ABOUT OSBIE

The Ontario School Boards’ Insurance Exchange (OSBIE) is a non-profit insurance company providing commercial lines of insurance to the school boards of Ontario. We classify ourselves as a boutique insurance company with a highly qualified and close group of employees. At OSBIE we foster a customer-focused culture and have great people working here, helping us ensure we provide excellent service to our subscribers. Our people are our greatest asset and at OSBIE we aim to balance work and play by providing our employees with hybrid work arrangements and a variety of social settings and events that promote a collaborative and connected work environment.

Position Summary

We are seeking an experienced IT & Business Project Manager to lead the successful delivery of strategic initiatives across both technology and business domains. As part of our growing IT Team, you will oversee complex, cross-functional projects that support operational efficiency, regulatory compliance, digital transformation, and customer value. This role bridges the gap between IT and business units, requiring strong industry insight in Information Technology, insurance, disciplined project execution, and effective stakeholder alignment.

Key Responsibilities

Project Leadership

Lead end-to-end planning and execution of medium to large-scale IT and business projects (e.g., system implementations, product rollouts, compliance programs).
Collaborate with stakeholders from Insurance Operations, Underwriting, Claims, IT, Security, Finance, and external vendors to define project scope, timelines, and deliverables.
Develop and manage detailed project plans, schedules, budgets, risk logs, and change controls.
Drive alignment between project goals and broader business strategy, ensuring measurable outcomes and ROI.

PMO Standards & Governance

Apply and enhance PMO frameworks, methodologies, and documentation standards to ensure consistency in delivery.
Support intake, prioritization, and portfolio reporting processes to facilitate executive decision-making.
Monitor and report on project health, resource capacity, and benefits realization through dashboards and KPIs.

Stakeholder Engagement & Communication

Act as the primary point of contact for project stakeholders, sponsors, and leadership.
Facilitate workshops, steering committees, and project updates to promote visibility, alignment, and risk mitigation.
Translate technical language into business terms and ensure transparency throughout the project lifecycle.

Team Collaboration & Coaching

Provide day-to-day leadership to project teams, including business analysts, developers, subject matter experts, and external consultants.
Coach team members on project management best practices and support continuous improvement.
Champion a culture of accountability, agility, and collaboration across departments.

Regulatory & Compliance Oversight

Ensure all project activities comply with insurance regulations, data privacy laws, cybersecurity controls, and internal audit standards.
Partner with Governance, Risk, and Compliance (GRC) teams to integrate controls into project lifecycles as needed.

Qualifications

Bachelor’s degree in business, Information Technology, or a related discipline.
PMP, PRINCE2, or Agile certification strongly preferred.
3-5 years’ project management experience, with at least 2 years in the IT, insurance, or financial services industry.
Proven track record in managing cross-functional projects that span IT systems and business operations (e.g., claims, underwriting, process transformation, third-party integrations).
Strong grasp of project delivery methodologies including Agile, Waterfall, and Hybrid approaches.
Proficient with tools such as MS Project, Jira, Smartsheet, Confluence, or similar platforms.
Exceptional communication, facilitation, and negotiation skills with the ability to influence both technical and non-technical stakeholders.

Preferred Attributes

Experience with insurance core systems (e.g., policy administration, claims, CRM, broker portals).
Familiarity with enterprise change management and organizational readiness planning.
Ability to drive alignment and collaboration across departments, vendors, and leadership.

To be considered for this position, please include a cover letter and current résumé with your application. Only those selected for an interview will be contacted.

OSBIE is committed to providing a barrier-free application and interview process for all candidates. Should you require accommodations due to a disability or medical condition at any point throughout the hiring process, please notify us and we will do our very best to meet your needs.

Job Type: Fixed term contract
Contract length: 12 months

Pay: $90,000.00-$120,000.00 per year

Work Location: Hybrid remote in Guelph, ON

Ontario School Boards' Insurance Exchange

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IT and Business Project Manager