Job Description

Why you'll love working here:

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 LinkedIn 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 Director, Compensation & Benefits, the Associate Director, Benefits is responsible for the design, implementation, and ongoing evaluation of HOOPP's benefits, disability management, and workplace accommodation programs. This role also partners with the team to deliver a holistic wellness strategy. Using data-driven insights, the Associate Director will continue to evolve HOOPP's market-competitive programs that differentiates HOOPP as an employer.


Anchored in HOOPP's values of Accountability, Compassion, and Trust, the Associate Director is expected to demonstrate these principles in how they lead, support employees, and collaborate across the organization. The role ensures alignment with HOOPP's Total Rewards philosophy and advances our people strategy by fostering resilience, embedding equity, diversity, and inclusion, and supporting a high-performing workforce. The Associate Director provides leadership to two direct reports: a Manager and a Senior Specialist.

What you will do:

Benefits Program

Lead the design and implementation of HOOPP's benefits program, ensuring compliance with legislation, market competitiveness, and alignment with HOOPP's Total Rewards philosophy. Lead the renewal process, including budget management, broker oversight, and rate/utilization review. Conduct annual data-driven program reviews to assess effectiveness, competitiveness, and cost efficiency. Regularly review and enhance benefits processes and policies. Monitor industry trends and apply best practices to continuously evolve the program. Build HOOPP's external reputation as a top employer by collaborating with peer plans and pursuing external recognition opportunities. Direct internal and external communications on benefits, in consultation with HOOPP's communications team. Manage relationships with third-party vendors to optimize employee experience and maintain service standards. Select and evaluate third-party vendors, ensuring quality service and cost-effectiveness, including recommending going to market for new vendors as necessary and leading the related request-for-proposal process. Analyze quarterly data to identify employee health trends and shape an evidence-based program.

Disability, Accommodations, and Leave Programs

Ensure consistent application of sick leave, accommodation, and leave policies across the organization. Continuously assess and evolve programs to enhance employee experience and ensure timely stakeholder communication (insurer, HR Business Partners, people leaders, employees). Manage disability claims alongside the Manager, Benefits, ensuring confidentiality, neutrality, and compassionate support. Partner with Employee Relations on cases involving performance or team dynamics. Work closely with the third-party vendors in managing claims. Manage medical accommodation requests alongside the Manager, Benefits; partner with HOOPP's corporate physician to develop and implement plans, engaging leaders and employees to ensure support and success of the accommodation plan. Work closely with third-party vendors in managing requests, as required. Oversee parental leave processes managed by the team, ensuring a seamless employee experience Provide training to HR Business Partners and people leaders on disability and accommodation practices. Manage relationships with third-party vendors to optimize employee experience and maintain service standards. Select and evaluate third-party vendors, ensuring quality service and cost-effectiveness, including recommending going to market for new vendors as necessary and leading the related request-for-proposal process. Analyze quarterly data to identify trends and inform program improvements.

Wellness Program

Partner with the Manager, Benefits to deliver a holistic wellness strategy that supports employee wellbeing, psychological safety, EDI goals, and hybrid work and implement a multi-faceted mental health program, maintaining HOOPP as a leader in this space. Stay current with best practices and actively participate in external networks. Use quarterly data insights to shape an evidence-based wellness program.

Health & Safety

Act as HR liaison to the Joint Health & Safety Committee, ensuring legislative compliance and training requirements are met. Collaborate with Facilities Management to define roles and responsibilities. Monitor industry trends and continuously evolve HOOPP's Health & Safety program.

Team Leadership

Foster a positive, engaged, and high-performing team environment built on empowerment, innovation, and collaboration. Communicate goals clearly, share knowledge and responsibility, and set high professional standards. Promote a service-oriented mindset in all stakeholder interactions. Champion continuous improvement in processes and practices.

What You Bring

University degree and/or College diploma, or an equivalent combination of education and experience. Certified Employee Benefits Specialist (CEBS) designation is an asset. 7+ years of experience in benefits and wellness, including program design, implementation, and management informed by data insights. Consulting/advisory background is an asset but not required. 3-5 years of direct experience managing disability, accommodations, and leave cases. Strong third-party vendor management skills. Global benefits and wellness program exposure is an asset. Proven ability to handle sensitive information with confidentiality and professionalism. Strong communication skills (written and verbal) across all organizational levels. Exceptional planning, decision-making, problem-solving, and troubleshooting abilities. Skilled at relationship building and providing advisory support. * Demonstrated ability to lead and inspire a team.