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Toby Lennox

Co-Founder & Investment Director

Toby Lennox is a bilingual senior executive and strategic leader with more than 30 years of experience leading complex organizations across the public, private, and non-profit sectors.  Known for his sound judgment and collaborative leadership style, he brings deep expertise in strategy, governance, and government relations.

 

Prior to co-founding Crosswalk Communities ,Toby served as the Founder and Chief Executive Officer of Toronto Global - the Greater Toronto Region’s investment promotion agency funded by all three levels of government. Under his leadership, the organization secured more than 100 greenfield investments and supported the creation of over 20,000 jobs, including leading the region’s successful bid to become an Amazon HQ2 finalist.

 

Toby began his career as a corporate lawyer at Osler, Hoskin & Harcourt, and then spent nearly two decades at the Greater Toronto Airports Authority, serving on the executive team and leading long-term strategy, public consultation, government relations, and crisis communications for Canada’s largest airport.

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