The Roadmap To Becoming A Great CTO: Skills, Strategy, and Rewards

A former co-worker reached out to me recently. They are a director of engineering at a midsize startup and just got their first headhunter inquiry for a CTO role. Having never been in the role before, they wanted to know what the position was like and how to prepare for the interviews.

I realized that while there are some books on technology leadership careers, there aren’t many resources explaining the most senior levels. My goal is to provide some insight and advice for those interested in someday becoming a CTO.

I’ve been a CTO for five and a half years

I’ve worked at a hundred-thousand-person company, seed-stage startups, and many of the variants in-between. I started as a developer and followed a traditional path of moving up to more senior levels on the development track and then moving to lead, engineering manager, director, VP, and now chief technology officer. I’ve been the CTO at three different companies in two countries and three parts of the technology industry. I’m part of a few networks where I meet and talk with CTOs of all sizes and stages of companies.

I’ve learned that one reason there isn’t a good reference for the role of the CTO is that the size of the company and the expectations of the CEO define the job. Some of my role expectations and responsibilities are like those of many of my peers at similar-size companies. However, there are also significant differences in our expectations from our executive peers and boards.

Because of the variability of the role, I will broadly share my direct experiences, joined with an understanding of the expectations of other CTOs that I know.

The early-stage company CTO is often the developer-in-chief

At earlier stage companies, the CTO is often the technical co-founder. They are likely the developer who built many of the earlier versions of the software and helped hire the original development team. Their responsibilities are primarily technical: driving architecture, doing advanced development tasks, and creating technical vision.

Frequently, the first CTO of the company is hired for their ability to code and not their ability to grow or manage a team. Depending on the person, they may also lead the development team. Still, often the team’s management will eventually move to another person, an experienced manager, who may report to the CTO or be a peer to them.

The early-stage CTO is the leading technical voice for the company externally, especially if they are a co-founder. They talk to investors and potential partners and meet with potential vendors. If they also manage the development team, they will solely represent engineering in the senior leadership team. As a result, they will have responsibility for the decisions made by the engineering team. Nevertheless, if they do not manage the team directly, they might not be involved in the decisions around the day-to-day operations.

A mistake that inexperienced founding CTOs often make is that they don’t understand their role beyond coder-in-chief. They focus solely on the technology and are not active participants in the company’s leadership. As a result, they do not work cross-functionally. CTOs fixated on the how without the why or what will not be in the role very long once the company grows.

If they have no experience leading an engineering team or organization, the early-stage CTO will be challenged to grow with the company. If they cannot scale, eventually they will end up in a subordinate role reporting to a more experienced CTO hired to replace them.

The midsize company CTO is responsible for leading the organization, corporate strategy, and making technical decisions

Once a company reaches a size at which it needs new processes and structures, the scrappy leaders who helped get the company off the ground are often replaced with more experienced leaders knowledgeable in taking companies through the next growth stage. If the CTO hasn’t grown into the larger role, they will be part of that replaced group.

The midsize company CTO is a full-fledged executive team member working cross-functionally and meeting with partners, investors, and customers. Frequently, the midsize company CTO will also manage the engineering organization. The CTO is responsible for setting technical direction, making sure good architectural decisions are being made, and establishing best practices and working methods. They are still expected to have good technical depth, but don’t often actively contribute to shipping code. A red flag for me personally is seeing a CTO role description where the expectation is to lead a 50-plus-person organization while also actively coding on the product. It means the executive team does not have appropriate expectations for the role.

A midsize company CTO spends significant time establishing culture and practices for the teams they are responsible for; they are also very directly accountable for the organization’s decisions and its track record of delivery. The CTO meets internally with members of the other functions, such as sales, marketing, HR, and finance, to share direction for the organization and get feedback. The CTO is responsible for the administration of the teams, including the budget.

The CTO is also responsible for hiring, performance management, and team structure and may be very active in their teams’ recruitment and interview processes, especially in a scale-up type of company.

A CTO leading a more extensive development organization must be a generalist, understanding different roles and responsibilities. Their remit may include Corporate IT and Technical Support. In some companies, they may also manage the business analytics, security, product, and UX teams. A CTO who is too focused on the areas closest to their background or does not respect non-coding functions will not succeed.

As a midsize company CTO, you will often spend as much time with your peers and their teams as you spend with your own. As a result, you will need to learn about their functions and how your teams can work together. CTOs who “stay in their lane” will not be seen as an equal member of the senior leadership team and may lose their say in decisions that affect the organization.

It is very unusual for someone to move into a midsize company CTO role without having some experience leading a multilevel-development organization and working with other business functions.

Growing (or moving) into the CTO role

If you are a manager or a manager of managers with the goal of being a CTO, there are a few things you can start to focus on that will help you on your path.

Learn about the business your company is in

Offer to sit in on sales calls, on user research interviews. Try to understand the company’s financials when the CFO presents them. If you can’t, make a friend in the finance team and ask them to explain them to you. Understand the KPIs not only for your team, but also for the teams around you.

Learn about the other functions

Get recommendations of reading or conference talks from your peers in the product, UX, and marketing teams. Think about how their work influences yours, and yours influences theirs.

Respect and learn other technology areas aside from your own

If you lead an area you don’t have personal experience in, approach the people in that function with respect and a genuine desire to understand their work. They want to help you know what they do and how they do it.

Hone your craft

Hopefully, you are already working on deepening your skill as an engineering manager or director, but are you trying to understand the bigger picture? Read other companies’ (public) handbooks, engineering blog posts, and conference presentations about their ways of working. What practices are interesting? Which can you try in your team? How do you think they will scale, or what issues do you think they may have?

Ask your CTO if there are tasks they can delegate to you

The best way to learn the job is to do the job. Even better is having someone who is already doing the job explain to you how they perform it so you can help them.

Start thinking in terms of strategy

The main difference between the expectations of line managers and senior managers is the emphasis on strategic thinking. Executives contribute to the company’s strategic planning and use their understanding of the company’s goals and the current situation to make sure that their teams are setting up the conditions for the company’s success. Strategic thinking is a learnable skill, but it takes practice.

The rewards of being a CTO

Being a CTO was not what I imagined it to be when I first decided it was my career goal. It is a lot of work, carries much stress, has fewer perks than you might think, and can be somewhat lonely. However, it is also the most personally rewarding job I have ever had. With the challenges, there is also incredible responsibility, tons to learn, the ability to influence the company’s direction, and the chance to affect the lives of dozens or hundreds of people on your team. I have yet to regret my choice to pursue this role.

Thanks to Laura Blackweell for editing assistance.