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Steven Caldwell is currently the Sport Advisor at Best Athletes. Prior to that, they were with the HORIZON LEADER GROUP. Steven has also held positions with the Oakville Blue Devils FC and MLSE (Maple Leaf Sports & Entertainment Partnership).

At MLSE, Steven was responsible for sales and marketing for clients across various industries such as BMO, Kia, Adidas, Expedia, Unilever and Tim Hortons. Steven was also a key player in several community initiatives, such as grassroots soccer clinics presented by BMO in partnership with TFC. Steven was chosen to run the grassroots soccer strategy for TFC. Steven was the only point of contact for all soccer clubs in GTA for large scale events such as TFC Kickzone fueled by Pioneer, including renewal and activation of the program.

Under Steven's leadership, TFC broke $20 million making it one of few MLS teams to do so.

Steven Caldwell has a certification from UEFA in UEFA A License Coaching Certificate.