John Winfrey serves as Director of IT at Ardmore Enterprises, a nonprofit organization in Lanham, Maryland, that empowers individuals with intellectual and developmental disabilities. Ardmore provides residential housing, community services, and employment programs that promote independence and inclusion. John brings over 30 years of experience to his role, spanning the IRS, Abacus Technology, and a two-decade tenure at Microsoft. His personal journey as a visually impaired technologist gives him a unique understanding of accessibility, innovation, and leadership in IT.

Here’s a Glimpse of What You’ll Learn

• How John built a successful IT career despite visual impairment

• Why accessible technology creates opportunity and loyalty in organizations

• The evolution of assistive tools from early magnifiers to adaptive software

• How Ardmore’s accessibility lab helps individuals discover life-changing tech

• The role of inclusive design in empowering employees with disabilities

• Leadership lessons from decades in both corporate and nonprofit environments

• Why community and challenge drive innovation in IT teams

In This Episode

John shares the story of how his career began with a Commodore 64 and evolved through persistence, adaptability, and purpose. After training at Lions World Services for the Blind, a program sponsored by the IRS, he began working in government IT and later joined Microsoft, where he spent 20 years helping to make technology more accessible. Today, at Ardmore Enterprises, he leads IT operations and drives forward-looking initiatives focused on adaptive equipment, AI, and inclusion.

He reflects on the early challenges of working in technology before accessibility was built into systems. In the early 1990s, he relied on oversized monitors and magnifying lenses to perform tasks. Now, modern accessibility features in Windows and other software make his work far more efficient. But he emphasizes that progress in technology must be matched by a change in mindset and helping others understand that disability is not a limitation but a perspective that enriches organizations.

John also discusses the creation of Ardmore’s accessibility lab, a new initiative that introduces individuals with disabilities to technologies that can improve their work and personal lives. Through partnerships with hardware and software developers, the lab allows participants to test tools and find those that best fit their needs. It is a place where innovation meets empowerment.

On leadership, John explains that the best IT teams thrive when leaders inspire creativity and ownership rather than control. He encourages team members to find their own solutions, collaborate openly, and share success. For him, great leadership is about creating an environment where people are motivated to build, learn, and grow together.