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Board of Directors
Meet the great stewards of Square Circle
BOARD MEMBER - Co-Chair
Robin Kay
Robin Kay is one of Canada’s most influential fashion leaders, recognized for positioning fashion as both a powerful industry and an art form. A self-made designer and entrepreneur, she built her eponymous label into one of North America’s most successful fashion enterprises, with 22 retail stores and over 600 wholesale accounts. Ahead of her time, she later pivoted to focus on sustainability with Robin Kay Home and Style, solidifying her reputation as a visionary voice in culture and commerce. In 2000, Kay reshaped the industry by founding Canada’s first Fashion Week, elevating Toronto into the ranks of the world’s top showcases. Under her leadership, it became a multimillion dollar platform that launched countless designers and drew global recognition, cementing her legacy as a driving force in Canadian fashion. After her retirement, Robin dedicated herself to giving back to the community by supporting programs such as Square Circle, where she became a board member in 2025. Since then, she has worked tirelessly to help drive meaningful social change.
BOARD MEMBER - Co-Chair
Ian C. Miller
Ian C. Miller brings over 27 years of expertise in finance and investment management, specializing in tailored wealth and estate planning solutions for high-net-worth families and professionals. He currently serves as Vice President at Mansha Plan, a leading multi-family advisory firm. Previously, Ian spent 16 years as Vice President of the Canadian Retail Division at Manulife Investment Management, holding senior roles at some of Canada's top investment firms. Ian holds a Bachelor of Arts in Political Science and Economics from Huron College at the University of Western Ontario. A long-time supporter of Square Circle, Ian first became involved as a guest before joining the Fundraising Committee in 2018. Ian currently serves as a board member at Square Circle. He is deeply committed to community service, working with supporting financial literacy for underserved students, and contributing to global charities such as Friends of Zambia and The Nelson Mandela Foundation. Outside of work, Ian enjoys traveling, backcountry skiing, golfing, and has completed the Marine Corps and Boston Marathons.
FOUNDING BOARD MEMBER
Judy Gladstone
Judy has an extensive background in overseeing the growth of not-for-profit organizations in the public and private sectors. She is a strong innovator, leader, risk taker and bridge-builder. Judy's peers have recognized her entrepreneurial and leadership skills with awards from Canadian Women in Communications, Women In Film and Television and Luminato. With a background in international development and arts administration, Judy has always looked for opportunities to support women. With strong production and technology skills, she has mentored numerous accomplished women, from unknown artists, to well known icons like Veronica Tennant and Karen Hines who, in mid-career, have transitioned from appearing on stage and in front of the camera into the director's chair, resulting in award-winning films. After attending the CWC Digital Media Career Accelerator in 2004, Judy had the groundbreaking insight to commission shorts to be shot with and screened on mobile devices, in addition to playing on traditional screens. She established, along with the National Film Board, the innovative and award-winning Shorts in Motion initiative in 2006. This program, part of Judy’s mission to build a strong creative community of women in the short film genre, created micro-movies for video cell phones while celebrating Canadian artists, well in advance of current mobile video platforms. Her specialties include creating new public-private partnerships, public and private-sector grants, television, film, and new media funding and production.
FOUNDING BOARD MEMBER
Gallant Law
Gallant Law is an award-winning marketing professional with over 15 years of experience turning consumer insights into impactful B2C and B2B strategies for tier-one organizations. He currently serves as Executive Advisor – Strategy & Growth and Client Relations Director at Coveted Co., providing strategic guidance in marketing, sponsorship, and social impact to drive client growth. Previously, Gallant was Head of Lifestyle Brand & Partnerships – The Americas at Cathay Pacific, overseeing partnerships across payment, holidays, shopping, wellness, and dining to enhance engagement with top-tier airline members. Before that, he was Director of Sponsorship Marketing Planning and Strategy at Scotiabank, leading national sponsorship strategy across sports, arts, and philanthropy. Gallant also held the role of Head of Brand, Sponsorship and Product Marketing at Visa Canada, managing strategic planning, national campaigns, promotions, sponsorship marketing, market research, and brand management, while representing Canada on the Visa International Sponsorship Committee. His extensive campaign and activation experience spans global and national properties including the Olympics and Paralympics, FIFA World Cup, TIFF, VIFF, Just for Laughs, Luminato, Stratford Festival, Hot Docs, and the Scotiabank Giller Prize.
FOUNDING BOARD MEMBER
Michael McGrath
Michael McGrath is a seasoned construction industry leader who co-founded Tucker HiRise in 2002 in partnership with Great Gulf, rapidly building the company into a nationally recognized expert in complex, large-scale construction projects. After successfully growing Tucker HiRise, Michael sold his interest in 2021 and founded Vertical 1, a cutting-edge, technology-driven construction platform.
Vertical 1 integrates advanced technologies like digital twins to create detailed, real-time digital replicas of construction projects. By converting paper plans into actionable data, the platform enhances coordination and provides valuable insights throughout the construction process. This early detection of potential issues minimizes delays and cost overruns, while simulations allow for optimized resource allocation and more efficient project timelines. Vertical 1 is revolutionizing the construction industry by combining innovation and efficiency to ensure projects are completed on time and within budget.
BOARD MEMBER - Secretary
Jennisa Visram
Jennisa Visram brings over 20 years of experience partnering with global brands including Macy’s, TJX, Nike, Disney, and Kotn in merchandising, assortment strategy, and brand growth. Known for bridging creativity with commercial discipline, she helps companies scale through consumer insight, financial strategy, and intentional product development. As founder of The Collective, Jennisa works with fashion and retail businesses to strengthen strategy, sharpen market position, and build sustainable growth rooted in collaboration and education. She is a committed mentor passionate about developing emerging talent and amplifying diverse voices. Rooted in Toronto and shaped by her time in New York, Jennisa brings a cross-cultural perspective to fashion and creative commerce, supporting organizations championing creativity, education, and equitable access in the industry.
BOARD MEMBER
Shawn Cuffie
Shawn Cuffie is an event producer, choreographer, and entertainment luminary with a three-decade journey marked by a visionary outlook and creative brilliance. Renowned for orchestrating triumphant events across North America, his expertise shines in crafting corporate and philanthropic gatherings for entities like Pepsi, TD Bank, Rogers Communications, Price Waterhouse Coopers, and Air Canada. Shawn's influence extends beyond corporate spheres, contributing to culturally resonant events such as the Mandela Legacy, Friday Night Live at the Royal Ontario Museum, the Art Gallery of Ontario, and the Toronto Design Exchange, demonstrating his commitment to community enrichment through the arts. Shawn Cuffie is a visionary who transforms concepts into captivating realities.
BOARD MEMBER
Yussuf Hussein
Yussuf Hussein is a community organizer and policy advocate whose experience spans government policy work, community organizing, and grassroots leadership. Growing up in Regent Park shaped his commitment to equity and informed his lived experience as a Black leader working within Toronto’s communities and policy landscape.
Yussuf has experience coordinating complex initiatives, managing budgets, guiding community engagement, leading development and revitalization projects, and delivering community-driven events and projects. His work connects multi-level governments, nonprofits, and grassroots partners, strengthening his ability to align diverse priorities and move projects from planning to implementation. He has contributed to committees and advisory groups focused on youth outcomes, community safety, equity, and strategic planning. Yussuf brings a community-rooted and systems-focused approach to partnership building, project coordination, and policy development, ensuring that both community insight and strategic goals are reflected in the work he supports.
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