A strategic IT leadership role for a seasoned director who brings disciplined planning, clear executive reporting and deliberate team development to a growing public-sector function.We're hiring aDirector of Information Technologyto join a small public-sector organization and lead its IT function. The organization is early in a multi-year digital strategy, and this role turns that strategy into detailed plans, keeps leadership informed on a regular cadence, and builds the team’s skills ahead of what the work will demand.The position is weighted toward strategy, stakeholder communication, and forecasting, with enough operational depth to guide a small team supporting a mix of on-premises and Microsoft cloud systems.Who You AreAn IT leader who operates at the strategic level, directing outcomes through plans, roadmaps, and documentation rather than hands-on configurationA forward-thinking planner who anticipates the organization’s technology and skills requirements six to twelve months aheadA proactive communicator who provides leadership with timely, structured updates on progress, risks and decisionsAn effective stakeholder manager who builds consensus and secures support for change across the organizationA committed people leader who invests in both the technical and professional development of their teamA discerning evaluator of new tools, including AI, who recommends adoption only where it serves the organizationWork TypeLocation:Sarnia, ON (Hybrid, 3 days per week)Vacancy Type:This role reflects an existing vacancyWhat You'll DoLead the expansion of the organization’s multi-year digital strategy into detailed IT roadmaps and initiatives,



in partnership with the CIODirect the planning, design, and communication of technology migrations and implementations, from approach and stakeholder engagement through deploymentProvide the leadership with regular reporting on progress, risks and forecastsBuild the team’s technical and professional capabilities, anticipating the competencies required six to twelve months aheadOversee IT operations across on-premises servers, Microsoft 365 cloud services and a TOPdesk-based service deskDirect the organization’s in-house cybersecurity program in collaboration with the team’s cybersecurity specialistManage IT budgets, technology lifecycle planning, and relationships with vendors and specialized service providersWhat We’re Looking For8+ yearsof progressive IT experience, including5+ yearsin leadership of technology teams and servicesPrior experience as a Director of IT or in an equivalent senior IT leadership positionDemonstrated success translating corporate strategy into multi-year IT roadmaps and directing technology migrations at the strategic and planning levelWorking knowledge of Microsoft 365 environments and hybrid on-premises and cloud infrastructureA solid foundation in cybersecurity principles, sufficient to direct an in-house security programProven experience managing IT budgets, vendor relationships,



and service-provider contractsExcellent written and verbal communication skills, with experience reporting to executive leadership and negotiating plans with stakeholdersEligibility to obtain a Secret security clearanceNice to haveAn active Secret security clearanceExperience supporting operational technology alongside corporate ITExperience rolling out Microsoft 365 Copilot or similar AI tools to staffWhat Makes This Role ExcitingStrategic Mandate:Report directly to the CIO and play a central role in determining how the organization’s multi-year digital strategy is prioritized and deliveredTeam Leadership:Lead a compact team that combines experienced and newer staff, with a clear mandate to develop their capabilitiesExpanding Scope:The data function may transition under IT as the strategy mDiverse Technology Setting:Oversee a technology estate encompassing Microsoft 365, on-premises infrastructure, and specialized operational systemsBase Salary:$130,000 - $155,000Paid Time Off:Competitive vacation and personal days to maintain a healthy work-life balanceHealth Benefits:Health and insurance benefits to support your overall well-beingRRSP Matching:Employer contributions to a group RRSP program, supporting your long-term financial securityWe're proud to support diversity and inclusion. Need accommodation during the hiring process? Just let us know - we're here to support you!AI Use Disclosure:STACK IT uses AI-enhanced tools to support initial candidate screening and interview note analysis. All assessments and hiring decisions remain human-led.#J-18808-Ljbffr

📌 Director Of Information Technology (Winnipeg)
🏢 Cressey Development Group
📍 Winnipeg