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Startup Jobs: What’s it like being a Chief Technology Officer (CTO)?

Insights & Trends

Startup Jobs: What’s it like being a Chief Technology Officer (CTO)?

Words Founders Factory

April 1st 2022 / 7 min read

Our Startups Jobs series dives deep into some of the most important roles you can do or hire in a startup, breaking down the responsibilities you have and the skills you need

When Jack Dorsey stepped down as Twitter CEO in November 2021, he named Parag Agrawal as his successor. As well as general excitement around the new direction and impetus behind a business which has largely stalled in recent years, many from the engineering community celebrated this announcement. Agrawal, after all, was formerly Twitter’s Chief Technology Officer.  

In startupland, we’re easily drawn into the cult of the founder: when we think of startup jobs, we think of the visionary leaders who occupy the headlines and act as figureheads for innovative business. Nowhere near as much attention goes to the CTO, often the second-in-command to the CEO, and the role that many engineers aspire to step into one day. As the name suggests, the CTO is responsible for the technical strategy of a business, both building the technology as well as creating and managing the team to maintain it.

So what is it really like to be a CTO? We interviewed a number of CTOs and technical leads from our startup community to find out:

  • What is it like stepping into the CTO/technical lead role?

  • What are your main roles & responsibilities?

  • What are the most important CTO skills? 

  • What advice would you give to aspiring CTOs?

Meet our experts

Paul Egan


Founders Factory

Previously CTO at Wonder, Rockpack

Kunal Varma

Helps asset owners assess value for money delivered by their asset managers

Kimberley McCann

Engineering Lead
Digital infrastructure for the circular economy

Richard Levy

Flight-free, slow travel company

Startup jobs: what’s it like being a startup CTO?

The term CTO is used at both multinational companies with millions of employees, as well as tiny startups with teams of less than 10. Experiences of the two positions, however, couldn’t be more different. 

At a startup, a CTO is likely to be a part of the founding team. CTOs are central to the search phase (discovering the direction of a business) and build phase of a business, especially if the CEO/co-founder(s) are from a non-technical background. Almost all CTOs come from technical backgrounds and it’s often the natural progression of responsibility for engineers or other technical professions. 

Stepping into a technical leadership position will grant you far more influence in the direction of a company. “I’m not in the startup world to sit quietly in the corner,” explains Paul Egan, CTO at Founders Factory. “You’re there to achieve bigger things, and have an impact on the business as a whole.”

This involves quite a transition, particularly in your way of thinking. CTOs should have an architectural view of the business and its technology, rather than focusing on the small minutiae. As a result, you should be empowering your team rather than doing it yourself. “Your mindset switches from ‘I need to do it’ to ‘I need to get it done’,” says Kunal Varma, CTO at ClearGlass. 

This can create a slight tension for many early stage CTOs—balancing the desire to get stuck in, with the need to be more managerial, can be tricky. Many will have chosen the career because of their love of programming, coding, etc, and it may feel difficult to leave that behind. 

Startup jobs: CTO roles & responsibilities

The roles and responsibilities of a CTO will change depending on what stage your startup is in. As a CTO, it’s your responsibility to:

🔦 Explore technological avenues
The CTO plays a crucial role in helping to define what is possible to deliver the mission of the business, as well as what may be the most effective applications of technology. You should be exploring many possible avenues to find the right technology; you’ll often find yourself going down dead-ends, and that’s part of the process.

At this stage, you need to be open-minded about the right methods to use. Don’t be fixated on your vision—always bring it back to what will deliver the best business/product. 

“I’ve always seen tech as an enabler. Our CEO has a vision, and it’s my role to bring that to life,” says Richard Levy, CTO at Byway.

⚒️ Build the technology that powers the product
After identifying the right direction of travel, and the appropriate technology to get you there, your next responsibility as CTO is to build the technological infrastructure for your product. This is where your technical expertise will prove invaluable—you’re likely to actually get your hands dirty. 

This early stage of a startup is crucial, and you have to build quickly and with agility. Fundamentally, your primary goal is to make sure that technology isn’t an obstacle to the growth of the business. 

Comfort with ‘technical debt’ is important. Basically, don’t spend your time poring over every detail: you need to build things quickly, without testing it thoroughly, even if it doesn’t feel particularly sustainable. You can worry about those problems once you start to scale and gain customers: at this point, just worry about getting a product on the table. It may not feel intuitive, so you need to get used to feeling comfortable cutting corners with things hanging together loosely. 

🤝 Hire
You’re not building the technology alone, so your role is to hire a team of engineers to build it with you. If you’re trying to attract top talent—especially someone coming from a highly paid technical role— you should approach hiring with humility. “​​Your startup means nothing to them, so you need to translate the proposition into exactly what’s going to be interesting for them,” Paul says.

Consider the following:

  • What’s interesting about the role to them - is it the mission of the company, the technology you’re using, or the team you’ve assembled so far?

  • Pay attention to messaging - consider each point of contact with them, from the first LinkedIn message to their interview

  • Focus on culture and values alignment - you may consider certain technical skills to be non-negotiable, but actually finding someone with aligned values will prove more beneficial in the long term

Manage and empower your team
As the business and your team grows, you’ll increasingly see yourself in a managerial position. A key responsibility is trying to remove any of the obstacles that prevent your team from doing their best work. 

“Don’t think that your engineers work for you, think instead that you work for them. They’re an expensive resource, and it’s your responsibility to work for them and make sure they’re productive and moving in the right direction,“ Kunal says.

💸 Fundraising
The bulk of this will usually fall to the CEO: there may, however, be a role for the technical lead to play when speaking to investors. This is most common when there’s a fairly complicated technology to explain. CTOs will need to translate the technology into language that’s accessible to investors, without diluting what’s impressive or unique about the tech. This authenticity will no doubt chime with investors.

Startup jobs: what skills and characteristics do startup CTOs need?

There are obvious technical skills that are important for any tech lead in a startup to have: this will largely depend on what you are building, and what sort of technology you are using. On top of this, however, there are several universal skills that will help you in your role as CTO.

This is one of the most important startup skills—but is particularly important for startup CTOs. Given its complexity, it’s easy for there to be a disconnect between the technology and the rest of the business, and it’s the responsibility of the CTO to ensure this doesn’t happen.  

Working between the CEO/founding team and the engineering team, CTOs act as a mediator. You need to translate the founding team’s vision into what that will look like from a practical perspective; and vice versa, you need to be able to communicate what your engineers are working on to the founding team.

Stakeholder management
This is no doubt linked to communication. Keeping the central technology in mind, you have to constantly interact with various functions of the business (internal and external) and ensure they’re fully informed on how the tech may impact what they’re doing. 

“Take your ​head of client success. They don’t want to know exactly what’s being built, they want to know whether they’re able to onboard a client, and how the technology will impact their KPIs,” Kunal says.

Sense of perspective

Stepping up into the role of CTO also requires taking a step back, and having a helicopter view of the technological architecture of the business. Is the technology fulfilling its function? Are all the parts operating smoothly? Do my team have everything they need to do their jobs effectively?

“Step back and look at the bigger picture. You can’t just be sucked into the code, and thinking of repairing tiny features,” says Kimberley McCann, Engineering Lead at Reath. 

This obviously means stepping back from the small detail tasks that you might do as an engineer. It means knowing what to prioritise, and where best to focus your efforts. But it also means seeing the technology as part of something bigger, something which is helping the business succeed.

Ability to question—and say no
There’s an innate ability of good CTOs to be able to question the direction of travel. 

This is true for deciding on what you should be building. Richard Levy, CTO of Byway, highlights the ‘five whys’ method—constantly questioning ‘why’ allows you to interrogate exactly what the founding team wants to achieve, and to drill down into the best way to achieve that.

It’s also about questioning the CEO/founding team’s decisions, and, when it's appropriate, to say no.

CTO interview questions

Examples for the type of topics and certain questions that you may face in CTO interviews

On leadership:

  • Experience of building a team from scratch

  • Comfort with attracting tech talent & managing a recruitment process without much support

  • Ability to clear explain technical solutions and manage stakeholder expectations

On strategy/startup experience:

  • Experience of working at a startup from an early stage or a lean environment

  • At ease with experimentation, prototyping, & MVP development: Have you built something that had to be thrown away?

  • Comfortable with ambiguity/constant change: How do you balance technical debt with the need to move quickly?

On product building:

  • Have you ever built your own product?

  • Experience of working with product managers & designers - how did that work?

  • Where does your satisfaction come from: data/tech architecture/scale, user/customer feedback, or driving business value?

Advice for aspiring CTOs?

“Find a good support network” - Kimberley McCann
In small teams, there may not be other people with a similar technical background to go to with questions and problems. Even for CTOs at larger startups, it may not feel appropriate to do this with more junior members of the team. Find a mentor or coach who can support you on both the technical side and personal side of your role. Check out organisations like CTO Craft which offer community and support for CTOs.

“Always think of maximising your team’s efficiency” - Kunal Varma
When you’re making decisions, don’t just think of it as you committing your time. You’re leading a team of engineers, valuable and costly resources to the business, and so the value they’re giving to the business has to be worth it. 

“Choose your battles” - Richard Levy
You may feel like an expert on the technical side, but sometimes you need to leave your ego at the door. There’s no point getting stuck on a hill on certain things, or getting involved in personality clashes. It all comes back to viewing technology as a servant—and your role is maximise that.

Interested in stepping into the CTO seat? We’re hiring CTOs to help build businesses in our Venture Studio

Explore CTO roles
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