232: A Family Business Succession Done Right with Jennifer Wilson, Oak Bay Coaching and Consulting
About this episode
Jennifer Wilson shares her experience in successfully transitioning leadership in a family business.
"These are long-term decisions that have far-reaching impacts — not just for us, but for future generations." Host Laurie Barkman sits down with Jennifer Wilson, founder of Oak Bay Coaching and Consulting and former CEO of the Canada Homestay Network — a family business her mother started in 1995 from a bed and breakfast in Toronto that has since placed over 100,000 international students across Canada. Jennifer joined the company as an accidental second-generation leader, grew into the CEO role after completing her MBA, and spent 17 years building the organization before transitioning to chair in 2022. She built a co-CEO structure, created a board of directors from scratch, and navigated a partial management buyout — all while keeping the family intact. Here's how she did it. Key Insights The CEO handoff is as much symbolic as it is structural. Jennifer's mother passed her a vintage recipe box — the company's original "analog database" — in front of the entire team at a company retreat. That moment publicly transferred authority and gave the whole organization clarity about who was leading. Succession isn't just paperwork — it's a signal. A co-CEO structure can work — but only…
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