Technology Jobs in Kitchener, ON

Senior Program Manager – Insurance Transformation

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.

What is in it for you:

• Salaried: $49-54 per hour.
• Incorporated Business Rate: $57-63 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.
• Hybrid work, with 3 days per week in the office.

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.

What you will need to succeed:

Required qualifications

• 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.

Required soft skills

• 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.

Preferred qualifications

• 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.

Why Recruit Action?

Recruit Action (agency permit: AP-2504511) provides recruitment services through quality support and a personalized approach. As part of the screening process, some applications may be reviewed using artificial intelligence tools. Only candidates who meet the hiring criteria will be contacted.