Working at LeadingIT means joining a group of people obsessed with taking on the real challenge of cybersecurity and helping businesses across Wisconsin, Illinois and Indiana. With locations in Woodstock, Downtown Chicago and Manteno, IL we are the areas premier IT company with a positive team culture.
Our values guide us to always deliver our very best
We are DRIVEN
We are motivated to grow, succeed, and push forward, both professionally and personally. Our effort fuels not only our own success, but the success of our clients and our company.
We are ACCOUNTABLE
We take ownership—for our results, our clients, and each other. This means following through, owning mistakes when they happen, and making things right without excuses.
We STAY POSITIVE
We keep a positive, solution-focused mindset. We choose to focus on what we can do instead of what we can’t—because how we think drives how we act.
We CHASE EXCELLENCE
We pursue EXCELLENCE in what we do; all day, every day. We hold a high standard for ourselves and our work, always striving to improve and deliver the best for our team and our clients.
We are HUMBLY CONFIDENT
We lead with confidence grounded in humility. We trust our abilities, continue to learn, and aren’t afraid to ask for help to get the best outcome.
Perks of Working at LeadingIT
$5 Million Dollar Pledge
Over the next decade, we’re committing $5 million in profit-sharing directly to our team, because real success means everyone wins.
Full Health Insurance
401k
My Time Off Policy – Open Door PTO
Yearly Raises
Free Lunch
Paid Certifications
Automatic COLA Raises
Anniversary Gifts
$100 for every year of service for milestone years. Personalized gift boxes for non-milestone years.
Fitness Incentives
Mental Health Focused
LeadingIT holds the Silver Bell Seal Certification. This award is a national certification program that recognizes employers who are committed to creating mentally healthy workplaces.
The Nation’s Best and Brightest in Wellness
LeadingIT is recognized as one of the 2025 Nation’s Best and Brightest in Wellness! This prestigious honor celebrates our outstanding commitment to employee well-being and workplace health.
At LeadingIT, we use EOS, the Entrepreneurial Operating System, to keep our company running smoothly and our team aligned. It’s a simple set of tools and processes that helps us set clear goals, stay accountable, and keep everyone rowing in the same direction.
Why does this matter to you as a candidate? Because at LeadingIT, you’ll always know what success looks like, how your role contributes to the bigger picture, and where the company is headed. You’ll work with a leadership team that values transparency, clarity, and accountability and you’ll be part of a team that gets the right stuff done.
EOS helps us work smarter, grow faster, and build a culture where people actually enjoy showing up every day. We’re serious about performance, but we don’t take ourselves too seriously and we know that success starts with living our core values. If you’re someone who chases excellence, has drive, owns your stuff, stays positive, and brings a humble confidence to your work, there’s a good chance you’ll thrive here.
