Jonathan Gillingham – CEO

Jonathan founded Boss Promotions in 1991 while in university. After establishing a well-respected name for his company, he moved his business out of his mother’s basement and moved into his first office space in 1992 – and the rest, as they say, is history!

Now the proud owner of a 20,000 sq ft office and warehouse in Toronto’s east end, along with the acquisition of two other companies in 2012 and 2015, his entrepreneurial spirit has helped grow Boss Promotions into a $10-million company. Jonathan’s philosophy on the promotional industry has always been simple: Find the right product, at the right price, with the right delivery for your client and you can’t go wrong. His energy and entrepreneurial spirit is infectious and has enabled him to build an incredible team.

Jonathan is the quintessential family man – his weekends are busy cheering on his two athletic children or relaxing up north at his family cottage with his wife. Always on the go, Jonathan spends some of his spare time organizing an annual golf tournament for his buddies that has them playing some of the finest courses in North America. He also hosts a neighborhood rib fest and supports many local charities.

Luckily for us, it’s not hard to convince him to have summer hours, Friday afternoon ice cream for the team, spontaneous lunches for his sales staff, or an office outing to the ballpark. Because Jonathan knows you have to work – and play – hard to win.

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