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40 Under 40: Thomas Winstanley

In The Magazine

40 Under 40: Thomas Winstanley

The marketing expert has led the growth of one of Massachusetts’ largest dispensary chains.

A decade in the trenches working in marketing at powerhouse brands Pfizer, Under Armour and Rémy Cointreau made Thomas Winstanley a genuine catch for Great Barrington, MA-based thriving cannabis company Theory Wellness.

But why Theory Wellness, a startup weed company with little recognition prior to his arrival in Summer 2018? Winstanley said he saw an opportunity to innovate in the nascent cannabis industry.

His impact since then has been undeniable: Theory Wellness has grown into one of Massachusetts’ largest dispensary chains while also expanding into Maine and Vermont. During that time, Winstanley has ascended up the ranks from marketing director to VP of marketing in 2020. In May 2022, he became Theory’s CMO.

His role with Theory, which boasts a portfolio of flower and production brands in addition to their distinctive brick-and-mortar stores, involves brand and creative development, public relations, media buying, social strategy, operational infrastructure and analytics reporting.

“I have a curiosity in trying to understand people and their habits,” Winstanley said. “I love threading the needle between the art and science of marketing.”

This story was originally published in the print edition of Cannabis Now.

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