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Meet Our Systems Administrator – Graig Wheelock

Meet Our Systems Administrator – Graig Wheelock

December 2, 2025
Graig Wheelock

Graig serves as a Systems Administrator at IT Insights, bringing over two decades of hands-on experience fueled by a passion for technology that started when a friend introduced him to online gaming and PC building. Known for his thoughtful, client-first approach, Graig focuses on building trust and delivering solutions that truly meet clients’ needs.

We sat down with Graig and asked him a few questions we thought our clients and partners would like to know:

Q: How did you get to where you are today in your career?

A: My interest in technology began about 25 years ago when a friend introduced me to online gaming and helped me build my first computer. At the time, I was working as a manager at McDonald’s, but the demanding schedule — nights, weekends, and holidays — along with the high-stress environment made me eager to transition into a new field.

I initially pursued a traditional college path but found the coursework wasn’t providing the practical skills I needed. I shifted my focus to professional certifications, which offered more relevant, hands-on learning and accelerated my career transition into IT.

Q: What do you prefer to work on?

A: Backup remediation, disaster recovery, and Hyper-V

Q: What’s the most unusual or interesting tech problem you’ve ever had to solve?

A: At a previous position, I was challenged to develop a comprehensive imaging solution for multiple departments across the company — with zero budget. The only constraint was that I could utilize existing resources.

After researching options, I identified FOG (Free Open-Source Ghost), an open-source deployment tool that met our requirements. I repurposed an older server, installed and configured FOG, then created customized base images for each department. I also configured the server as a PXE (Preboot Execution Environment) server, enabling network-based deployment without physical media.

This project exemplified what I find most rewarding in IT: creative problem-solving under constraints. I was able to deliver a zero-cost solution that streamlined our deployment process while making full use of existing infrastructure. The hands-on nature of the work — from hardware repurposing to network configuration — made it particularly satisfying.

Q: How do you stay updated with the ever-evolving technology landscape?

A: I listen to podcasts like This Week in Tech (TWiT), read Hacker News (news.ycombinator.com), and subscribe to Udemy for continued training/courses.

Q: What is your favorite tech tool or trend you’d recommend to everyone?

A: A good password manager (i.e., LastPass).

Q: What’s your go-to tech gadget or app that you can’t live without?

A: My phone.

Q: What’s your approach when advising clients on technological solutions?

A: Good advisors act as trusted partners, not just vendors. My goal is to understand their unique situation, present well reasoned options, and guide them toward solutions that genuinely meet their needs — even if that means recommending something simpler or less profitable for us. Building this trust leads to long-term client relationships and referrals.

Q: What advice would you give to someone getting started in your field?

A: Certifications, certifications, certifications.

Q: If you weren’t working in IT, what alternative career path would you have pursued?

A: Food service. I left this field due to the demanding hours and stress.

Q: What do you do in your free time?

A: Fishing, camping, hiking, spending time with the kids, and reading.

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Categories:IT Insights Life, Team|Tags:Employee Recognition, IT Team
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