Lisa Osachoff

With extensive executive-level experience in Human Resources, I have consistently delivered high-impact people and talent strategies that drive organizational performance and support long-term business goals. As a trusted strategic partner to senior leadership, I have led enterprise-wide initiatives in talent management, organizational design, and culture transformation—resulting in measurable improvements in employee engagement, leadership capability, and operational effectiveness. Known for balancing empathy with accountability, I bring the courage to challenge constructively and contribute meaningfully as a member of the executive team, fostering alignment, trust, and execution excellence across the organization.

I am an accomplished Human Resources executive with a strong track record of aligning people strategies with business objectives to drive performance, culture, and organizational growth. Most recently serving as Senior Vice President and Chief People & Culture Officer at Wawanesa Insurance, I led enterprise-wide initiatives in talent development, organizational effectiveness, and employee experience, with a clear focus on delivering measurable results and long-term business value.

Prior to this, as Chief People & Culture Officer at Western Financial Group, I guided the organization through transformational change, including the challenges of the COVID-19 pandemic. My leadership enabled the successful implementation of flexible work strategies, strengthened wellness programming, and reinforced a resilient and values-based culture. During this time, our HR team was recognized as a finalist for the Canadian HR Team of the Year (Insurance or Finance), highlighting our commitment to excellence and innovation.

With a strategic mindset, sound business acumen, and a deep belief in the power of inclusive leadership, I have consistently been a trusted partner at the executive table. I am now actively seeking a new executive opportunity where I can continue to contribute to business transformation, enable high-performing teams, and drive sustainable organizational success.

I hold a Bachelor of Arts in Sociology from the University of Lethbridge, which has provided me with a strong foundation in understanding human behavior, organizational dynamics, and societal trends—insights that have been invaluable throughout my HR and business leadership career.

Currently, I am further enhancing my governance expertise by completing the Independent Corporate Director Certificate through McMaster University, deepening my knowledge of boardroom leadership, fiduciary responsibility, and strategic oversight.