Sr. Specialist

Position: Sr. Specialist, Benefits (12-14 month contract)
Overview  high-performance, people-focused culture
our commitment that equity, diversity, and inclusion are fundamental to our work environment and business success, which helps employees feel valued and empowered to be their authentic selves
learning and development initiatives, including workshops, Speaker Series events and access to Linked In Learning, that support employees’ career growth
membership in HOOPP’s world class defined benefit pension plan, which can serve as an important part of your retirement security
competitive, 100% company-paid extended health and dental benefits for permanent employees, including coverage supporting our team's diversity and mental health (e.g., gender affirmation, fertility and drug treatment, psychological support benefits of $2,500 per year, parental leave top-up, and a health spending account).
optional post-retirement health and dental benefits subsidized at 50%
yoga classes, meditation workshops, nutritional consultations, and wellness seminars
the opportunity to make a difference and help take care of those who care for us, by providing a financially secure retirement for Ontario healthcare workers

Job Summary  Reporting to the Associate Director, Benefits, the  Sr. Specialist, Benefits  plays a critical role in the effective administration and delivery of HOOPP’s benefits and wellness programs. This role supports day‑to‑day benefits operations for employees in Canada and the UK, ensuring accuracy, compliance, and a positive employee experience. The Sr. Specialist will administer benefits in Workday, manage benefits billing, maintain accurate documentation, and collaborate closely with internal partners such as Payroll, HR Operations, and external vendors.

The Sr. Specialist will also support the execution and implementation of the wellness programs, provide guidance and support to employees and managers throughout the disability and return‑to‑work process, and provide comprehensive support for employees taking parental leaves and other leaves of absences. The ideal candidate is passionate about benefits, highly detail‑oriented, customer‑focused, and committed to maintaining data integrity across systems and processes.
Benefits Administration

What you will do:

Execute end‑to‑end administration of employee benefit and pension records across various vendor platforms, including processing enrolments, terminations, and coverage updates, conducting routine data audits and reconciliations, and resolving discrepancies to ensure accuracy and seamless operational delivery
Facilitate weekly benefits orientation sessions for new hires, providing an overview of programs and ensuring employees understand how to access available benefits.
Maintain accurate and up‑to‑date benefits‑related documentation, SOPs, and process records.
Manage, and monitor the benefits billing process, including validating monthly carrier invoices, resolving discrepancies with vendors, and ensuring accurate, timely payment.
Employee Support & Advisory   Provide timely and professional responses to employee benefits and leave inquiries, ensuring an exceptional level of customer service.
Support employees applying for Short‑Term Disability, providing guidance through the process, and ensuring confidentiality, compliance, and compassion.
Provide end‑to‑end support for employees taking parental leaves, including advising on leave entitlements, system updates and required documentation
Provide expert support to employees transitioning into retirement by responding to inquiries, guiding them through post‑retirement benefit options, and ensuring they have clear, timely information to make informed enrollment decisions
Develop and promote clear, engaging benefits resources for communication channels such as employee intranet —collaborating with internal communications partners to build awareness and enhance employee understanding of the full benefits offering.
Wellness Program Execution   Support the execution, implementation, and ongoing coordination of wellness programs across the organization.
Track wellness program participation and outcomes and support data analysis for program enhancement.
Collaborate…