Anna Filice

Anna Filice

Anna is Chief People Officer at the Workplace Safety & Insurance Board (WSIB), one of North America’s largest insurance organizations, serving more than five million people across 300,000 Ontario workplaces. As a member of the executive leadership team, she plays a pivotal role in advancing the WSIB’s transformation mandate by shaping its people strategy, brand strategy, and strategic agenda.

With experience across a diverse range of sectors and industries, Anna has guided Human Resources and Corporate Service functions through transformation and growth in both unionized and non-unionized environments. She is known for integrating people, change, and communications strategies to build high-performing cultures and engaged, empowered workforces. Guided by a passion for continuous learning and talent development at all levels, her work leverages people analytics and enabling technologies to equip leaders with critical insights to support their teams and strengthen business performance. More recently, Anna has been focused on the advancement of AI enablement strategies to help her organization lead through change and prepare for the future of work.

Prior to joining the WSIB, Anna served as the first civilian executive at one of Ontario’s largest police services, where she led enterprise modernization across all corporate service functions. She holds the ICD.D designation from the Rotman Directors Education Program and brings extensive experience in strategy development and governance, most recently serving as Chair of the Mohawk College Board of Governors.