Job Title: Senior Project Manager
Location: Waterloo, ON (3 days onsite)
Duration: 06 months
Description:
We are seeking a Senior Project Manager to lead the delivery of a complex, multi-workstream claims and operations implementation in partnership with an external vendor. This role will be responsible for the end-to-end orchestration of a multi-track program, ensuring successful execution from initial discovery through to go-live and production readiness.
The successful candidate will operate within a vendor-led delivery model, providing strong execution leadership, structured governance, and clear, executive-level reporting. This is a hands-on delivery role requiring a strong operator who can drive outcomes across multiple concurrent workstreams, manage interdependencies, and ensure alignment between technology, operations, and customer experience objectives.
Key Deliverables
- End-to-End Program Delivery
Lead and coordinate multiple concurrent workstreams to ensure integrated and timely delivery, including:
Discovery and requirements definition
Customer and marketing communications
System configuration and development
Claims operations and assistance model design and implementation
Production readiness and go-live execution
Ensure all workstreams are aligned to a single integrated delivery plan, with clear milestones, dependencies, and outcomes.
- Vendor Management & Accountability
Act as the primary day-to-day interface, ensuring strong partnership and accountability
Monitor vendor performance against agreed scope, deliverables, timelines, and milestones
Proactively identify and escalate risks, delays, or performance gaps
Translate contractual commitments (SOW) into clear execution plans and measurable deliverables
Ensure effective coordination between vendor teams and internal stakeholders
- Execution Governance
Establish and maintain strong program governance to support disciplined execution:
Develop and manage an integrated delivery plan across all workstreams
Track and manage cross-functional dependencies and sequencing
Maintain risk, issue, and decision logs, with clear ownership and escalation paths
Drive a structured weekly execution cadence, including status reporting and milestone tracking
Ensure transparency of delivery status, risks, and mitigation plans across stakeholders
- Operational Readiness
Ensure the organization is fully prepared for go-live and ongoing operations:
Oversee development and implementation of claims handling processes
Support creation of standard operating procedures (SOPs), documentation, and job aids
Coordinate development of training materials and readiness plans
Ensure alignment between system capabilities and operational processes
Validate readiness across operations, vendor delivery, and customer experience prior to launch
- Executive Reporting & Stakeholder Management
Prepare clear, concise updates for senior leadership (COO/GM level)
Provide forward-looking insights on delivery risks, dependencies, and readiness
Support governance forums and decision-making processes
Develop and maintain go/no-go frameworks and readiness assessments
Ensure cross-functional alignment across operations, technology, and business stakeholders
Required Experience
- 9 years of project and/or program management experience
- Proven track record delivering complex, multi-workstream implementations involving external vendors
- Experience operating within vendor-led delivery models, including managing third-party accountability
- Demonstrated ability to lead cross-functional programs involving:
- Operations
- Technology
- Customer and communication functions
- Proven delivery of end-to-end program lifecycle, from discovery through to go-live and stabilization
- Industry experience in insurance, claims, or financial services operations is strongly preferred.
Key Capabilities
- Strong execution focus, with ability to drive delivery outcomes (not purely PMO or reporting-focused)
- Experience leading operational build and implementation, in addition to technology delivery
- Deep capability in risk management, issue resolution, and escalation management
- Ability to manage complexity, ambiguity, and evolving priorities in a fast-paced environment
- Strong vendor management and negotiation capability
- Excellent communication and stakeholder management skills, including executive-level reporting
- Ability to connect strategy to execution and ensure alignment across multiple delivery streams
Background
- Experience supporting claims operations setup, transformation, or outsourcing models
- Exposure to assistance / case management operations
- Experience with customer communication channels, including telephony, digital, and chatbot solutions
- Background in consulting (e.g., Big 4 or equivalent) is considered an asset
- Experience supporting go-live readiness, production launches, and operational stabilization
Dexian stands at the forefront of Talent + Technology solutions with a presence spanning more than 70 locations worldwide and a team exceeding 10,000 professionals. As one of the largest technology and professional staffing companies and one of the largest minority-owned staffing companies in the United States, Dexian combines over 30 years of industry expertise with cutting-edge technologies to deliver comprehensive global services and support.
Dexian connects the right talent and the right technology with the right organizations to deliver trajectory-changing results that help everyone achieve their ambitions and goals. To learn more, please visit https://dexian.com/.
Dexian is an Equal Opportunity Employer that recruits and hires qualified candidates without regard to race, religion, sex, sexual orientation, gender identity, age, national origin, ancestry, citizenship, disability, or veteran status.
