Project Manager – Software Implementation (Health & Welfare)

Location: Toronto, Ontario, Canada; flexibility to work in-office, virtually, or in a combination of both.

Salary: $70,000–$90,000 CAD annually.

Company

Deliver technology solutions that improve physical, mental, and financial health, including modern platforms for employee benefits administration.

What you will do

• Coordinate software implementation activities across Configuration, Data, QA, Product, Development, Integration, Operations, and client teams.
• Facilitate cross-functional meetings, document decisions and actions, and maintain follow-up communications.
• Maintain project plans, milestone trackers, RAID logs, dependency records, and status reports.
• Identify risks, issues, and dependencies; support mitigation planning and escalate concerns when required.
• Support benefits implementation activities including eligibility, enrollment, plan configuration, data migration, carrier and vendor interfaces, testing, and go-live.
• Apply Agile and modern delivery practices, including AI-powered copilots and automation for meeting notes, status reporting, and follow-ups.

Requirements

• 2–3 years of project management experience, ideally supporting client-facing software implementations or benefits technology projects.
• Foundational knowledge of Waterfall, Agile, and hybrid delivery methodologies.
• Strong organizational and communication skills, with the ability to manage competing priorities and keep teams aligned.
• Proficiency with project tools such as MS Project, Jira, Smartsheet, or Azure DevOps.
• Practical experience using copilots, automation, or generative AI to improve productivity and work quality.
• Willingness to learn Health & Welfare benefits concepts, including eligibility, enrollment, plan rules, life events, interfaces, and data migration.

Nice to have

• Experience with Health & Welfare benefits platforms covering medical, dental, vision, life, disability, spending accounts, or leave programs.
• Familiarity with carrier and vendor integrations, eligibility file feeds, payroll interfaces, or data migration.
• Exposure to open enrollment, annual enrollment, or client onboarding projects.
• PMP certification or progress toward certification.

Culture & Benefits

• Comprehensive rewards package with salary, bonus structures, flexible benefits, and at least three weeks of vacation.
• Flexible work options: in-office, virtual, or combined.
• Company-matched pension.
• Career growth and learning and development opportunities.
• Collaborative, inclusive, customer-focused culture centered on continuous improvement and community impact.