OUR COMPANY BACKGROUND & CULTURE
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.
Join us in building a bright future for our members, our organization, and each other.
THE ROLE
The Director, Cyclical Transactions is accountable for the end-to-end design, governance, and execution of cyclical pension administration transactions across annual, monthly, quarterly, and ad-hoc cadences within Pension Services.
This role owns the cyclical operating model and ensures that all recurring pension processes – including annual statements, valuation data extracts, regulatory filings and statutory reporting – are delivered accurately, completely, and in compliance with plan rules, legislative requirements, and established governance frameworks.
Reporting to the Managing Director, Specialized Operations, the Director, Cyclical Transactions translates Pension Services strategy into a scalable, controlled, and audit-ready cyclical administration framework. While enterprise regulatory policy and risk appetite are set at the executive level, this role is accountable for ensuring cyclical administration is executed within those frameworks and for escalating material risks appropriately.
A core focus of the role is safeguarding trust and transparency in UPP’s recurring pension outputs, ensuring members, employers, and regulators receive accurate, timely, and compliant information.
In addition to execution accountability, this role leads the continuous modernization and optimization of cyclical pension administration processes, strengthening operational resilience and scalability as UPP grows.
This role is based in downtown Toronto in a hybrid work environment, allowing employees the flexibility to work remotely and in-office (minimum two days per week in-office).
This posting is for an existing vacancy.
SPECIFIC ACCOUNTABILITIES
The Director, Cyclical Transactions will have responsibility for but not limited to the following:
- Own the end-to-end planning, execution, and governance of cyclical pension administration transactions across annual, monthly, quarterly, and ad-hoc cadences, including annual member statements for active, retired, and deferred members, recurring statutory filings, and regulatory reporting.
- Accountable for providing accurate data for the liability valuation of the Plan to UPP’s Actuarial team.
- Accountable for the accurate and timely delivery of year-end activities, including the application of interest to annual contributions, management of year-end updates to system rules and factor tables, and related compliance outputs.
- Oversee regulatory and statutory processing, including CRA filings, preparation of pension adjustments for participating employers (PAs), amended PAs, PAR and PSPA filings, age-based retirement requirements, and other legislated recurring obligations.
- Oversee cyclical member lifecycle calculations, including optional member enrollment options, pension “true ups,” and other rule-driven recalculations required under plan provisions or pension legislation.
- Accountable for the governance and maintenance of missing member processes, including periodic reviews to locate missing members and beneficiaries with outstanding pension benefits, ensuring fiduciary and regulatory obligations are met.
- Design, maintain, and continuously enhance the cyclical pension administration operating model, ensuring scalability, auditability, and alignment with Pension Services strategy.
- Maintain and execute the enterprise calendar of cyclical transactions and ensure readiness across Actuarial, Product, Technology, Finance, Communications, and Enablement & Controls functions.
- Ensure data completeness, reconciliation, validation, and financial integrity for all cyclical batches, filings, statements, and regulatory outputs.
- Accountable for delivering cyclical legislative and service-level agreement results and meeting or exceeding scorecard metrics related to accuracy, timeliness, and compliance.
- Act as subject-matter expert for configuration of cyclical transactions and workflows in the pension administration system.
- Establish and enforce operational controls and quality assurance standards specific to cyclical processing, partnering with Enablement & Controls to ensure appropriate sampling, validation, and compliance coverage.
- Coordinate cross-functional dependencies with Actuarial, IT, Product, Process and Controls function, Finance, and Communications to ensure timely and accurate cyclical delivery.
- Partner with external vendors and internal technology teams to oversee cyclical calculation methodologies and system functionality as it relates to recurring transactions.
- Act as subject matter expert in plan provisions and cyclical calculation rules, ensuring consistent interpretation and application across recurring processes.
- Resolve escalated cyclical issues, document adjudication decisions, and partner with Policy and Legal as required.
- Use data, insights, and feedback to measure, refine, and enhance cyclical delivery performance and customer experience across channels.
- Translate organizational strategy into effective cyclical operational practices and identify automation and modernization opportunities.
- Support change management and adoption activities during transformation or rollout phases impacting cyclical transactions.
- Provide executive-level reporting and insight on cyclical readiness, risks, outcomes, and performance.
- Create an environment in which team members are mentored and coached for continuous improvement and career development.
Enablement & Controls
- Accountable for the design, implementation, and ongoing effectiveness of processes and controls across assigned functions, ensuring alignment with the Target Operating Model and enterprise risk frameworks.
- Fosters 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.
- Promotes 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.
QUALIFICATIONS & EXPERIENCE
- Bachelor’s degree required; postgraduate degree is an asset.
- Minimum 10-12 years of progressive experience in Canadian defined benefit pension administration or a comparable regulated financial services environment.
- Deep, applied knowledge of Canadian pensions administration, including pension calculations, pension adjustments, statutory reporting, and recurring regulatory requirements.
- Demonstrated experience designing and governing recurring operational cycles in a highly regulated environment.
- Proven experience leading cross-functional teams and influencing senior stakeholders across actuarial, legal, technology, and finance functions.
- Strong understanding of operational controls, reconciliation processes, audit requirements, and compliance frameworks.
- Experience overseeing pension administration system functionality and recurring calculation methodologies.
- Demonstrated ability to translate strategy into scalable operational execution.
- Professional designations such as CEBS or PPAC are considered assets.
- Experience in university-sector or unionized environments is an asset.
ATTRIBUTES
- Strong operational discipline and structured approach to recurring delivery cycles.
- High level of accountability and ownership for compliance-sensitive outputs.
- Calm and decisive under pressure when managing regulatory deadlines.
- Risk-aware and governance-focused mindset.
- Collaborative and influential in coordinating across complex stakeholder groups.
- Data-driven, analytical, and improvement-oriented.
- High integrity and commitment to financial and regulatory accuracy.
- Dedicated to maintaining transparency and trust in member and employer communications.
LIFE AT UPP
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. Check out some highlights of our inclusive employee-focused benefits program including:
- 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
This posting will remain open for a minimum of seven (7) days and will remain open until a sufficient number of qualified applications are received or finalist candidates have been identified.
Artificial intelligence (AI) tools may be used to support certain stages of the recruitment process, including sourcing, screening, and assessment. All hiring decisions involve human review and intervention by UPP employees.
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.
UPP respects your privacy. For information on how UPP handles the personal information you provide during the application process, please see our Job Applicant Privacy Statement.
