When Two Hats are Better than One – Interview with Bobby Singh

Some leaders pay lip service to the notion of lifelong learning, opting instead to settle for what they already know. Bobby Singh was taught to learn something new every day and continues to follow this sage advice.

“Almost 20 years ago, I made a commitment to myself that each day I would do something that would help me become a better person, or a better leader, or a better technical expert,” says Singh, CISO and CTO of TMX Group, which owns a number of stock exchanges, including the Toronto Stock Exchange and the Montreal Stock Exchange. “At the end of the day, I still ask myself what I learned that I didn’t know the day before.”

A frequent presenter on cyber, blockchain, and cloud technologies, Singh joined ITWC CIO Jim Love for a June 2022 episode of Leadership in the Digital Enterprise, an ITWC podcast series focused on in-depth conversations about leadership in the digital era. In conversing with Love, Singh traced a fascinating career path that led to his dual role managing and securing TMX’s technology.

The Dual Role Advantage 

“There’s always a healthy friction between the technology folks and the cyber folks, so wearing those two hats and being able to manage both has resulted in a kind of crosspollination of resources and knowledge,” he observes. “I don’t know if I would have been able to achieve this if I was still only wearing my CISO hat.”

When asked to describe a defining moment in his life, Singh shares the impact of completing high school in New Delhi, India at the age of 18 and moving to New York City. “Coming to a brand new country with a different culture and a different environment was probably the biggest shock in my life,” he recalls. “Keep in mind that we’re talking about decades ago, when there was no texting and no cell phone availability. Maintaining friendships and family connections were the biggest issues.”

Exemplary Leadership

Fast-forwarding to today, Singh reflects on leadership, stressing the importance of bringing others along and making them even better at what they do. “If you can’t bring out the best in people, I don’t think you’re a great leader,” he says. “And making it to an executive level doesn’t make you a great leader. Leadership qualities can be found at any level.”

Pivoting to the pandemic experience, Singh speaks to the critical importance of empathic leaders who understood the complexity of what was happening in the early days of COVID 19 – not only from a technical point of view, but also from a people perspective. As well, he stresses the gains made by leaders who were able to be agile in their decision-making and make decisions on the fly as the pandemic unfolded.

On the subject of cybersecurity leadership in particular, Singh recommends demonstrating confidence when conveying information to the executive team and making them feel at ease. “That doesn’t mean making them think that everything is resolved,” he notes. “It’s more about  demonstrating that somebody is educated enough, smart enough, and experienced enough to have it all under control.”

Strength in Numbers

Singh does his best to ensure that team members work as collaboratively as possible. “As we get more data from different sources, we have to be able to make sense out of it and I don’t think one individual is able to do that,” he says. “I’m relying on my network team, my cyber team, and my infrastructure teams to collectively figure out what the data is and how we are going to handle it.”

Looking Ahead

Commenting on what the future may hold in terms of promising technologies, Singh identifies the cloud as one of TMX Group’s key drivers. The organization is also looking into machine learning and blockchain. As for big lessons learned, he points to the need for accountability, saying he holds himself accountable all the time and expects the same from his team. 

“You just have to care about the team that you are responsible for,” he concludes. “I probably didn’t put the care piece high enough on my list two years ago, but today it is much higher.”


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Jim Love, Chief Content Officer, IT World Canada

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Suzanne Robicheau
Suzanne Robicheau
Suzanne Robicheau is a communications specialist based in Wolfville, Nova Scotia, where working remotely continues to fuel her passion for new mobile technologies -- especially on snowy days.

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