Faces of CompTIA AITP: Darryl McCaskill

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After Forging His Own Path to Tech, This Atlanta IT Executive Wants to Close the Confidence Gap for the Next Generation.

Darryl McCaskill is a tech industry veteran and CompTIA AITP member who spent more than three decades in various IT roles at Macys. But his career path into technology was by no means laid out for him.

Neither of his parents graduated from college and no one in his family worked in tech.Darrtyl McCaskill Headshot Despite not having a mentor in the tech industry when he was young, Darryl has always been technically curious. He remembers being fascinated by gadgets as a kid and often spent free time using a keyboard to program his Atari as a young adult.

Down the road, this curiosity would play a key role in jumpstarting his career in tech. “To be successful in technology you need to have an innate, natural curiosity,” says Darryl. 

After landing a job as a collector for Rich’s—a retail chain based in Atlanta that eventually merged with Macys—he seized an opportunity to work on a system conversion project the company was undertaking. His efforts on the project paved his way into the IT department.

“I remember being so excited that I made my way into IT,” says Darryl. “I knew it was a lucrative field and I grew up kind of simple. My dad ran a Piggly Wiggly grocery store and my mother managed the home. Like Winnie-the-Pooh, I fell into a pot of honey.”

Darryl worked his way up in the Macys IT department, eventually becoming group vice president of application development. However, his legacy at the retail company stretches far beyond the technology he implemented and supported. In fact, by fostering a more inclusive workplace, his biggest impact was on company culture.

In the early 2000s, Macy’s Technology launched a diversity program to promote a more inclusive culture at work. Darryl helped drive initiatives that included making diversity leadership a part of the company’s review process. They also implemented mentorship programs and learning communities that encouraged people from different backgrounds to work together on training and skills development programs, a critical step to closing the confidence gap—where the lack of diversity in the IT industry can cause individuals to think that a career in tech is not for them.

Darryl now works with Mogean, a cutting-edge startup that uses geospatial location analytics to help retailers better understand how their customers behave. He says the ability to be a mentor for other people who grew up without a background in IT is what he likes most about working in tech. “Nothing in my background said I would one day be a senior executive in IT. It was something I built myself, and now I enjoy helping others grow in their careers and discover how they can create opportunities.” 

Darryl believes the tech industry can continue to improve around diversity and inclusion, but he’s excited that things are evolving in the right direction. He joined CompTIA AITP Atlanta in October 2017 and his experience with the chapter reflects this. “The tech industry is really growing in Atlanta and the mix of diversity across race, gender, and age I see at our chapter meetings is a great sign of where the industry is heading.”