How CIOs can get inside the CEO’s head

When Jay Woo enrolled in the IT Leadership Development program at Toronto’s Ryerson University, he couldn’t have known that four years later the experience would help earn him a promotion to chief operating officer for a $350-million business.

In 2006, Woo was working for Cooperators Insurance in Toronto as the VP of IT when his boss encouraged him to take the Ryerson program. Her goal was to develop him to take on his next role: CIO. Woo calls the course an eye-opener that gave him insight into how other business leaders in the organization think.

“The program was a great way to understand how a CEO thinks,” says Woo. “A lot of times IT focuses on technology without a clear connection to business objectives. The course focused on what drives the CEO and what’s on his or her radar. Bringing IT and translating that into business nomenclature was the biggest takeaway.”

Woo says his professional development experience gave him an opportunity to network with other companies and to understand the best practices across industries, another invaluable lesson.

“You can lose touch with the other functions of a company, and there is a danger in not getting that kind of exposure to the other disciplines within the company,” he says.

Fast forward to November 2008. Woo accepts a job as CIO of CAA South Central Ontario where he has an opportunity to apply the lessons he’s learned in the IT Leadership program and transform the CAA’s IT department from a cost centre to a revenue generator.

“Over the last several decades, every time the CAA bought a new system or added a new product, the IT strategy was to add another data centre to support that,” Woo explains. In the end, CAA had four data centres for each line of business, each operating as a silo.

During the assessment phase of this overhaul, Woo says it was a challenge to convince CAA’s executive to make the necessary investments that would translate into bottom-line savings.

“It took about two months for them to buy into the vision, but we clearly articulated the impact of the bottom-line expenses and how technology could address that.”

Under Woo’s oversight, CAA consolidated the four data centres into one, and built an enterprise data warehouse, enabling advanced business intelligence and a key competitive edge.

“Excess maintenance costs were eliminated and the investment in the data warehouse actually helps the business’s bottom line,” say Woo. Now, the CAA has a clear view of where they have poor market penetration and the company is able to do targeted marketing to that specific segment.

In November 2009, after the successful implementation of the data warehouse, Woo was appointed chief operating officer of CAA South Central Ontario – not a typical career move for an IT professional, but one where Woo feels he can make a “positive impact on the organization as a whole.”

“My CEO wanted me to have a greater responsibility for the business; to take the same discipline and creativity in the IT space and move it into the entire business.”

Woo credits the Ryerson IT Leadership program as a catalyst for all the success he’s enjoyed in his career, but he says that overall, executive leadership programs are missing a critical component.

“The one thing executives need to learn to do better is to make a connection to the front-line associates in a company; those people who will executive the vision,” he says. “I’ve spent a lot of time with front-line associates to understand what each role does, who they are and what their motivations are. This is critical because these are the people who will give you feedback on what’s working and what’s not.”

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