Chief Operating Officer

December 3, 2026 St John's, Newfoundland and Labrador
November 30 - December 3, 2026 Winnipeg, Manitoba
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GLP-1 medications are changing the conversation around workplace drug benefits. As demand grows and new treatments emerge, plan sponsors face a difficult question: how do they balance the immediate cost of coverage with the possibility of better long-term health outcomes?
Canadians are living longer, and the assumptions used to calculate pension obligations are evolving. New research from the Canadian Institute of Actuaries is giving defined benefit (DB) pension plans a more current picture of longevity risk, with implications for valuations, funding and long-term planning.
Location: Regina
Job Start Date:
DescriptionFor the people who rely on Plannera, pensions and benefits are personal. They support decisions about work, family and retirement, and confidence in what comes next. As Chief Operating Officer, you will help ensure those members receive service that is clear, coordinated and responsive to their needs.
Plannera is a purpose-driven, not-for-profit corporation serving more than 114,000 plan members and over 900 employers across Saskatchewan. With a history dating back to 1983, the organization administers 11 pension plans and 16 benefit plans, with more than $20 billion in pension assets under administration. Following its transition to an independent corporation in 2024, Plannera is building on that foundation to strengthen service, modernize operations and pursue thoughtful growth.
The Opportunity
Reporting to the Chief Executive Officer and serving on the Executive Committee, the COO leads a broad portfolio encompassing pension and benefits administration, marketing, communications and brand, corporate and client planning, and business development. You will lead corporate and client planning processes, ensuring priorities are translated into coordinated operational plans with clear ownership and measurable outcomes. This is an opportunity to influence both the daily experience of members and the long-term direction of the organization.
At the centre of the mandate is a clear ambition: “one member, one experience.” Working with experienced directors and executive colleagues, you will bring administration, communications, education and engagement together around the individual. You will turn member insights and strategic priorities into practical improvements, establish a disciplined approach to operational performance and service costs, and help build the capacity to serve additional employers and clients. You will also lead major corporate projects from planning through implementation, coordinating work across departments, establishing accountability and ensuring projects are completed.
Plannera believes in the value and impact of strong leadership. You will give capable leaders clear direction and room to act, strengthen management capacity and help teams sustain progress through change. Within Plannera’s complex governance structure, you will work directly and independently with Boards and governing bodies, building trusted relationships and ensuring their priorities and commitments are reflected in planning and delivery. You will foster strong relationships with plan governing bodies, employers and other stakeholders whose confidence is essential to Plannera’s work.
RequirementsThe Leader We’re Seeking
The successful candidate will bring senior leadership experience in complex service operations, a record of improving customer or member experience, and sound financial and operational judgment. You know how to lead planning processes, coordinate major projects across functions and translate plans into measurable results. Colleagues value your ability to listen, ask thoughtful questions, address difficult issues constructively and follow through. Experience working with boards or within complex governance structures would be an asset.
Experience in pensions, financial services, or regulated environments is an asset, but not required. We welcome leaders from diverse backgrounds who bring strong transferable skills, quick learning ability, and the drive to lead in a complex organization.
Based in Regina, this role offers meaningful executive responsibility in an organization that values professional excellence, collaboration and a sustainable working life.
Plannera is an equal opportunity employer and welcomes applications from qualified candidates of all backgrounds. Accommodation is available throughout the recruitment process by contacting Leadership Source confidentially.
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