Fifty shades of CTO

“What is a CTO? What do they do all day? How do I find a good one?”, I hear you asking. Well, I have the same questions and I am a CTO, so you’re in good company.

The answer is, of course, that there is no single answer. However, there are common themes. This post describes models I find helpful to reason about the different types of CTO roles. If you’re thinking about hiring a CTO, hopefully this will help you figure out what profile you need and what to hire for.

The 4 CTO archetypes

If you look at job postings for CTOs you’ll see quite quickly that there’s no archetypal job description. Instead, you’ll find widely varying responsibilities and requirements. That’s because “CTO” has very different meanings for different companies, from infrastructure management to technical strategy to managing engineering and product teams.

In what is arguably the best-known article about what a CTO does, Werner Vogels (CTO of AWS) describes 4 types of CTO roles:

Infrastructure Manager

“takes on the responsibilities for infrastructure and IT operations: data center operations, network operations, application development and maintenance, security, and other line functions. The CIO retains the responsibility for how technology is actually used within the organization”

Technology Visionary and Operations Manager

“is responsible for determining how technology can be used to implement the business strategy […] then subsequently, is responsible for actually integrating and running the technology”

External Facing Technologist

“the intermediary between clients and internal development and the main influencer in the development of the product portfolio” (note that in this model, you can have several CTOs: by vertical, product range or geography)

Big Thinker

“spend their time evaluating how technology can be used internally to developed new business models and business lines, and how to preempt competitor’s attempts to use technology to disrupt the markets”

The typical start-up/scale-up CTO falls squarely in the Technology visionary and Operations manager quadrant, but (at least judging from LinkedIn job postings) it’s also common to see External facing technologist and Infrastructure manager CTOs. I’d argue that Big Thinker roles are rarer1 but there are some well-known examples: for instance, Bill Gates stepped down as CEO of Microsoft to become its Chief Software Architect and concentrate on product and strategy.

There are some very clear differences between these 4 archetypes. Some profiles are external-facing, while others turn their attention primarily inwards. Some roles are very operational, focusing on implementing the roadmap or supporting the business, while others are less hands-on and more strategic. Some manage large teams, some are individual contributors. And the role can either be considered a pure cost center (infrastructure manager), be part of a profit center (tech visionary and operations manager), or even belong to the commercial team (external facing technologist)!

So internal vs external, operational vs strategic, management responsibilities and position in the value chain are our first criteria to calibrate a CTO role.

Mad Skillz

Expanding on these criteria, Mark Ridley identifies 9 skills required by different CTO roles.

9 axes of CTO skills

The CTO skillset wheel - from What flavour CTO does your business need?

These skills are :

  • Domain knowledge: is domain-specific knowledge or previous experience in the field required to fulfill the role?
  • Engineering: producing software or platforms; ability to make technical and architecture decisions; knowledge of software development practices
  • Strategy: ability to help define the company strategy, interface with board members or investors, build out long-term plans
  • Product: defining and building the products of the company, prioritizing features, managing a product team
  • Business technology (aka IT): managing internal/employee tools (CRM, email, etc.)
  • Data: knowledge of data science and data engineering; ability to organize, manage and extract business insights from the company data
  • Large teams: management skills, especially management of large teams and HR experience
  • Commercial: the original article describes this as the capacity to build complex financial models and experience with M&A and procurement. I’d expand this definition to cover customer interactions and pre-sales
  • Security & compliance: focus on regulatory, compliance and security topics; knowledge of relevant standards and certifications

Using this model, you can recast the previous 4 archetypes in terms of main skills.

Infrastructure Managers will score high on Business Technology, Engineering, Large Teams and Security & Compliance, but have little say in Product or Strategy and usually don’t need a lot of Domain Knowledge.

Big Thinkers on the other hand essentially focus on Product and Strategy, applying their Domain Knowledge and past Engineering experience, to the exclusion of the other skills.

External Facing Technologists score highly on Commercial, have strong Domain Knowledge and enough Engineering and Product know-how to be an efficient go-between between customers and product/engineering teams.

Technology Visionaries and Operations Managers have a firm grasp of Product and Engineering as well as Strategy. In larger companies, they also need strong Large Teams skills. In smaller start-ups, they usually have to dabble with a bit of all the other skills.

Of course, you don’t have to stop there! These skills are non-exclusive, so you can combine them in other ways, according to your specific company context.

You could even imagine a CTO role requiring high skills on all 9 dimensions. However, I encourage you to think about what this means.

Do you need someone who has expert domain knowledge in your field, who can define a world-class strategy, masterfully execute it along both product and engineering dimensions, and then sell it to your customers? Who also knows how to build and manage an entire engineering organization, can navigate regulatory and security topics blindfolded and science the shit out of your data? Oh, and who will gladly set up WiFi routers and troubleshoot printer drivers?2

Now, can you imagine how exceedingly rare and sought-after (not to mention eye-wateringly expensive) such a person is?

Size matters

There’s a final facet to take into account when defining a CTO role. It only applies to start-up/scale-up CTOs, but in this case it’s in my opinion the most important factor to take into account: companies of different sizes need different types of CTO.

This article (in French) outlines 3 different profiles.

The hacker CTO thrives in small start-ups, where he is the lead dev/product owner/primary builder of the solution. This profile is first and foremost a developer, whose skills are critical for the company to iterate quickly and find product-market fit. Jack of all trades, this CTO is able to find inventive solutions on a shoestring budget, and is not afraid to throw everything away and start again when the startup pivots or the technical context changes.

Once the company starts to find traction and grow, it becomes necessary to structure the platform, the tech team and its processes; this is where the stabilizer CTO comes in. They focus on building a sustainable platform (while not slowing growth!) by introducing best practices and methodology and consolidating all the technical choices (and debt) from the first phase of the company. They also build out the tech team, by hiring and coaching new developers.

When the company becomes a scale-up, it needs an industrializer CTO who will focus on tech leadership. Strategic vision and a good relationship with critical stakeholders (other CxOs, the company board, etc.) are required to steer the company in its expansion, and the bulk of the role is centered on leadership and strategy. At this stage, the company will often have hired a VP of Engineering to steer the day-to-day activities of the tech team.

Another way to look at these three profiles is through the metaphor of commandos, infantry and commander in chief3.

Commandos are the first wave of troops to see battle; their main advantage is speed, and their goal is to establish a beachhead as fast as possible. Commandos are not afraid to take risks, they move fast, and they are comfortable in uncertain, volatile situations. However, they soon get bored and start looking for the next beach to storm. Likewise, our hacker CTO thrives on building new things and dreams of disrupting the market, but may have trouble transitioning to a more orderly way of working.

The infantry hits the beach en masse and consolidate the commandos' early gain, securing the beach, building defenses and moving inland. Because there are many more soldiers, with more varied duties, they need processes and rules to work efficiently. The stabilizer CTO is akin to an infantry captain whose job is to take over the early product and “secure” it, building and relying on a tech squad working from a common playbook.

Then comes the rest of the expeditionary force, led by a commander in chief. Its role is to establish a sustainable presence, coordinate with allies and other armed forces, oversee the progress of the front line and decide where and how the next battles should be fought. Accordingly, the focus of the commander in chief is on logistics, coordination with stakeholders, and strategy, much as what is expected from the industrializer CTO.

Recap

4 CTO archetypes, 9 skill families, and 3 company sizes make for a lot of combinations, and a lot of differences in the day-to-day responsibilities of a CTO. Do you need an infrastructure manager, or a big thinker? Someone who will parachute behind enemy lines or oversee the battlefield from afar? I hope that thinking about the role through these prisms will help you determine what the “right” CTO is for your company and your current context.

Addendum

As always, it took me a long time to write this article. While I was procrastinating, Daniel Jarjoura published an article describing the startup CTO growth cycle. He outlines 4 steps in a startup CTO’s evolution, with the skills required for each. Go read it!

  1. At any rate, they are not usually advertised externally ↩︎

  2. I am painfully aware that I just summarized the typical start-up CTO job posting. ↩︎

  3. this is an adpatation of the commandos, infantry and police metaphor. In it, the police steps in to administer the territory once the battle is won. Their job is to keep the situation stable and maybe make incremental progress, which would fit in with how a large, established company operates once its scale-up days are behind it. ↩︎