Federal Government Clearance Level Required:NoneAbout UsMaplesoft Group is currently seeking a hybrid Group Benefits Specialist for our client in Mississauga, ON.This is a hybrid position with a mandatory 1 day/week on site (Tuesdays).Position SummaryThe Group Benefits Specialist plays a critical role supporting the end‑to‑end administration and ongoing operations of group benefit plans for a diverse portfolio of clients across Canada. This is a hands‑on, business‑facing role that blends deep industry knowledge with strong operational aptitude. The successful candidate will be comfortable working directly within benefits administration platforms and troubleshooting issues to resolution. This role requires someone who understands group insurance workflows, can translate plan requirements into system configuration, and demonstrates strong agility to quickly learn and adapt to new platforms and tools. In addition to day‑to‑day plan administration, this role leads group implementations, resolves complex issues through root‑cause analysis, supports continuous process improvement, and acts as a mentor to junior team members. A client‑focused, detail‑oriented mindset and sound professional judgment are essential to success. This position offers a flexible hybrid work model and career growth opportunities.Key ResponsibilitiesServe as a senior point of contact for assigned clients, advisors, and insurer partners, ensuring timely, professional, and inclusive service delivery.Manage full cycle group benefits administration, including:New employee enrollments, terminations, life event updates, and salary changesEligibility management and contract maintenancePremium billing reconciliation and adjustmentsOngoing reporting, audits and compliance supportPlan sponsor billingInterpret plan designs, insurer contracts, and administrative rules to ensure accurate, compliant processing across all systems.Liaise with insurance carriers to resolve escalated issues, manage service expectations, and coordinate ongoing plan requirements.Hands‑on configuration of group benefit plans within administration platforms,



using front‑end system screens and available tools. Performance end‑to‑end testing, including payroll, carrier and premium.Set up new groups and plan designs by translating client and carrier requirements into accurate system configuration, including:Group and plan setup, coverage tiers, rates configuration and eligibility rules in the benefits systemOnboard and validate client and employee data, ensuring accuracy and completeness throughout implementations and transitions.Conduct root‑cause analysis on operational errors, system issues, or client escalations.Identify gaps between plan requirements, workflows, and system behavior, and recommend practical solutions. Be the voice of the client to our products team.Support operational improvements by aligning business processes with system capabilities.Act as a mentor and subject‑matter resource for junior team members, particularly on:System usage and configurationBest practices in group benefits administrationProvide coaching, peer review, and informal training to support skill development.Participate in team meetings, implementation reviews, and continuous improvement discussions.Contribute to the creation, refinement, and maintenance of standard operating procedures (SOPs), workflows, and job aids.Identify opportunities to improve accuracy, efficiency, and client experience through better processes and clearer documentation.Maintain comprehensive, up‑to‑date documentation for assigned client accounts in accordance with company standards.Required QualificationsMinimum 5 years of experience in group benefits administration, ideally within a TPA or insurer.



Proven experience with plan set‑up and administration of group benefit plans.Strong understanding of group benefits workflows and administrative best practices.Demonstrated ability to troubleshoot complex issues and perform root‑cause analysis.High attention to detail, strong organizational skills, and respect for confidentiality.Ability to manage multiple priorities and deadlines in a fast‑paced, client‑focused environment.Excellent written and verbal communication skills.Advanced proficiency in Microsoft Office (Excel, Word, Outlook).Preferred / Assets QualificationsExperience leading or supporting group benefit implementations.Prior experience mentoring, coaching, or informally training team members.Experience working with benefits administration platforms or TPA systems.CEBS, GBA, or other industry related designations is an asset, but not required.Bilingualism (English/French) is an asset but not required.CompensationSalary Range: $75,000 – $85,000BenefitsComprehensive health, dental, and vision advantages to help you and your family stay well.Financial literacy tools and resources to help you feel confident managing your money today and planning for the future.Employee discount program with savings across a variety of products and services.A full Employee Assistance Program (EAP) with virtual health access, making it easier to connect with a doctor or get support when you need it.Retirement savings program to support your long‑term financial goals.Paid time off, including support for new and growing families.Hybrid work model that offers flexibility and supports work‑life balance.Career growth opportunities with mentorship, learning, and advancement across different experience levels.A collaborative, supportive team environment with exposure to diverse clients and complex group benefits plans.Submission DeadlineFriday, May 1 2026, 12:00pm ESTHow to ApplySubmit your resume (and cover letter) to the provided links.https://www.Maplesoftgroup.Com/Careers/Career-OpportunitiesEqual OpportunityMaplesoft is an equal opportunity employer and welcomes applications from all qualified candidates. Accommodations are available upon request throughout the recruitment process.#J-18808-Ljbffr

📌 Benefits Specialist - C$75,000 - C$85,000 A Year (Winnipeg)
🏢 Maplesoft Group
📍 Winnipeg