Name: Rob Zuber

Current position: CTO at CircleCI

Bio: Rob Zuber is a 20-year veteran of software startups; a three-time founder, and five-time CTO. Since joining CircleCI, Rob has seen the company through multiple rounds of funding and an acquisition, while leading a team of 200+ engineers distributed worldwide.

While he’s not solving complex software problems, Rob enjoys snowboarding, playing the guitar, and spending time with his wife and two children. He holds a Bachelor’s degree in Applied Science from Queen’s University in Kingston, Ontario, and lives in Oakland, California.

Tell us about your life before leadership – what kind of roles and projects did you work on?

I went to college during a time when the parameters of the software industry were less obvious than they are today. I studied engineering physics, did a little bit of software development, then afterward went to work in a production facility analysing production defects and optimising factory processes.

I found myself really enamoured with the software part of it all. Then a couple of friends created a startup, which I later joined. I started out doing things like running a QA team and then something we called systems engineering. I even wrote our first build script. I’ve been thinking about delivering software ever since.

How did your first leadership position come about, and was it intentional on your part?

I held multiple management roles early in my career, but I drifted in and out of them because I was always more interested in building products and systems than I was in teams. I’d bring people along with me, but a small startup in the late 90s wasn’t a place where people were wondering about their career path. We were all just holding on for the ride.

About 10 years into my career I joined a different small startup, AdPerk, as the CTO. That was the first time I made a conscious decision to take a leadership role and really own it. I began thinking about building a team and driving a business. We were small enough that I also wrote huge parts of the product. So it was definitely that pace-setting, lead-by-example model that so many new leaders fall into.

How did you manage the transition? What came easily / what was difficult?

I’d say I handled it about as well as your average new leader. Setting direction and helping others see where we were trying to go, was something I developed quickly. I was taking over for an outsourced team that had built something quite unwieldy. I put together a small group of great people and we executed on stabilising and growing the platform while continuing to meet customer needs and expand product capability. That path can be hard to navigate, but we pulled it off.

On the other hand, I was terrible at stakeholder management. Even though we were delivering value beyond what could probably be expected from the small team we had, I didn’t always ensure we all agreed on priorities. I also didn’t set expectations effectively, so even our great results weren’t seen as such.

What was your biggest failure in that first leadership role?

Pretty classic, but as it was my first time working with an entirely new group of people in 10 years, I felt like I had something to prove and set out to do it on my first day. While there were plenty of opportunities for improvement and I would ultimately be accountable for those improvements, I didn’t take the time to understand the limitations that led to any of the choices that had been made. Instead, I just started pointing out issues and charging towards fixes. I created a pretty significant trust deficit around minor things that made it a lot harder to navigate the major ones for a long time.

I ultimately left because I didn’t believe in the business we were pursuing, but I could have made a lot more of my time there. 

What made you keep doing it?

I actually took a break after that to do some consulting and contract work, which was very focused on delivering projects. After a year, my desire to be more invested in the things I was building, combined with my entrepreneurial spirit, led me to start a company. That was later acquired and I immediately started another.

Starting and growing companies always begins with building a product and then transitions into building teams. For me, I’m not sure that leadership was on my mind when I started doing that; I just loved the pursuit of the idea and the business. Then you get to the scale where your most valuable contribution is influencing those outcomes through leadership, and that’s where I’ve shifted my focus.

Tell us a fun fact that nobody knows about you

After all the years I’ve been in software, I guarantee I own at least one t-shirt or hat that has your tech company’s logo on it.  

What are the three key skills you think every leader needs?

  • Storytelling. We live in a world of data. Every day we have more data and we use it to achieve amazing insights. We’re also getting better and better at understanding the metrics that drive our businesses. But at the end of the day, human knowledge is shared through stories and that’s what we’re wired to accept. As a leader, you need to incorporate the signals from this data – along with all the surrounding ambiguity – and weave together a story to motivate and align people. When they have that picture, the numbers will speak for themselves.
  • Comfort with ambiguity. You’ll never have all the information. As your scope broadens, the consequences of your direction increase, while clarity about the right direction reduces. That doesn’t mean it’s all ‘YOLO’. You need to develop tools for dealing with that ambiguity, such as finding ways to drive forward while insulating yourself from the consequences of bad information. Or learning to effectively incorporate risk into your decision-making. Then your job is helping disambiguate for those around you. Filling in the missing pieces of the puzzle in a way that allows members of your organisation to make their own good decisions is a major part of the role of a leader. Don’t paint a false picture of clarity when there is none. But saying: “This is our hypothesis and we can de-risk it by learning more about the following unknowns” gives people the room to define clear next steps for themselves. 
  • Focus on learning. This comes in two parts for me. First of all, every single one of us can improve in various ways. Learning might come in the form of building new skills, collecting feedback, or just practising the skills that you already have. Aiming to be a little bit better every day not only opens the doors to actually being better but helps to build a broader culture of being open to learning and continuous improvement. The second part of learning ties to the decisions we make and the information we have at the time. As humans, we’ve somehow managed to create negative associations with people who change their minds. But we’re constantly uncovering new information. We’re more likely to make good decisions if we continue to incorporate all of the information that we have and stop worrying that we were ‘wrong’.

What have you learned about acquiring and retaining talent?

The most valuable thing I’ve learned about both acquiring and retaining talent is something I discovered in my first job out of university, but it took longer for me to see it in practice.

My first day on that job, I was told what I would be doing and it didn’t really match anything I had been told when offered the role. I felt deflated and not off to a great start. While I found ways to learn interesting things in the year I spent there, I was an attrition risk from the word go.

To this day, I do my best to be completely transparent with anyone I meet during the hiring process. I tell them what I’m excited about and where our challenges are. I find myself repeatedly saying: “Everyone has their problems, the question is whether those are the problems you want to work on.”

Companies are so much more than their external brand or their valuation. A person who blows the doors off in one organisation may struggle to make progress in another. We spend way too much of our lives at work to be in the wrong place. Be honest with your candidates about who you are as a company and you’ll find the ones that not only want to join, but will also be the ones to stay.

How do you motivate your team and manage their stress levels?

I spend a lot of time ensuring the people on my team have the full picture regarding what we’re trying to do and the role they play in it. Everyone has their own internal motivations and stressors, so for me, this is about finding ways to tap into those motivators and connect them to the shared objectives, rather than find a universal motivator. That requires investing in sharing the bigger context and understanding individuals better, to help tie their own aspirations to that context.

Understanding shared goals, and that the work you are motivated to do is moving towards those goals, is an important tool in reducing most people’s anxiety and stress.

How do you manage your own stress levels and productivity?

From a productivity perspective, I know myself well enough to know when I should focus on different types of work. Luckily, I always have plenty to do, so knowing what’s going to be energising at any given time helps me get the most out of my time. And as long as I feel like I’m making progress, I can generally keep stress to a minimum.

When I do need a break, I’ve slowly gravitated towards activities that require me to be present. For example, I play the guitar and when I’m playing music, I’m thinking about only the music, not about work. When I snowboard, things are happening fast enough that I have to be focused. Immersing myself in something else is the best tool I have to really separate myself from anything causing me stress.

How do you stay in sync with other parts of the business?

As a member of the executive team, my peers represent the rest of the business, so that’s my primary avenue. I understand their goals and what makes them successful, and we talk regularly about where we’re succeeding and where we can help each other. I pay attention to the metrics, but I look to the other execs to help me understand the narrative behind those metrics and how I can help.

I’ve done my best in recent years to shift from someone who focuses on engineering and technology to someone who focuses on the business and brings the expertise from an engineering and technology perspective. Having ridiculously talented and knowledgeable peers has made that transition easy.

Where do you see yourself in five years’ time?

Solving hard problems, working with great people, and learning. That’s all I can say for certain.

What product do you wish you’d invented?

Ride-sharing. In the film Zootopia, there’s even a billboard for a ridesharing company called ‘Zuber’. In 2003, my wife and I had the opportunity to visit Moscow and stay with our friend, Andrei, who lived there. We would get around town by walking out to the street and waving at cars until someone stopped. We’d tell them where we were headed and see if they would take us there for a negotiated price (this was all done in Russian by our friend). At the time we couldn’t believe that people just got into the cars of complete strangers without a more regulated taxi system. I’d call this a failure of imagination on our part!

Thank you, Rob!


If you or your CTO / technology lead would benefit from any of the services offered by the CTO Craft community, use the Contact Us button at the top or email us here and we’ll be in touch!

Subscribe to Tech Manager Weekly for a free weekly dose of tech culture, hiring, development, process and more