Senior Transformation Project Manager (Claims & Operations)

Recrute Action • Woolwich, ON

3d • CA$50 - CA$62 • Hybrid

About The Position

Play a key role in a major transformation initiative within the insurance sector, overseeing the delivery of complex programs that connect operations, technology, customer communications, and vendor partnerships. This hybrid opportunity offers executive visibility, cross-functional collaboration, and the ability to influence outcomes from planning through go-live and operational readiness.

Requirements

• Bachelor’s degree in Business, Technology, Engineering, or a related field.
• PMP certification or equivalent project/program management certification.
• 9 years of project and/or program management experience.
• Proven experience delivering complex, multi-workstream programs involving external vendors.
• Experience managing end-to-end program delivery from discovery through go-live and stabilization.
• Experience working within vendor-led delivery models and managing third-party accountability.
• Demonstrated experience leading cross-functional initiatives involving operations, technology, and customer communication functions.
• Strong expertise in integrated program delivery management.
• Strong vendor management capabilities.
• Experience with program governance, including risk management, issue management, dependency tracking, escalation management, and executive reporting.
• Strong leadership skills with the ability to drive execution in complex environments.
• Excellent stakeholder management and executive communication skills.
• Strong problem-solving abilities and the capacity to manage ambiguity and evolving priorities.
• Ability to align strategy and execution across multiple delivery streams.

Nice To Haves

• Experience in insurance, claims, or financial services operations is preferred.
• Experience supporting claims operations setup, transformation, or outsourcing models is preferred.
• Exposure to assistance or case management operations is considered an asset.
• Experience with customer communication channels, including telephony, digital, and chatbot solutions, is considered an asset.
• Consulting experience within a Big Four firm or similar environment is considered an asset.
• Experience supporting go-live readiness, production launches, and operational stabilization is considered an asset.

Responsibilities

• Lead and coordinate multiple concurrent workstreams, including technology, operations, communications, vendor delivery, discovery and requirements definition, customer and marketing communications, system configuration and development, claims operations design and implementation, and production readiness activities.
• Manage and maintain an integrated program delivery plan, including milestones, dependencies, sequencing, and outcomes across all workstreams.
• Act as the primary day-to-day interface with the external vendor, ensuring accountability, strong partnership, and performance against agreed scope, deliverables, timelines, and milestones.
• Monitor vendor performance and proactively identify, manage, and escalate risks, delays, issues, and performance gaps.
• Translate contractual commitments into execution plans and measurable deliverables.
• Establish and maintain program governance, including risk, issue, decision, and dependency tracking, with clear ownership and escalation paths.
• Facilitate structured execution governance through status reporting, milestone tracking, and weekly delivery cadences.
• Drive alignment and collaboration across internal stakeholders and vendor teams.
• Oversee operational readiness activities, including claims handling processes, standard operating procedures, documentation, job aids, training materials, readiness plans, and go-live preparation.
• Ensure alignment between system capabilities and operational processes.
• Validate readiness across operations, vendor delivery, and customer experience functions before launch.
• Prepare executive-level updates, dashboards, governance materials, readiness assessments, and decision-support documentation.
• Provide visibility into delivery status, risks, dependencies, mitigation plans, and readiness indicators.
• Support governance forums, decision-making processes, and go/no-go assessments.
• Lead production launch execution and support operational stabilization activities following implementation.

Benefits

• Salaried: $50-54 per hour.
• Incorporated Business Rate: $58-62 per hour.
• 9-month contract with the potential for permanent employment.
• Full-time position: 37.50 hours per week.
• Weekday schedule from 9 am to 5 pm.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior