We make tech work for growing NYC businesses.
We're the tech team that actually shows up, responds fast, and treats your business like our own.
%20(1).avif)
About us
Since 2023, we've been doing IT differently in New York City. No long-term contracts. No hidden fees. No corporate jargon. Just straightforward tech support from a team that cares about your success.
We bring enterprise-level IT to growing businesses, handling everything from daily tech hiccups to long-term strategy. Whether you need immediate support for a system failure or expert guidance on your next big tech move, we've got your back.
Think of us as your in-house IT team – except we cost less, respond faster, and bring 20+ years of experience to the table. Plus, a portion of every dollar you spend with us goes toward helping NYC families in need. That's what we call a win-win.
%20(1).avif)
Gary Whittaker, Founder & CEO
at Chief Second
Meet Gary Whittaker
After 16 years climbing the corporate IT ladder, I hit a breaking point. As the second-in-command at my previous company, I watched clients get lost in the shuffle of contracts, hidden fees, and slow response times. I knew there had to be a better way.
In October 2023, I felt called to start something different. A tech company that puts relationships first. Where we actually listen to what clients need instead of pushing our own agenda. Where profits fuel our mission to help NYC families in need.
Today, Chief Second is that vision come to life. We're building an IT company that measures success not just by our bottom line, but by how many lives we can impact through radical generosity.
Our Mission
Our values
Honor God
Approach every task with dedication and excellence, as if working for The Lord.
Generosity
Rooted in selfless service, we freely give our resources, time, talents, and innovations, going beyond expectations for the benefit of others.
Growth Mindset
We surround ourselves with remarkable people who elevate the mission, core values and vision.
Constructive Empowerment
Individuals are encouraged and supported to take initiative, make decisions, and contribute meaningfully to both our organization and the community.
Commitment to Community
Dedicated to fostering strong, supportive relationships and creating a positive impact in the communities we proudly work alongside and serve.
In everything we do at Chief Second, we follow a simple mantra: Show up. Listen first. Solve problems proactively. Give generously. This guides how we approach our work, treat our clients, and invest back into NYC.
Our commitment to ethical business and radical generosity isn't just talk – it's baked into our monthly budget and daily decisions. Every interaction, project, and dollar serves a greater purpose.
Join Our Team
Want to use your tech skills to make a real difference? We're always looking for talented people who share our vision of using business as a force for good in NYC.
%20(1).avif)
%20(1).avif)
Ready to experience IT done differently?
Let's talk about how we can help your business thrive while making a positive impact in NYC.
No pressure, no obligations. Just a friendly chat about your business needs and how we can help.