At the young age of 17, Christopher Stewart embarked on a career with the United States Air Force as a Communications Computer Systems Operator. He later transitioned to the City of Austin, initially as a System Support Technician, beginning a dedicated journey in public services. Little did he know that this journey would culminate in his retirement as the CIO of the City of Austin, marking 22 years and 11 months of service to this government entity. The trajectory from a System Support Technician to CIO epitomizes a keen eye for opportunities, a commitment to continuous learning, and unyielding perseverance.
His foray into leadership at the City of Austin began when he volunteered for night shifts after successfully implementing a 911 dispatch system. This opportunity propelled him to lead a small team of system-dedicated support personnel. Simultaneously, he seized the chance to pursue a BBA in Business and Management during the day. Subsequently, he stepped into an interim supervisor role, overseeing two public safety IT support teams, eventually securing the position permanently. Throughout this period, he pursued further education, earning his Master’s in Public Administration. The fusion of an enterprising attitude, hands-on experience, and educational enrichment positioned Chris as a reliable executive who consistently rose to the occasion. Consequently, he ascended to the roles of CIO of Austin Water and later the CIO of the City of Austin.
Assuming the CIO role at the City of Austin during the COVID-19 pandemic, Chris was pivotal in establishing digital service capabilities that supported employees in both remote and hybrid work setups.
Upon retiring as the CIO of the City of Austin and completing an impressive 27 years of public service, Stewart founded Resolute Executive Consulting. In this capacity, he serves as an IT Executive Consultant, leveraging his extensive experience in developing and implementing innovative technology solutions to assist executives.
I present to you the inspiring career journey of Chris and his invaluable advice to advance in your career.
Describe your career progression from the start to where you are and what pivotal decisions, moves you made, circumstances, and other facts that facilitated your growth.
At 17, I joined the United States Air Force as a Communications Computer Systems Operator stationed at NORAD supporting satellite communications. Growing up in a military household, I was drawn to service. I also knew I could take advantage of the many educational benefits the military offered and was able to earn my AAS in Computer Information Systems while enlisted. Shortly after moving back home, I decided to continue my fledgling IT career and joined the City of Austin with the electric utility.
The job was desktop support and, at the time, the most entry-level IT position in the city. I was incredibly excited for the opportunity but had no idea it would turn into a 23-year career. Always wanting to be the best at what I did, I made sure to make an impact early. We tracked ticket closures weekly and I was determined to be at or near the top as often as possible. I was never very competitive with others, just myself. After a couple of years, I knew I was ready to be promoted into a more technical role and moved from Austin Energy to the city’s central IT division focused on building out one of the world’s first multi-agency 911 and emergency communications centers CTECC.
I was privileged to be in an atmosphere where we had to build everything from scratch. It was a learning environment like no other. We were a small, but mighty team, and had to figure everything out as we went. We pushed the limits of public safety technology and had a great time doing it. This culture allowed me to grow immensely and move into more systems and network administrator roles. I took ownership of anything I could such as data backups, email, and various network devices. After implementing our new 911 dispatch system I volunteered to work nights focused on support of that system and eventually ran a small team of system-dedicated support personnel. This was my first shot at a leadership role and I knew it would be the direction my career would go. I took advantage of working nights and returned to school during the days earning a BBA in Business and Management.
Working with a great manager, I was able to take an interim supervisor role eventually earning the position full time. It was time to put my education and limited experience to the test. Managing a team was very difficult, but a wonderful learning experience and one that solidified my decision to pursue management as a career. I supervised two public safety IT support teams and started looking around for my next step. It was hard to admit it, but I had to look outside the public safety sphere to really move up in the city. Thanks again to great management for making me believe this absolute truth. Public safety is an incredibly rewarding field to be a part of, but it is 24/7/365 and can be very stressful. The good part about working in that environment for so long was I knew I could work pretty much anywhere with no troubles. I also realized from an educational standpoint that a master’s degree would be necessary to be competitive so I returned to school and earned my MPA (Master’s in Public Administration).
I started talking to other IT managers and saw an opportunity coming at City Hall. City Hall is not the epicenter of technology for the city, but there’s no better place to learn how the city operates as an organization and how politics plays a role in decision making. I let the CIO know if he ever needed an interim manager there to call me first. He was very supportive and as we thought, the role soon opened up and I quickly moved in. I learned immensely in that building making many strong relationships with officials and getting a much better understanding of how everything worked. I would watch council, board, and commission meetings daily soaking up as much as I could. This knowledge became useful faster than I had expected as the water utility called and I earned a role there managing their IT infrastructure.
This was my first experience managing supervisors, a major win for me personally, and another moment where I knew I was moving in the right direction. Not only could I influence and support direct reports, but I was now in a position to help others do the same. I felt this was how I could really impact the organization and was not ready to stop there. I wanted to prove my value to the executive team and volunteered to be the technology lead of a new $100 million Advanced Metering Infrastructure (AMI) project. It was the utility’s first such system and would dramatically increase technology’s reach and impact on the organization and community. My focus on modernization drove the utility forward in very noticeable ways and when an opportunity arose for the utility to find a new CIO, I was more than ready to fight for it. Thankfully, the executive team had faith in me and I became the CIO of Austin Water. It was an amazing opportunity and I thought I would eventually end my career with the city. Of course, life had another plan for me and I was ready for the challenge.
The city’s CIO had been offered an opportunity in the private sector and the deputy city manager asked if I would be willing to serve as the interim CIO. I was happy to do so. After all, I had about 20 years with the city by this time and thought I had a pretty good idea of what to expect. I figured I’d see the organization through this change and head back to my role at Austin Water. I was happy to serve and honored to be thought of. The job was incredibly difficult and very public. I was used to significant organizational change, but this was at a level I had not expected or experienced before. When the nationwide search for a new CIO kicked off, I decided to throw my hat in the ring. I had worked so hard and wanted to see things through. I was again blessed with an amazing opportunity and offered the role of CIO for the City of Austin which had just become the 10th largest city in the country. I was humbled, a little nervous, and incredibly motivated to be as effective as humanly possible. We achieved a lot in a short amount of time and built strategies to lead the city forward for years to come.
I never planned on, or could even dream of, a journey taking me from an entry-level desktop role to a Chief Information Officer. I may not have seen the road ahead of me, but I always wanted to be prepared for any twists or turns along the way and I’m grateful I was able to be in the right place, at the right time, with the right knowledge and experience to make it happen.
What are the key skills and qualifications that aspiring tech executives in the tech industry should focus on developing to enhance their career prospects?
Before worrying about skills and qualifications, please make sure you’re in it for the right reasons. Executive management can be a lonely journey and not at all made for people looking to get their name in print. You’re there to support and serve others ahead of yourself. If you are recognized, it’s because of their work and talent. Be honest with your intentions and if you’re ready to give of yourself for the team, go for it.
If you’re ready to start the journey, pay special attention to everything other than your technical skills. Communication is key. I know you’re tired of hearing it, but it’s true. You have to be able to effectively communicate with elected officials, top executives, boards, department directors, your staff, and the public. These are all very different audiences and require skill to navigate the intricacies of each. Be persuasive while not demanding. If you can’t convince others of anything, you’re not much use to the organization and cannot lead your team anywhere. Time management is critical and much more challenging at this phase of your career. You should be good with your time by now, but you’ll have far more than you can achieve on any given day and must rely on others for your success. This level of delegation can be uncomfortable but is an invaluable skill for a great leader.
What are some key milestones or achievements that tech executives should aim for at various stages of their career to demonstrate their growth and readiness for higher-level roles?
There’s no one path to take and I think we’ve seen that with so many IT executives. Some come from very technical backgrounds of heavy coding, administration, security, etc. while many have very little hands-on technical experience and have relied on their management and executive skills to achieve great results.
As with any executive position, I highly recommend becoming very versed in the non-technical areas of the business. Budget and finance and crucial understandings for an IT executive. Know how the money works for your company and industry so you can more effectively plan and implement your strategies. HR is your friend, learn your company’s HR culture to make everything go smoother for you and your staff.
Manage people of varying backgrounds, experiences, and abilities. Grow your leadership skills and get a strong foundation to lead you through your executive career. Knowing how to effectively communicate, influence, mentor, and manage large groups of employees sets you up for success when the opportunity arises. Don’t wait to start bolstering your leadership skills.
How important is it for tech executives to actively seek out mentorship or coaching opportunities to advance their careers? What benefits can they derive from such relationships?
I’m sure there are incredibly talented executives who were not mentored, but the ones I know all sought out mentors. The executive space can be lonely. Your peer group dwindles the higher up you go. Having people you can go to for support and advice is very useful. Mentors have been there before and can give an external perspective like few others can. Mentors don’t even have to be experts in your particular field. Sometimes it’s just as helpful to get ideas and perspectives from very different viewpoints than your own. Seek out people you trust and admire. The hardest part is reaching out and asking for their time.
In your experience, what role does professional networking play in the career progression of tech executives? How can tech executives effectively build and leverage their networks?
Professional networking is essential to the career of a tech executive. Not only does a great network help get your name in front of potential employers, but it also allows you to reach out to all of your connections when necessary (and it will be necessary). You could always try to take the journey alone, but I wouldn’t recommend it and I can’t imagine wanting to.
Your network can help with any number of issues you’ll run into. I have yet to meet an exec who was completely satisfied with their talent pipeline. Your network is often your best resource for available talent. Tackling a new initiative or taking on a once-in-a-career project? Someone in your network can help. There’s no end to the benefits of having a great network, but I can’t think of any positives in going at it solo.
Are there any specific certifications, advanced degrees, or executive education programs that can significantly enhance the career prospects of tech executives in the tech industry? Which ones would you recommend?
Your education and certification level are very personal and should reflect your desire to pursue particular interests in your field. That said, be aware of your competition. Are you seeing mandatory CISSP, CGCIO, MPA/MBA, etc. in the majority of the jobs you’re researching (hopefully not, but it does happen)? If so, don’t wait a moment to start that process. Even if the requirements disappear, you’re now even more competitive than many of your peers.
Many large employers, especially government agencies, have internal management/leadership programs. If this is the case where you are, you should definitely see how you can become involved. Show your employer you’re not only skilled in the industry’s best practices, but your company’s as well.
Can you share any examples of notable tech executives who have successfully transitioned from one role (e.g., CIO) to another (e.g., CEO) within the same organization or industry? What factors contributed to their success?
I am really excited to see what former State of Florida CIO Jamie Grant is doing. He’s started a project/company/community called RedLeif focusing on cybersecurity, digital transformation, and SLED as a Service. I’m definitely keeping an eye on RedLeif and Jamie.
How important is it for tech executives to cultivate a personal brand and establish thought leadership within the industry? What are some effective ways for tech executives to showcase their expertise and gain visibility?
I never focused on a personal brand. Instead, I focused on my core values and ensured everyone knew what those were and why they were so important to me. “Integrity, Accountability, Diversity and Inclusion” When you know every decision you make is through the lens of those values, you automatically know what direction you’re going and have a much clearer idea of how to make day-to-day decisions.
Whether you call it a personal brand or not, people need to understand where you’re coming from. You can accomplish this in many different ways, but regardless if you’re trying to lead an organization through transformational change or get your name out there, your “brand” should be clear.
Get out of your comfort zone. Not everyone is drawn to the attention and exposure that comes from executive positions, especially when it’s with a major corporation or highly visible government agency. I never enjoyed marketing myself, but I always accepted opportunities that allowed me to showcase my team and what we were accomplishing as an organization. This helped me, as a fairly introverted person, to be more visible as uncomfortable as that was.
Lastly, what advice would you give to aspiring tech executives who are looking to accelerate their career progression and make a lasting impact in the tech industry?
I urge executives in all fields of expertise to stop playing it safe. We’ve all seen the paralysis this can cause and it’s often caused by real pressures and a fear of losing the position you’ve worked so hard to achieve. Our jobs are hard; they should be hard. You’re letting your team and entire organization down if you’re not speaking up and ensuring your knowledge and experience drive change. The status quo never impressed anyone.
Creating a lasting impact comes with sacrifice and challenge. Push boundaries, be humble, and never lose sight of your core values. You might scare some of your colleagues, but your team will be motivated and excited to help you achieve your vision. Sticking with the same old gets you the same old with diminishing returns. Not very motivating or inspiring at all.
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