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About the Role

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.

Responsibilities

Take end-to-end accountability for translating a five-year technology heatmap and remediation roadmap into an executable portfolio of projects.
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.

Requirements

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.
Successful applicant must commit to an on-site in-office work arrangement up to 5 days a week.
Prospective candidates must undergo a criminal records name check.

Skills

Technology modernization
Technology remediation
Applications
Infrastructure
Data
Cybersecurity
Systems integration
Project governance
Risk management
Issue management
Financial management
Resource planning
Dependency management
Executive reporting
Vendor management
Procurement
Contract negotiation
Service-level agreement negotiation
PMI practices

Location

On-site

Work Type

On-site
Temporary

Experience Level

Senior
7-10+ years project/program management
3-5+ years vendor management

Education Level

University degree in Business, Finance, Computer Science or related discipline, or equivalent relevant experience
PMP certification
PgMP certification
Master's degree
Technical credentials

Salary/Compensations

$132,000.00 - $165,000.00

Benefits

Competitive salary
May be eligible to participate in our health and dental plan

About the Company

The Workplace Safety and Insurance Board (WSIB) helps Ontarians when a workplace injury or illness occurs by providing wage-loss benefits, medical coverage and support to help people get back to work.
Funded by businesses, WSIB provides no-fault collective liability insurance and access to industry-specific health and safety information.
WSIB is one of the largest insurance organizations in North America covering over five million people in more than 300,000 workplaces across Ontario.
At WSIB, employees have the opportunity to explore career paths, continuously learn and grow professionally, be recognized for great work, and participate in programs that support health and wellbeing.
Technology supports an important public purpose: helping Ontarians when a workplace injury or illness occurs.
As a public sector organization, WSIB offers the opportunity to work on complex, meaningful initiatives where strong technology delivery contributes to the resilience of an organization that serves people across Ontario.

Equal Opportunity

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 talentacquisitioncentre@wsib.on.ca.
If you are invited to participate in the interview or assessment process, you can advise our Recruiter of your accommodation needs at that time.
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.
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.