying to find a place to land and figure out what I wanted to do. And I was kind of at the tail end of that exploration process when I heard about Superhuman and met with the founding team. I think when I joined the company, it was like 7 or 8 people or something like that. So it was very small. And I liked a lot, I liked that the vision was huge. Like it was just an absolutely massive vision. I was at a point in my career where I knew I wanted to be a driver. I didn't want to be a passenger on that ride. And I thought that there was like really good role alignment. You know, I just really gelled with the team. And I actually, when I joined, I was the head of, I think it was the head of mobile initially, and eventually became the head of engineering. Yeah. Yeah, there's a lot of space for me at the company. I know if you'd been like a year earlier, hey, do you want to work on email? I'd been like, what? Email because I'd only done consumer, consumer-ish kinds of things. And that's kind of where my heart was. But I liked that they were taking a consumer approach to email. I used to always say it was kind of like if Apple built mail, this is what you would expect. I mean, of course Apple does have mail, but this is kind of what you'd expect. So yeah, that kind of led me to Superhuman.
And like I said, it's like it's a movement. I would say Superhuman literally like showed How a startup should grow, you know, with their— I think, I don't know if they patented it, but I think they should have done it. Like, you know, the waitlist concept is ridiculously phenomenal, right? Like, you only invite a few people, like, you know, you share and you get more access. You get like, you know, the number changes your role. So that is so like gamified the whole system. Yeah. You being part of the team in those early days, what was it like to kind of like, again, changing different, different hats, right? You, I'm sure that you wouldn't just like do 9 to 5, you would have done many things. What are some external things that you did that actually helped you become, you know, who you are right now as a, as an engineering, you know, product person? I want to also talk about the product side, but let's, let's kind of like, you know, unpack the engineering side.
Yeah. Yeah. Superhuman, it's, you talked about, you know, sort of the pride that I'm sure you're picking up on from my Apple days. I definitely am proud of that experience and it's really cool to have worked on something that's been impactful. And I said that I feel very fortunate to have been in some of these roles because I think Superhuman also had a lot of impact on how startups execute. There's a lot of things that we did. Yeah. I see product launches. I see, you know, of course the waitlist. You know, the way that companies approach finding product-market fit, some of these different techniques that we executed there, I see those having shifted the landscape of startups, which I think is very cool. Yeah, I did get to wear a lot of hats. I think one of the things that's been helpful for me kind of since post-Superhuman has been I was involved in hiring a lot of the early company. Mm-hmm. So whether it was creating hiring plans, whether it was, you know, actually sourcing candidates, interviewing, um, I think I interviewed probably the, the, you know, if you look at the next 50 people after me, I think I interviewed almost every person, if not everyone. Um, and was like a, a, you know, a major part of bringing them onto the team and that in, in every role, which I think has been really interesting now that I've transitioned to, to being a founder because, mm-hmm. you know, a lot of building the team is, of course, there's a lot of engineering, but there's a lot of other roles. And it helped me going off and researching what skills do we think would be successful for this particular role? What are we looking for? What do we need this person to do when we had something we needed in the company? Actually showed me quite a lot about how companies function and like the different roles and the different, the types of people that you need to bring in. So I think that's been really helpful. And then on the engineering side, you know, lots and lots of learnings. You know, one of the things that I think carried over from my Apple days was our team was really small. We probably were too small for too long. But I think small teams can accomplish quite a lot, and you don't have the overhead of— you don't have the overhead in terms of communication costs and a lot of the things that management costs that you have for— bigger teams, you have it, but to a lesser extent. So that was one of sort of the lessons that kind of carried through and I think was helpful for that early. We had a very senior, very small team with a pretty large surface area. Email's actually a really hard technical problem.
Of course.
Yeah.
So I'm fortunate as well to kind of experience that side when I was at Product Hunt, which is so lean for such a big platform. I kind of experienced why, you know, certain founders think lean teams are really, you know, the right way to, you know, right path to put success for, right? I think there is, there is a, there is a level of trust and there is a level of focus that lean teams bring into, and there is less distraction. If you think about it, it's more about we need this, let's get it done, right? You know, that jobs-to-be-done mindset is really, really, I think, something I've If I were to build a startup, for sure it's definitely going to be lean regardless of the stage, money, and all
that.
So you've briefly touched about hiring. I want to understand what are the things that founders should learn, especially early stage. They don't have recruitment teams or they don't have bigger teams be involved. What are the things that they should learn from your experience that you want to like pass it on?
Yeah, I think interviewing and hiring, you know, we talk a lot about hiring in startups, but I think we don't talk very much about interviewing and how important that actually is to company building. It's a skill that I think, I mean, I think, you know, founders, of course, there's a lot they have to do. There's a lot they have to do well. You can't be great at everything, can't just even be good at everything. But that's one I think that Surprisingly, there's not a lot of emphasis on like how do you figure out what skills you need? How do you create a process to select those skills and evaluate those skills in candidates? And then how do you iterate that process as you, you know, have kind of people moving through the company? So I think that's a skill we should actually flex a bit more than we do in startups. And I think there's a lot of, you know, there are materials out there in terms of how do you get better at interviewing. It's just there isn't an emphasis on it. You know, there's a lot of talk about hiring, but how do you hire if you don't interview, right? So that's definitely something I think quite a lot about. I think it's important for the early team to be pretty involved on the hiring side and to be careful and sort of craft that team. I also think setting values early on and using that as part of the criteria for how— they don't necessarily have to— it doesn't have to be a formal process, but being intentional about it is important, I think, to then be able to select for those values. And if you don't do that, I think one of the things that can come through is sort of you end up with these accidental values, things that the company is sort of either intrinsic to the people at the company or the company's accidentally selecting for in its existing hires. And so I think that's something that's really worth being intentional about. And crafting that early team is unbelievably important. Yeah, it's tough though. I mean, you know, you've got to sort of lean on network. And if you don't have network, I think you have to lean on, you have to sort of find recruiters or other ways of sourcing. I spent a lot of my career sourcing or, you know, looking at resumes and, and that kind of thing to build these early teams.
And, uh, do you have a particular hiring strategy that worked for you that you want to share? Like, you know, let's get into like tactical stuff, right? Where do you start? Uh, what is like the process, like 0 to 1, and how do you close it? Like, is there a proper I would love to know about the interview tips as well. Like what would exactly, like what kind of questions do you ask to, you know, kind of understand other people, the candidates? So do you wanna share something that you did at even like, you wanna understand about, you know, how to establish like an engineering team from that hiring strategy as well as generally like founders, what can they learn from that process?
Yeah, I think one of the components on the tactical side that's important is research, right? Like Anything that you want to hire for, any skill that you need, someone has done that before, right? So actually going and looking at interview plans, reading them, trying to make sure you have like a full process before you start hiring and the process that you're going to iterate, I think is very important. There's lots of good resources out there and it's not even important that you pick the best one. It's sort of, you know, getting that overview and picking and choosing different elements from different ones. Processes to create your own and craft your own, I think is quite important. You know, I think the other thing is really thinking about what's important to the particular needs of the company. So I mentioned at Superhuman, we had a pretty senior team. I think that was critical because it was— there are lots of very hard technical challenges that let us be lean, that let us kind of operate with a smaller team. And then we needed to, at some point, we wanted to transition that because I think having Like diversity in a lot of different ways is incredibly important to teams as well, including the sort of energy that you get with, with many times that you get with youth, right? Or people who are at least earlier in their journey. So being able to create a support layer was something that we wanted to establish before we then brought on, really scaled in terms of people who were earlier in their journey. And again, I think it's less important exactly what approach you take, and more important, that it's an intentional approach and you're thinking through, okay, here's what I need. I've done this research to see how other people select for these skills. I'm now trying a process. We've made this hire. It is— it worked or it didn't work. And I've now— I've created a loop to integrate that into any, you know, output back into the process.
Interesting. In any interview, uh, like, specific tips that you want to share, like what kind of questions that that, uh, that people generally miss when they actually want to interview people, or any things that you want to mention about, hey, these things are so obvious but they just miss it for whatever reason?
What do people miss when they're interviewing? Hmm. Um, I think one of the things people miss is— so interviews are, you know, it's, it's an hour, it's, you know, a couple hours. It is both— first of all, it's, it's a 2-way interview. I think a lot of the times We treat it like the only, you know, person interviewing is the candidate, but in reality, they should also be evaluating the company. So that's something I look forward to. If the person doesn't have any questions, if they don't, if they're not really trying to understand, it's not that they won't be successful, but it's completely random whether or not they are successful then. Right. Right. And so I wanna make sure and push whoever I'm interviewing to make sure that they're treating it like a two-way interview. That's just gonna help with kind of get to the best fit. Mm-hmm. But the other thing I would say is you've got this, you know, couple hours that you need to put your best foot forward. If you aren't putting your best foot forward in those couple hours, I don't optimize for false negatives. I don't optimize for saying no when I should have said yes. Like, I just, I'm okay with that. I'm okay with this didn't work. We, you know, for whatever reason, you know, whether it's we've set forth our criteria and the person, you know, didn't meet it in certain ways, or, uh, it didn't go well, you know, all of those things, I'm okay just, you know, putting my time into a different candidate.
Interesting. I like that. I think, uh, they have to put skin in the game is what you're saying. In a way, uh, it's not like one way where you sit, you hear these questions, and you answer. It's like, you know, kind of like a conversation. I like that a lot. Uh, so what advice would you give for someone you know, who's kind of transitioning from big corporations to startups? Like, what are the, what are the things that they look for? They probably, like, you know, in, in your case, you moved from kind of Apple to Superhuman, right, through many years. But, uh, what do you— what, what's— what, what advice would you give?
Um, I'm not sure this is advice, but at least one of the things that really shocked me, um, so at Apple we don't use any, we didn't use any existing software. Like I had, you know, this is the era of Stack Overflow, but I didn't even really know what that was because you have access to the other people who've built the software you're depending on. You can call them. Mm-hmm. So I was like absolutely shocked to be, when I left the company, I was sort of like, everything was black box about all the tools I was using. And instead of calling the person who wrote the software, I had to like go look up like, how do you do that? How do you, you know, I'd look on Stack Overflow and find people who didn't actually know the inner workings that were trying to answer these questions. That was something that was actually one of the more interesting transitions that I needed to make. But in terms of what advice I would say, I sort of stumbled through a lot of things and I think I ended up finding my way. But, you know, take some time to explore and find things you are interested in using and actually touching and working with, and then talk to those companies. And when you're with a big company, there's often this like very, you know, established point of connection if you want to get a job. I'm a huge fan of, I find a product I like, and then I just email the people who work on it. And I'm like, hey, I want to work on this. Like, and then kind of go from there and see. So I think there's no closed door, I would say also when it's a startup world. It may not lead to a job, but it might.
Yeah, you should shoot your shot, right? Yeah. Now that you're— I think you are part of— you're not part of Superhuman, but I think last 2 years, 3 years, I'm excited to learn what you're working on next. What's next for Imue? What's going on in your life?
Yeah. So I started a company. It's always hard to say when because I was kind of tinkering around with some things and that sort of turned into a company, but we're super small. You know, the origin story is really, I was exploring what I wanted to do next, talking with a lot of different companies. And I was mostly looking for VP Eng or head of product kinds of roles. And almost every company I talked to had the same set of problems. The reason they were you know, hiring for that role is because they were having trouble prioritizing, aligning on the priorities, and communicating around the priorities on their product teams. And so, yeah, well, we're, you know, working on that. We're calling it Udo, and we're trying to solve that problem. And we want to make it easier for product teams to make better data-driven decisions faster. Yeah, so it's early days, but, and we're kind of cranking away building, but it's been a lot of fun.
Excited. We haven't touched your product side of expertise. So I think every builder has some side of product knowledge or product intuition, right? Whether even like take Steve Jobs, he's a builder. It doesn't matter if he writes the code or not. he knows how a product works, right? So in your case, you actually build things. Like, you're a developer, you're like a technical person. So how much of you, uh, of your experience helped you become— develop that, you know, skill as a product person or a product leader?
Yeah, it's actually something I was interested in even before. I think I'm a builder because I love products, right? That was the— that happens to be sort of my tool, my hammer to actually get things I'm interested in. into the world, but it's actually the user experience, like how people interact with technology. That's the thing I was interested in before I ever even, you know, kind of went down the CS and eventually engineering path. And that got cultivated, I think, at Apple where there weren't any product managers. So that engineering team, like I mentioned, there, you know, were 5 to 10 people. We had one designer and then their product decisions were sort of made At every level of leadership, there was no real process. And that meant there was a lot of filling in the gaps on the engineering team. And since it was something I was already super interested in, I spent a lot of time thinking about how people were going to interact with product. And then after that, I sort of continued to foster that sort of level of thinking at different jobs. I think you can be one or the other, and I think you can be both. I think you're right that most of the time, you know, the builders we think about, some part of why they're building or what's interesting to them is actually the end goal as opposed to the tools and technologies themselves. Yeah. But I've seen great engineers who, you know, they're in it for the technology. They, you know, they, the sort of the process of building the thing is more important than the end goal. Yeah, that happens to not be the case for me
though. Yeah. I know we're on time, so we'd love to like, you know, close it off on one question, which is how do the phases of a startup from early stage to subsequent growth stages impact decision-making in leadership roles? Like in this case, you are, you had like engineering role leadership. So what is kind of that, do that, is that like really a thing where as you grow, you make decisions in a different way versus, you know, Early stage?
I think you absolutely should. I think the lesson I've learned here is we get so attached to these things, like they become our babies, like they become the thing we're very passionate about. And I think it's important to really think about, is it when that starts to get in the way, right? So I think one of the things we should fold into our decision-making as the company scales, as the company grows, it has different needs. We talked about pattern recognition. There's going to be a lot of things, a lot of patterns that we can't recognize because we're, you know, individuals. So making sure to surround yourself with people who have seen that stage, have done that thing, and whether it's, you know, as an advisor, as an employee to the company, but being okay, you know, we go from, you make every decision at a really early stage company and at some point that actually gets in the way of the company and making sure that you're not trying to make those decisions because it's your baby, but because you— and making sure you have the right set of people, the most knowledgeable set of people around it. I think that's a really important lesson that I've sort of learned throughout my career.
I love that. Thank you so much. This has been so knowledgeable. I think I've learned a lot about hiring and setting up interviews, like, you know, that whole process. And I really, really appreciate you for sharing some of the, uh, some of the experiences or memories from Apple, which is, which is, which are always like, you know, good to hear. Uh, such a, you know, amazing company making a lot of impact on our lives. Uh, any closing thoughts before we wrap
up? Well, I just wanted to say I appreciate you, uh, having me on. It's been a great chat. Uh, it's been fun reminiscing about some of these past experiences. Yeah. So thank you so much.
Awesome. That, yeah, you know, hopefully like listeners, you learned one or two things and we do this for that, like basically like enhance your, either like put a plant in your, you know, in your mind about whatever it is. In this case, how to hire, how to hire scale engineering teams in the right way. Muye, thank you so much. Appreciate you. And that's a wrap, folks. See you all in the next episode. Cheers.
Merci.
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