We’re excited to introduce you to the always interesting and insightful Gary Whittaker. We hope you’ll enjoy our conversation with Gary below.

Gary, appreciate you joining us today. Naming anything – including a business – is so hard. Right? What’s the story behind how you came up with the name of your brand?

I always knew that I didn’t want a “tech-y” name for my company even though we would provide IT services. I wanted it to be meaningful in many levels.

When naming the company, Chief Second, two influences came together. At the time, I was actively boxing, and in that world, a “chief second” is the head coach in a fighter’s corner—the person guiding strategy, offering support between rounds, and ensuring the fighter is set up for success. That role resonated with me deeply. I saw a parallel between that and how I wanted our company to serve clients: not in the spotlight, but essential to their success—always in their corner, making sure everything runs smoothly so that they would continue to shine.

Though that was a great driving force for the name, the greater inspiration was spiritual. I believe this company ultimately belongs to God. The name Chief Second reflects our posture of humility—we are second to Him in all we do.
Every decision, service, and relationship we build is shaped by these two truths: we are strategic support for our clients, and faithful stewards of a mission that’s bigger than us.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

My journey into technology began in an unexpected place—while working at Publix, a local supermarket. A French colleague and I often found ourselves deep in conversation while bagging groceries about tech, and he suggested I explore a degree in Management Information Systems. That recommendation changed everything. The more I studied, the more I realized how passionate I was about technology—not just using it, but understanding it, building with it, and helping others benefit from it.

That passion led to an internship at NetCor Technologies in Miami, which to led to an even greater leap, moving to New York City! There I worked for over 16 years at Method Group, where I gained hands-on experience and a deeper appreciation for the impact technology can have on a business. Eventually, I founded my own company, Chief Second, an IT consulting firm based in Manhattan.

At Chief Second, we serve small to mid-sized businesses by fixing their tech issues, offering strategic technology planning, and providing ongoing security. But more than that, we’re a trusted partner in our clients’ growth. We empower them to stay focused on what they do best, knowing their technology is aligned, protected, and ready to scale.

What sets us apart? It’s how we treat people. I’m most proud of the way we support our clients—and each other—with generosity. Relationships matter, and our clients feel that in every interaction. It’s not just about solving problems; it’s about helping people thrive.

That same spirit of generosity extends beyond our company. We believe the resources we receive are meant to be a blessing to others. Whether it’s local needs or global impact, we’re intentional about using our success to serve those who may never become clients—but still matter deeply to us.

For anyone getting to know us for the first time, know this: we’re not just tech experts—we’re in your corner, ready to help you build something excellent and meaningful.

How about pivoting – can you share the story of a time you’ve had to pivot?

I’ve been in tech for over 20 years—but really, it started when I was just a kid. I still remember sitting on my dad’s lap, mesmerized by the glowing green text on his old-school black monitor in the mid-80s. I was hooked from that moment on.

In my previous role, I worked my way up from entry-level technician to second in command, overseeing operations. But something deeper kept stirring—an inner pull I couldn’t ignore. It wasn’t just about starting a tech company. It was about building something with purpose.

A company that doesn’t just solve problems, but changes lives. One where success isn’t measured only by profit, but by generosity—using what we earn to lift up those in need.

This wasn’t just a career move. It was a calling.
As our mission statement ends: “…for the well-being of others, and the glory of God.”

Are there any books, videos, essays or other resources that have significantly impacted your management and entrepreneurial thinking and philosophy?

Throughout my journey there have been so many books that I have gleaned from, but particularly two books by Mark Batterson have deeply shaped my leadership and decision-making.

1. Chase the Lion
I read this book at a time when I was praying for direction. Batterson’s message — that God often calls us to take the first step of faith before He reveals the second — hit me hard. It gave me the clarity and courage to leave full-time employment and step into entrepreneurship. I still reference this book often as a reminder that obedience sometimes means moving before the map is drawn.

2. The Circle Maker
This book taught me the power of bold, persistent prayer. When I believe in something, I “circle” it in prayer until I see God move. Not because of my strength, but because I trust God to do what only He can. I’ve watched Him show up and show off time and time again.

These books didn’t just inspire me — they confirmed that God is in the details, and leadership begins with listening to Him.

Contact Info:

• Website: https://chiefsecond.com
• Linkedin: https://www.linkedin.com/in/gary-whittaker/