Cassandra Chowdhury is a Senior Manager in EY’s Technology Consulting practice, specializing in the P&C insurance industry with deep experience across claims transformation and large-scale technology delivery. With nearly a decade of experience, she leads complex transformation, application development, and data and analytics programs, and is recognized for building high-performing teams in fast-evolving environments. Cassandra is also the Co-Chair of EY Toronto’s Professional Women’s Network, where she helps lead a large mentorship program and designs initiatives focused on developing, engaging, and retaining the next generation of leaders. Cassandra is a passionate advocate for diversity, equity, and inclusion and is deeply committed to human-centred leadership. She believes in showing up authentically, creating space for diverse perspectives, and ensuring that empathy and humaneness remain at the heart of technology and transformation.
Jolee Crosby is CEO of Reinsurance Canada, where she oversees the Property & Casualty and Life & Health reinsurance market units as Chief Agent for Canada.
Jolee has held a number of leadership roles of increasing responsibility since joining Swiss Re in 1998, including Head of Asia Medical Products and Operations, and most recently, Global Head of Life & Health Underwriting and Medical Reinsurance.
Jolee also has a P&C background in both direct insurance and reinsurance. She started her career in Corporate Solutions, handling Agents and Brokers Errors & Omissions claims, before ultimately leading the FinPro Claims department.
She then transitioned to Reinsurance, where she led a global Governance team, ensuring the appropriate framework was in place to assess and manage operational risk. Her remit also included compliance related topics such as international trade controls, fraud detection initiatives, data protection and business continuity management.
After three years in a governance role, Jolee was appointed Head of US Casualty Claims for Reinsurance, where she focused on helping clients manage their portfolio risks as well as individual claims utilizing data analytics.
Earlier in her career Jolee practiced law at an insurance defense firm, where she represented insurance
Pamela Derksen brings a distinctive and well-rounded perspective to the insurance industry, having held executive roles on both the brokerage and carrier sides of the business across Commercial and Personal Insurance. With a national footprint, Pam is currently licensed in all Canadian jurisdictions and serves as the Principal Broker and Designated Representative for NFP Canada Corp. and its affiliated legal entities.
As Chief Compliance Officer for NFP in Canada, Pam oversees compliance across Property & Casualty, Life, and Benefits. She plays a critical role in helping the business and its clients navigate evolving regulatory landscapes, resolve complex claims, manage carrier relationships, and implement practical, client-focused solutions when faced with Privacy questions and client escalations. Her leadership has been instrumental in initiatives such as Quebec francization, M&A due diligence and onboarding, Lloyd’s program audits, and the development of educational insurance content for brokers across North America.
Pam completed the Certificate in Regulatory Compliance and Legal Risk Management for Financial Institutions at Osgoode Hall Law School (April 2025), further strengthening her expertise in governance and risk. She also serves as a skills-based Director on the Board of the Insurance Brokers Association of Ontario (IBAO), contributing her strategic insight to the broader industry.
Known for her pragmatic and collaborative leadership style, Pam is committed to fostering ethical, compliant, and positive business practices. Outside of work, she enjoys time at the cottage with her family and dogs, concerts, and hunting for mid-century modern vintage items at flea markets.
Geneviève Fortier has been serving as Chief Executive Officer of Promutuel Insurance since 2019, becoming the first woman to hold this role in the company’s 170+ year history.Over the course of her career, Geneviève has held several senior leadership positions within the pharmaceutical and, more recently, insurance industries.Celebrated for her results-oriented yet human-centric leadership approach, she has been instrumental in driving the continued growth and success of the Group and its network of mutual insurance associationsacross Quebec.
Recipient of numerous honors, Geneviève Fortier was awarded the title of « Grande diplômée » by Université Laval in 2025. She was also named CEO of the Year 2024 by Les Affaires in the Large Enterprise category and recognized among the Top 20 Most Dynamic CEOs in Canada in 2021. In June 2023, she was also appointed to the National Order of Quebec, the highest distinction awarded by the Quebec government.
A seasoned governance expert, Geneviève is Chair of the Board of Directors at Investissement Québec and a board member of METRO Inc. and Équité Association. Until recently, she was also Chair of the Canadian Association of Mutual Insurance Companies (CAMIC) and Chair of the Insurance Bureau of Canada's Quebec Chapter. Deeply committed to community engagement, she actively supports young people and women in achieving their career aspirations.
Rose Freeman, Founder & CEO, is the sole owner of Willow Insurance Corp., an independent Saskatchewan brokerage established in 2013 with offices in Shell Lake and Debden. Serving rural markets including agriculture, small business, and resort communities, she has built a reputation for growth, leadership, and resilience. Rose has been recognized nationally multiple times throughout her career for her impact on the Canadian insurance industry. In 2025 alone, she earned three distinguished honors: Elite Woman of Insurance, Broker of the Year – Regional (Prairies & Maritimes) by Insurance Business Canada, and IBC Top Broker 2025, amplifying her continued commitment to excellence and advancing women in insurance.
Lisa Kack is the Founder & CEO of Royal City Recruitment, where her extensive industry knowledge and entrepreneurial spirit drive the company's success. With over 20 years of hands-on experience in the Canadian insurance and financial sectors, Lisa is uniquely positioned to offer specialized, full-cycle recruitment services.
Her career began in sales, working at an agency and selling all lines of business from Auto to Life insurance. Over the years, she expanded her expertise into roles such as underwriting, coaching, broker acquisitions, talent acquisition, and management. This diverse experience has given Lisa depth in her ability to understand the skills and attributes required to succeed in the insurance and financial industries.
Lisa's passion for connecting top talent with the right opportunities and her commitment to building effective recruitment processes are the cornerstones of her professional journey.
Her goal is to help businesses grow by delivering exceptional recruitment solutions tailored to their specific needs.
Mackenzie Oldfield joined as an Associate on Chubb’s Financial Lines Underwriting Team in 2022, after graduating from Wilfrid Laurier University with a Bachelor of Business Administration. Based in Toronto, Mackenzie’s focus is on underwriting private and not-for-profit organizations to provide Directors & Officers, Employment Practices Liability, Fiduciary, Crime, and Kidnap/Ransom coverage. As she's grown into the Senior Underwriter role, she focuses on more complex and large-scale clients, while providing guidance and mentorship to newer team members. She previously held a wide variety of roles in the industry through Laurier’s co-op program: in claims, risk consulting, and underwriting.
Celyeste is President and CEO of the Insurance Bureau of Canada (IBC), where she works with governments and industry leaders to strengthen Canada’s property and casualty insurance sector and advance a safer, more resilient country.
She previously served as Executive Vice-President, Strategic Initiatives and Advocacy, leading national advocacy priorities for the industry. Over her career at IBC, Celyeste has held senior roles including Chief Strategy Officer, Vice-President, Western, Executive Director of Strategy and Member Engagement, and National Corporate Spokesperson. Before joining IBC, she held senior positions with the Government of Canada, including Issues Manager to the Prime Minister.
Celyeste is Chair of The Insurance Supper Club Canada, supporting the advancement of women in insurance leadership. She was named a Woman of Distinction at the 2022 Insurance Business Canada Awards and holds a BA from the University of Ottawa and an MBA certificate from the University of Toronto.
Susan DuHamel is Vice President, National Distribution & Field Leader at CNA Canada. A respected leader in the Canadian insurance industry, Susan is passionate about developing talent, fostering inclusive leadership, and supporting the advancement of women. She brings a thoughtful, practical perspective shaped by years of experience in commercial insurance and leadership.
With more than 30 years in insurance and risk management, - across both brokerage and industry-diverse corporate risk management roles – the common thread in Erin’s career has been building and growing business through periods of significant transformation. Known for stepping into complex, evolving environments, Erin is recognized for building world-class teams and guiding transformation with empathy, clarity, and purpose, while advancing innovation, elevating client service, and strengthening organizational resilience.
Prior to joining HUB, Erin led Willis Canada. Through her corporate experience at RBC, Manulife and Bentall Kennedy, and her brokerage experience at Marsh and Aon, Erin brings extensive experience in strategic growth, sales and client service delivery excellence.
Erin is a past president of the Ontario chapter of RIMS and a previous advisory board member of the Insurance Supper Club.
Jaime is a seasoned leader with over 25 years of experience in the commercial risk and insurance industry, bringing a uniquely diverse background in broking, underwriting, risk management and business development. She began her career at Aon, spending a decade placing complex commercial property and casualty insurance risks across various industries. She then joined Markel International as an underwriter, progressing to National Product Line Leader, where she oversaw the Canadian environmental book of business. Jaime later brought her expertise to a technology startup in Montreal, focusing on digital asset risks and innovative insurance solutions. At Aviva, she led the Client Relationship Management team, supporting Global Corporate & Specialty’s value proposition and strengthening Aviva’s national relationships with key broker partners. Jaime currently leads Distribution for Canada at Sompo, driving long-term profitable growth and building meaningful partnerships with clients and brokers.
Jaime holds a CRM, FCIP, and a Bachelor of Arts Honours in Applied Economics from Queen’s University. She lives in Toronto with her husband and two children.
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