Associate Director, Group Benefits – Trusteed MarketRegular Full Time7 days ago Requisition ID: 1234Salary Range: $120,000.00 To $140,000.00 AnnuallyAt Eckler, we know it’s our people that make us great at what we do.We are looking to add a senior consultant with expertise in Trusteed accounts to our growing Group Benefits Team, based in our Toronto office to support Eckler’s clients across Canada.A typical day-in-the life of an Associate Director, Group Benefits involves managing relationships with clients, coordinating complex project deliverables, analyzing underwriting arrangements, assessing client needs, work with and delegating effectively to a team of analysts and technical staff, and proactively developing business opportunities within the trusteed benefits market.We are looking for an individual with robust interpersonal skills who can fit into a tightly knit team and effectively manage competing priorities in a busy consulting practice. If you thrive on delivering customized solutions and working collaboratively with industry-leading professionals, this role may be perfect for you!Roles and Responsibilities:Serve as key relationship lead for a portfolio of trusteed clients, with accountability for client outcomes, satisfaction, and retentionLead client strategy and oversee delivery across engagements, ensuring alignment with client objectives while partnering with Directors on complex or high-risk mattersSet direction for client work, translating business challenges into strategic recommendations on plan design, funding, and risk managementOversee execution across multiple concurrent projects, delegating effectively while maintaining accountability for quality, timelines,



and financial performancePlay a key role in business development, leading components of proposals, contributing to win strategies, and expanding relationships within existing clientsProvide leadership in collective bargaining engagements, shaping costing approaches, scenarios, and strategic positioningLead and develop analysts and junior team members, including workflow management, coaching, and contributing to performance management decisionsDrive quality and consistency of deliverables across the team, establishing expectations and reviewing outputs as neededBuild and leverage insurer, administrator, and other market relationships to inform client strategies and enhance negotiation outcomesContribute to broader practice initiatives, including process improvements, knowledge sharing, and development of intellectual capitalWhat we offer:Collaborative and engaging atmosphereVariety in work and ability to evolve and grow your careerWorking with colleagues across Canada and across multiple practice areasOpportunities to help build and evolve our practiceCompetitive total rewards package in terms of salary, bonus and benefits (commensurate with experience level)An entrepreneurial,



collegial work environmentHybrid working policy and dress for your day approach (3 days in office minimum)What you offer:Direct experience and in-depth knowledge of group insurance, underwriting arrangements, and their application specifically in trusteed market scenariosExperience in large and complex multi-employer or trusteed benefit plans, including interaction with Board of Trustees and navigating union-employer dynamicsExcellent oral and written communication skills, proven ability to respond appropriately to trustees, clients, administrators, and vendors in real-timeStrong business acumen – demonstrated ability to assess complex situations, distill complex discussions, understand strategic and operational impacts, and make informed and actionable decisions that align with client goals.Stakeholder management and governance engagement – comfortable attending trustee meetings and navigating differing priorities among stakeholders.Proven ability to thrive in a collaborative team environment while managing multiple prioritiesReal passion for their work and a desire to contribute positively to Eckler’s leading cultureCommitment to exceptional client satisfaction and attention to detailStrong planning, organizational, and time management skillsStrong analytical skills and proficiency in Microsoft Excel, Word and PowerPointCEBS certification preferredPrior experience with trusteed accounts requiredAt Eckler, we are committed to an inclusive, diverse, and accessible workplace and encourage all interested applicants to submit a cover letter and resume for consideration. Persons with disabilities who need accommodation in the application process or those needing job postings in an alternative format may e-mail a request to [email protected] .#J-18808-Ljbffr

📌 Associate Director, Group Benefits – Trusteed Market - $120,000 - $140,000 A Year (Winnipeg)
🏢 Eckler
📍 Winnipeg