One CTO wrote about this problem on the alphalist CTO Slack.
“Hey Alphalist!I'm currently struggling with my role after the luxury problem of bootstrapping our company all the way to Series B stage as a cofounding CTO. With a headcount of 100+ and growing, I'm a creator, visionary and architect at heart, but these days I'm torn between getting the zero to one projects off the ground where I historically created the most value (but it's getting weirder for both the teams and me to work on something directly together with the CTO) — and the ever-growing organizational workload that's something that doesn't fulfill me as much and that I frankly suck at. In Simon Wardley's model, I'm a 100% Pioneer personality who's grown himself into a Town Planner role that doesn't fit me well right now.I'm looking for good resources, but first and foremost an experience share from someone who's dealt with this kind of situation and reinvented themselves in some kind of way (and/or rebuilt the organization in order to suit their strengths and weaknesses)” - post on alphalist CTO slack
Of course, the alphalist community rallied around their peer with offers to discuss their learnings and some even wrote down some things they learned. In this article, you will have a round-up of some suggestions as well as some tips from alphalist CTO podcast episodes - all arranged in a cohesive manner.
Discover where you can add value
What do you love?
“Find your value inside a growing organization [which is often] not being attached to titles (which can be harmful). It's more important to be fulfilled and work on things you really enjoy rather than keeping a title for posterity's sake and being miserable every day because you hate managing people. I see way too many founders who pigeonhole themselves into not doing what they love. And that's a bit sad. Like, as a founder especially you have a choice as to what you spend your time on. “ - Renaud Visage, co-founder and ex-CTO of Eventbrite, speaking on the alphalist CTO podcast episode #67
What does your company need?
You need to think about how your personal skillset and interests can be matched with what the company now needs.
“I think you should think about how can I bring the most value to my company every day. And that's something I tell all the founders I invest in.If you're not a [good] CEO for this company - realize it quickly so you can hire the right person. You are first and foremost a shareholder. And as a shareholder, you should think about what's best for the business and make that compatible with what you love doing. And we know life is short, especially after Covid made us realize that sickness can come at any time and strike. So being very thoughtful about what you spend on your time on finding the right balance between work and life has always been something I've put a lot of emphasis on. And Eventbrite especially puts a lot of emphasis on.”- Renaud Visage, co-founder and ex-CTO of Eventbrite, speaking on the alphalist CTO podcast episode #67
Delegate that which you don’t like doing
I think the best advice I received was to make myself unnecessary for all the “boring” stuff” -Joa Ebert
First of all, you need to decide if this organizational load interests you or not.
More specifically you should think about if you want to become an inspiring people lead that is able to hands-off drive the companies technology through your directs.” - O. on the alphalist CTO Slack
If you don’t want that, “you should think of an alternative VP engineering structure that takes over a lot of the organizational/operational tasks and gives you the room to concentrate on strategic or explorative topics rather with a smaller team” suggests O. Another way this was implemented in a different company was that they hired a Head of IT who paired with the CTO and took care of all the organizational responsibilities.
Mistakes when Delegating
Delegating by creating a new role is not as simple as it seems. If you keep your CTO title, you risk undoing whatever work your new hire is doing.
“The difficulty that I see and that I experienced (as the new hire) is if you hire a Director/VP/Head of Eng [you usually] hire someone to ship reliably at high and constant velocity. They take over all the organizational and process-driven things you grew tired of.Now, when you are a pioneering personality, your desire is to be innovative and try disruptive things. So you take a small team of engineers and start disrupting, going against everything that you hired your Director/VP/Head for. However, since you are the higher ranking member in the org, people will follow you instead of the Director/VP and you make it a "Mission Impossible" for them” - T. on the alphalist CTO Slack
The solution that T. recommends is for you to hire someone else as the CTO and for you to change your title to something like VP of Innovation. But that might be frustrating for you.
“It can work if you have very mature personalities in your team with not a lot of ego. However, my experience is that at the executive level you are very likely to have strong egos and you'll likely run into a situation where you achieve exactly the opposite of what you originally intended to achieve. My success rate so far: 1x with a very humble, low-ego, results-driven person as my superior: awesome experience. 2x with strong egos, goal-driven personalities: easily worst time of my career" - T. on the alphalist CTO Slack
Do What You Love
How CTOs can code
In the initial Slack message, the poster voiced that they would like to go back to getting their zero-to-one project off the ground but were concerned that it would be weird for their team to work on something directly with the CTO. While this is a concern that needs to be addressed. (Perhaps you, dear reader, have some advice), Renaud didn't mention is as a problem.
I always like building and I always found it more impactful for me to spend time on whatever the next big project we had. So, that's how I evolved in the organization. Every six months to one year, [I'd pick] whatever was the biggest hurdle to our growth that I could solve with a small team [which I would handpick myself]. - Renaud Visage, co-founder and ex-CTO of Eventbrite, speaking on the alphalist CTO podcast episode #67
One project Renaud worked on was internationalization. When they decided to launch in Europe, they had to make the site work for each country in Europe. They built an MVP for each country. They had to translate the site into German, French etc., and deal with local taxes and unique features. Renaud headed up this project which involved migrating to Django and doing all the string extractions, automatic translations, etc. He would cycle around the company working on building new features that way.
How CTOs can focus on Tech Innovation
Perhaps as a CTO you want to be at the forefront of whatever innovation your company is working on.
There's always these large projects that the CTO wants to remain hands-on with and not be purely managing. [Where the CTO] can spend time on them. Those are the nuggets that enable the company to go further and are equally important as to how well you manage your team.- Renaud Visage, co-founder and ex-CTO of Eventbrite, speaking on the alphalist CTO podcast episode #67
One project Renaud was involved in was discovering other software tools that would enable Eventbrite to diversify its revenue streams.
Recently.. we realized that we needed to diversify our revenue. Until then, we were very like purely transactional. A ticket is sold on the event site for a price and we take a commission. That's our business model. We wanted to introduce some recurring revenue, so we looked at all the potential other fields that we could build software on and ended up picking event marketing as one of the options. So we built a suite of tools and acquired a company that was doing event marketing and bundled that into a [nice] size offering for event organizers. - Renaud Visage, co-founder and ex-CTO of Eventbrite, speaking on the alphalist CTO podcast episode #67
When To Move On
Moving on is a personal decision. It could be tough to move on as the founder of a company. For Renaud, it took 16 years before he was ready to move on. At that point, he realized he just didn’t have it in him to spend the next 3-4 on the event topic anymore. He has exhausted his interest in that space.
“And at the end of 2021, I realized that maybe I didn't have it in me to spend the next three or four years on the event topics anymore. I think I had exhausted my interest in the space and, and my value inside the company. Because I was coding less and less, I was investing on the side more and more as an angel. I was working with venture funds and I decided that's what I wanted to do full-time. So it made sense for me to step down and, and go do something else. And 16 years is a long time already. “ - Renaud Visage, co-founder and ex-CTO of Eventbrite, speaking on the alphalist CTO podcast episode #67
Conclusion: In this article, we discussed how the founding CTO can evolve their role within their company, by delegating that which they don’t like (perhaps making changes to the org structure) and finding areas where they can contribute the most value. This is a loop you can continue on as a CTO until you realize, like Renaud did, that you have nothing more to contribute to the company.