WISF Fireside Chat: Leading in the Age of AI
Toronto Chapter Event
Wednesday, May 27th, 2026
12:00pm - 1:30pm
Delta Hotel Toronto
75 Lower Simcoe St, Toronto, ON M5J 3A6
Join us for an engaging fireside chat with Cindy Hoots as she shares her insights on modern leadership and what it takes to succeed in an AI-driven world.
Drawing from her extensive experience, Cindy will explore how leaders can adapt, stay resilient and foster innovation amid rapid technological change. She will also discuss the importance of leading across generations, offering practical strategies for building cohesive teams that leverage diverse perspectives, experiences and working styles. This conversation will provide valuable perspectives on navigating uncertainty, strengthening collaboration and thriving at the intersection of leadership and artificial intelligence.
Thank you to Osler for kindly sponsoring this event.
Register
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Lisa Mantello
Lisa Mantello is an experienced transactional lawyer recognized for her creative problem-solving and strategic counsel. She practices across all areas of financial services, with specialized expertise in domestic and cross-border financing transactions, structured finance, and derivatives.
Advising pension funds and other institutional investors, Lisa draws on deep practical experience from her involvement in the most complex and dynamic Canadian structured finance transactions of the last decade.
Leveraging her exceptional background in derivatives, Lisa has strategically built a market-leading practice at Osler, establishing the firm as the legal advisor of choice for derivatives in Canada. She serves as primary Canadian counsel for the International Swaps and Derivatives Association (ISDA). In this capacity, her work includes drafting and publishing the Netting and Collateral opinions for Canada, Ontario, Alberta, British Columbia, and Québec, which are relied upon globally by ISDA members and market participants.
Lisa is consistently recognized as a leading lawyer by the Canadian Legal Lexpert Directory for derivatives, by Best Lawyers in Canada for banking and finance, and is Highly Regarded by IFLR 1000 for banking, finance, derivatives, and financial restructuring. Named one of the Top 25 Most Influential Lawyers in Canada for 2023, she speaks and writes extensively on the derivatives industry, fintech, and cross-border financings. She also serves on the Finance Advisory Board for Practical Law Canada, established by Carswell.
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Cindy Hoots
Cindy is an accomplished, award-winning Chief Digital Officer/CIO and Non-Executive Director who is known as a business-focused, consumer-centric, transformational leader. She is widely recognized for leveraging technology to drive top-line growth and bottom-line profitability by applying advanced technologies to create measurable business outcomes.
A thought leader in AI, data, and emerging technologies, Cindy advises organizations on innovative business models, customer-centric strategies, and accelerated value creation. Her deep technical expertise and pragmatic execution enable responsible, scalable adoption of new technologies in large, complex and geographically dispersed companies.
Cindy is known for creating high performing organizations and is particularly skilled at mentoring people to reach their personal and professional goals. She has a passion for advising companies and startups and strategizing together on how they can reach their growth ambitions.
She brings strong capabilities in board governance, risk management, organizational effectiveness, go to market, cyber and AI. Her purpose... to be a catalyst of growth for business, people and the planet. International speaker on topics including: AI, future technology trends, exponential organizations, ethical implications of technology and the role of IT in driving top line and bottom line business performance.

