Senior Program Manager – Insurance Transformation

Recrute Action•Woolwich, ON

4d•CA$49 - CA$63•Hybrid

About The Position

Step into a pivotal role within a major insurance transformation initiative where complex business, operations, technology, and customer experience streams come together to drive meaningful change. This opportunity offers the chance to contribute to a high-visibility program, collaborate with senior stakeholders, and support the delivery of critical business capabilities from planning through launch.

Requirements

Bachelor’s degree in Business, Technology, Engineering, or a related field.
PMP certification or an equivalent project or program management certification.
9 years of project and/or program management experience.
Proven experience delivering complex, multi-workstream implementations involving external vendors.
Experience working within vendor-led delivery models and managing third-party accountability.
Experience leading cross-functional programs involving operations, technology, and customer or communication functions.
Proven experience delivering end-to-end program lifecycles from discovery through go-live and stabilization.
Strong expertise in end-to-end program delivery management across multi-workstream initiatives.
Strong vendor management experience.
Expertise in program governance, including risk management, issue management, dependency tracking, executive reporting, and escalation management.
Experience leading operational build and implementation initiatives in addition to technology delivery.
Strong execution focus with the ability to drive delivery outcomes.
Deep capability in risk management, issue resolution, and escalation management.
Strong vendor management and negotiation capability.
Ability to align strategy with execution across multiple delivery streams.
Strong leadership skills and the ability to drive execution in complex environments.
Excellent stakeholder management skills.
Excellent executive communication skills.
Strong problem-solving skills.
Ability to manage ambiguity and shifting priorities in a fast-paced environment.

Nice To Haves

Experience in insurance, claims, or financial services operations.
Experience supporting claims operations setup, transformation, or outsourcing models.
Exposure to assistance or case management operations.
Experience supporting go-live readiness, production launches, and operational stabilization.
Experience with customer communication channels, including telephony, digital, and chatbot solutions.
Consulting experience within a Big 4 environment or equivalent.
Experience in large-scale transformation programs.

Responsibilities

Lead and coordinate multiple concurrent workstreams, including technology, operations, communications, and vendor delivery activities.
Manage and track the integrated program delivery plan, milestones, dependencies, and outcomes.
Act as the primary day-to-day interface with the external vendor, ensuring accountability and performance.
Monitor vendor performance against agreed scope, deliverables, timelines, and milestones.
Translate contractual commitments into execution plans and measurable deliverables.
Facilitate execution governance, including status reporting, milestone tracking, risk and issue management, decision logs, and escalation management.
Drive cross-functional alignment across internal stakeholders and vendor teams.
Develop and manage an integrated delivery plan across all workstreams.
Track and manage cross-functional dependencies and sequencing.
Ensure transparency of delivery status, risks, issues, and mitigation plans.
Lead and coordinate activities related to discovery, requirements definition, customer and marketing communications, system configuration and development, claims operations design, assistance model implementation, production readiness, and go-live execution.
Oversee operational readiness activities, including claims process implementation, SOP development, documentation, job aids, training materials, readiness plans, and go-live planning.
Ensure alignment between system capabilities and operational processes.
Validate readiness across operations, vendor delivery, and customer experience prior to launch.
Prepare executive-level updates, dashboards, decision materials, and senior leadership reports.
Provide insights on delivery risks, dependencies, and readiness.
Support governance forums, decision-making processes, go/no-go frameworks, and readiness assessments.
Monitor program risks and proactively implement mitigation strategies.
Support production launch execution and operational stabilization activities.