iOCO Chief technology officer David Gray reflects on building technology that endures, taking on difficult projects, creating safe spaces for people to grow and the personal interests that keep challenges in perspective.
David Gray is drawn to things that are a little broken. For iOCO’s chief technology officer, they present an opportunity to make a difference.
“I like things that are a little bit broken, because it gives us the opportunity to do things,” he says. “That’s my special power, in terms of what I do. I’m a fixer. Things that break or are broken, I fix.”
That instinct shapes his career as much as it shapes his patriotism. David, who grew up in Cape Town, is candid about South Africa’s flaws but remains focused on the potential beneath them.
“There’s so much potential. If we just harness it, that would turn out amazing. We’ll be unstoppable. Literally, there will be nobody to stop us,” he says.
From accountant-in-waiting to software developer
David grew up in the 1980s and early 1990s, when a home computer was still a luxury. He enrolled at the University of Cape Town intending to become a chartered accountant. A mandatory first-year IT101 module changed that trajectory.
“Literally within three days behind a computer, I was like, this is pretty cool,” he recalls.
He stayed on the accounting track until his third year, when two back-to-back lectures tipped the scale. His auditing lecturer warned that only 10 percent of the class would find jobs, while his IT lecturer promised the opposite: 90 percent employment.
“For somebody who was a little bit unsure what I would do afterwards, that got me. Let me do the IT thing,” David says.
He skipped his postgraduate studies and went straight into a software development internship in Johannesburg, moving there alone at 21.
Asked why building appealed to him more than auditing, while stressing that he has nothing but respect for the profession, David’s answer comes back to creating something of value.
“I wanted to build something, something that people would find value in.”
That instinct paid off in a way he did not expect. Code he wrote for a client at 22 was still running 15 years later.
“For someone to approach you and say that your code still works and is running after 15 years is super cool,” he says.
Why the hard projects are the point
Careers rarely run in a straight line, and David is matter-of-fact about the stretches of his career that have been difficult. What has kept him in place is loyalty rather than obligation and the people around him.
“It’s because I’m bought into the people I work with and the vision. The people I work with are cool, want to make a difference and they’re ethical.”
It is not the only bet David has made on people over comfort. In 2012, after his “delivery confidence had taken a knock”, he took a pay cut to rebuild it.
“The rest is history,” he says.
David is candid that rescuing distressed development projects, including ERP and supply chain systems, is not glamorous work.
“It’s hard work. It’s not easy. If it’s salvageable, you’ve got to surround yourself with the right team, the right skills, and you’ve got to get your head down into dark places to make things successful.”
He believes the discomfort is part of the value of taking on difficult work.
“I think it makes you a better person to go through a little bit of pain in your career, to understand how hard it can actually be.”
Managing a team that spans three generations
David, a self-described “comfortably Gen X” leader, now spends as much energy on people as on technology. He has watched Gen Z employees arrive with fewer opportunities to fail safely.
“We need to create a safe space, specifically for the Gen Zs of the world, to come in and have a space of safety to make mistakes and grow from them, learn from them and become more mature,” he says.
He has also seen changes across the other generations in the workplace.
“The millennials are starting to behave like Gen Xs, right?”
One of the clearest signs of how quickly the technology landscape is moving sits at David’s own dinner table. His 18-year-old son was using Claude long before David had heard of it.
“From that perspective, he’s coaching me,” he says. “There’s an app for this, and he doesn’t have to always ask me for my opinion, because he knows the answer probably better than I would anyway.”
Trench poetry and a Thursday-night airport ritual
Away from the office, David reads for perspective as much as pleasure. On travel Thursdays, he buys at least one book at the airport so that he does not have to open his laptop on the flight home. He gets through roughly 12 books a year.
He gravitates towards leadership, South African political non-fiction and military history, with a particular love for First World War poetry.
“The really big moment, the shift from structured poetry into something more contemporary, was the First World War. Ordinary people, in very horrible situations, found an outlet to express themselves,” he says of poets such as Wilfred Owen.
The perspective it offers has stayed with him from his time managing implementation teams.
“You’d rather have code that doesn’t deploy properly than be sitting in a muddy trench on the Western Front. Sometimes a tech lead would come to me complaining about something reasonably mundane and I’d say: read this poetry book, get some perspective that things could be much worse. This typically broke the ice and led to problems being overcome rather than dwelt on.”
Friday braais, South African music and team sport
Fridays were traditionally braai days in David’s home, indoors or out, come rain or shine. It was a simple family ritual rather than a production: a fire, a glass of red wine and time together at the end of the working week.
His South African playlist includes Seether, Arno Carstens, Johnny Clegg, Brenda Fassie, éVoid and Bright Blue’s “Weeping”.
Team sport is another constant. David played rugby and cricket into his early thirties, and participation in a team sport was non-negotiable for his two sons.
“I didn’t mind what team sport they played, but they were going to play one team sport. You learn so much about interacting and working with a wide range of people, cultures and differences in a team setting, and generally make lifelong friends,” he says.
“I love standing on the side of a school rugby field on a Saturday morning, watching all the teams. From the G team to the A teams, that’s where the real passion for the game is.”
