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Steven appears in the Top 100

Canadian Professionals Magazine

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Steven Fry

An ambitious and successful entrepreneur, Steven Fry has first-hand experience of humble beginnings. He grew up north of Toronto, Canada, where, for parts of his life, he lived in government subsidized housing with his single mother and six blended siblings. Steven worked throughout elementary and high school, learning that hard work and hustle makes you stand out in the workplace. After a lucky break, whereby his high school provided him an exception to enroll in pre-university courses without all the prerequisites, Steven excelled and obtained a scholarship to Brock University’s, Business Co-Op Program. After graduating with honors and earning a Bachelor of Business Administration degree, Steven applied to over 50 jobs per day for months until he landed an opportunity to work in healthcare administration. 


Armed with his newly learned skills and sheer grit, Steven quickly rose through the ranks and became vice president of operations, overseeing the supply chain of 14 hospital organizations across Ontario, with responsibilities for over 100 staff and hundreds of millions in yearly contracts. During this time, Steven completed an MBA from McMaster University and designations as a certified associate in project management and certified health executive. However, Steven states that his most recent accomplishment is his self-proclaimed PhD in retail cannabis, as he holds the title of co-founder and chief executive officer at Sessions Cannabis, the fastest growing and largest licensed cannabis retailer in Ontario


Sessions Cannabis started after Canada legalized recreational cannabis and Steven was selected as part of a cannabis retail operator license lottery. Struggling to meet inconceivable deadlines and large capital requirements to open a historic store, Steven licensed a store concept and borrowed funds from another brand. After working around the clock and making every mistake in the book, he ultimately grew his store to become one of the top performing stores in the nation, with over $14M in sales in just 10 months, and subsequently sold the business to generate the funds required to create Sessions Cannabis. 


Staying true to Steven’s life mission “to be the wild card that ups the ante and redefines the game,” Sessions Cannabis was co-founded to differentiate and provide an enhanced customer experience. Working through the minutiae of a highly regulated and lottery-based licensing system, Sessions was successful in partnering with two cannabis retail operator license lottery recipients and opened its first two branded stores in December ‘19 and February ‘20. Sessions has not slowed down one bit and currently has the largest Ontario footprint of any cannabis retailer, with over 31 stores scheduled to open this year. 


Steven notes that what he is most proud of is the company’s ability to relate to customers and offer a complete experience, as embodied in its slogan “Your next session starts here.” The name of the company was borrowed from the cannabis culture term “session” which refers to people coming together to consume cannabis. “We are very locally focused, embracing the community by hiring local, featuring local artwork, and housing locally grown cannabis,” says Steven. The team also takes pride in educating people on the different forms of cannabis as well as navigating the stigmas associated with its use. Sessions offers a broad curated range of cannabis products, full suite of life-style accessories, apparel, growing supplies and services. The Sessions Cannabis mission is to bring people together and enhance their moments by providing a cannabis retail experience that is inviting, comfortable and informative.  



Steven Fry

Co-Founder & CEO

Sessions Cannabis

Toronto, Ontario, Canada


Instagram: @sessionscannabiz

Twitter: @SessionsCannab1

Facebook: ꟾ @sessionscannabiz

LinkedIn:   ꟾ

Download the Top 100 Canadian Professionals magazine and check out Steven's feature on page 109.

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