First jobs: How PC support gave a future CEO experience

Like a blue-raspberry Warhead or a Mortal Kombat finishing move, tech support in the ’90s was intense.

When it came to fixing that pre-Y2K hardware, sometimes you had to ask the caller to put their phone down and grab their toolbox.

Chris Rozum, now founder and CEO of Insite Managed Solutions, a contact-center operations consultancy, began his IT career at the service desk, guiding customers via phone through problems with their Gateway 2000 desktops (those computers that arrived in cow-print boxes, familiar to many a millennial).

That kind of repair work meant walking customers of varying levels of expertise through at-home repairs. “Think of your grandma. You’re saying, ‘Go find the screwdriver with the star on it, and we’re gonna go take things apart,’” Rozum told IT Brew.

The Gateway 2000 support role became a “stepping stone” to subsequent stops along Rozum’s career path, giving him the IT fundamentals essential for call-center tech expertise, as well as a knack for translating those concepts for non-technical people—skills he uses today as he bridges the knowledge gaps between COOs and CIOs/CTOs.

At your service. A Gateway 2000 computer, for those unfamiliar with the technology of the era, sometimes featured a beige tower (with CD-ROM and floppy-disk drives), old-school cathode-ray tube monitors, a keyboard with high raised keys, and a mouse. It was a big, heavy device for Excel, Word, and the cutting-edge gaming experiences Solitaire and Minesweeper.

Rozum had to know that computer inside and out, literally. His early training involved assembling and dissembling the machines, so he could help customers do the same over the phone.

In 1993 or so, when Rozum was an engineering student at South Dakota State University, Gateway recruiters visited a campus class, offering the attendees a chance to “learn computers” and get some technical work. Rozum leapt at a chance to work for one the era’s main hardware players.

The job, he learned, consisted mostly of phone-based technical support, walking customers both young and grandma through cable inspections, processor reseating, and installing drivers from disks. For very difficult problems, he could recreate a configuration in the company’s test lab and work out the solution.

And at least once a month, Rozum told us, someone called in about a broken coffee cup holder—their mistaken term for the CD-ROM drive.

Moving on! Rozum advanced from frontline tech support supervisor (and cupholder repair supervisor) at Gateway. After studying up on Microsoft system engineering and gaining multiple certifications, he moved to Y2K consulting at Keane, then founded Insite Managed Solutions in 2007.

Rozum regularly meets with operations teams and COOs, he said, who are “not always deep in the technology,” which can require explaining sophisticated technology in simple terms. That contrasts with his meetings with CIOs and CTOs who are “really deep in technology.”

“We’re often a translator or a bridge,” he said, for people with varying levels of understanding. He still sees the service desk as a valuable starting point for IT careers today, even if troubleshooting involves fewer screwdrivers than it used to.

“The fundamentals you learn there will port forever,” he said. “You get to see how the users do things.”

(And break things.)