Job Description
Insight Global is seeking an experienced Senior IT Project Manager on a 6-month contract (with high possibility of extension) to support two high-impact solution investigation initiatives for a leading Canadian insurance organization. The selected candidate will oversee parallel projects replacing legacy commercial audit and risk engineering tools, drive solution analysis, and proof of concept for the project. This role includes managing Agile delivery processes, coordinating with teams, building project schedules within diverse teams, and maintaining reporting across financial and operational metrics. The Project Manager will initiate and maintain sponsor and PO connections, facilitate daily standups and biweekly portfolio reviews, and lead communication across stakeholder groups. As both projects progress through scoping and feasibility assessment, the PM will guide vendor selection, requirement gathering, and capability comparison. The most important aspect of the position is schedule creation and management for the two projects, where the successful candidate will have a strong background managing end-to-end or proof of concept projects. The ideal candidate will be located in Calgary or Toronto, with the requirement of being in office two days per week.
Required Skills & Experience
• 7+ years of experience as a Project Manager in IT environments
• Proven track record managing multiple concurrent projects from initiation through delivery
• Proficiency in JIRA, Confluence, and SharePoint for task and document management
• Solid experience in project scheduling using MS Project or Excel
• Strong command of financial reporting and tracking, including rate logs and budget reviews
• Exceptional stakeholder communication skills, with the ability to bridge technical and business conversations Experience delivering presentations to senior-level stakeholders
Nice to Have Skills & Experience
• 5+ years’ expertise in Agile delivery frameworks, including backlog grooming, standups, and sprint reporting
• Familiarity with the insurance industry, particularly commercial lines
• Experience evaluating enterprise tools for RFP/RFI or proof-of-concept initiatives Comfort working with cross-functional teams and managing vendor engagement
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