Gary Hensley is not just stepping away from a ten-year journey at Follett Software he’s stepping into something deeper, more profound. In his own words, this week marks the end of one chapter, but the beginning of another filled with curiosity, purpose, and the same passion that ignited his path a decade ago. As Vice President of Business Development at Follett Software, Gary Hensley wasn’t just a title-holder he was a visionary, constantly seeking ways to make systems better, more human, and more accessible. His recent reflection on LinkedIn is a poignant reminder that transitions, while bittersweet, can be powerful springboards toward greater impact.
Ten years ago, Gary Hensley stood at a school fundraiser table, holding a checkbook and wondering why it wasn’t easier to support something as important as education. That moment simple, even mundane planted the seed for a transformative idea. He asked the question so many of us overlook in everyday life: Why is something so valuable still so hard to do? From that moment, Gary Hensley began to chase a solution, not out of obligation but out of a genuine desire to serve educators, families, and communities in a more meaningful way.
Throughout his time at Follett Software, Gary Hensley became known not only for his strategic acumen but for the clarity and purpose he brought to the table. His journey is not just one of career progression, but of personal evolution a deepening of mission over time. For many, technology is about efficiency. For Gary Hensley, it’s about people. It’s about asking better questions, solving real-world problems, and making systems that work for people, not the other way around.
What sets Gary Hensley apart is not a list of accomplishments, though there are many, but the intentionality with which he pursues them. His LinkedIn post doesn’t focus on accolades; it focuses on lessons lessons earned through building, exiting, and starting again. His message is clear and actionable: Work with people who challenge and inspire you. Choose missions that matter. Be bold. These are not just entrepreneurial philosophies; they are life values.
Gary Hensley’s entrepreneurial mindset doesn’t just belong in startups it belongs in education, in philanthropy, in every space where systems need reimagining. His insight into school fundraising is one example of how an overlooked pain point can become a catalyst for innovation. It’s a reminder that sometimes, the spark for the biggest changes comes from the smallest frustrations.
This isn’t the first time Gary Hensley has stood at the edge of something new. With three exits behind him, he understands that reinvention isn’t a phase it’s a pattern, a rhythm. It’s the willingness to look at a blank page and see not uncertainty, but opportunity. To stand in front of the unknown and feel energized, not afraid.
There’s an incredible amount of freedom in that mindset. While many professionals focus on climbing a ladder, Gary Hensley focuses on building new ones ladders that others can climb, bridges that others can cross. His impact extends beyond software and systems; it touches on something essential: how we show up for others, especially those doing the often thankless work of educating the next generation.
Gary Hensley’s decision to move on from Follett Software isn’t about stepping away; it’s about stepping toward something that matters deeply to him. And though the next chapter is, as he puts it, “still unwritten,” it’s clear that whatever he chooses will be guided by the same principles that have marked his journey so far collaboration, mission, and boldness.
In a world that often values speed and noise, Gary Hensley moves with intention and clarity. He listens deeply, asks hard questions, and builds with a long view. It’s no surprise that those who’ve worked alongside him speak not only of his leadership but of his heart.
Transitions like this can be hard. Letting go of a decade of work is never easy. But Gary Hensley reminds us that change isn’t just necessary it’s magical. It’s a chance to realign with purpose, to rediscover curiosity, and to recommit to making a difference.
Whether the next chapter brings another startup, a new role in education innovation, or something entirely unexpected, Gary Hensley will undoubtedly continue to be a force for good. He’s someone who doesn’t just adapt to the future he helps shape it.
So what’s next for Gary Hensley? Only time will tell. But if his past is any indicator, it will be meaningful, challenging, and driven by the same spirit that brought him here in the first place.
In the meantime, his words and example serve as a compass for anyone at a crossroads: Choose people who inspire you. Choose missions that matter. Be bold.
