Jaimie Grossman

Jaimie Grossman is a three-time founder and CEO with full ownership-cycle experience across digital marketplaces, on-demand consumer services, healthcare services, and advertising. Based in Toronto, Jaimie brings the operator’s perspective to Beacon’s lower middle market sell-side and growth-stage mandates, with two exits delivered to TSX-listed strategic acquirers.

Jaimie was co-founder and CEO of UPTREND Media, which grew to become the largest independent advertising representation network in Canada before being acquired by Yellow Pages Group (TSX: Y) in 2010 as part of the formation of Mediative, YPG’s digital advertising platform.

In 2015 he co-founded Jiffy Inc., a mobile marketplace that connects homeowners with vetted service professionals in real time based on proximity and availability. Jaimie served as CEO through 2018 and then as Chairman through the company’s sale to Intact Financial Corporation (TSX: IFC) in November 2024. At exit, Jiffy was operating in the Greater Toronto Area, Ottawa, and Calgary, and was described by the acquirer as Canada’s leading home maintenance app.

In late 2023, Jaimie acquired Golden Care Dental, now operating as Golden Care Health, where he serves as Executive Chairman. Golden Care is a leading provider of on-site oral health services to long-term care facilities and retirement homes across Ontario, partnering with hundreds of facilities and supporting residents under both private coverage and the Canadian Dental Care Plan.

Across his career as a founder and board chair, Jaimie has raised capital from and managed ongoing relationships with institutional venture investors across Canada and the United States. He has led founder-side fundraising processes through seed, growth, and pre-exit rounds, negotiated term sheets with both Canadian and US-based funds, and managed the governance and reporting cadence that institutional investors expect through to liquidity.

Jaimie holds an MBA from the Schulich School of Business at York University and a certificate in American Foreign Policy from American University in Washington, D.C. He currently sits on the boards of technology companies including Tow4Tech and LiveBarn, and serves as Chair of the Larry Grossman Forest Hill Memorial Arena. He has previously served on the boards of Mount Sinai Hospital’s Leadership Sinai, Kensington Health, and the Kensington Health Foundation.

At Beacon Advisors, Jaimie advises founders and shareholders on transaction readiness, growth-stage capital strategy, and exit positioning, with particular focus on founder-led businesses navigating sale to strategic and financial acquirers in digital marketplaces, tech-enabled consumer services, and healthcare services.