The Director, Benefits and Retirement is responsible for the strategic design, implementation, and governance of the organization’s benefits, retirement, and pension programs. This leadership role ensures that all programs are competitive, compliant, and aligned with both employee needs and long-term organizational sustainability.

You will oversee the administration and continuous improvement of employee benefit programs—including health/life, wellness, retirement, and leave policies, ensuring they are effectively managed and support the organization’s talent and business goals.

Reporting to the Senior Director, Payroll, Benefits and Total Rewards, the Director role leads a team of professionals focused on delivering valued employee programs.

This role will be based at our head office in Markham, Ontario. Extendicare offers a hybrid working environment

Key responsibilities include:

Lead the design, implementation, and governance of competitive benefits, wellness, retirement, and leave programs tailored to a unionized Canadian workforce, ensuring alignment with organizational goals, employee needs, and evolving market trends.
Ensure full compliance of programs with federal and provincial legislation, pension laws, and collective bargaining agreements.
Oversee the administration and governance of registered pension plans and group RRSPs, collaborating with actuaries, legal advisors, and pension committees to ensure sustainability and legal compliance.
Partner with and manage vendors to design, deliver, and evaluate cost-effective programs that enhance the employee experience, ensuring continuous improvement and favorable contract terms.
Develop and manage leave policies (statutory and non-statutory) such as parental, medical, and compassionate care, ensuring consistency with legislation, internal equity, and collective agreements.
Lead benefits due diligence and integration planning during mergers and acquisitions, supporting business continuity and employee retention.
Drive communication and education strategies to increase employee understanding and engagement with benefits and retirement programs, including onboarding, offboarding, and retirement planning initiatives.
Collaborate cross-functionally with HR, Finance, Legal, and Payroll to ensure seamless program delivery and alignment with broader people strategies.
Act as a strategic advisor to senior leadership, preparing presentations and recommendations for the Executive Leadership Team.
Contribute to HR leadership goals by leading strategic initiatives that drive continuous improvement and operational efficiency.
Utilize data analytics and AI tools to gain insights into program utilization, cost-effectiveness, and employee engagement.
Provide leadership and coaching to a team of professionals, fostering development, accountability, and ownership.
Manage competing priorities effectively, focusing on high-impact initiatives that support business objectives while respecting organizational capacity.
Influence and align cross-functional teams by defining processes, capabilities, and environments that support strategic goals and an exceptional employee experience.

What we are looking for:

A strategic mindset with the ability to balance employee experience, cost management, and compliance
Deep expertise in the design, governance, and optimization of benefits, retirement, and leave programs, with a strong grasp of current trends and regulatory environments
Experience navigating complex, unionized environments with sound judgment and discretion
Confident working across functional areas and leadership levels, influencing outcomes and driving collaboration
Skilled in leading change and integration efforts, particularly during organizational growth or transformation
Strong analytical thinker, comfortable using data and technology to inform decisions and improve outcomes
A clear, engaging communicator who can simplify complexity for diverse audiences
Demonstrated ability to lead and develop teams, fostering accountability, growth, and innovation
Agile and solutions-oriented, with a track record of executing in fast-paced environments

At Extendicare, we believe that working as a team creates an environment that allows us to reach our potential. We value each employee, encourage equal opportunity for growth and recognize achievement. As a valued member of our team, you can expect:

Continuous mentorship, support for life-long learning and growth opportunities
Opportunities for advancement and career growth within the organization
A rewarding and meaningful work experience where you can enrich your life and the lives of others through your work.
Employee Family Assistance Program.
Robust benefits package

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Extendicare

Open Positions

Director, Benefits and Retirement