For better or for worse, a company’s corporate culture is often created and shaped by the attitudes, mores and actions of leadership that are observed by their charges, a.k.a. the team members. This is why many office technology dealers that value their reputation within the market are focused on constructive, repeatable interactions that reflect positively upon the organization and its clients.
Consistency is key. When asked one day why he always plays so hard, baseball Hall of Famer Joe DiMaggio observed, “Because there might have been somebody in the stands today who’d never seen my play before and might never see me again.” It only takes one moment to solidify an impression, and for Hayden Free, that came early in his career with San Antonio-based DOCUmation.
DOCUmation is among those companies that encourage autonomy, particularly whenever a team member makes a decision in the best interests of its clients. But what really captured Free’s attention one day was when an employee’s best interests were placed above those of the dealership. That DiMaggio moment convinced Free that he was in the right place professionally.
“The situation was handled by putting the employees’ interests as top priority without a second thought. That moment confirmed that I was part of something rare—an organization where doing the right thing isn’t optional,” said Free, a 2025 ENX Magazine Difference Maker. “It laid the groundwork for how I approach my team every day.”
A graduate of Abilene Christian University (ACU) in 2016, Free jumped on the opportunity to serve as an intern with DOCUmation beginning in 2015. The opportunity was something of a mystery, and the only guidelines he set was to not have a desk job that involved crunching numbers or pushing papers. Free longed to be interacting with people and developing a better understanding of the cadence of real business. Fortunately, DOCUmation checked off those boxes. By the time he completed the internship, it was clear the dealership valued people as much as profit, perhaps even more so.
Free had found his professional home, and it would serve him well in providing for his growing family. They were, and remain, his ultimate motivation.
“Early in my career, I heard a saying that stuck with me: ‘If you don’t know where you’re going, any road will get you there,’” he said. “I know exactly where I’m going, and that’s building a life for my family. They’re the reason I keep my foot on the gas.”
The vice president of DOCUmation’s West Texas branch, Free appreciates how the Midland operation grew from a single technician to an established regional office. He saw it as validation of the idea that when you remain above reproach in all areas and work hard, success will follow.
But the man with his foot on the accelerator is more driven to double down than to bask in glory. Territorial expansion sits atop the priority list.
“I’m fueled by competition and the drive to keep expanding our footprint and earning the West Texas marketplace and then pushing into the Panhandle,” he added. “Continued growth will come from investing in young talent, maintaining high standards of service and developing the next generation of leaders who share that same drive.”
On the home front, Free and his wife, Chandler, met at ACU and were married in 2016. The couple have a three-year-old son and are expecting a daughter in the near future. Family activities dominate his docket, but he also enjoys traveling and hunting (“I’m an avid upland bird hunter and will take any excuse to be outside,” he added). Free also loves vacationing in the mountains.
