Stephen Taylor

Always tied to technology, Stephen Taylor focuses on bringing the best technology to businesses.  He has been the driving force behind LeadingIT – the energy, the vision, and the success. LeadingIT has since become a standout in the Crystal Lake area for technology and cloud support companies, honored locally as well as in the industry.

Stephen was always involved in technology at a young age and studied at Milwaukee School of Engineering for Computer Science, he is also Microsoft Certified for Small Business Server. Interesting enough is the fact that everything Stephen knows has been learned hands-on, not in the classroom.

Stephen is also the author of “Technology Should Just Work” which provides a basic, non-techie education on how to avoid overpaying for IT services, what questions to ask your IT consultant before signing a contract and how to spot an incompetent or dishonest IT person before giving them access to your computer network.

LeadingIT currently serves over 2500 staff members, at 80 client businesses across Chicagoland, with an internal staff of 10 full-time engineers – all on a monthly flat fee basis (saving our clients well over $25,000/month collectively). We hold a 95%+ client satisfaction rating. And we’re just getting started! Under Stephen’s direction, LeadingIT is on track to continue growing more than +30% every year since opening in 2010.

At LeadingIT, Stephen and his team support the Crystal Lake community — in 2013-2016 raised more than $5,000 towards Extra Life (benefiting local children’s hospitals). They plan to earn more at the 2017 event and to do even more work this year for the community. LeadingIT gives back locally to Big Brothers Big Sisters and other non-profits as well.

“Go with what you FEEL”

Stephen serves on the Crystal Lake Chamber Finance Committee and is a Chair in the Young Professionals group.  He is also Captain of the “Marketing Madness” IT owners accountability group in Nashville, which earned “Accountability Group of the Year in 2016”. Stephen also serves on the Board for Big Brothers Big Sisters McHenry County.

Outside of working hard and giving back, Stephen enjoys going fast in karts and cars, summertime, good food and cooking, and great music from around the world.

“I started our company LeadingIT when I was 25 back in 2010 (I know, I thought I would start younger too). I had a crazy idea to start an IT company and quit a well paying full-time job. Today, we support a multitude of businesses and their teams across Chicagoland with all of their technology. And we have one of the fastest and friendliest teams around.