Matthew Dicker
Senior Commercial Sponsorship Manager @OLG
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WORK HISTORY
Senior Commercial Sponsorship Manager @OLG
Toronto, ON, CA
Currently responsible for the strategic direction, planning, and execution of OLG’s corporate sponsorship portfolio, shaping how flagship brands like Proline, Lotto Max, Lotto 6/49, Instants, and the Masterbrand connect with Ontarians. My role is focused on building partnerships that drive measurable impact, amplify brand equity, and strengthen OLG’s presence across sport, entertainment, and community.Key Highlights- Co-led the evolution of OLG’s Home Court and Home Ice Advantage programs with MLSE, amplifying the profit-to-Ontario message through broadcast, digital, and in-arena activations- Evolved marquee MLSE programs, including Max Contract Fan (Lotto Max) and Most Interesting Seats in the House (Proline), to maximize brand relevance and fan engagement- Created the most successful social post in PROLINE+ history with NFL Canada, generating 8.6M views and 103K engagements- Played a lead role in Proline’s NFL Playoffs / Super Bowl “ALL BETS ARE ON” campaign, integrating sponsorships, activations, social storytelling, and paid media- Delivered large-scale experiences including PROLINE+ Night with Toronto FC and the Instant “Money Machine” event with the Maple Leafs, engaging live audiences, broadcast viewers, and digital communities- Conceptualized and launched a retail sweepstakes with the Toronto Raptors, driving 46K entrants,$250K in revenue, 6K re-engaged customers, and 1K new OLG.ca signups.
EDUCATION
Dalhousie University
Bachelor of Management, Marketing
SKILLS
ABOUT MATTHEW DICKER
I am an award-winning sponsorship marketing professional with a decade of experience leading high-impact partnerships across sports and entertainment. I specialize in transforming sponsorships into brand platforms that drive equity, engagement, and measurable results.At OLG, I oversee partnerships that bring PROLINE, Lotto Max, and the Masterbrand to life through collaborations with MLSE, NFL Canada, Live Nation, Fallsview Casino, the CEBL, and the Canadian Olympic Committee. I have led the creation and evolution of flagship programs including Most Interesting Seats in the House for PROLINE, Sponsored by You for OLG, and Home Ice and Court Advantage with MLSE, all designed to connect fans with our brands in meaningful and memorable ways.At Scotiabank, I developed the award-winning Hockey for All platform, a two-time Best of the Best winner at the Sponsorship Marketing Awards and the bank’s marquee DE & I platform. I also managed the bank’s relationships with major league and team partners across hockey, football, golf, and the arts, and led initiatives such as The Art of Storytelling and The Hockey Jersey Book.Earlier in my career, I deliberately started agency side, seeking exposure to a wide variety of clients and industries. This allowed me to hone my skills and selling tactics early, and to bring bold and effective campaign ideas to clients in diverse sectors. I managed clients at Narrative PR and drove social and content strategies at Bensimon Byrne, supporting brands including Nike, Amsterdam Brewery, and Jackson-Triggs.
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