Jason has spent his career doing something rare: leading large-scale transformation from the inside of some of the most recognized brands, including Microsoft, Bell Canada, and Cadillac Fairview. Not as a consultant parachuted in with a framework, but as a leader accountable for outcomes, culture, and the long game.

Jason founded Pinecone & Co in 2025, a brand and marketing advisory firm. His signature is to get immersed in a business, connect brand and marketing strategy directly to business goals, and then build the structure, talent, and metrics to make it stick.

As Senior Vice President of Brand and Marketing at Cadillac Fairview, Jason led a multi-year transformation to shift CF into a purpose-driven, experience-led organization, ultimately establishing it as the pre-eminent brand in the industry. He oversaw Marketing, Brand Strategy, Research and Insights, and Corporate Communications across a decade of sustained leadership.

Before CF, Jason spent ten years at Microsoft Canada as Vice President of Retail Sales and Marketing, where he led the Xbox business to achieve one of the first number one market share positions anywhere in the world.

Earlier in his career, Jason was a founding member of Bell ExpressVu's first Marketing team, growing Bell into Canada's largest digital TV provider. He began at Procter & Gamble, widely regarded as the birthplace of brand management.

Jason holds a Board Director certification from the Rotman School of Management at the University of Toronto, an Advanced Certificate in Management, Innovation, and Technology from MIT Executive Education, and a Bachelor of Business Administration from Wilfrid Laurier University.