From devops to CTO: 5 things to start doing now

I was promoted to CTO in my late twenties, and while it is common to see young CTOs leading startups these days, it was unusual in the ’90s. I was far less experienced back then, and still developing my business acumen. While I was a strong software developer, it wasn’t my architecture and coding skills that helped me transition to a C-level role.

Of all the technical skills I had back then, my devops skills were the most critical. Of course, we didn’t call it devops, as the term hadn’t been invented yet. We didn’t yet have CI/CD pipelines or infrastructure-as-code capabilities. Nonetheless, I automated our builds, scripted the deployments, standardized infrastructure configurations, and monitored systems performance.

Developing all that scaffolding enabled the development teams to focus on building and testing applications while operations managed infrastructure improvements. With automation in place and a team focused on the technology, I was able to focus on higher-level tasks such as understanding customer needs, partnering with product managers, learning marketing objectives, and learning about sales operations. When our CTO left for another opportunity, I was given the chance to step into the leadership role.

In my book, Digital Trailblazer, I elaborate on my journey from developer to CTO and CIO. Since the book came out, many readers have asked me for advice about how to accelerate their career trajectories. In this article, I focus on how high-potential employees in devops roles—including developers and engineers—can start making moves toward a CTO role.

Develop platforms teams want to use

If you want to be recognized for promotions and greater responsibilities, the first place to start is in your areas of expertise and with your team, peers, and technology leaders. However, shift your focus from getting something done to a practice leadership mindset. Develop a practice or platform your team and colleagues want to use and demonstrate its benefits to the organization.

Devops engineers can position themselves for a leadership role by focusing on initiatives that deliver business impacts and building systems that teams want to use. Look to deliver incremental small wins and guide solutions that help teams make continuous improvements in key areas.

Another important area of work is reviewing platform engineering approaches that improve developer experience and creating self-service solutions. Leaders seeking recognition can also help teams adopt shift-left security and improve continuous testing practices.

Recommendation: Don’t leave it to chance that leadership will recognize your accomplishments. Track your activities, adoption, and impacts in technology areas that deliver scalable and reusable patterns.

Shift your mindset to tech facilitator and planner

One of the bigger challenges for engineers when taking on larger technical responsibilities is shifting their mindset from getting work done today to deciding what work to prioritize and influencing longer-term implementation decisions. Instead of developing immediate solutions, the path to CTO requires planning architecture, establishing governance, and influencing teams to adopt self-organizing standards.

Martin Davis, managing partner at Dunelm Associates, says to become a CTO, engineers must shift from tactical problem-solving to big-picture, longer-term strategic planning. He suggests the following three questions to evaluate platforms and technologies and shift to a more strategic mindset:

How will these technologies handle future expansion, both business and technology?

How will they adapt to changing circumstances?

How will they allow the addition and integration of other tools?

“There are rarely right and wrong answers, and technology changes fast, so be pragmatic and be prepared to abandon previous decisions as circumstances change,” recommends Davis.

Recommendation: One of the hardest mindset transitions for CTOs is shifting from being the technology expert and go-to problem-solver to becoming a leader facilitating the conversation around technology implementations. If you want to be a CTO, learn to take a step back to see the big picture and engage the team in recommending technology solutions.

Extend your technology expertise across disciplines

To ascend to a leadership role, gaining expertise in a handful of practices and technologies is insufficient. CTOs are expected to lead innovation, establish architecture patterns, oversee the full software development lifecycle, and collaborate and sometimes manage aspects of IT operations.

“If devops professionals want to be considered for the role of CTO, they need to take the time to master a wide range of skills,” says Alok Uniyal, SVP and head of IT process consulting practice at Infosys. “You cannot become a CTO without understanding areas such as enterprise architecture, core software engineering and operations, fostering tech innovation, the company’s business, and technology’s role in driving business value. Showing leadership that you understand all technology workstreams at a company as well as key tech trends and innovations in the industry is critical for CTO consideration.”

Devops professionals seeking to develop a deep and wide breadth of technology knowledge and expertise recognize it requires a commitment to lifelong learning. You can’t easily invest all the time required to dive into technology expertise, take classes in every technology, or wait for the right opportunities to join programs and teams where you can develop new skills. The most successful candidates find efficient ways to learn through reading, learning from peers, and finding mentors.

Recommendation: Add learning to your sprint commitments and chronicle your best practices in a journal or blog. Writing helps with retention and adds an important CTO skill of sharing and teaching.

Embrace experiences outside your comfort zone

In Digital Trailblazer, I recommend that leadership requires getting out of your comfort zone and seeking experiences beyond your expertise.

My devops career checklist includes several recommendations for embracing transformation experiences and seeking challenges that will train you to listen, question how things work today, and challenge people to think differently. For example, consider volunteering to manage an end-to-end major incident response to better understand being under pressure and finding problem root causes. That certainly will grow your appreciation of why observability is important and the value of monitoring systems.

However, to be a CTO, the more important challenge is to lead efforts that require participation from stakeholders, customers, and business teams. Seek out opportunities to experience change leadership:

Lead a journey mapping exercise to document the end-user flows through a critical transaction and discover pain points.

Participate in a change management program and learn the practices required to accelerate end-user adoption of a new technology.

Go on a customer tour or spend time with operational teams to learn firsthand how well—and often not well—technology is working for them.

“One of the best ways I personally achieved an uplift in the value I brought to a business came from experiencing change, says Reggie Best, director of product management at IBM. “Within my current organization, that usually happened by changing projects or teams—gaining new experiences, developing an understanding of new technologies, and working with different people.”

John Pettit, CTO at Promevo, says to rise from devops professional to CTO, embrace leadership opportunities, manage teams, and align with your organization’s strategic goals. “Build business acumen by understanding how technology impacts company performance. Invest in soft skills like communication, negotiation, and strategic thinking.”

Petit recommends that aspiring CTOs build relationships across departments, read books on digital transformation, mentor junior engineers, develop a network by attending events, and find a mentor in a non-tech C-level leadership role.

Recommendation: The path to CTO requires spending more time with people and less time working with technology. Don’t wait for experience opportunities—seek them out and get used to being uncomfortable: it’s a key aspect of learning leadership.

Develop a vision and deliver results

CTOs see their roles beyond delivering technology, architecture, data, and AI capabilities. They learn the business, customers, and employees while developing executive relationships that inform their technology strategies and roadmaps.

Davis of Dunelm Associates recommends, “Think strategically, think holistically. Always look at the bigger picture and the longer term and how the decisions you make now play out as the organization builds, grows, and develops.”

My recent research of top leadership competencies of digital leaders includes strategic thinking, value creation, influencing, and passion for making a difference. These are all competencies that aspiring CTOs develop over time by taking on more challenging assignments and focusing on collaborating with people over technical problem-solving.

Beyond strategies and roadmaps, the best CTOs are vision painters who articulate a destiny and objectives that leaders and employees embrace. They then have the leadership chops to create competitive, differentiating technical, data, and AI capabilities while reducing risks and improving security.

You can’t control when a CTO opportunity will present itself, but if technology leadership is your goal, you can take steps to prepare. Start by changing your mindset from doing to leading, then look for opportunities to guide teams and increase collaboration with business stakeholders.