Sleeper Spotlight on David McKibbon – Top Fundraiser


The first year David McKibbon participated in Sleep Out Executives Edition was the coldest of his five years since.

“We had two inches of snow on the ground,” the Senior Vice President of Project Management & Development at Cadillac Fairview said, “It turned to sleet when we got to sleep site.”

More impactful than the conditions that night, however, was what David learned about the young people who come through the doors of Covenant House Toronto.

“Probably the best thing for me was hearing the stories of how youth have endured and come through the system and are doing things with their lives now,” he said. “Thanks in large part to Covenant House Toronto.”

He found himself drawn to the cause of supporting young people experiencing homelessness and trafficking and hasn’t looked back.

This year will be David’s sixth Executives Sleep Out, now an annual tradition and commitment to supporting young people on their paths towards a brighter future.

But he hasn’t just shown up year after year: He’s also been Sleep Out Executives’ top fundraiser multiple times over – a title he humbly plays down.

“The five years I’ve participated so far, three or four years I was the top fundraiser, but that’s not without the support of everybody within my network,” he said. “I’ve learned that people are extremely generous but only if you really become a pest.”

This year, he is aiming to raise $65,000, the highest target of all participants.

For David, it’s about far more than fundraising – it’s about always looking for new ways to help, whether that’s making connections between people or organizations who can help or pursuing new partnerships.

“As executives, you’ve got to walk the talk,” he said. “All you can do is do the right thing as a leader and hope that people see you’re doing and what you’re talking about and do their part to give back to the community in their own way.”