Proper Sky began with a simple idea: that information technology could be both deeply human and operationally excellent. Jim Smith, founder and chief executive officer, always had the drive to build, solve problems and create something meaningful. Guided by an entrepreneurial streak and a desire to do things differently, he transformed a small IT venture into a dynamic force known for partnership, clarity and measurable results.
Smith’s career traces back to early experiences that shaped his commitment to integrity and innovation. With entrepreneurship hardwired into his thinking, he wasn’t content to follow established paths. Instead, he created Proper Sky with a model that emphasized strategic alignment over transactional service. Clients weren’t customers—they were partners. And support wasn’t just technical—it was built around understanding business needs and long-term goals.
The company’s rise wasn’t accidental. It was crafted through discipline, data and a commitment to doing the right thing when it was hardest. Smith steered the organization through key moments of reinvention, always insisting that people—clients and employees alike—come first. That perspective powered growth, pushed boundaries and has earned him distinction as a Titan 100 Honoree, a title reflecting more than accolades: it reflects how he leads.
Over the next five years, Smith sees Proper Sky redefining managed services through innovation and automation. But the goal isn’t disruption—it’s clarity. He’s building tools that give clients transparency into their tech health and enable smarter decisions. Cybersecurity will be deeply embedded, support will be increasingly proactive and service will remain anchored in trust. As others race to automate, Smith is focused on intelligent, intentional transformation.
His energy comes from being in the arena. Solving hard problems, pushing for excellence and creating moments of real progress are what reignite his passion day after day. The entrepreneurial fire doesn’t fade—it evolves. And he shares that fire with his team through mentoring, transparency and a culture that celebrates impact over noise.
Among his proudest achievements is Proper Sky’s 95% client retention rate. This metric isn’t just a number—it represents trust, reliability and the tangible value Proper Sky delivers to its clients. In an industry where churn is common, maintaining such a high retention rate is a testament to Proper Sky’s unwavering commitment to its customers.
The skill he most wishes he could master instantly? Patience. Not out of frustration but from an understanding that real transformation—whether personal or professional—takes time, and that slowing down can often be the most strategic move of all.
Smith’s approach to leadership defies flash. He doesn’t seek attention; he seeks results. With a compass grounded in ethics and a strategy rooted in client success, he’s not just running a business—he’s building a standard.
