Leo Bailey is a strategist and community builder based in the Greater Toronto Area and the founder of Fresh Wind Consulting. He helps nonprofits, small businesses, and public sector organizations gain clarity, strengthen operations, and drive sustainable growth, guiding clients through strategic advisory, digital transformation, and risk consulting engagements that turn complexity into practical, actionable plans.

Leo’s career spans financial services, digital transformation, grassroots community leadership, and board governance. He spent over a decade at RBC and Interac, most recently as Director of Small Business Partnerships and Director of Diversity & Inclusion in the Office of the CEO, where he built national partnerships, led crisis response frameworks, and managed budgets and portfolios with the rigor of a risk and governance background. That discipline, paired with deep empathy for mission-driven work, gives Fresh Wind its practical, people-centred approach to solving complex challenges.

Governance is central to how Leo leads. He serves as Board Trustee and Treasurer at Black Urbanism TO and as Board Trustee at SickKids Community Mental Health, bringing financial oversight and strategic counsel to organizations working at the intersection of community and care. He has also served as University Councilor at Queen’s University and as a grant reviewer for the Ontario Trillium Foundation, reflecting a long-standing commitment to stewarding resources responsibly on behalf of the communities he serves.

Leo is also an educator and emerging academic. He teaches Business Concepts and Small Business Management at George Brown Polytechnic and serves as Entrepreneur in Residence with the Black Entrepreneurial Alliance at York University’s YSpace, mentoring the next generation of Black founders. Starting in October, he will take on a new role as Entrepreneur in Residence at Yorkwoods Public Library. He is currently pursuing a PhD at Carleton University’s Sprott School of Business, researching the entrepreneurial ecosystem of Black Canadians and the pathways from small business to thriving enterprise, alongside an MBA from Queen’s Smith School of Business.

Leo is from Rexdale and a proud graduate of North Albion Collegiate Institute (NACI). That upbringing continues to shape his commitment to servant leadership and community impact, fueling Fresh Wind’s philosophy and the work the firm does.