Chicago Managed IT Services Company, LeadingIT, Pledges $5 Million in Employee Profit Sharing
The announcement reflects a years-long personal and organizational evolution for Taylor, who founded LeadingIT from zero resources at age 25 with no clients, no savings, and no safety net. Over more than a decade, the company earned three Inc. 5000 designations, completed four acquisitions, and built a reputation for reliable technology partnerships with businesses across Chicagoland.
LeadingIT’s Chicago office, now a central hub for managed IT services, cybersecurity, and cloud solutions throughout the region, is at the heart of this next chapter. As a managed service provider supporting organizations across healthcare, legal, finance, and professional services, the firm operates as a trusted technology partner for Chicago-area businesses, with a team of IT professionals, cybersecurity analysts, and IT help desk specialists whose work directly shapes the reliability and security of businesses throughout the city and suburbs.
“I know what zero feels like,” said Stephen Taylor, CEO of LeadingIT. “I was out on my own at 16. For years I measured success by revenue because revenue was the safety net I never had. But I realized the higher I climbed, the deeper the hurt locker got. What I truly wanted, what I think most people want, is a wholly successful life: health, family, relationships, impact, presence. And real success isn’t solo. It’s shared. That’s why we’re committed to putting $5 million back into the hands of the people who build this company every day. Freedom for a hundred families, not just mine.”
The $5 million commitment will be distributed through structured profit-sharing over a ten-year horizon, with the goal of giving LeadingIT team members genuine financial participation in the company’s continued growth. Taylor described the initiative as inseparable from a broader operational transformation: the adoption of the Entrepreneurial Operating System (EOS) to build sustainable team-based leadership, and a personal commitment to building a company that outlives any single leader.
The announcement also serves as a direct recruiting signal. LeadingIT is actively expanding its team across managed IT services, IT support, cybersecurity, and client success roles throughout Chicago and the surrounding Chicagoland market. For the right people, this is not simply a job change. It is a chance to see what a purpose-driven IT MSP looks like from the inside: a three-time Inc. 5000 company running on a structured EOS operating model, serving businesses that have trusted LeadingIT with their IT outsourcing across healthcare, legal, and finance, and publicly on record committing real profit back to its team. People who join LeadingIT are not just filling a role; they are building equity in a culture that is intentionally designed to reward contribution. The managed IT services and cybersecurity work happening out of LeadingIT’s Chicago office is where that kind of career gets built.
LeadingIT’s path to this announcement was not without difficulty. Taylor described a period in which the company churned 80 percent of its team in a single year, an acquisition that went significantly wrong, and a 20 percent revenue decline, all while he was reorienting the company’s leadership structure and culture. Rather than retreat, the company held to its long-term vision and continued investing in people and process. That resilience, Taylor argues, is what makes the profit-sharing pledge credible rather than aspirational.
Chicago-area businesses seeking managed IT services and cybersecurity support, as well as technology professionals exploring new opportunities in the market, can learn more at LeadingIT or view current open IT positions on the company’s careers page.
About LeadingIT
LeadingIT is a managed IT services and cybersecurity firm serving businesses throughout Chicago, IL and the surrounding Chicagoland area including the West Loop, River North, Lincoln Park, and suburban communities across Cook and DuPage counties. Located at 600 W Jackson Blvd, Chicago, IL 60661, LeadingIT specializes in proactive IT management, network security, cloud solutions, help desk support, and compliance-focused cybersecurity services for small and mid-sized businesses.
For inquiries, call (815) 308-2095, visit https://goleadingit.com/chicago-managed-it-services
or explore career opportunities at https://goleadingit.com/careers/
Stephen Taylor
LeadingIT
+1 815-308-2095
info@goleadingit.com
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