IT Project Director (12 month temporary)

Workplace Safety and Insurance Board (WSIB); Canada; On-site; CAD 132,000 - 165,000; Full time

Benefits offered by this job

Health plan

Dental plan

Job summary

Workplace Safety and Insurance Board (WSIB) in Ontario is seeking an IT Project Director to lead a significant portfolio of technology modernization and remediation work. This role focuses on coordinating multiple complex projects, securing governance, and delivering shared outcomes across IT teams and stakeholders.

The position requires 7–10+ years of senior PM experience, a strong track record in multi-year transformations, and experience with sizable budgets.

Qualifications

• 7-10+ years of progressively senior project/program management experience leading complex technology initiatives.
• Experience managing multiple concurrent IT projects or interdependent workstreams (Program Manager, Project Director, or Senior IT Project Manager).
• Experience delivering technology transformation, modernization, remediation or technology risk initiatives.
• Experience managing significant project budgets, ideally $5M+, with portfolios or programs exceeding $10M as an asset.
• Strong governance, risk and executive reporting capabilities, and vendor/contract management.

Responsibilities

• Lead a portfolio of multiple concurrent IT projects across applications, infrastructure, data, cybersecurity and systems integration.
• Translate multi-year modernization priorities into sequenced, achievable delivery plans.
• Develop and manage multi-year, multi-phase implementation plans across workstreams.
• Ensure governance and reporting to senior leaders and IT governance forums.
• Manage major budgets, forecasts, change requests and financial reporting; coordinate resources.

Skills

Program management

IT project leadership

Budget management

Vendor management

Governance & risk

Stakeholder influence

Education

University degree

PM certification (PMP/PgMP) and related credentials

Job description

Job Description

About the Workplace Safety and Insurance Board (WSIB)

We’re here to help. When an injury or illness happens on the job, we move quickly to provide wage-loss benefits, medical coverage and support to help people get back to work. Funded by businesses, we also provide no-fault collective liability insurance and access to industry-specific health and safety information. We are one of the largest insurance organizations in North America covering over five million people in more than 300,000 workplaces across Ontario. For more information, visit wsib.ca.

At The WSIB, You’ll Have The Opportunity To

• explore many career paths and follow your passion
• continuously learn and grow professionally
• be recognized for the great work you do
• participate in programs that support your health and wellbeing

You’ll also receive a competitive salary and may be eligible to participate in our health and dental plan.

Salary Grade: N10 From: $132,000.00 To: $165,000.00

IT Project Director (12 month temporary)

Make an impact through technology modernization

At WSIB, technology supports an important public purpose: helping Ontarians when a workplace injury or illness occurs. As a public sector organization, we offer the opportunity to work on complex, meaningful initiatives where strong technology delivery contributes to the resilience of an organization that serves people across Ontario. We are looking for an experienced IT Project Director to lead a significant portfolio of technology modernization and remediation work. This multi-year program is focused on addressing technology debt and risk while modernizing and strengthening the resilience, security and sustainability of WSIB's technology environment. This is an individual contributor role focused on program and project leadership rather than direct people management. We’re looking for someone who has operated at a senior level leading multiple complex technology projects, managing dependencies, and bringing together technical teams and stakeholders to deliver shared outcomes.

What You'll Be Responsible For

Reporting to the Senior Director, IT Portfolio & Project Management, you will take end-to-end accountability for translating a five-year technology heatmap and remediation roadmap into an executable portfolio of projects.

You Will

• Lead a portfolio of multiple concurrent, highly technical IT projects across areas such as applications, infrastructure, data, cybersecurity and systems integration.
• Translate longer-term technology modernization and remediation priorities into sequenced, achievable delivery plans.
• Develop and integrate multi‑year, multi‑phase implementation plans across multiple project workstreams.
• Manage dependencies, risks, issues, constraints and competing priorities across interconnected technology initiatives.
• Provide strong project and program governance, including reporting, escalation and communication to senior leadership and IT governance forums.
• Manage significant project budgets, financial forecasts, change requests and project financial reporting.
• Develop resource plans and coordinate project resources across technical teams, addressing resource conflicts and delivery constraints.
• Partner closely with Architecture, Application Delivery, Infrastructure, Security, IT Finance and other technology teams.
• Build strong relationships with senior IT leaders and bring together stakeholders with different priorities to drive decisions and maintain momentum.
• Manage third‑party vendors and procurement requirements, including supporting contract and service‑level agreement negotiations and holding vendors accountable for delivery.
• Lead through influence, providing direction and coordination to multidisciplinary project teams without having direct people‑management responsibility.
• Champion WSIB project management methodologies and recognized PMI practices.

What You'll Bring

Strong IT and technology project delivery experience is essential. You will be leading complex technical initiatives and need enough depth and experience to effectively work with, challenge and coordinate specialized technology teams and leaders.

We Are Looking For Someone With

• 7-10+ years of progressively senior project/program management experience, with substantial experience leading complex technology initiatives.
• Demonstrated experience managing multiple concurrent IT projects or interconnected project workstreams, ideally as a Program Manager, Project Director, or highly experienced Senior IT Project Manager level.
• Strong experience delivering technical projects involving several areas such as applications, infrastructure, data, cybersecurity and systems integration.
• Experience leading large, multi-year technology transformation, modernization, remediation or technology risk initiatives.
• Experience managing significant project budgets, ideally $5M+, with experience managing portfolios or programs exceeding $10M considered an asset.
• A strong technology foundation is a significant asset, whether gained through project/program management or broader hands‑on experience within IT. Familiarity with domains such as applications, IT infrastructure, data, cybersecurity, systems integration and architecture will help you effectively lead complex technical initiatives and collaborate with specialized technology teams.
• 3-5+ years of experience working with third-party technology vendors and partners.
• Strong understanding of project governance, risk and issue management, financial management, resource planning, dependency management and executive reporting.
• Demonstrated ability to influence senior leaders, bring alignment across technical teams and resolve complex delivery challenges.
• A university degree in Business, Finance, Computer Science or a related discipline, or equivalent relevant experience.
• Project management certification such as PMP. PgMP, a master's degree and/or additional technical credentials are considered assets.

The Kind Of Experience That Will Help You Succeed

You may have built your experience as an IT Project Director, IT Program Manager, Senior IT Project Manager, Technology Transformation Lead, or through another technology delivery role with similar scope and complexity. More important than your current title is the experience you bring: successfully leading multiple complex technical initiatives, navigating interdependencies, working across specialized IT teams, managing significant budgets and partnering with senior stakeholders to deliver against a broader technology roadmap.

Our commitment to equity, diversity and inclusion

We respect and value the diversity of our people. We strive to create an environment where employees can be themselves and where our differences are celebrated. We value and celebrate diversity and are committed to creating inclusive experiences for both our employees and prospective employees. We invite all interested individuals to apply. If you require accommodations in order to apply to this position please contact [e-mail] . If you are invited to participate in the interview or assessment process, you can advise our Recruiter of your accommodation needs at that time. Please visit our EDI Vision to learn more about what actions WSIB are taking to advance our commitment to equity, diversity and inclusion and to support all employees participating and contributing to their full potential

Disclosing conflicts of interest

As public servants, employees at the WSIB have a responsibility to act in an ethical way at all times to create a respectful workplace and maintain public trust. Job applicants are required to disclose any circumstance that could result in a real, potential or perceived conflict of interest. A conflict of interest is any situation where your private interests may impair or be perceived to impair the decisions you make in your official capacity. This may include: political activity, directorship, other outside employment and certain personal relationships (e.g. with current WSIB employees, customers and/or stakeholders). If you have any questions about conflict of interest obligations and/or how to make a disclosure, please contact the Talent Acquisition Centre at [e-mail] .

Privacy information

We collect personal information from your resume, application, cover letter and references under the authority of the Workplace Safety and Insurance Act, 1997. The Talent Acquisition Centre and WSIB hiring parties will used this information to assess/validate your qualifications, determine if you meet the requirements of vacant positions and/or gather information relevant for recruitment purposes. If you have questions or concerns regarding the collection and use of your personal information, please contact the WSIB’s Privacy Office at [e-mail] . The Privacy Office cannot provide information about the status of your application. As a precondition of employment, the WSIB requires that prospective candidates undergo a criminal records name check any time before or after they are hired.