This is the third in a three-part series, ParadigmShift Speaker Sessions, designed to bring you closer than ever to our speakers. This month we’re featuring Toby Lennox, CEO of Toronto Global, a not-for-profit investment-attraction agency that supports the expansion of foreign-owned businesses to the Toronto region.

Join us at ParadigmShift where you’ll have the opportunity to meet and talk with Toby and many of our other keynote and executive speakers.

A City of Opportunity and Optimism

We first announced the location for ParadigmShift 2018 one year ago and since then, we’ve been asked “Why Toronto?” more than a few times. At first, we prepared a list of facts about the city’s tech giants; 200,000 tech workers; 4,000+ startups; 230 ethnic groups, and its recognition as the most diverse city in the world. From AI and self-driving cars to connected cities and advanced medical technology - this city is making strides, and headlines. But the more we learned about Toronto, the more we learned it cannot be reduced to data points. 


Getting to know Toronto led us to Toronto Global, which acts as an advocate, consultant, and connector to foreign companies, helping them to expand and succeed in the Toronto Region. 


We recently sat down with Toby Lennox, the CEO of Toronto Global, to learn more about his own leadership journey and his perspective on the city dubbed, “The Silicon Valley of the North.” 


ThoughtWorks: Toronto and Montreal are historic rivals in sports, business, and culture. So what’s a native Montrealer doing heading up Toronto Global?


Toby Lennox: It’s true, I grew up in Montreal. I was a lawyer for several years and then legal counsel for the Greater Toronto Airports Authority. I transitioned into the role of Vice President of Strategy Development and Stakeholder Engagement and it was there that I found a passion for connecting people and organizations to empower change. 


For more than a decade, I implemented community and industry relations engagement programs, including chairing public, industry, and community committees.


Because of the civic work I did in Toronto, I had the opportunity to operate the first investment promotion agency for the entire Toronto Region, so despite being born in Montreal, I jumped at the chance. I love Toronto; it is such a privilege to promote what’s going on across the region.


TW: Our theme for ParadigmShift this year is Action Required: The Future in Real Time. Toronto was an obvious choice because there is real innovation work happening. So we were surprised how many people asked, “Why Toronto?”


TL: We hear ‘Why Toronto?’ all the time. On a personal, corporate, and a regional level, it’s fascinating to be in a city and a region that is on this kind of growth trajectory. We regularly rise to the top of rankings in education, innovation, business opportunities, talent, and cultural diversity. It’s funny to be in a position that requires me to brag about the region. Canadians, and Torontonians, are notoriously humble. But people are becoming much more aware of the remarkable things happening here and we’re becoming more comfortable talking about it. 


TW: Toronto is the only Canadian city to make the short list for Amazon’s new HQ2. That’s something worth bragging about!


TL: The most exciting part of completing the Amazon bid was that it allowed us to hold up a mirror to people across the Toronto Region and say, ‘This is who you are now!’ We’re not trying to regain a faded, past glory, and we’re not striving to become something we can’t be. 


TW: Toronto has really embraced innovation; it’s even a required subject in school. Has Toronto always been so forward thinking? 


TL: Growing up, Montreal was the financial center of Canada and people moved there to find opportunity in what was then Canada’s fastest-growing city. Toronto, on the other hand, was a backwater; it was a bit repressed. Spaghetti with meatballs was considered exotic! For a very long time, Toronto was trying to figure out what it was. 


Now the region is a global innovation center. We’re the most diverse city on Earth. You can find any kind of food, any kind of people, any kind of activity. 


TW: What do you think led to this transformation? What has the city experienced as a result?


TL: Two factors have largely contributed to the region’s overall population, innovation, and business growth: The first is that the government has helped build this region through immigration policy. Canada has always been a country of immigrants, primarily from the U.K. and western Europe, but we’ve seen a huge influx from the Caribbean, China, and Southeast Asia. Immigration is really about optimism; Toronto has a very strong spirit of optimism that fuels its growth. Secondly, we have a fantastic university system in Canada and Ontario that supports research, technology, and innovation. 


In terms of business, the transformation of Toronto has helped it surpass Montreal as the business center. But it’s not just the city: five of the six largest banks in Canada are based in Toronto, and these banks are also transforming [from financial services companies] to meet the demand for emerging tech in financial services. There are also VCs, investors, incubators, and public-private partnerships; the business community recognizes that it's in its own best interest to invest in the tech community. 


TW: How do you sustain a rapidly growing ecosystem like Toronto?


TL: We’re well aware that rapid growth can be a fragile thing, so we talk a lot about how to sustain it with the right investments, the right partners. I hear from companies all over the world that say, ‘I want a piece of Toronto.’ There’s a bit of FOMO: they want to be where the next big tech discovery is going to happen. So it’s a balance. We don’t want someone to come in like the loud kid in the library, demanding attention, when everyone is working really hard together. 


TW: What are you most excited about when it comes to Toronto?


TL: I love that everything we’re doing is creating opportunity for people. Recently, two young women, each about 15 years old, born to Somalian immigrants, delivered a beautiful speech at city hall. They talked about the opportunities they have here that they would not have in their home country. The opportunity to go to university. To study what they want. To start a business. That is what is going to sustain the Toronto Region well into the future. 


Toby Lennox will share more about this booming ecosystem during his talk, The Role of the Enterprise in the Citizen Economy: Transformation and Innovation in Toronto, Monday, October 22 at ParadigmShift 2018.

More from the 3-Part Series

Part 1: Craig Miller, Chief Digital and Information Officer at Planet Fitness

Part 2: Lucie Glenday, Founder and CIO at