2025 Men of the Year: Kevin Waterland

Kevin Waterland is a driving force for technological development in southern Missouri. As general manager and co-owner of Pitt Technology Group LLC, he shares his expertise with employees, clients and nonprofits to advance his local community.

Waterland co-founded Pitt Technology Group with Doug Pitt in 2017 as an information technology provider. The company has since expanded through multiple acquisitions to include additional services such as software development and artificial intelligence infrastructure.

“Our AI offerings enable organizations to train and deploy AI models on-premise, ensuring data security, cost-efficiency and business intelligence advancements,” he says. “This shift positions Springfield as a technology leader, giving regional businesses a competitive edge.”

Waterland manages a team of approximately 50 employees, and Pitt Technology Group brings in $11 million in annual revenue. The company has received the Springfield Business Journal Economic Impact Award and Community Impact Award, as well as the Springfield Tech Council Community Impact Award and Best Technology Provider Award.

Investing in employees is essential to this success, Waterland says. Pitt Technology Group offers flexible schedules, a robust benefits package and annual employee bonuses average between $300,000 and $400,000, nearly 10% of total payroll.

“These investments ensure our staff feel valued, motivated and secure in their careers,” he says.

Waterland’s empathetic, mentorship-based approach to leadership stems from personal experience. He left high school early to enter the workforce, beginning to work for Pitt’s ServiceWorld Computer Center at 18 years old. Within four years, he became a senior level network engineer and team leader. Waterland is passionate about helping others with a nontraditional background gain the skills needed for successful tech careers. He emphasizes apprenticeship and mentorship programs which allow entry-level employees to grow into leadership roles.

“Having started my career without a high school diploma, I understand the importance of mentorship, opportunity and resilience,” he says, “and I strive to create those same opportunities for others through my work, leadership and community engagement.”

Waterland is involved with numerous community efforts and causes. He leads Pitt Technology Group’s philanthropic initiatives including the donation of more than $600,000 worth of IT services to local nonprofits including Care to Learn, the Drew Lewis Foundation and the Springfield Regional Arts Council.

“We build long-term technology strategies that lower nonprofit operational costs and allow them to reinvest resources directly into their missions,” he says. “From equipping organizations with AI-powered tools to donating high-performance IT infrastructure, we are strengthening the nonprofit sector with the same innovation we bring to businesses.”

Family: I’ve got a wonderful wife and four amazing kids, ranging in age from 10 to 21. None of them are into tech, which makes home life refreshingly different from work. They keep me balanced, humble and constantly entertained – and they remind me that what I build at work is ultimately for them.

Advice to other men: Be real. Don’t let pride keep you from learning or listening. Show up, do the work and build something that lasts.