A number of Canadians have risen through the ranks at Uber, bringing lessons from Toronto to global leadership positions.

These leaders have taken on roles helping bring Uber to more than 70 countries, driving engineering innovation from Silicon Valley, and tackling marketing challenges across markets. 

“There’s a broader narrative right now that if you have a certain level of ambition in tech, your path is out of Canada. I’m just not a supporter of that viewpoint.”

Andrew Macdonald, Uber

Canadians can be found in leadership roles across Uber’s global operations. Adam Blinick, now overseeing public policy and communications at Uber from San Francisco, previously held senior policy positions within the Canadian government, including a role with Canada’s federal minister of transport. 

David Cinanni, who leads Uber’s performance marketing team in Amsterdam, once held a role at Health Canada, while Diane Rodgers, Uber’s global head of insurance legal in San Francisco, previously worked as senior counsel at Toronto-Dominion Bank.

The following stories reveal how the skills and experiences developed in the great north helped three Canadian Uber leaders navigate global markets, solve problems at scale, and prove that growth is not always defined by location.

Andrew Macdonald, Senior Vice President of Mobility and Business Operations

In 2012, Andrew Macdonald was winding down his retail tech startup when a chance conversation in his co-working space at MaRS changed the trajectory of his career.

A fellow entrepreneur mentioned that a new rideshare company called Uber was looking to staff up in Canada. By May, Macdonald was on a plane to San Francisco to interview for Uber’s Toronto General Manager position.

“I never would have been hired by Uber for my role, had I not been a failed entrepreneur,” Macdonald said. “Entrepreneurs don’t just endure failure – they learn from and grow stronger from it. Travis Kalanick, our founder and CEO at the time, had also experienced failure before he found success, and Uber embraced those of us with that background and entrepreneurial mindset.”

When Macdonald joined, Uber was “ultra-scrappy”, he said, and only operating in a few cities. 

“There were only 60 people globally,” he said. “In Toronto, it was just the three of us.” 

At the time, Uber was a black car service, and Macdonald’s first role involved signing up drivers, navigating the city’s complex regulatory environment, and building Uber’s brand in Toronto from the ground up. 

He spent evenings handing out promo codes at events like the Toronto International Film Festival, pitching Uber as a solution for getting home from social outings. Driver engagement was just as hands-on, often literally involving “knocking on limo windows” at the airport.

Adoption in Toronto was slower than in other markets at first, he said, due to its widespread adoption of tech from another local company.

“Toronto’s professional class, our early adopters, disproportionately used BlackBerrys,” Macdonald remembered, noting that initial hurdle limited Uber’s growth until it launched a workaround that allowed people to order rides via text message.

Despite growing pains, Canada quickly became one of Uber’s strongest markets. 

“Canada is a top five market for Uber in both delivery and mobility, so it’s big. We’ve built a strong talent hub here, and now we’ve got hundreds of people working in our Toronto office across pretty much every function that exists at Uber,” MacDonald added.

Macdonald’s own ascent mirrored Uber’s Canadian success. Just one year into his role, he was tapped to lead operations in the US Midwest, while still running Canada. That role meant moving from Toronto to Chicago on “24 hours’ notice.”

In the following years, MacDonald took on oversight of Latin America and Asia-Pacific.

In 2016, he moved back to Toronto, where he now serves as Senior Vice President of Mobility and Business Operations at Uber and oversees the mobility business in over 70 countries. This includes ridesharing, taxis, micromobility, rentals, public transit, high-capacity vehicles, and more. He also oversees Uber’s sustainability efforts, autonomous mobility and delivery operations, business development, Uber for Business, and Uber Health.

He credits his experience as a failed entrepreneur in preparing him for Uber’s fast-paced environment, which he describes as focused on “doing, not just talking or analyzing.”

“I’m not a fan of the ‘move fast and break things’ mantra,” he added. “But I do believe speed matters.”

MacDonald also sees his career as proof that Canadian leaders can still achieve global impact while remaining rooted in Canada.

“There’s a broader narrative right now that if you have a certain level of ambition in tech, your path is out of Canada,” he said. “I’m just not a supporter of that viewpoint.”

Neil Barakat, Director of Engineering

As a Winnipeg-born engineer with a PhD from the University of Toronto, Neil Barakat had spent years in academia before transitioning into roles in the tech industry. After working in software development at Amazon, a team member from Uber approached him with an opportunity. 

It was 2018, and Uber was just beginning to build a Toronto tech hub. 

Skeptical but curious, Barakat decided to go through the interview process. He said three things ultimately sold him on Uber: its rapid pace, the ambitious mission, and the company’s approach to solving problems by blending tech with the physical world.

“As an engineer, that interface between software and the real world is super interesting,” he added.

At Uber, Barakat’s first task was building teams for the Toronto tech hub. He wanted to take a unique approach to building the site that involved creating “centres of excellence,” rather than scattering teams and roles.

He anchored the Toronto office around key charters—teams that owned critical areas like Uber’s ad offerings on Uber Eats and rider-driver matching for trips scheduled in advance. He said the idea was to build ownership and pride locally, rather than having teams simply report to San Francisco for direction.

The strategy worked. Toronto’s matching team, which paired riders with nearby drivers, played a pivotal role in the launch of Uber Reserve, a feature that allows riders to schedule rides ahead of time. Barakat said this required rethinking Uber’s entire approach to matching.

“Real-time matching is about finding the closest car,” Barakat explained. “But for a ride scheduled tomorrow, you need to take a totally different approach that takes into account where cars will be in the future.”

Another standout success was Uber Ads, the company’s advertising division that allows businesses to reach consumers with ads integrated into Uber Eats. Barakat said the engineering team for this product development “was born in Toronto, and now it’s one of the most important businesses in Uber.”

After five years of building Toronto into a thriving tech hub, Barakat recently relocated to San Francisco to serve as Director of Engineering. Today, he leads engineering and science teams for Uber’s experimentation and mapping platforms.  

“The transition to San Francisco was a pragmatic decision—how can I serve my teams best, represent them to leadership, and drive more impact?” he said. 

Barakat finds that his Canadian background offers a distinct advantage south of the border. He said the Canadian approach to brokering deals on compromise has proven effective in situations where an American ‘win-or-lose’ mindset falls short.

“I’ve heard people half-jokingly refer to the fact that I’m a Canadian, just because I’m always friendly and polite in these interactions,” he added. “That can go a long way in building people’s trust.”

Ceili Hubbard, Head of Marketing, UK Mobility 

By 2020, Uber had firmly established itself as a vital element of Toronto’s transportation landscape. Regulations were in place, ridership was growing steadily, and the company was a natural part of the daily lives of locals.

Ceili Hubbard thought it might be time to leave town. 

As the Canada Marketing Lead, she had contributed to solidifying the company’s brand nationwide, and was eager for a new challenge. When a role emerged in London, England, she jumped at the opportunity.

“Toronto was quite a stable environment,” Hubbard said. “The UK market has had historical challenges that were quite unique and represented some unique brand marketing challenges and opportunities.”

Born and raised in Oakville, Ont., Hubbard studied at Western University’s Ivey Business School before landing a role in consumer-packaged goods marketing at General Mills. It was a friend from Ivey who recommended her for a marketing role at Uber in 2018.

“Uber had always been in my line of sight,” she said. “I used Uber and Uber Eats every day in some capacity even before I worked at Uber, and I had a lot of respect for the impact that Uber has had globally.”

Her first assignment at Uber was helping the platform launch a service at Toronto Pearson Airport, and she went on to lead Uber’s collaboration with Mothers Against Drink Driving to promote responsible transportation.

“I think that felt impactful not only because we were able to drive more trips for Uber, but we were also doing some good for the world,” she added.

In the UK, she was part of a team rebuilding Uber’s rideshare business post-pandemic, building trust with policymakers, and improving benefits for drivers.

“I think we’ve come a long way in making sure that we’re always doing the right thing and operating as safe a business as you possibly can and putting drivers first,” she said.

Under her leadership in the UK, Uber also launched one of its most celebrated campaigns. ‘Trains, now on Uber,’ promoted a new service that allows users to book train tickets through the app. The campaign won a Cannes Lion award and set a blueprint for other European markets. For Hubbard, this is one of the most rewarding aspects of her job.

“A lot of things are developed in the local markets, which is part of why I love working at Uber,” she added. “We get the best of both worlds by developing locally and leveraging those learnings globally.”

When asked if there was anything unique about her Canadian roots that she brings to her global role, she pointed to a quality that can be surprisingly effective in tough conversations.

“Canadians have a reputation of being quite friendly and kind, but it is actually the case,” she said. To Hubbard, bringing that energy means “we can have challenging conversations coming from a place of positive intent.”​

Learn more about Uber’s tech hub in Toronto and careers here.

Photos courtesy of Uber and LinkedIn. Feature image produced by BetaKit.

The post Meet the Canadians shaping Uber’s global vision first appeared on BetaKit.