Transitioning from Developer to CEO

I used to find it really easy to write. I didn’t know very much about business and wrote about startups constantly – so I probably suffered from Dunning Kruger effect. Don’t laugh, my blog posts back then consistently ended up on Hacker News’s front page.

These days I find blogging about business very hard. I work with a team of people who are smart and have experience and areas of expertise far outside my own. So my first thought as I try to dispense advice to other company founders is “Oh shit, so-and-so is going to read this and know what an idiot I am.”

I think most of my team may already  know how ignorant I am so I probably shouldn’t worry as much.

Anyway, to the point. I used to be a developer  – part of a two person founder team that for over a decade tried to create a business out of thin air, ambition and whatever capital we could scrounge up. At some point the engine actually sprang to life and started running and then quite quickly sped up.

These days we have a going concern with a growing team and whatdyaknow! An actual business on our hands.

Around early 2015 I made a hard transition into beginning to be a CEO as we hired our first team members. The team grew rapidly and today it ranges between 25 to 30 people. The business is busy, we have more than one business ‘division’, three execs, tons of financial throughput and lots going on.


The transition from developer to executive or CEO can be quite challenging I think. To be a developer you need to disappear into your head for around 40+ hours a week and do that for years if you want to be a good developer.

When I’ve been coding for several days, I have found that my ability to communicate verbally suffers. I stutter more – I don’t actually have a stutter, but I have more verbal hesitation. When I’m “on my game” and have had plenty of phone calls and in-person conversations, I find communication easy and I have the ability to make it flow if it gets a bit stuck. I think this is one of the challenges devs face when becoming execs – they need to learn how to communicate and how to make it flow.

As a chief executive, you need to talk to teams or groups of people frequently. The conversation tends to be one sided because you are describing a vision, a goal, a challenge. Even when it is collaborative, you tend to be the one doing most of the talking in a room. You’re the facilitator. Being in many meetings a week where you have to play that role is an acquired skill, but I’ve gotten better at it over time and I’ve also gotten more comfortable with it.

When I started out and our team was just 5 to 10 people, I found our Monday team meetings and Wednesday product meetings quite tiring. We would have them at 10:30am and an hour or two later once the call wrapped, I was just finished. I didn’t have much energy left for a couple of hours until I recovered. As I did more and more of them, I found that they became easier, and then much easier. Now they energize me. It took about 2 years to get there.


Writing is one of the most valuable skills I think any exec needs. The ability to clearly articulate your ideas in individual or group emails, blog posts and documents is absolutely critical. I happen to enjoy writing. I don’t do much personal writing anymore – obviously trying to get back into it with this post. But blogging is, I think, what really helped me become a better writer.

Writing is also an acquired skill and a muscle that you have to keep fit. When I have written several blog posts over a period of weeks, I find things flow when I need to write another. When I’m rusty, the page is an abyss and the abyss stares back.

Writing is probably what connected me with the amazing early investors we had in Defiant (called Feedjit back then). It also served as a source of early marketing, gave me the ability to write compelling copy on our first website and today, writing is how I communicate with our team.


I think leadership and power are often confused. Power is something desired by many. It is seductive and TV and film dramas are filled with scenes of people ‘flexing’ in some way. The fantasy of having someone bend to your will is irresistible if the ratings are anything to go by.

I think when it comes to inspirational leadership, power, a desire for power, the exercising of power and the confusion between power and leadership can be incredibly destructive and toxic for an organization. History has shown that accumulating power and using power devices and structures to manipulate people and groups can get things done. But I choose not to live that way and I don’t want to work for or be part of an organization that conducts itself that way.

My leadership style is still evolving. I’m relatively new to leading a team. I’ve only been doing it for about 3 years now. Perhaps that’s why I’m so willing to write about it – I don’t yet know how little I know. But I would describe my style as follows:

  • Know that there is much that you don’t know and many skills you don’t have and will never acquire. Get really comfortable with that. You’re a hilarious ass. Get over yourself!
  • Assemble a team of talented people who you trust and who are equally realistic about their strengths and weaknesses.
  • Trust your team. In other words, collaborate, and then give them the space they need to exercise their talents and to an amazing job.
  • Collaborate with the team to gather data and then come up with a shared vision for the organization. I find that having many conversations with no whiteboard helps because you are forced to clearly visualize in your minds eye the vision and path forward. That helps you and the team remember it.
  • Once the vision is clear, as CEO you are the custodian and keeper of that vision. It is your job to repeat it to the team when the opportunity arises. The way I do that is to describe where we are headed, why we are going there, how we will get there and what it will look like on Monday morning once we have arrived. [Kudos to my father who was a brilliant CEO and is a great strategic planner for some of that. Dankie Pa!]
  • I generally treat others the way I would like to be treated and the way I want my team to treat each other. I think that requires empathy because everyone has a bad day.
  • I try to create space in conversations so that others can fill that space with their intellectual contribution. I think this may have resulted in others in the organization taking the same approach to running meetings and collaborating.

I no longer code

These days I no longer write code. As with speaking and writing, code is a muscle and if you don’t exercise it, you lose it. If I look at code – usually when I’m evaluating a job applicant or understanding a new vulnerability or exploit – it takes me a few minutes to switch modes and get into the right head-space.

If you are a developer and become an executive or chief exec, I think that it comes with that sacrifice. You may not be the incredibly productive and talented developer that you used to be as you start using different intellectual muscles.


I started my career in operations and did that for about a decade. Then switched to being a full-time developer. So I’m an ops and dev guy. I think that one of the things that is very challenging for technical founders who transition into being a CEO is that you have to step back and trust someone to do a job that is equal to or better than the job that you did.

Stepping back takes a leap of faith. It takes trust. To be completely honest, when Matt B  joined our organization as our first dev hire and I completely stepped back from being the only dev on the product, I actually could not believe the incredibly job he did from day one. I thought “Holy crap, the guy can code and I think he may code better than I do. And he works for us? What is a guy this good doing working for us?”

I think I had a touch of imposter syndrome. I felt like we weren’t a real company even though we were making quite a lot of money and that cash flow was rapidly growing. On a side-note, I suspect this may be why many founders go and raise money – they too suffer from imposter syndrome and by raising money from an investor it makes you a ‘real’ business.

Once Matt and Tim, our first two team members joined, I found that I had to delegate an increasing number of tasks as we hired more people and each time it’s a new leap of faith. You trust that the person you’re hiring is going to do a great job, take your hands off the wheel and every time I was surprised for some inexplicable reason that they did an amazing job.

These days I carefully monitor myself to make sure that I am giving our team the space they need. A day ago I was having a conversation with the team about something technical. It required the developers to discuss whether going a certain technical route was good for the organization, strategically. I initially started leading the meeting and I realized that I was creating an imbalance in the conversation. Because I’m CEO, I was dominating the room and even if someone held a strong opinion they might not voice it if it disagreed with something that I said. Or perhaps they would voice it but my opinion might carry the day by default. So I recused myself from the conversation and asked our lead developer to facilitate the meeting going forward and let me know what the team decides. I also explained why I was recusing myself.


As we scale, leaders are beginning to emerge in the organization. This isn’t the kind of awkward “leadership ability” they teach in high-school where the noisiest or brashest or biggest kid is described as having leadership abilities. Because of the mutual respect we have for each other and the intellectual space we provide for each other in conversations, our leaders are emerging organically and in a very comfortable way. They tend to be the people that simply take on a particular role through passion or necessity or both and the rest of the team acknowledge them as the person to turn to when they have certain kinds of questions or need guidance.

I’m beginning to notice that as we scale, our team is in some cases having to go through the same kind of “stepping back” process that I went through. When we were just a handful of people, we all had many roles. As we grow, some of us are going to have to acknowledge that someone else needs to do a job that we used to do – and perhaps enjoyed very much. That process will be a challenge and we’re just beginning to see that emerge.

Going forward

I’m confident in my ability to continue to grow as a CEO and to grow with the team. We are not a public company working to goose a stock price and we are not a private company that has a high pressure board with a risk of executives being changed out if targets are not met.

One of the benefits of this is that it has created a culture within the company of knowing that it is safe to fail. Kerry (my wife and co-founder) and I failed many times for more than a decade before we created our current successful business. As executives, we are in an environment where we can do risky experiments using large chunks of our cashflow and we know that no board is going to fire us for failing.

Our team knows the same thing. We just started building a completely new department in the company and one of our team members has stepped up to lead that effort. She knows that she can take a risk, step out of her comfort zone and give it her absolute best shot and it’s OK to get it wrong. We’re all in the experiment together and if it doesn’t work out, we’ll just try a different way.

That’s it

If you are a technical startup founder or aspiring founder, I hope you have found this useful. You are welcome to comment here or shoot me an email at and I will do my best to respond to any questions.