Entrepreneur of the Year 2024: How Apollo co-founder Jeff McCann is expanding the insurance industry

THE KICKOFF: If there’s a type of insurance that doesn’t exist yet, Jeff McCann is probably busy creating it. After graduating from SFU and serving as the president of its student society, McCann thought maybe he’d go to law school or get a job with a big corporation.

Instead, he got a gig driving around to different Western Canadian ski resorts and trying to sell them insurance. “It was the coolest job ever,” he says. Within a couple of years, he had learned enough about the industry—“you wouldn’t believe how complicated drone insurance is”—to start his own company: one that would bring insurance online and into the 21st century.

ACTION PLAN: McCann and co-founder David Dyck started Apollo with about five people in an office in Vancouver’s Gastown. There’s been some trial and error since—“we launched logging truck insurance; that wasn’t my best product,” says McCann with a self-deprecating smile. The company ballooned to well over 100 people after COVID-19 lockdowns lent more urgency to bringing things online but later had to consolidate; in 2022, Apollo focused its efforts on tenant insurance.

Now the company is designing more insurance products for the renter. “We can sell you pet insurance, help you with moving, add cleaning services,” he says. “Let’s do a good job at making it easier for renters in Canada—building an ecosystem around that customer is going to set us apart.”

CLOSING STATEMENT: Apollo, which was founded in Vancouver but is now a remote-first company, has some 50 employees and will serve some 135,000 customers in 2024. “No kid says, ‘When I grow up I’m going to be the largest insurance provider to dogwalkers,’ but you learn and you find a way to do a great job for the customer and build a great product,” says McCann.

Q+A

What’s the best leadership advice you’ve ever received?

Calm waters. Somebody’s upset with you, calm. The deal’s going great, calm.