Stephen Taylor

Meet Stephen Taylor

Entrepreneur. Visionary. Technology Problem Solver.

Most IT companies talk about technology.

Stephen Taylor talks about what technology is actually supposed to do:

Help businesses move faster, stay secure, and stop wasting time fighting broken systems.

Stephen founded LeadingIT in 2010 with a simple belief:

Technology should just work.

Not create bottlenecks.
Not leave businesses waiting days for support.
Not become a liability every time a cyberattack hits the news.

Today, LeadingIT has become one of Chicagoland’s premier managed IT and cybersecurity firms, supporting businesses, nonprofits, manufacturers, municipalities, and professional organizations that rely on technology to operate every single day.

But none of this started in a boardroom.

It started with a kid taking computers apart just to figure out how they worked.

Built Through Real Experience

Stephen’s story is not the polished “serial entrepreneur” story people expect.

He lost his mother at a young age. His father had already left. Growing up, life was unstable, and technology became an escape, something he could control, understand, and solve.

That mindset never left him.

Even after studying computer science at the Milwaukee School of Engineering, Stephen realized quickly that experience was teaching him more than a classroom ever could.

So he bet on himself.

In 2010, he quit his job and started LeadingIT from scratch.

No giant investor backing.
No massive team.
No safety net.

Just a vision to build the kind of IT company businesses actually wanted to work with.

“There’s Nothing Unsolvable”

That mentality became the foundation of LeadingIT.

Stephen built the company around responsiveness, accountability, and solving problems other providers ignore, avoid, or overcomplicate.

Around here, the mindset is simple:

We Figure IT The F*ck Out.

That philosophy helped LeadingIT grow from a one-person operation into an award-winning IT and cybersecurity company supporting organizations across Chicagoland.

Today, LeadingIT is known for:

• All-inclusive managed IT services
• Advanced cybersecurity protection
• Fast, friendly live-answer support
• Strategic technology leadership
• Vendor management and concierge support
• Local onsite service across Chicagoland
• A team that actually answers the phone and gets things done

Stephen has always believed businesses deserve an IT partner that takes ownership instead of making excuses.

That’s a big reason clients stay.

Leadership That Puts People First

Stephen’s leadership style is direct, honest, and people-first.

He believes culture matters. Accountability matters. Speed matters.

But taking care of people matters too.

Under Stephen’s leadership, LeadingIT has built a team culture centered around autonomy, trust, personal growth, and continuous improvement.

He has also led the company through rapid growth while maintaining a strong reputation for customer experience and employee investment.

LeadingIT has:

• Been recognized 3X on the Inc. 5000 list
• Expanded to 4 Chicagoland locations
• Been named one of Chicago’s Best and Brightest Companies to Work For
• Created a $5 Million Dollar Pledge to share $5 million in profit-sharing with our team
• Supported thousands of end users across the region
• Maintained 98% positive customer satisfaction ratings over the past 10 years

Stephen also pushes his team to stay involved locally through nonprofit partnerships, charity work, and community initiatives throughout Chicagoland and McHenry County.

Because business is bigger than revenue.

Author, Speaker & Technology Advocate

Stephen is also the author of Technology Should Just Work and Unsolvable Solved, business-focused guides designed to help organizations avoid overpaying for IT services and make smarter technology decisions.

His approach is intentionally straightforward and practical, translating complicated technology topics into clear business conversations that executives can actually use.

Outside of Work?

Stephen likes fast cars, racing, great food, and moving quickly.

One phrase that often follows him around is:

“Go Fast, Don’t Die.”

Which honestly sums up both his personality and the culture at LeadingIT pretty well.

Move with urgency.
Take care of people.
Solve problems.
Keep improving.

That’s the standard.

Work With LeadingIT

If your business is tired of reactive IT support, slow response times, cybersecurity uncertainty, or technology vendors pointing fingers at each other, Stephen Taylor and the LeadingIT team are ready to help.

Ready to have a real conversation about your technology?