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OverviewOur Company Background & CultureUPP is the first pension plan of its kind in Ontario’s university sector, proudly serving members across six universities and eighteen sector organizations. Our purpose is to bring retirement peace of mind to the university sector by investing with integrity and serving members with care. We are a sector-wide plan designed for growth and open to all Ontario universities. UPP is recognized as one of Greater Toronto’s Top Employers for 2026. We are a team of progressive thinkers operating within a fast-paced culture of collaboration and respect, with values of integrity, inclusivity, ingenuity, and impact. Our culture is rooted in equity, diversity, inclusion, and reconciliation (EDI&R). We believe diverse teams and lived experiences contribute to better decisions and a better workplace. As a pension plan, we invest with a long-term view, considering risks to generate risk-adjusted returns to meet members’ needs. Join us in building a bright future for our members and organization. RoleThe 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 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 governance frameworks. Reporting to the MD, Specialized Operations, the Director translates Pension Services strategy into a scalable, controlled, and audit-ready cyclical administration framework. The role ensures cyclical administration is executed within enterprise policy and risk appetites and escalates material risks as needed. A core focus is safeguarding trust and transparency in UPP’s recurring pension outputs for members, employers, and regulators. The role also leads the continuous modernization and optimization of cyclical pension administration processes, strengthening operational resilience and scalability as UPP grows. This position is based in Downtown Toronto in a hybrid work environment (minimum two days per week in-office). This posting is for an existing vacancy. Specific AccountabilitiesOwn 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. Ensure accurate and timely delivery of year-end activities, including application of interest to annual contributions, 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. Govern missing member processes, including periodic reviews to locate missing members and beneficiaries with outstanding benefits, ensuring fiduciary and regulatory obligations are met. Design, maintain, and enhance the cyclical pension administration operating model for 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. Deliver cyclical legislative and service-level agreement results and meet or exceed 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 for cyclical processing, partnering with Enablement & Controls for sampling, validation, and compliance coverage. Coordinate cross-functional dependencies with Actuarial, IT, Product, Process and Controls, 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 related 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 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 insights on cyclical readiness, risks, outcomes, and performance. Create an environment in which team members are mentored and coached for continuous improvement and career development. Qualifications & ExperienceBachelor’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 knowledge of Canadian pensions administration, including pension calculations, pension adjustments, statutory reporting,



and recurring regulatory requirements. 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. Ability to translate strategy into scalable operational execution. Professional designations such as CEBS or PPAC are assets. Experience in university-sector or unionized environments is an asset. AttributesStrong operational discipline and structured delivery cycles. High accountability for compliance-sensitive outputs. Calm and decisive under pressure when managing regulatory deadlines. Risk-aware and governance-focused mindset. Collaborative and influential 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 UPPDo work that matters. We are duty-bound to serve our members’ interests and sustainability is embedded in our work to ensure a resilient future for members today and in generations to come. Stronger together.Collaboration is how UPP was born and how we work with each other and our partners. Every win is a shared win. Grow every day.You’ll have opportunities to work on unique projects that maximize your skill set and grow with you. BenefitsPrioritize wellness. Highlights of our inclusive employee-focused advantages program include: 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.#J-18808-Ljbffr

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📌 Director, Cyclical Transactions (Toronto)
🏢 University Pension Plan Ontario
📍 Toronto