Job Description Insight Global is seeking a Senior Project Manager to join a growing insurance organization in the Waterloo region. Reporting into the VP of Digital Modernization, this individual will lead strategic digital transformation initiatives that sit at the intersection of business and technology.

This role is responsible for driving the delivery of complex, client-facing digital programs, including portal enhancements, system integrations, and modernization initiatives that impact multiple business units. The successful candidate will act as the bridge between business stakeholders and technical teams, ensuring strategic objectives are translated into executable plans and delivered successfully. The ideal candidate is a self-starter who can quickly ramp up in a new environment, navigate ambiguity, build credibility with stakeholders, and confidently lead cross-functional teams through change. This is a true Business PM role—the successful individual must understand both business drivers and technical delivery, while maintaining a focus on business outcomes and customer experience.

REQUIRED SKILLS AND EXPERIENCE -10+ years of Project Management experience leading complex business and technology transformation initiatives -Experience within the insurance, financial services, fintech, or broader financial industry -Proven experience delivering large-scale digital modernization projects, including customer/client portals, digital platforms, or enterprise applications -Experience working between business stakeholders and technical teams, translating business objectives into delivery plans -Strong understanding of both business processes and technology concepts, with the ability to communicate effectively to technical and non-technical audiences -Experience leading multi-functional project teams with cross-departmental dependencies -Ability to quickly assess environments, ramp up rapidly, and independently drive initiatives forward with minimal onboarding -Strong stakeholder management skills with experience influencing senior leaders and executive teams -Demonstrated success managing risks, dependencies, timelines, and project governance across multiple workstreams -Excellent communication, facilitation, and relationship-building skills -Self-starter mentality with a proactive, solutions-oriented approach to problem solving

Please Note We may use artificial intelligence tools to assist with the screening, assessment, or selection of potential applicants for this position.