Justin Sider’s path to CIO wasn’t the traditional one. He didn’t start with a computer science degree and neatly map out his future IT career. He started as a teenage park ranger.
“I was walking around parks, picking up trash and telling people what they can and can’t do,” Sider recalled. The ranger gig began at age 15 and Sider kept at it through high school and a bit beyond. “It was an absolute blast.”
His career in IT began with a full-time, entry-level job on a help desk. From there, things took off. He eventually became a self-taught system engineer and then an IT director. In 2011, he joined Belay Technologies Inc., a technology and engineering defense contractor based in Columbia, Md.
One year later, he was named Belay’s chief information officer, in charge of the small company’s IT needs. Last year, he was elected to serve on the Board of Directors of VMUG, the VMware Users Group, an independent, global group focused on how to get the most out of VMware software through training, collaboration and events.
Discovering VMUG
Sider discovered VMUG about the same time he joined Belay. He remembers being drawn into a VMUG trade show booth. “They were giving stuff away, so, you know, you go over to the booth, you check them out.” But what kept him at the booth wasn’t the swag. It was the people.
“It’s a great following of people who are just energized around the technology,” he said. “And I wanted to be part of it.”
His decision to join VMUG was a pivotal one. The community became a space for Sider to learn, share, and grow in ways that weren’t always available on the job. Working largely for government clients, he didn’t always have the same access to resources or technologies as those in the private sector. VMUG bridged that gap.
“For me, VMUG has been consistent in providing that opportunity to network and learn from my peers,” he said.
Building Skills Through Community
Sider’s technical focus has long been on automation, especially PowerShell and PowerCLI. VMUG gave him an avenue to deepen those skills and learn how others were solving similar automation challenges.
That sense of exchange is central to his view of VMUG and its role in the VMware and IT ecosystems. It’s not just about learning from others, it’s also about giving back.
Over time, Sider moved from being strictly a VMUG consumer to one who presented and mentored others. “VMUG gives the community an opportunity to come together, to challenge each other, and then teach,” he said.
Those connections are real. For some of Sider’s VMUG friends, VMware’s annual Explore events are the only time of year they see each other in person. “There’s a huge, tight-knit group of VMUG users. Over the years I jokingly tell them ‘Happy New Year’ when I see them at Explore.”
Brad Tompkins, VMUG’s executive director, said Sider has been an asset to VMUG, having provided a wealth of knowledge to the organization for the past decade. In 2026, Sider will take on the role of VMUG vice president.
"Drawing from his deep expertise in local chapter operations, dynamic public speaking skills, and forward-thinking strategic guidance, he empowers VMUG members to navigate and succeed in the rapidly evolving technology landscape,” Tompkins said.
VMUG and VMware: A Stronger Connection
Sider said the relationship between VMUG and VMware has strengthened since Broadcom acquired VMware in 2023. Some users worried about the impact on community engagement.
“It’s actually gotten a bit better,” he said. “As far as the VMUG relationship with Broadcom, I think it’s probably as strong as I’ve ever seen.”
A big part of that, he said, comes from leadership visibility. He points to Hock Tan, Broadcom’s president and CEO, who’s made a point of regularly showing up at VMUG UserCons and connecting with the community.
“It’s an interesting dynamic,” he said. “You can see that he wants to make the product better, and he knows that in order to make the product better, he needs users, he needs people to advocate about things that they want to see in the product. So it’s great to see him at events, it’s great for him to be so open and honest.”
A Career Without a Degree
Another aspect of Sider’s career story that stands out is how far he’s come without a four-year degree. He earned a two-year degree in general studies and picked up certifications along the way, but most of his skills came through hands-on work.
“I got a little discouraged when I was going to online classes at night, and I knew more than the professors based on my day-to-day experiences,” he said.
Instead, he focused on community and practical experience.
“I think that’s one of the things where VMUG and the VMware community excel is in engaging people and getting them excited about technology. I don’t know if my trajectory would have been the same had I not wanted to be a part of the community and challenge myself.”
That perspective shapes how he leads his team today. Of the 16 people working under him on a project, only four have degrees. For Sider, passion and problem-solving skills often matter more than formal credentials.
Problem-Solving Like an Animal
Speaking of problem-solving, Sider has a unique take on it, one that ties back to his days as a park ranger. At this year’s Explore in Las Vegas, he gave a well-attended talk on “Improving Your Problem-Solving Skills by Studying Nature’s Best Hunters.”
In his presentation, Sider compares the different ways engineers solve problems to different types of predatory animals. For example, he said, one of his friends approaches problems like a snake: “He takes a look at a problem, just tries to swallow it whole.”
Engineers are problem solvers. And finding creative ways to approach challenges is part of what keeps the work interesting, Sider said.
When he’s not running IT operations, mentoring engineers, or serving the VMUG community, Sider is a family guy. He and his wife have two teen children and live in San Antonio, Texas. He spends a lot of his free time on the soccer field, both coaching and refereeing. And when he needs some downtime, you’ll find him on the golf course.
Why VMUG Matters
Looking back on his career, Sider views VMUG as more than just another professional network. It’s a community that has given him mentors, friends, and a platform to grow both technically and personally.
“You initially never feel like you fit in until you can look back and see you’ve made all these friends that you look forward to seeing at different conferences,” he said.
That sense of belonging is what keeps Sider and thousands of others invested in VMUG. Whether you’re a seasoned CIO or just starting out on a help desk, the group offers a place to learn, connect, and challenge yourself. Read more about how VMUG leaders are shaping the future of private cloud and IT here, and to learn more about VMUG, please visit: www.vmug.com.