Why Listen: You want to lead like a founder—even if you’re not in tech.
Episode Description:
What does it really take to lead a small, mission-driven organization through massive growth? In this conversation, we speak with Allan Reesor-McDowell, Executive Director at the John Howard Society of Ottawa, about his earlier experience rapidly scaling Matthew House Ottawa from a tiny charity into a multi-million-dollar, multi-program organization. Allan shares how embracing his generalist mindset, rather than chasing expertise, helped him prioritize, pivot, and make smart decisions that enabled sustainable growth. For anyone navigating leadership in uncertain times, especially within nonprofits or systems under pressure, this episode explores how broad thinking, strategic listening, and confident humility can be powerful levers for change.
Key Highlights:
Being Agnostic: Why being agnostic to tools and approaches allowed Allan to adapt quickly and lead effectively through organizational change.
Smart Growth: How Allan helped scale Matthew House Ottawa from 3 to 55 staff and $300K to $5M in budget, using agile planning and resourceful outsourcing.
Decision-Making: The importance of reversible decisions, risk management, and knowing when to pause versus push forward.
Outsourcing Strategy: How fractional expertise (e.g., HR, finance) enabled big capabilities on a small budget.
Confidence with Humility: Balancing imposter syndrome with clarity on the value of broad-based competence, and leading without needing to be the expert.
About Allan Reesor-McDowell:
Allan grew up in Canada but work, studies and travel led him for many years to the US, Haiti, and England as well as to more than 60 countries throughout Africa, the Middle East, Europe, and Latin America. Allan has served in leadership and governance roles in politics and nonprofits, including serving on the boards of the Social Housing Registry of Ottawa, The Alliance to End Homelessness Ottawa, the Canadian Council for Refugees and currently sits on the board for the Ottawa Community Foundation.
Allan currently serves as Executive Director of John Howard Society of Ottawa. He holds an MSc in Development Studies from SOAS, University of London and was a recipient of the Forty Under 40 award in 2021.
Find Allan Here
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