The Modern Recruiter #20: The story of Reddit and its founding engineer-turned-CTO, with Chris Slowe, CTO & Founding Engineer @ Reddit,

Talent wins games, but teamwork wins championships. Welcome to a Players the Podcast where we'll tell you how to target, hire, retain and train top performers for your team.

I think at every milestone, it just feels like, increasingly humbling. I remember really early on when the first time we hit 40,000 dailies and Steve just had this moment where it like, you realize there's an entire like college football stadium of people showed up today. And now we're like, you know, extra three zeros on top of that. It's kind of, it's kind of insane.

I am Robin Choi, CEO at Hiresuite, and we are sourcing automation software that helps 900 tech companies hire the best talent. Add me and follow me now on LinkedIn if you want to keep an eye on us. Hi everyone. Today we're having Chris, who is CTO at Reddit. So Reddit needs no introduction, I guess. Welcome, Chris. My first question will be can you tell us more about your own story? So I heard the Reddit story before, but can you tell us about Reddit story your own story as a founding engineer and then we'll talk about a players and top performers?

Sure. I think my story is kind of intertwined with Reddit, so maybe I'll start kind of at the beginning. So my original career path was in science. I was an academic for most of my early adulthood. Originally wanted to get a, you know, got a PhD in experimental physics, wanted to be a professor, got a little disenchanted later in grad school and ended up getting roped into what ended up being a startup with a friend. And the side effect of that was by summer of 2005, I had a failed company, two free rooms in my apartment, and became the first employee at Reddit. So it was kind of a whirlwind adventure. Definitely wouldn't have predicted this particular career path. And that's kind of, that is to say, it's history. So, yeah, so by, by October. So it wasn't the first Y Combinator batch. Summer, Summer Bill 5 I think at the time there were 10 companies. And if I remember right, the first company imploded one or two weeks into yc. Like, I'm not even sure they made it to the first dinner. It was like they had an initial like, blow up over IP assignment, which was also like totally enlightening for me, being an academic. Like, oh, assignment of ip, what a, what a novel concept. And then proceeded to, you know, get into it and then get into, get into Reddit and then the rest of the state is history. So at the company for the first five years, saw it through our initial acquisition by Connie and Aston, late 06, stuck around for five years, then went on to another YC company, also founded by Steve Huffman, Hipmunk in 2010, and then five years there and now five years back at Reddit ever since mid 2015.

Right, so I heard about that one. Before you sold the company, you sold Reddit, create a new company with the same people and then join Reddit again, right?

Pretty much, yeah. I think it was a little bit different. My time at Reddit was a little bit staggered relative to Steve's, for example, in that. So Steve originally left Reddit kind of end of 09 and went off and just kind of took an extended vacation and thought about startups. I stuck around through 10, and then by about midway through 10, Steve had kind of kicked off Hipmunk and they'd gotten into the summer of 10 yc batch and he's like, hey, Chris, want a new job? Sure. So it was a bit of a. It was initially a bit of. Some convincing was required, but not a heck of a lot. And so that was actually a heck of a lot of fun. If anything, I think that the theme for the early years of Reddit is we actually never really got much into building the company. We got acquired so early. You know, we were basically a four man shop at the end of 06, and we never really grew much past that point. So we never had more than about five engineers for the first five years, which is a crazy thing to think about in retrospect. At the end of 2010, we were just, I mean, we were so measuring. We're still measuring in units of page views, but we're doing like a billion page views a month, which is just crazy to do with a team of five. I'd scale up at that point.

Right. And so I checked your curse page, actually, so that Today's Reddit is 52 million daily active users. Right?

Yeah. Yep, yep, yep.

Nice. And congrats.

Yeah, no, it's great. I think at every milestone it just feels like increasingly humbling. I remember like really early on when the first time we hit like 40,000 dailies and Steve just had this moment where it's like you realize there's an entire college football stadium of people showed up today, and now we're like, you know, extra three zeros on top of that. It's kind of a country, right? It's a decently sized country.

And can you give us a few numbers about how that user Base grew over the years just to for us to have the milestones and how the company grew. And then we'll talk about how you grew the team at the same time.

Yeah, so I think in terms of like Reddit's growth has always been very steady. We're kind of different from most of the other players in the social space insofar as we've never seen explosive growth and we've never seen not growth. It's always been kind of a slow, continuous increase. So, you know, at this point we have more than 100,000 active communities. We do something like 49 billion comments in 2020 and we've got something like 300 million posts last year. And those numbers are always bigger than the year before it by a decent fraction, something like a 30% roughly year over year growth at this point. I remember the early years, we were kind of more in doubling every three months. And so you can kind of extrapolate the line in between of how the growth has been. It's probably a quick little logistic regression to figure out what the curve looks like, but it's been pretty consistent. The nice thing about that, of course, is that because we've always seen steady growth, it also means we've never seen the kind of viral implosion that you see in some places where it's like you take off really fast and then all of a sudden it crashes when the target group moves on. Which also has meant though that we've kind of had this constant sustained pressure to kind of keep the tech stack working and improve it and iterate it and make sure that we can actually deal with tomorrow's traffic, which is always going to be greater.

Right. That can be a huge challenge. And so when you were back at Reddit in 20, what is it? 2015? 2016.

2016, yeah. So 2015 started dabbling and then 2016 was kind of full speed ahead, back on full time.

Okay, and how big was the company at this stage?

At that point we were at around 70 people. And so that was mostly based out here in San Francisco with a small but mighty contingent in New York doing sales and also another even tinier contingent in LA also doing sales. And so at that point engineering was probably all of 30 people. Now that said for me, that was like the biggest I had ever seen Reddit by far because prior to 2010 there was never more than about five engineers. And so the idea of like, oh my gosh, oh my goodness, with a luxury of 30 people, just fantastic. And from that point on, it's been just kind of rapid growth. So we're currently at about 750 globally. We've since opened offices in Chicago, in Dublin, and we just actually kicked off in London just a couple months ago, if I remember right. And engineering is a good half of that across all of our teams. Engineering, product and design probably is about 350, give or take. So it's a very different scale. Wow. Okay.

So you hired close to 300 people, 300 engineers in three years, right?

Yeah, give or take three or four years. Well, probably more than that when you take into account the fact that people move on in the meantime. But yeah, it's been a Right. So, you know, a couple VPs, got a bunch of lots of directors. It's been a fun challenge. Cool.

And if we look at recruiting now and building the team. So you could probably give a lot of career advice yourself, and you reached that position, and that will be interesting as well. But now let's think of other founders, other CTOs of VP Engineering listening to us. So what's the main advice that you'd give to someone hiring engineers today?

I think my advice is going to depend a little bit on scale of company. And I think that when you're not to suggest that every hire isn't to some extent essential to the business, because they are. And in fact, one of the nice things about our current positioning of being, we're talking about 700 people, which sounds large even to me. But honestly, given our reach and our size, we still have a fair amount of. Every person has a huge impact. Right. At our size, when you're smaller, every employee can almost be sink or swim. You really need to have that initial group of people kind of be very focused on the mission, very focused on the growth of the business. And the trick is to keep that alive as long as you can. At some point, if you have the luxury of being a big company and you can worry about things like management structure and organization and organizational design, then you kind of made it at least as your first pass as a technology leader. But those early days where you have to make sure that everything is covered and you have to basically decide what's essential, it's really sink or swim with your hires. One bad apple spoiled the bunch is the aphorism that fits here. It's like if you have a bad hire in your first 10, that means 10% of your company is in trouble. That's not a good spot to be in.

Okay, and how do you avoid those bad hires then? How do you find the top performers. Do you have a secret sauce here in the assessment in the interviews?

I wish I had a secret sauce. I would say that I think that one thing that is actually really critical is the cultural component. I think that we put a lot of emphasis as technology leaders into kind of looking for the next badass hire, looking for the person who's going to really scale the team up and push hard on something. Those people are decidedly essential, but you also have to make sure that they don't operate by demotivating the rest of your team. I remember when I got early into this, there used to be this whole mythos around the 10x engineer. Those people who basically, I believe they write code by directly imprinting on the dram. They don't actually use a keyboard because that would sully their perfect vision that they have for how they write. And those people do exist. And I've met a bunch over my times. And the overlap between those people and people who are also kind of like humble experts is not as big as you would like. And again, it's a question of stage of company. I think early on, when everyone's operating autonomously and kind of lone soldier and able to pick an area and excel there, that's when you really do need to have the kind of heavy hitters in place, people who know what they're doing and who are going to not be be distracted. As you grow, you've got to start getting people who actually are going to have an impact to the entire team, not just to their own, you know, their own output. And that's when things start to shift around. That's when you start seeing things like the old guard, new guard splits that appear in older companies where it's like, you know, those first 50 employees have a slightly different ethos than the next 150. And you have to kind of like account for that as you start hiring. That's why little things like management appear as being a critical component. It's not that people need to be told what to do. It's that humans are messy. Humans are the worst Turing machines imaginable. From my experience as an engineer, I have to say it's like, give them clear instructions and then somehow don't follow. Like the tape doesn't move, what happened, Right?

So humans are messy. There's a lot of biases in the recruiting. There's a lot of human errors. And not everything can be automated in recruiting. So that's probably one of the biggest challenge, especially when you're hiring engineers. When you're an engineer, Yourself. So what's your biggest surprise? When you had to scale a team from 30 engineers to 300 engineers, what didn't you expect? And what was the biggest surprise as the cto?

I mean, like, this is a little trite, but honestly, I think I mentioned a little bit too, like, the value of management. Like, there is actually a skill. Speaking as somebody who I spent the first half of my career as kind of like more of an IC architect, and I think there was a shift when I kind of came back to Reddit in 1516 where I kind of got dragged into being a full time manager, somewhat kicking and screaming. I've described my career path as being almost like whatever the inverse of a land grab is, where it's like, here, Chris, you're doing great with those teams. So we have another. It's like, great, cool. I'll figure this out then. Management is a skill. It's not the same kind of step in your career ladder as a technologist as I think cranking up in your ability to code or architecture or building out, like any skill it has to be invested in. And also like any skill, you have to kind of learn by doing. So. I think the value, in the same way that one kind of alluded to one bad apple can spoil the bunch early on. The impact of a bad manager is just outmoded compared to their composition of the team. Because now you're talking about they've not only messed up their own career, they've messed up an entire team in the process. And of course that just kind of goes up. Not to entirely emphasize the downside here, I think the inverse is that I really should say this as hiring a fantastic manager, a fantastic director, is one of those things. It pays dividends. You get a team that you thought was effective and you find out that actually they were barely operating on all cylinders and you get those moments of almost. I think what I miss being an IC is I don't get those moments of beautiful code or that you build this thing and it works the first time. Because first of all, it never works the first time. But we all pretend it does, but it never works the first time. You do see that with orgs as well, where you hire somebody who kind of knows what they're doing, or you kind of get it in a setup and like, you just see people operating at full capacity and it's great.

Yeah. And so you can learn by doing, obviously. And you also mentioned that you can invest in this skill. How did you do that? Do you have any good reads to recommend or tricks or frameworks or how would you recommend investing in this?

Definitely reading is one part of it. I mean, I think, like, one of the good and bad parts about management is that everybody thinks that they're an expert and writes a book on it. And so separating out the good from the bad is difficult. This is a case where, honestly, getting mentorship is really important. Like, making sure to actually seek out mentors who've done it before is critical because these are things where you can't. At least with software engineering, you can mostly kind of like, figure it out, live, you know, alone at your computer. When you're talking about management, you're talking about people and their lives and their complicated stories. And so you need a framework to be able to think in, and you need to actually be able to do it, to kind of do it as you learn it as you go. And so finding somebody who's actually already done it or having a senior leader, you can actually kind of tap for questions is very essential. One of the books I did really like, especially as I was kind of growing up as a director, is a book by Ben Horowitz, the Hard Thing About Hard Things. And it's just fantastic. And I think it's fantastic. It's more fantastic after you've already been in the deep end of the pool, because it's like a reminder that no matter how bad it is, it could be much, much worse. There's a. There's. There's. You know, it's always hard to make tough decisions, and there's always going to be more tough decisions. So you have to get it kind of figured out.

I love that book as well. And among all these ocean of management books, is there another one that you'd recommend? I don't know if there is specific things for engineering or.

You know, I am a fan of also the conscientious leadership approach. It's kind of grown on me over time. I think that it's also one of those things where I'd also add the asterisks here of the first time reading some of the books that I think I've kind of taken and internalized. I don't think they had the same impact on me as the second read. And that's just also a sign of. You do have to kind of mature in your craft to kind of really get where the tricks are. So I think for consciousness leadership, the main focus on kind of curiosity being the cornerstone of how you think about the world and asking questions from a place of genuine curiosity, as an essential component that didn't really resonate until, I think, much later in my career when you start seeing that, oh, hey, cool. I actually do have biases and I have personal experience and I have things that are going to cloud my judgment. And so let's go into this assuming that good intent on the part of the person who I'm talking to and kind of going from there.

Right. Okay. There's two other books that we hear people recommend a lot. The first one is Radical Candor by Kim Scott. I don't know if you heard about this one.

Radical Candor. I've had many people tell me I should read that book. It's actually been. I think it's one of those books that's been on my reading list for a little bit too long. So consider that's another. Another, like fuel for the fire. I'll try and pop it further up on the. On the reading list. Other problem with having all of my books being digital these days is I don't realize how big my pile is because.

You should switch to podcasts.

And.

We'Ll actually have Kim Scott on this podcast in a few weeks. So very looking forward to it as well.

Oh, that's fantastic.

So consciously leadership. Radical Candor. The hard thing about how things. Do you read any blogs or do you have while you're there, any other recommendation, I don't know, podcasts or things that you'd recommend for?

You know, it's funny, I think that this is one of those things that's also changed for me in the last year is that having lost a commute in the process of being sheltered in place, initially it was kind of nice because it meant that, well, I lost my commute. It means I can actually just kind of go to work and leave work. The flip side of that is I realized after about a month that my commute was the time when I would do all those things that were kind of like the read the book and listen to the podcast. And because, you know, I would commute and then I'd walk. And so I would have this time to kind of like, you know, sit and sit and listen and think that's kind of fallen to the wayside, which I try to figure out a good way to recover, I think. I mean, honestly, the other thing that's fallen to the wayside, to be totally frank, is like exercise. Geez, it's a lot harder these days. I don't know if you're having that problem. You know, I'm happy to say that I have not gained any weight during COVID I am unhappy to say that I have not lost in either. So I think I've just become like a wagyu steak, well marbled. But yeah, no, I think in terms of podcasts, I haven't been listening to as many recently as I used to is the problem. I used to start my day actually honestly listening to the BBC, getting their radio broadcast. Used to be a big fan of. I'm just going down the list I always loved for economics, just for the little vignettes and little bits of useful information that turned into oh, this is a book I should read. Radiolab, same category for me for the development of personal skills. Trying to think what I was also listening to. Those are definitely the top contenders for just mostly broadening horizons I think was the approach I took with podcasts.

And so the last thing that you mentioned is getting mentors. How would you do this? So it's probably now much easier to talk to people. But when you were at the beginning when Reddit wasn't known, how did you find your first mentors? How do you engage with them, what you tell them? How do you find those people?

I know this is unsatisfying for your listeners probably, but just good old fashioned. Fortuitously this is the value to me of just getting out and going to conferences as well, just meeting people. I think that not every interaction has to be transactional and sometimes you meet somebody who you end up re encountering years later that you find out that all of a sudden you could strike up a friendship or strike up a professional relationship where that might not have happened before. I think that you can't really underplay the amount of value and serendipity. To be totally honest, opportunities and fortuitous connections happen out of nowhere. I think the more scaled approach, honestly is like things that I currently do. There is an SFCTO club that I joined a couple years ago. This has been fantastic and in part it's because the organization of it is. It's a lovely combination of a good talking series, a good breakfast club, a good dinner club back in the before times where we went out to breakfast and dinner and it's a great chance to kind of like cavech and chat with people of similar experience because I think that the CTO job is one that is always a little bit undefined. I think, I think most C level jobs fall into that category of you're kind of doing what needs to be done at any given time. And so finding a. Finding a good support group is A good way to also find group, you know, good connections to mentors, find people who are further along than you are and therefore be able to tap their expertise. Because, you know, you can solve a lot of things just by brute force doing it yourself, but honestly, it's better to find somebody who's actually done it before to kind of get some advice. You can at least get a shortcut or you can find some of the pitfalls you fall into.

And I'm always surprised to see the extent to which people are happy to help. If you just ask them, just send them an email and people will reply. I've been surprised about this time and time again.

I think that's actually the underpinnings of why Reddit as a platform works. What I've learned over the years from being on Reddit for 15 years on Reddit, it's kind of crazy to say, is that, hey, on average people are actually kind of interesting and funny and curious, or at the very least just want to be left alone to do their thing and read and enjoy. A lot of the work that goes into a platform of our size is just kind of making sure that those 1% of AD apples don't spoil it for everyone else.

And do you actually use Reddit itself for recruiting? Do you post your jobs on the subreddit or is it any good for sourcing, especially engineers?

Not as much as I'd like to. I think that actually we did that a lot in the early years. In fact, if anything, it was a lot easier in the early years where we had precious few jobs posted. I remember at one point, you know, we didn't have very many job openings in the early years. And we hired an employee who's now been at the company for, for more than a decade. And I have this great picture that I love of, of just like us, like, trying to sort through this stack of like 500 resumes we got for this one job. I'm just like, you know, laying around the floor. The flip side is the inverse of that is like one place we have actually sourced pretty aggressively on platform is interns. So we started doing internships three years ago, I want to say. And that first batch of interns, oh my God, like, I, I was so. Speaking of somebody who did, actually. So I went to Harvard. Harvard has like, notoriously tight interviewing and like, the pool is always huge and the number of slots is always small. I think we had something like 6,000 resumes for like six slots. So it was just like the initial winnowing pass was just the hardest of like all these fantastic people applying for this small number of internships. And we've since increased our pool and like we've. But ultimately the launch was just a blog post by me on Reddit.

So you had to hire 300 engineers in three years in San Francisco, so probably one of the most competitive place in the world for tech talent. How did you do it? Did you have to write a lot of blog posts? Do you have an engineering blog? How do you create this engineering employee brand? Because the employee brand for Reddit is already here, right? That's already something that's done. Don't have to work more on this. But then there's the engineering employee brand, right?

Yeah. So in our case, we've had kind of a low key blog for a while, a tech blog that actually I kind of constantly want to see more fuel add to the fire. You know, it's like the hard part with the tech blog for us right now is like we've got so much that we're doing and we're building so much that it's always, it's kind of like hard to find time to write about, write about it. I remember one of, one of those lessons I kind of learned early in school was like, the ones that are writing the books aren't the ones that are doing the active research. You have to like, you know, you have to kind of like if you're in the middle of the thing, you're not writing up how to do the thing. You know, that doesn't mean we can't actually spend some time to be deliberate and actually write up, write up more of our learnings wherever possible. But I will say that honestly, the inverse of that is like, because we run a social platform, we can kind of show what we're doing. And also the third thing that is still a very big strategic advantage for us is the fact that we are relatively small. So, you know, for us, we opened a brand new office in Dublin last year and that office is up to, up to a good 35 people, which is, you know, for us is fantastic. That's a drop in the bucket for the tech talent in Dublin. Right. And so, you know, we kind of have the luxury of being able to be kind of picky and like, have people kind of come to us in these situations where we're opening something new. Now that's, that's definitely not the case anymore in SF where it's a, you know, tight hiring market and we have to actually, you know, I don't want to, by the way, underplay this, like, oh, yeah, we just kind of like, our resumes just come to us. It's like, no, we have, like a really good recruiting team that also spends a lot of time, like, sourcing and looking for things, looking for good people, looking for talent. And it takes a fair amount of active work to hire at the rate that we're looking to hire.

Right. So it's proactive sourcing, engaging with people.

With passive candidates, proactive sourcing, reaching out as much as possible. I think that I find the best way, honestly, again, to meet talent is I do miss the days where I could actually go to a conference and meet people in person is great. It's a great way to get people giving talks. I do enjoy that. Talking on platform, just kind of talking about technology, something I actually enjoy. That's the part of the career that I love the most, doing technology. Being a technologist and so kind of showing by example what we're doing and being able to rep for all the work that my team is doing is really what kind of gets me going. And then, so at the moment, it's also like word of mouth, referring, you know, as. As we kind of grow, we. We have a broader base of people that we're connected to that we kind of use as a, As a means to also grow the team. And again, can't say enough nice things about our recruiting team. Just, just a fantastic group of people who are very talented and of course, our hiring managers who put a lot of. A lot of time and effort into growing our team.

How big is the recruiting team today?

I have to double check. We actually just grew it really fast to kind of ramp up for the year. So I want to say that if you kind of go all in, sourcers, sources, recruiters and the like, we're at about 20 people, which is a good, A good chunk of. And of course, the tricky part is we're talking about our target for this year is probably a good 50% growth. And so it's just a lot of time. It's going to have to be spent by everybody in recruiting and sourcing.

Yeah. Interesting to see this multiple. So 20 people for a team of 750.

Okay. Yeah.

Well, congrats for the last 15 years then at Reddit. Looking forward to the next year. Let's keep that growth and let's keep that 50% growth in the team. Thanks a lot for sharing your tips. Is there anything else you'd like to say? Any final word?

No, other than it's been a fun ride. And like I said, I think the best thing about being a CTO has been that every day is a little different because the job is intrinsically what you make it.

People become CTOs. Thanks Chris. Thanks a lot.

You bet.

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