Meet the
B Street Team
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Heather was born and raised in Winnipeg, Canada, and now resides in Toronto. Heather is the Managing Director at Jessiman Family Investments Inc., a private investment company, and Managing Director of The Jessiman Foundation, both headquartered in Winnipeg.
Driven by her passion for the arts, Heather founded B Street Collaborative, an arts incubator, featuring an innovative culture space that opened in 2023 in Toronto’s vibrant Annex neighborhood.
Heather is a board member of Crow’s Theatre and has previously chaired the Board of First Book Canada and served on the board of Brands for Canada. She actively participates in several volunteer committees, including Chair of the Conservatory Circle at the Royal Conservatory of Music, Member of the Winnipeg Symphony Orchestra Futures Committee, and Past Chair of the Opening Night of Art Toronto Fundraiser for the Art Gallery of Ontario.
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Dylan (he/him) is an award-winning actor, director and acting coach. He has performed at The Stratford Festival, The Shaw Festival, Mirvish Productions and on London’s West End. As a director, Dylan’s productions with Toronto’s Eldritch Theatre—including Requiem for a Gumshoe, Space Opera Zero! and The Harrowing of Brimstone McReedy— have garnered multiple Dora Award nominations. Other directing credits include La Bete (Harbourfront Centre/TIFT); Wakey, Wakey (Stratford Festival/CSC); Cock, Herringbone, The Yalta Game (TIFT); Every Brilliant Thing (CSC). Associate Director: The Shape of Home (CSC/Crow’s). Dylan taught fourth year acting at The University of Toronto and Co-Founded the online mentorship platform Ghostlight. He was a founding member of Theatrefront and served as Associate Artistic Director of Festival Players from 2018-2023. Film and TV Credits include: Cross, Reacher, The Handmaid’s Tale, Titans and Workin’ Moms.
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From the bustling arenas of real estate, private equity, and venture capital to the vibrant world of the arts, Cathy has charted a dynamic career path that bridges the realms of business acumen and creative expression.
With a wealth of experience as a long-time executive assistant for C-Suite leaders, she has honed invaluable skills in organization, communication, and problem-solving.
However, the call of creativity and a deep-seated appreciation for the arts led Cathy to embark on a new chapter, joining forces with Heather Jessiman, the founder and visionary behind the B Street brand. Here, Cathy has found a perfect intersection of professional expertise and personal passion in supporting Heather and the entire crew at B Street Collaborative.
On a personal note, Cathy takes pride in her two grown children. She holds a deep affection for all animals, loves the outdoors, finds joy in music and dancing, and has a keen appreciation for old architecture.
