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About the Role

The Associate Director, Member Education & Engagement is accountable for the delivery and continuous improvement of UPP's technical member presentation program, serving as UPP's primary liaison for member-facing presentations. This role owns the development and delivery of member-facing education and engagement activities, ensuring members and participating employers receive consistent, accurate, and engaging pension education. The successful candidate will personally lead and deliver complex pension work while acting as a trusted advisor to stakeholders.

Responsibilities

Own the development and delivery, and continuous improvement of UPP's technical member education and engagement program across participating employers
Serve as UPP's primary representative and facilitator for member-facing education and engagement activities
Communicate complex technical information in plain language appropriate to the audience while maintaining technical accuracy
Serve as a recognized subject matter expert on pension plan provisions, pension administration practices, and regulatory requirements
Lead the planning, coordination, and delivery of webinars, presentations, workshops, retirement education sessions, and other member engagement opportunities
Develop and manage the annual member presentation and engagement calendar, ensuring effective coordination across employers, internal stakeholders, and business priorities
Build strong relationships with participating employers and employee representatives to understand education needs, identify engagement opportunities, and support employer readiness
Tailor presentation delivery to meet the needs of diverse member audiences while maintaining approved messaging, content, and communication standards established by Strategy & Communications
Maintain expert knowledge of UPP's pension plan, member services, digital tools, and member experience to effectively facilitate education activities and respond to member and employer questions
Identify when specialized expertise is required and coordinate participation from subject matter experts across Pension Operations, Actuarial, Investments, Product, Legal, and other business areas
Monitor education program effectiveness through participation metrics, member feedback, employer feedback, and engagement insights, using findings to continuously improve delivery approaches
Lead, coach, and develop team members responsible for member education and engagement activities, fostering a culture of collaboration, innovation, and continuous improvement
Prepare and present program performance updates, engagement metrics, emerging trends, and recommendations to senior leadership
Represent UPP at employer meetings, conferences, onboarding events, retirement planning sessions, and other external engagement opportunities as required
Lead the execution of the design, implementation, and ongoing effectiveness of processes and controls across assigned functions, ensuring alignment with the Target Operating Model and enterprise risk frameworks
Foster a culture of constructive challenge by actively engaging with Second- and Third-Line functions, ensuring effective oversight and assurance, and driving timely and transparent responses to feedback, findings, and requests
Promote a culture of ownership, accountability, and constructive challenge, where feedback from oversight and assurance functions is actively sought and used to strengthen processes and controls

Requirements

Bachelor’s degree required
Minimum 8-10 years of progressive experience in Canadian defined benefit pension administration or a comparable regulated financial services environment
Demonstrated experience leading education, engagement, or client-facing programs within a complex, regulated environment
Strong understanding of Canadian defined benefit pension administration, including complex and employer-specific scenarios
Exceptional presentation, facilitation, and public speaking skills with experience presenting to diverse audiences, including executive stakeholders, employers, unions, and plan members
Demonstrated ability to build trusted relationships and influence stakeholders across multiple organizational levels
Experience using member feedback and performance metrics to improve service delivery and engagement outcomes
Exceptional verbal and written communication skills, with a proven ability to explain complex pension, actuarial, and regulatory concepts to technical and non-technical audiences
Experience in university-sector or unionized environments is an asset
Professional designations such as CEBS or PPAC are considered assets

Skills

Member-focused leadership
Confident facilitation
Relationship building
Presenting to large and diverse audiences
Strategic thinking
Operational excellence
Risk-aware mindset
Governance-focused mindset
Collaboration
Influence
Data-driven analysis
Improvement orientation
Innovation
Transparency
Trust building
Accountability
Service orientation

Location

Downtown Toronto
Hybrid

Work Type

Hybrid work environment
Work remotely up to eight weeks/year

Experience Level

Associate Director
8-10 years of progressive experience

Education Level

Bachelor’s degree
Postgraduate degree is an asset
CEBS or PPAC designations are assets

Benefits

Defined benefit pension plan
Flexible hybrid work model
Paid time off – vacations, personal days and wellness days
Work remotely up to eight weeks/year
Comprehensive group benefits including medical, dental, vision, etc.
Extended paramedical and mental health service coverage
Health care and lifestyle spending accounts
Fertility treatments, paid parental leave, and gender affirmation coverage
Education Assistance program

About the Company

UPP is the first pension plan of its kind in Ontario’s university sector, proudly serving over 46,000 members across six universities and nineteen sector organizations.
Our purpose is to bring greater retirement peace of mind to the university sector by investing with integrity and serving members with care.
As a sector-wide plan designed for growth, our doors are open to all Ontario universities.
UPP is recognized as one of Greater Toronto’s Top Employers for 2026.
Together, we’re a team of progressive thinkers and agile doers operating within a fast-paced culture of collaboration and respect.
We believe in bringing smart and capable people together to create, solve, and grow with a clear shared vision and values of integrity, inclusivity, ingenuity, and impact.
Our culture is intentionally welcoming and purposefully rooted in equity, diversity, inclusion, and reconciliation (EDI&R).
We believe diverse teams, perspectives, and lived experiences contribute to better decisions and a better workplace.
As a pension plan, UPP approaches investing through a long-term lens to generate and safeguard value.
Our commitment to investing responsibly accounts for material risks that impact our investment portfolio to generate sufficient risk-adjusted returns to meet the pension needs of our members.
Do work that matters. We are duty-bound to serve our members’ interests, and it’s a responsibility we don’t take lightly.
That’s why we’ve ingrained sustainability in our work from day one—to ensure our members have a resilient future to retire into, both today and for generations to come.
Stronger together. Collaboration is how UPP was born, and it’s how we work with each other and our partners day in, day out.
No one at UPP is just a number (even if they are excellent at math) and every win is a shared win.
Grow every day. You’ll have the opportunity to work on unique, once-in-a-career projects that maximize your skill set and probably teach you some new ones—at any stage in your career.
Prioritize wellness. At UPP, wellness takes many forms. Ultimately, it’s about ensuring our people are cared for in the ways that matter to them.

Equal Opportunity

UPP enthusiastically welcomes applications from all qualified applicants and especially invites people with lived experience as an Indigenous person, a person with a disability or as a member of another Human Rights Code protected group that faces barriers to employment to apply.
Our goal is to create a barrier-free experience for every candidate throughout the recruitment process.