Job ID: 67960 Job Category: Information & Technology Division & Section: Toronto Cyber Security, Cyber Operations Work Location: Metro Hall, 55 John St., Toronto, ON M5V 0C4 Job Type & Duration: Full-time, Permanent Vacancy Salary Range: $105,241.00 - $160,649.00 Shift Information: Monday to Friday, 35 hours per week Affiliation: Non-Union Number of Positions Open: 1 Posting Period: 30-Oct-2026 to 13-Nov-2026 The Specialist, Cyber Diplomacy & Governance provides senior-level technical and business advice, support, and services to City divisions, agencies, and corporations on cyber security projects, programs, and initiatives. The role supports the execution of the Chief Information Security Officer’s (CISO) mandate, vision, and strategy by building strong relationships with internal partners, suppliers, and stakeholders and helping ensure that cyber security services align with organizational priorities and compliance obligations. The Specialist works collaboratively with Purchasing and Materials Management Division (PMMD) and other relevant stakeholders on procurement activities related to cybersecurity programs, services, and technology solutions in accordance with the City’s procurement policies, procedures and bylaws. The Specialist develops and implements detailed cyber security plans and recommends policies and procedures tailored to specific program requirements. The successful candidate leads complex initiatives aligned with organizational goals, fosters cross-functional collaboration, and integrates change management throughout the project lifecycle. The role assesses cyber security needs in relation to business strategies, recommends appropriate solutions, supports the deployment of cyber programs and initiatives, and conducts research to inform strategic decisions in alignment with industry developments, corporate policies, and legislative requirements. A key responsibility of the role is supporting the Manager in the administration and oversight of cyber security vendor agreements, ensuring compliance with contractual obligations, service standards, and performance requirements. The Specialist maintains vendor performance records, risk assessments, and operational issue logs; develops and supports procurement solicitations and contract documentation, including Statements of Work, MOUs, and SLAs; and provides cybersecurity technical and business requirements for incorporation into technical specifications, security controls, and related deliverables for inclusion in procurement documents in collaboration with PMMD and procurement leads. The role provides subject matter expertise in the review, negotiation, drafting, and management of contracts related to managed services, cloud solutions, software licensing, and hardware procurement, while coordinating with Procurement, Legal, vendors, and internal stakeholders to ensure contracts are properly reviewed, approved, and implemented. The role establishes and monitors governance structures, deliverables, budgets, and cross-project activities to support effective program delivery. The Specialist develops metrics to track milestones, risks, financial performance, and service outcomes; establishes and monitors SLAs and contractual performance objectives; and participates in performance reviews with service leaders and subject matter experts. The Specialist also acts as the primary representative on financial management matters, planning and coordinating activities that support fiscal accountability. The Specialist develops internal communication strategies that address stakeholder needs and external strategies that showcase achievements and outcomes. The role prepares and presents reports, briefing notes, and presentations; communicates findings, recommendations, options, and implications; and handles confidential information that may influence staffing, resource allocation, and cyber infrastructure. The Specialist also supports the integration of strategic initiatives across the organization. The Specialist maintains accurate cyber risk metrics and reports and stays current with emerging threats, technologies, and industry trends. Working closely with senior management, the role helps address internal and external cyber threats, participates in strategic meetings, and takes timely action when required. The successful candidate also recommends improvements to cyber solutions, business processes, policies, and resource models to strengthen organizational resilience. The Specialist leads assigned projects from initiation through completion, coordinating teams, stakeholders, and resources to deliver high-quality results while promoting collaboration, strong performance, and continuous learning. The Specialist oversees the day-to-day work of project staff and contract resources, including assigning and reviewing work, scheduling, coaching, training, and supporting performance and employee-relations matters. The role identifies emerging needs and organizational impacts, recommends and coordinates solutions to complex or sensitive issues using sound judgment, negotiation, and conflict-resolution skills, and provides technical expertise on cybersecurity risks, security requirements, controls, and technology solutions, including identifying cybersecurity requirements and deliverables to support procurement initiatives in accordance with established PMMD processes and governance. In addition, the Specialist leads the development and delivery of the organization's cybersecurity awareness and training strategy to strengthen workforce knowledge and risk awareness. The Specialist will create and develop content, toolkits, and awareness materials that support the successful implementation and adoption of transformative divisional initiatives. Ensures resources are practical, engaging, and aligned with organizational objectives to enhance stakeholder understanding and program outcomes. What you bring to the role Post-secondary degree in financial management, business administration, or a related discipline, or an equivalent combination of education, training, and experience. Considerable experience in vendor/contract management, compliance monitoring, or related functions within a large, complex organization; public sector experience preferred. Experience providing cybersecurity or IT subject matter expertise to the procurement, negotiation, and management of complex technology contracts in a public sector or municipal environment. Experience supporting operating and capital budgets, including budget tracking, expenditure monitoring, and financial reporting. Experience assessing cybersecurity risks and requirements in complex business and technology environments, including defining security controls, recommending mitigation measures, and translating technical requirements into business and operational solutions. Experience in SAP Ariba platform, or S4 HANA is considered an asset. Ability to lead internal and external resources and work effectively both independently and collaboratively within multidisciplinary teams. Ability to prepare clear, concise, and professional reports, dashboards, presentations, and other materials for a variety of audiences. In-depth knowledge of cybersecurity controls, risks, emerging threats, technologies, and industry best practices; professional certifications in cybersecurity, project management, or vendor management are considered an asset. Excellent written and verbal communication skills, with the ability to communicate effectively with leadership, stakeholders, business partners, divisional teams, and vendors, and to identify communication gaps and develop content strategies aligned with business objectives. Strong creative, critical, analytical, and strategic thinking skills, with the ability to solve complex problems, exercise sound judgment, identify practical solutions, and respond effectively to cyber-related incidents. Ability to influence and build effective relationships with key stakeholders to achieve business objectives, while managing competing priorities, projects, and initiatives in a fast-paced environment. Highly organized, proactive, and self-motivated, with the ability to take initiative, work independently, manage pressure, maintain professionalism. Please Note: As a condition of employment, the successful candidate will be required to undergo and maintain a satisfactory police record check, background screening, psychological assessment, and any other security clearances deemed necessary. This requirement reflects the highly sensitive and confidential nature of the information managed by the Toronto Cyber Security Division. A normal work week is 35 hours, however, unforeseen situation may require extended hours of work with little or no prior notice. In case of a cyber incident or breach, rotation shift, continuous extended hours may be required with little or no prior notice. Equity, Diversity and Inclusion The City is an equal opportunity employer, dedicated to creating a workplace culture of inclusiveness that reflects the diverse residents that we serve. Learn more about the City’s commitment to employment equity . Accommodation The City of Toronto is committed to creating an accessible and inclusive organization. We are committed to providing barrier-free and accessible employment practices in compliance with the Accessibility for Ontarians with Disabilities Act (AODA). Should you require Code-protected accommodation through any stage of the recruitment process, please make them known when contacted and we will work with you to meet your needs. Disability-related accommodation during the application process is available upon request . Learn more about the City’s Hiring Policies and Accommodation Process .