Chief Officer Awards Finalist Jeff Gallimore: ‘A Worthwhile Career is Full of Risks’

Editor’s note: The winner of the Chief Officer Awards Private Company CTO Award announced June 17 is Allen Badeau of NCI.

On June 17, WashingtonExec will be virtually celebrating the most impactful and innovative C-suite executives in government and industry. These chief officers work in technology, security, data, operations, finance, business and more, excelling on both sides of the government contracting sector. Our team of judges have chosen the finalists for the inaugural Chief Officer Awards, so before we announce the winners during the event, we wanted to get to know those in the running a bit better. This Q&A series highlights their careers, successes, proud professional moments and notable risks.

Jeff Gallimore, Excella

Jeff Gallimore is chief technology and innovation officer at Excella and a finalist in the Private Company CTO Award category.

What was a turning point or inflection point in your career?

I started my professional career as a developer. I worked in command lines and with code editors most of my day and often into the night and on weekends. I loved creating systems and making computers do useful things. I loved technical problem-solving, the creativity involved and the power of what technology could do. I discovered the world of technology changes quickly and there were always new tools, new techniques and new tricks to try out.

Shortly after starting my company, Excella, I found myself on a government contract in a program management office. At the time, I didn’t even really know what a program management office did. We weren’t building any systems (directly, anyway). I wouldn’t be coding. In fact, there was no code in sight anywhere. What on Earth was I supposed to be doing? It was uncomfortable for me not knowing how to contribute confidently.

I eventually figured out what I was supposed to do, and that engagement became one of the most professionally rewarding and transformative experiences of my career.

I learned the roles of people and process in accomplishing business goals, in addition to the technology. I learned process was more important than technology and people were much more important than anything. I learned about the human element of technology. This experience opened my eyes to what the real power of technology was — to make an impact on people’s lives. I’m so thankful for the opportunity because of what I learned through it.

What’s the biggest professional risk you’ve ever taken?

I’m a big believer a worthwhile career is full of risks and the biggest risk I’ve taken was starting Excella in early 2002. Of course, starting a company is a risk, but the circumstances surrounding Excella’s launch were what made it so risky. I had good stability and career growth at my employer, I had a family and a mortgage, and in mid-2001, the dot-com bubble had burst, the telecom market had crashed and 9/11 had just happened. It was the rock bottom of the IT economy. What a perfect time to start an IT consulting firm, right? It was definitely a professional — and personal — true leap of faith.

What was your biggest career struggle and how did you overcome it?

I was a bad boss early in my career. What’s worse is I didn’t even realize it at the time. I micromanaged. I was impractical. I didn’t give meaningful feedback. I cared about the people on my team, but I didn’t show it all that constructively. There’s even a quote on the back of a t-shirt from a project I was on 20 years ago that memorializes my less-than-effective management style.

With the help of some others I respect and trust, I learned that leadership was a real thing and included skills I could develop, just like coding or writing or anything else. That realization set me on a lifelong journey to become a better leader. Leadership is now a passion of mine. I read books and articles, listen to podcasts and watch talks on the subject of leadership frequently. I share leadership lessons and principles with my team and others at Excella (and they share them with me — which is really cool).

Even still, I often fail to be the leader I want to be and my team deserves. I fall into micromanagement. I forget the team only has a limited capacity for “new” and change. I don’t always communicate effectively. But I’m better today than I was 10 years ago. I hope to be better in 10 years than I am today.

What has made you successful in your current role?

I believe I have two qualities that prepare me for success in my role as chief technology and innovation officer. The first quality I’ve always had: a natural curiosity, a hunger for learning and a growth mindset. I’ve always loved learning new things and I have an eclectic mix of interests. My bookshelf is probably the most obvious reflection of that. I’ve also believed that whatever new situation I encounter, I can learn what I need to succeed.

The second quality I developed later in my career after I had gained more perspective on what’s important: The power of technology is in solving real problems and impacting peoples’ lives in a positive way. Earlier in my career, I made decisions that were sometimes “technology for technology’s sake.” It took me some time to learn the impact of solving the problem was most important and the technology needed to be in service of that.

What are your primary focuses areas going forward, and why are those so important to the future of the nation?

My primary focus is changing how we manage technology and transforming into better ways of working. There is so much waste and inefficiency in our use of technology, particularly in large, complex organizations. Not only are many organizations not achieving their goals (and wasting a lot of time and money in the process), there are also so many people who are frustrated, checked out or burned out as result.

Because of the DevOps community, we know there’s a better way of helping our organizations win and at the same time helping the people we work with find more joy in their work. This transformation is hard because it challenges much of our conventional wisdom. Science and experience are now telling us much of what we accepted as “best practice” for decades is not only not best practice, it’s actually counterproductive. But if we go through the transformation journey, it’s worth the trip.

We can create so much more value and impact and accomplish so much more so much faster for our organizations and our stakeholders. And we can increase the engagement of our colleagues, helping them find joy in their work — maybe for the first time in their careers. That’s a worthwhile endeavor.

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