Project Manager

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

1. 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.

2. 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

3. 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

4. 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

5. 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.