From individual developer advocate to the C suite

DevRel career paths aren’t always clear. Here Simon Maple describes his career journey from individual contributor, through director and VP of DevRel, to the C-suite.

Transcript

Simon: Thank you for inviting me to speak at DevRelCon. A real pleasure to be here and talk to so many amazing people both in the audience as well as those running, so a big, big thank you there. So yes, this is going to be over the next 30 minutes or so. This is going to be a story really about my particular path from being really an engineer, but joining developer advocacy and developer relations, to my current role, which is the field CTO here at Snyk.

So, yeah, this is my DevRel journey. And I think all DevRel journeys tend to be different. And there’s no one correct path, or maybe even most common path through a DevRel career. But I think it’s important to talk about our own individual journeys to share those so that people who find specific parts of that journey most relevant can kind of take that on board. So let’s jump in.

And the agenda that we’re going to be talking about here today is really going to start off with my path, you know, the different roles I did in the different companies. And we’ll talk about that per company as well as the different areas of the organizations that I worked into, and talk in some depth around some of the key turning points, some of the decisions I made, or the areas that I decided to focus on which I feel were some of the big moments of change that drove my career.

And then look at things a little bit more reflectively and talk about what I would have done differently, you know, hindsight is always 20/20. But how I would have perhaps changed my approach, or sped things up, or not done other things as well.

So, let’s jump in and talk about what my path into DevRel looked like. And I would say my build up really happened through work from 2001, which is when I first joined my first company that we’ll talk about, and it was an engineering role that I held up until 2010-ish before I really took my first leap into an official DevRel role.

So, let’s start a little bit before that, just to give some background into how I even got into this industry. And realistically, I took a fairly…I would say standard, if not boring, approach into my DevRel group.

I would say I’m the double maths physics, A-level person who did, you know, straight computer science as a BSc at the University of Reading. It was a fairly standard, or maybe I shouldn’t say standard, but a fairly predictable path into a technical route. Now, if you’ve not been to Reading before, that’s probably okay.

There’s no need to change that. But one of the things that I did, you know, just starting more, or probably midway through my third year at Reading University, is I went to the student union and got hideously drunk. I figured that that was probably the best time for me to decide to apply to as many different roles, organizations that I could do for my first role.

And I do remember going back to the computer science department, grabbing a PC, grabbing a computer there, and just making as many online submissions as I can. I specifically remember the IBM submission form because one of the questions they asked me was why I wanted to work there. And I had answered this question plenty of times already that day. And I can’t exactly remember the words I used.

But I do remember the sentiment and it was 100% pure cheese, I would be embarrassed to read that back. Anyway. I got that job at IBM in 2001. And I actually joined as a tester on WebSphere Application Server. And I joined in an organization called BP Deans at the time. It was the feature, it was a low code addition into WebSphere Application Server.

To be honest, I felt like I needed to be a developer. I felt like that was what I wanted to do. And the first question I pretty much asked on my first day is, okay, how do I get into development, rather than test? Test didn’t feel important enough when I was, you know, going from university doing nothing but development, and very, very little test.

I felt like why am I going into test rather than development? I couldn’t have been any more wrong. I learnt so much. I really enjoyed the breadth of what I was learning, the integrations of, you know, pulling…various products together, building all that up. I learnt a lot there. I moved into a team lead role after a probably a year or so. I got some really good leadership experience.

And it was the first time that I really kind of felt that ambition, that drive to want to build up my career fairly early on. At this stage, I would say I have felt very much like a people pleaser. And I think it was probably just because I was lacking a little bit of experience. So I just kind of did whatever I needed to do to make other people happy, rather than what I felt was right for that role.

So it’s still very, very much an IC in that space. After a few years, I moved into development, and I built up a production-level developer skills, the test part that I built up over the previous few years really did help me in that development role, having that breadth and understanding of how products work together. I owned some major features in the transaction service and places like that in WebSphere Application Server, and I had some really, really fond memories.

I remember the very first…the first presentation I gave at IBM, and this was actually someone who couldn’t make a conference trip at the time. It was in the U.S., I think it was New York, maybe. They couldn’t give the presentation. They were ill or busy, I can’t remember which but they had slides, they prepared the narrative, all I had to do was learn the narrative, go on stage, and speak.

So, I did that. I had a little bit of presenting experience, but never in front of a, you know, tons of customers or prospects who were paying thousands of pounds to be there that week. So, it was a little bit nerve-wracking that first time. And of course, you know, with travel over to the U.S. and things like that, it was tough. But everything went really well. And I started doing it more and more. I got the bug.

Still, pretty much, you know, presenting other people’s slides rather than my own, but it was really great experience. I enjoyed the stage. I wanted to do more and more. And I grew into building up my own slides, building up my own narrative, giving sessions, still very, very technical sessions, though, rather than anything too storytelling. I built up, oh, sorry…I rather, I did other things like high availability workshops, did things for services and support, which isn’t my strongest thing, it was outside of my comfort zone, but when the opportunity arose, it was something I wanted to take.

I still remember having that kind of carefree, if it goes wrong, it goes wrong, I can do anything without consequence, I’m bulletproof nature, which I think, you know, when you’re younger, you kind of have that feeling of less to lose. And it slowly replaced that, my feelings slowly were replaced by very much an imposter syndrome, which of course, we’ve all experienced and something that I still have today.

Of course, everyone mostly does. But what I’ve really just done is learnt how to deal with it, learnt how to accept it, recognizing it’s there, and understanding why it’s there. But that was my first kind of presentation experience that I did as part of my engineering role. I also did some tech blogs. I did some writing for developerWorks. I got paid for it extra.

But that wasn’t the only reason why I did that. I really wanted to get my name publicly out there. My name next to some articles that I wrote. I also did some community work in and around the London Java Community. I interacted with other DevRels. And I talked to a lovely amazing person called Zoe Slattery, incredible DevRel, who really introduced me into the role.

And I didn’t even realize a role like this existed in the past. I’d never heard of it before. But I was very, very interested in what she did. I’d also say someone at IBM who I think influenced my decision to go into DevRel would be Andy Piper, who I, you know, very much admire, and he’s absolutely someone I looked up to, and look up to today, and learned from just listening, seeing how people do things, watching how…that people present and things like that.

But I remember, Zoe and Andy were absolutely my first kind of people that you admire that you want to aspire to looking into their roles. So, I tried doing a 50/50 role. And I looked at it. I was essentially rather than splitting my time between the two 50/50. I was two doing jobs, I was doing two full-time jobs. And it was hard.

And I had to make a decision. I was worried about that jump of going from an engineering role, something that people consider very, very technical, to DevRel, which sometimes when you think about it being, you know, less development, maybe looking at it as less technical. But, you know, it’s not, it’s a different type of technical role. And I was quite worried about that jump, I’m really pleased I made it.

I didn’t need to be. And even if it’s something I didn’t want to do, I could always just jump straight back into a Dev role I’m sure, particularly at IBM, where people move around all the time. So I continued to do that DevRel role for two years at IBM. And I’d say, you know, being a product developer, I did a lot of things that were outside of my job, very uncomfortable for me, doing communication, representing IBM, learning from other people, listening, sharing, collaborating, it’s uncomfortable to be put into that position straightaway to be able to do those things.

But actually, it happened very, very naturally, and I grew that thirst and hunger for those types of activities. I would say that of my career, these are some of the most important skills I’ve learnt. Everything else I would say is far less transferable. And these are things that I use everywhere, not just in my job, but across, you know, with friends, family, my wife, my kids, you know, the communication and listening, the collaboration is super important to be able to learn all those, and things that I feel are some of the most important things I want to teach my kids as well.

But let’s talk about my actual roles now and how I progress them. So, first of all, a couple of things here, everyone’s roles and everyone’s journey is going to be quite different. I would say there’s a huge amount of hard work in here that I’m sure everyone is already doing themselves as well. But let’s not forget how much everyone has luck in their career path and their career journeys.

And I feel like I had a lot of luck in mine as well in terms of, you know, having the right opportunities and being able to grab those, having people that believe in you, having the right people that are mentors at the time. That is one of the things that is absolutely priceless for you to find and hold on to in your journeys as well.

So, I found some old business cards, this is my first DevRel business card or, in fact, in this case, it was technical evangelist back in the day. At IBM, I had to do a lot on brand. I had to understand how webSphere can be more relatable to developers. Lucky, I worked on Liberty Profile, fast, Dev-friendly version of the app server. So, it’s something I was able to be passionate about and be able to present.

I did find interesting things like getting that running on a Raspberry Pi even before they were released and being able to show that IBM impact which was IBM’s premiere kinda WebSphere conference at the time. There were a few things that, at the time, really frustrated me, red tape, bureaucracy, DevRel was still fairly new to the industry, and certainly new to IBM, and groups, and individuals, and teams were learning how to navigate it.

So, that was tough. I ended up, kind of, like, feeling like I was explaining my existence too much. And really, every week trying to justify my role. And it was getting very, very tiresome. So, I realized I needed something else. Also a product set and suite that some kind of experience that Dev’s absolutely craved and needed.

So, a company I needed that got DevRel all the way to the top with far less red tape and things like that. So, I felt I needed a startup, which was a big, big jump for me going from, you know, 12 years or so in a massive company over to a startup. And that’s where I moved to ZeroTurnaround. I was around a 70th higher. I was a tech evangelist, which of course, I soon realized should have been rebranded to a developer advocate there.

And of course, note the great and interesting business cards here, which are quite different. I still put my telephone number on…my personal telephone number on my business cards, which was something I did because I felt like it was right at the time, but that’s another discussion. But in this role, I felt like I could really express myself, and I feel like that was really important for doing a DevRel role. And I feel like, you know, doing things like, I did a music video to Carly Rae Jepsen’s, “Call Me Maybe,” silly things like that, that pulled in, you know, some interesting product stuff.

I created a virtual user group for Java, which is almost a decade old now. And that virtual user group almost has 20,000 members today. So, I started thinking outside the box. One of the things I needed was a Post-it note next to my monitor that said, “JFDI, just fucking do it.” Right?

And this was because I was previously asking permission to do everything. And I kept getting back, when I was asking permission to do things in my new company, in ZeroTurnaround, Why you asking me? Just do it. And I needed to put that there just to remind me to have more self-belief in my own actions. And to understand that what I was trying to do, I was doing for the right reasons and justifying that. And actually getting on to do it and being judged by my results rather than my way of getting them.

So, IBM sometimes I felt like I almost too inward facing, and ZeroTurnaround was the first time that I actually existed in other people’s communities, rather than, you know, things like the big IBM conferences and things like that. This was the first time that I really met some amazing people on that journey as well, and the communities that I was growing into were really important to me.

I would say amazing people like, you know, Josh Long, Venkat Subramaniam, who I really, really respected both as incredible speakers. Trisha Gee, who is simply just an amazing DevRel person and great leader. Martijn Verburg, Arun Gupta, Barook, Matt Raybould, Markus Eisele, Sam Hepburn, hundreds of people that I haven’t mentioned here as well that I could kind of list, but it would take the rest of the presentation, that people that I learnt from that helped me on that journey.

I would say in this role, I became a team lead as the company grew to around 150, 120 people, that kind of number. And I grew a team of a few people. I felt like they were more an extension of my activities than me actually becoming a real true leader. I felt more like this was just an ability to scale what I was doing rather than really an extension of the function of DevRel.

So, I got promoted to my next role which is director of DevRel. And this wasn’t as a result of me being a manager or the team getting big enough, it was as a result of my ability to show a strategic plan. And I talked to many others that, you know, really grew my plan together. And that plan was, you know, understanding KPIs, understanding my goals, and these were some of the most important career steps still that I’ll cover in a little bit more depth.

But this was one of my biggest deviations, I would say, from my main job. Six years later, I joined, sorry, ZeroTurnaround was acquired, and I moved to another startup in 2018, called Snyk. This time, it was a little earlier, I was the lucky 13th employee in London and around the 20th worldwide, high 20s worldwide.

It’s a very, very much earlier startup, I would say than ZeroTurnaround, just announcing Series A. Greater risk, but, you know, today, there are almost 1000 employees just 4 years later. But this brings its own challenges. You know, this is a startup that is growing the same speed as Stripe, Datadog, those kinds of companies, ramp up and growth is very, very, very, very tough to deal with.

You have less time to fail, you have more chance of personal growth, though, and opportunity. So, as the sole DevRel, I built up a team of around 10 people plus in EMEA, APJ, and Americas. My role turned more into a second line manager role. But I feel like the area which grew myself into the VP role was really about how I built other teams’ goals and needs into my own.

It was about how I could make others successful as well as the DevRel team. And this was the VP of DevRel. And I was given an option here to go the senior IC route, or VP managerial route. And I didn’t expect I would 100% love the VP route because it was more a managerial route and, was a manager what I actually wanted to do? I had, you know, history of kind of hands-on roles by then.

And I knew that was what I most enjoyed. But I would say, this role and my previous role, that I definitely couldn’t do everything myself. And it was really important to give things away that I already knew I was very successful about. And it always feels hard to do that because you feel like that’s what people are saying thank you, that’s what people are encouraging you and giving you the appreciation for, but you need to give that away in order for you to learn the next skills in terms of growing yourself.

And I hired some amazing people, Liran Tal, a great example of incredible DevRel. Very, very natural DevRel. But he was the first person I appointed to director role beneath me, and that was giving him not just the team, right, a part of a team to run with, but also asking him to do the strategy and build up the goals and KPIs for his part of the DevRel team.

And that allowed me to do more with other wider parts of Snyk. So, yeah, my new role was very, very managerial. I had a couple of years experience in the role, but I was ready for my next challenge. And I knew that wasn’t in the pure manager space. Because as this team grows even further, I would pretty much just be 100% managerial. So, that time, I knew I needed to go more into a contributor role.

But it was going to be a senior contribution role that I wanted to get back to that IC vibe a little bit. One of my other best hires, Patrick Dubois. And I know I shouldn’t have favorites. But hey, Patrick Dubois once told me he was a reluctant manager, he was a manager when he needed to be, which is a wonderful phrase that he mentioned to me, and I realized it fit me well as well.

It’s not something that I need as my role to be a manager. But it’s something I’ll do if I need to be. So, and my next role was the field CTO at Snyk. And this is a role that requires me to have much higher-level vision style sessions with C levels and customers, understand the market better and make them successful. I needed to now make not just our team, the rest of the business successful, I need to make others successful as well.

So, this is a role that I applied for. And while I didn’t meet the job description of this traditional ex-CTO, somebody who had operational experience, I felt my DevRel background had a lot to give to that as well. Someone who is able to really communicate, build content, learn from others, and then share that experience back to others to make them successful to share best practices and pitfalls.

So, I brought my DevRel skills to this role, which I felt was very, very important. Now, if we was to take a look at the decisions that I’ve made from a company point of view that I think are equally important, when I moved from IBM, it was because I wanted to take more control of my role, like I said, less bureaucracy, etc. I didn’t really want to justify my job all the time.

But to get such a role, I needed to make sure that there were three things, really, that I thought about. One, that DevRel was truly needed in that company, it was actually going to be valuable to the company. Secondly, that the company was Dev-first, they had freemium offerings, they had good trials, it was self-serve, they valued developers. Then that from the top down, from the CEO down, they understood DevRel.

And I made sure that in my interviews, luckily, it was a startup, so I could speak to the DevRel, speak to the CEO, and understand what they wanted from DevRel, how they understood it. I think that was really, really important. And while these were met with both ZeroTurnaround and Snyk, by the way, these are the backs of my business cards, and it’s great to see how each company deals with this differently.

But yeah, while, you know, I wanted that at each company, for each of those three to be addressed, what I really needed was to understand where red flags were because that’s the easiest thing to be able to spot where a company is not right for you. Where a company is right for you, it’s hard to decide, right?

Because it’s you need to really live that, you need to understand the culture. And it’s hard to do that just in interviews. But to spot red flags is a little bit easier. So, one of the core things that I needed in each of these companies was mentors. And I was lucky enough actually that some of my mentors were also the co-founders. So, Jevgeni, JK, at ZeroTurnaround, Guypo at Snyk, really helped me, and I was being very, very transparent with them in order to be able to say, “You know what? This is where I want to go. How can you help me spot what I’m missing and what I need to do to go through that journey?”

So, I’ll finish off with just, kind of, like, some of the career turning points. And then we’ll take some questions. I think some of the career turning points here, first of all me just getting into DevRel in the first place and taking those steps, even though they were uncomfortable, and even though sometimes I wasn’t getting huge amounts of appreciation in the engineering role, it was what I wanted to do and I recognized that early on.

I’d say going from an IC to a team lead really built some of my managerial skills, but it didn’t really help me strategize or anything like that. I would say doing that into the…that was probably one of my biggest turning points actually, stopping and assessing why I’m doing things, trying to pin that back to company goals, pin that back to different parts of the organization, and why it’s helping them and understanding their goals.

And I think that’s really what led me into that VP role, where I’m actually looking at others and working with others to help achieve their goals and make sure that our team, the activities that our team are doing are aligned with those as well. And I think moving more into the field CTO, the big turning point now is really actually understanding what I was passionate about. And that wasn’t necessarily the managerial space.

The piece that I was passionate about was my own contributions, my own learnings. And I felt like while VP was absolutely something that built me up as a person as well, doing that IC piece was what actually makes me happy day to day. And I think that’s the core DevRel in me wanting to break out.

So, what would I have done differently? There’s three things that I’ll say before I jump over to questions. The three things that I would do differently, I would say is I would definitely give my Legos away earlier, understanding what you are, when you are being really successful, people often think that’s where I need to focus, where I’m most successful, where I’m able to deliver.

But if you’re not learning stuff, if you’re just doing the same thing, you’re not actually going to grow your career, it’s important to be able to give that away and master the next thing, if it’s seen as a place that you want to grow. So, helping others grow faster will actually take more away from you. So, you have more time to spend on the areas that are going to grow you. I would have spent more time hiring, particularly at Snyk here, whereby, you know, 30%, 50% your time, by hiring, you’re actually going to build up more of those people who you can give your Legos away to, of course, this requires a company that has, you know, is in active hiring mode and growth mode.

But that was a core thing that I took way too long to learn. So, actually spending that time early really, really helps six months, even a year down the line. And I’d have got into DevRel earlier. I think joining a startup earlier as well would have really helped me, you know, with that growth and speed of my career.

So, I think jumping into something that I knew I had passion around, that gut feeling that I wanted to be in DevRel. I wish I would have taken those steps earlier. But those are probably the three things that I would have personally done differently. And with that, I’m happy to take questions. I feel like there’s some in the chat already, Matthew or Joe.

Joe Nash: Oh, indeed, some in the chat. Thank you very much, Simon. That was wonderful. And thank you to everyone for asking so many questions. We do only have time for two, but Simon is in the Discord, and I believe will probably jump in over there. There’s some great questions, particularly around your enjoyment of Carly Rae Jepsen’s back catalog. Let’s begin with the first of the questions, which I think this one from Chatterbox Coder Nathanial, is a great one to kick us off, which is, “How did your priorities change the higher you moved in seniority?

I.e., have you found yourself serving developers less?” is the example Nathanial gives.

Simon: I think I haven’t found… Well, in my specific activities, I have directly I would say engaged with developers less probably. But that’s just because I have less time to kind of do more of that hands-on stuff. That said, I don’t think, my actions I feel actually have a greater chance of serving devs more, because I can put a better plan together, a better strategy with a team that can actually have more of an impact on them.

So, I would say, my individual activities, yes, I was serving developers less with my individual activities. But across the team, I was doing a much greater job and serving more developers as a result by, you know, having a team that I could work with to do so.

Joe: Wonderful. And then I think this question is a great one. “Do you have some examples on how you have made other teams and other people in your organization succeed alongside your DevRel team as you’ve advanced into these leadership roles?”

Simon: Yeah, great question. I mean, I think one of the core areas is ownership. Being able to give anyone ownership is an extremely strong way for them actually to put their own mark on something. So, I always ask people to take ownership, build a plan around something, and give me their opinion, rather than just do what I say, you know, that’s not leadership.

Or, you know, that’s really something you would do if someone only ever wants to do a specific job and be told what to do. That’s not how you grow people. So, finding ownership, that’s not necessarily a team ownership. That could be anything from, “Hey, I want you to own the cheat sheet strategy, or the report strategy, or owner events, or…”, you know, there could be lots of different things as well as geographies. So, ownership is extremely important to be able to grow people.

Joe: Wonderful. That’s a fantastic answer. And again, thank you very much, Simon. We are going to release you into the Discord to answer as many of those questions as you want and to hang out for the rest of the day. I really appreciate you kicking DevRelCon off and giving us such a fantastic start. Enjoy the rest of your day.

Simon: Thank you.