Do you need to go to CTO School?

What CTOs at fast-growing startups can learn with continuing education? Project A’s CTO, Stephan Schulze, shares recommended resources

By Merlin Carter

If you’ve made it to C-level, you’re probably confident that you have all the skills to cover every aspect of the job. Except, perhaps if you’re a founder at an early-stage startup. In this case, founders sometimes take on C-level titles before they’ve really grown into the role. This issue is particularly common for the CTO, who often starts off as a highly technical specialist.

As the startup grows, the founding CTO has to undergo a painful metamorphosis into a fully-fledged executive. Or not. Some eventually step aside and allow a more experienced hire to assume the role.

Could continuing education help technical founders evolve into well-rounded CTOs who stick around for the long haul? Something like a… CTO school?

I recently chatted with our own CTO, Stephan Schulze, to address this very question. As usual, the answer is “it depends”. On what exactly? Well, you’ll have to either listen or read our conversation to find out:

All of a sudden, you’re CTO, and you don’t necessarily have the right skills. Do you think there should be more CTO schools?

Merlin: Hello, Stephan. I hope you’re going well. today I would like to talk about something that I’ve observed a lot, and that is educational material about becoming a CTO. There seem to be more and more books coming out and even courses. I noticed that someone had started a course for CTOs at companies that suddenly became unicorns.

And there are also more established CTO academies. And I know that even you participated in some kind of CTO program at Project A, and my guess is that these are becoming more popular because people realize that the job of developer and the job of CTO is they’re both extremely different jobs. with completely different skill sets to some degree.

And quite often, it’s the case at startups, you are the lead developer, and you’re maybe a technical founder. You help build a product, it grows, and you hire more developers. You become their boss by default, and all of a sudden, you’re CTO, and you don’t necessarily have the right skills, or you have to just learn everything as you grow.

So given that, do you think that the concept of a CTO school is useful, do you think there should be more CTO schools?

“I would say a CTO school, makes sense. You would ideally come out… more like a generalist”

Stephan: Thanks for the question. I think it’s a very interesting question. And I think the main reason behind it is: like in a lot of things in IT or tech, it heavily depends.

If you’re starting a startup for the very first time, founding a startup as a technical co-founder, I definitely think it can make sense to run through something like a CTO school. And the main reason behind that is that you normally deal with things that are beyond the technical scope.

Normally, if you, like the example that you mentioned, like your elite developer or a technical founder, then you are relatively good or strong building the product and in the first versions of the product…but you’re normally not that strong in all of the other areas like finance, like HR, like recruiting processes and all of that.

And to get an insight into that area, I would say a CTO school makes sense. You would ideally come out of such a CTO school more like a generalist person, still with a very strong tech focus, and that can help.

If I see you as somebody who already is in a company being like a lead engineer, or team lead, I could also imagine this can make sense because it will extend the knowledge that you have.

I would still doubt that it will prepare you for a CTO role in a larger company or even a medium-sized company. This is something I would not expect because, very often, these companies like to take someone with proven experience in that specific CTO craft or having a history in that.

And this is nothing you would just get by “Hey, I run through three months or nine weeks through a CTO school”.

I’m just thinking about different types of CTOs; the ones that are in the early stage, what kinds of things do they generally struggle with?

Merlin: Interesting. Just so I’m just thinking about the portfolio. Some of the companies in our portfolio are early-stage startups. Some of them, as you say, are more mature companies, and some of them have gone through very quick hyper-growth and started early-stage but then became middle-stage companies very quickly.

So they obviously all have probably different types of CTOs with different backgrounds. But if you think about the ones that are in the early stage, What kinds of things do they generally struggle with? I mean, you mentioned a few subjects like finance and team management. Could you elaborate on common themes that you see when talking to some of the early-stage CTOs?

“Where they are not very good… sometimes… is… translating this very tech-heavy language into something that is also understandable by others”

Stephan: Yeah, I think one of the typical patterns that I see is… early-stage CTOs… they are very often very technical. So they build the product from scratch. They know every corner and every dark area of the product. And can tell you exactly from the very beginning until the very end how the product works and how the internals are.

Where they are not very good… at least sometimes… is the point of translating this very tech-heavy language into something that is also understandable by others, right? Because if you see the journey of a CTO in the very beginning, you are the tech person, And maybe also the only tech person, but when the company grows, your area of focus will actually shift.

And if we go more into the team management direction, it will go more into stakeholder management, we will also probably touch on budgeting and all of the different areas that are not very strong in the very early stage. And so the pattern that I typically see is that companies start with the very technical CTO.

And then, at a certain point in time, these CTOs maybe also leave the company, or they take a different role in the company because they just feel for the current stage that they are maybe not the right fit anymore because they still prefer to do the full technical stuff and just don’t want to do the management part.

So the management part becomes more and more important the further the company grows, and not everyone is happy with that. And I think this management part is what most people then struggle with.

You’re saying that the technical lead generally gives way to someone who they hire from the outside?

Merlin: Okay. You’re saying basically that, at some point, the technical lead or the lead developer generally gives way to someone who they hire from the outside and becomes like a proper CTO rather than growing into that role themselves and taking it over?

“…very often the tech leads… know their limits, because they never grew a company from 25 to 150 people”

Stephan: Yeah…it’s not that black and white. So there are also people who can grow into that role. I think for a company to get some kind of external CTO, there are typically two reasons.

  • So one could be that the current CTO, head of software engineering, whatever, is not interested… so he or she is going to leave, and then you get somebody in who just takes over here.
  • The second core reason could also be to say, “look, we found product-market fit … we need to scale our whole organization, the way we work, and so on and so forth, and we would explicitly like to get someone in who has done that before, who brings the experience, who brings like a network with him or her and who’s actually able to execute and apply whatever experience that person already has”.

So it’s not about, hey, I’m learning that, and I’m growing the company on the way, but sometimes we have the situation where you will say: “I don’t have time that you are learning all of these process steps and doing all the mistakes”. I would just like to get someone who has done that one or two times or even more times already because this will provide the speed that we need to reach the next level. And this is typically a discussion that happens between the founders.

And also, what I see here is very often, the tech leads or the CTOs, they know their limits because they never grew a company from 25 to 150 people, for example. So it’s something they, they trust themselves [to handle] “Yeah. I would somehow manage that”. But if you take the priority of the company, and the company is more important, then you probably also say, “look, I’ve never done it”. Maybe it’s a very good chance to learn it from somebody who has done it already. So I’m prepared for my next adventure. Or you actually say, “look, yes, let’s please take somebody because the company is more valuable than my personal ego”.

Do you not think it’s unsustainable to only have CTOs learn on the job because otherwise, your pipeline is just going to be very small?

Merlin: Yeah. But I think that’s the whole point of the CTO school idea because, obviously, these more experienced CTOs are extremely hard to find.

I think the strategy there is….people who aren’t confident with growing a company or dealing with all of these new challenges..maybe they want to, but they just don’t know how that’s, why they capitulate or, step aside.

So the idea is, I think to increase the pipeline. Of CTOs, who at least know how to deal with these challenges in theory. And I think some of these schools even have practical exercises and round tables and scenarios and what have you, because… do you not think it’s unsustainable to only have CTOs learn on the job because otherwise, your pipeline is just going to be very small?

“…it’s mainly theory, right?… in reality, we still need to have the flexibility to say, okay, I know this is not the perfect process…”

Stephan: Yeah, I agree. I think there are two parts to that, and I mean we speak of a CTO school or university. So what do you typically learn in school or university is, and this is what you said already… it’s mainly theory, right?

So theoretically, you know how to do a proper recruiting process, to do a good interview, and so on because you’ve read a lot of books, you talk to many people, but… then there’s reality… and reality is very often different because things just develop differently.

I don’t say that a school can’t be very good preparation for that because they at least have the toolset at hand and have the methodologies and all of that. I think the main question is are you then able to apply them and especially also adapt them to the specific situation.

Because this may be a very important thing: we all know how to do things in the best case, but in reality, we still need to have the flexibility to say, okay, I know this is not the perfect process in a particular area, but we understand what kind of toolset we have and take the right tool out of our toolbox say, okay, for that specific station, I’m going to do this and that knowing exactly what I want to achieve with that. And also maybe knowing that this is like an adaptation of a best practice, but it’s the perfect solution for my specific case. And this is something you learn by experience, and this cannot be taught at school.

I don’t think it’s a binary choice between only learning theory and learning on the job. It’s like continuous education

Merlin: But I think… maybe you’re talking about two different things because I don’t think it’s an either-or situation. And what I see in these curriculums for these schools, they’re not doing them full time. They’re going to school while, at the same time, dealing with the real-life problems that they’re learning in the curriculum. So the point is these are people who are still holding the position of CTO. They are just not sure how to deal with these new challenges. And then, so they’re attending, maybe, some meetups or what have you, or doing it on the side while having their normal job. So I don’t think it’s a binary choice between only learning theory and learning on the job. It’s like continuous education.

“All of us are doing that by reading books, by listening to podcasts, by attending any conferences and meetups… the advantage would be that you can consume that in a very structured, curriculum”

Stephan: Absolutely. And if you do it that way, then I agree. But I think there are also CTO schools out there who do like a similar promise of these boot camps, right? “You are nine months with us, you learn all of the foundations and also have a bit of practice, and then you’re ready to become a CTO”.

And this is something where I would say you get like the foundation… you’re probably a better fit to start a startup because you’re better prepared, but at the very end, it will not prepare you for the reality.

If you do it next to your job, then it’s more like further education, right? All of us are doing that by reading books, listening to podcasts, attending conferences and meetups, and whatever. This is some kind of permanent development. I think the advantage would be that you can consume that in a very structured curriculum. And you can heavily connect it with your personal experience.

Can you talk a little bit about how you learned on the job as a CTO?

Merlin: Yeah. And that reminds me of Project A’s own attempts at, I guess, a CTO program. So can you talk a little bit about how you learned on the job as a CTO as part of Project A’s CTO program?

“…the idea was actually to say, ‘hey, we bake our new CTOs ourselves’”

Stephan: We had this CTO or trainee program, I think it was now five years ago, and I also joined Project A as a CTO trainee. And I think we actually wanted to address exactly the same problem that you described because we didn’t have enough CTO candidates for our portfolio companies and incubations in the funnel.

So it was pretty hard to find good people. And the idea at this time was okay. let’s take team leads, heads of IT, engineering, and so on and so forth. Let’s work them together in incubation with the team and build the product and all of that stuff.

And then, after six to nine months, they actually transitioned as a CTO and then into the portfolio company. So that was the original idea. And I went through the program as well, and I also had my first venture, where I learned quite a lot. But still, the idea there was that you are not already a CTO and just learning things on top. But the idea was actually to say, Hey, we bake our new CTOs ourselves.

If you were to restart such a program, would you have a curriculum—what would you focus on?

Merlin: Okay. Yeah. So that’s quite a unique opportunity because you actually get on the field and test your knowledge with our portfolio companies, as opposed to just learning theory. But still having a safety net of having colleagues to back you up. And so, having said that, if you were to design or restart such a program, would you have a curriculum and a more structured way of learning? And if you would, what would you focus on?

“I would… I think it would cover a lot of different topics… the majority of the topics would not go on tech and engineering… more about the rest of the role.”

Stephan: Yeah, I think it’s a very good question. If I would design such a school, I would definitely create a curriculum that I think would cover a lot of different topics, and then one part of that would be tech-related things, but very much on a high level. But, the majority of the topics would not go on tech and engineering, but it’s more about the rest of the role.

  • How do you build a proper tech organization?
  • What kind of processes and approaches should you focus on in different stages of your startup? and at what stage are you?
  • Are you a single person? Do you already have a team of three or four people?
  • What becomes more important to deliver the product in an efficient way?

Having all of these topics around stakeholder management, project management, budgeting, planning, forecasting, and also in other fields of your whole company, right?

So there’s marketing, and I personally think that the CTO should also know a bit about marketing and about the fundamentals of that. You must not be a marketing expert, but you should know about the basics. The same goes for product, data engineering, data science… and also for one of the other areas that are part of your company.

And this would be part of my curriculum if I would say, “let’s start a CTO school”. So the idea is that at the very end, you come out, you have a way broader knowledge than you had before, but not necessarily in tech, that’s one part, but mainly in all other areas that are part of the company as well.

Is there anything that you would still like to learn or improve on?

Merlin: Yeah. And then that makes me think a bit more about your own experience. Again, I know you’ve had plenty of experience now, and you’ve learned all of these skills on the job. But is there anything that you would still like to learn or improve on… that maybe you would like to learn as part of some kind of structured program?

“…I think understanding how to put the right priorities and focus on important things…”

Stephan: Yeah. I would say there are endless things to learn, for sure, a couple of the things that I have in mind is… so one very good example is time management and maybe not time management and how to better organize myself….but I think understanding to put the right priorities and the right focus on important things and to also be aware of situations in terms of, okay: Is it …maybe “cancel like a one-on-one, with a counterpart?”, compared to, “Hey, I have to create some kind of budgeting, and I actually need a lot of time for that”.

So putting the right things in focus to be able to support the company… is something I definitely need to improve and learn more about.

The second thing is… gaining more knowledge in all of the other areas. So I would say I have a bit of a blind spot in the area of data science. That’s definitely something I know I should know more about, even if it’s not touching my current role…but developing a deeper understanding of data science would definitely make sense. And this is because… in the role of a CTO, at least a Project A, I’m not just talking to tech people, but I’m mainly talking to a broad variety of other departments. And therefore, it’s a must for me to have a good understanding of what they’re doing.

Merlin: Great. Our time is almost up, but thank you again for your thoughts. And also, if anyone out there is listening (or reading) and would be interested in a CTO school and particularly as part of Project A, then feel free to raise your hand and let us know. And..maybe we’ll start something again.

Stephan: Absolutely.