Job ID: 64469
Job Category: Information & Technology
Division & Section: Technology Services, Enterprise Services & Operations
Work Location: Metro Hall, 55 John St, Toronto, ON M5V 0C4
Job Type & Duration: Full-time, Permanent Vacancy
Salary Range: $126,000.00 - 176,140.00
Hiring Zone: $139,659.00 - $151,419.00
Shift Information: Monday to Friday, 35 hours per week
Affiliation: Non-Union
Number of Positions Open: 1
Posting Period: 01-Jun-2026 to 15-Jun-2026
As Senior Enterprise Solutions Technical Lead, Microsoft 365, you will report to the Portfolio Manager - Strategic Enablement and will be part of a Technology team providing both oversight, as well as leading implementation of multiple strategic initiatives including Collaboration and Microsoft 365. With a focus on the Customer, you will be a driving force within the Programs.
This key role will focus on strategy, planning, solutioning, rollout, and evolution of the Microsoft 365 platform tools and services, with a forward-looking approach to meet evolving business needs throughout the city.
As Technical Lead, you will be hands-on, engaging in solution analysis, formulation, coordination as well as advising managers and teams on programs and services at both strategic and operational levels. You will provide innovative, resourceful solutions, identifying approaches, concepts, and methods of analyzing complex and sometimes competing priorities. Management will count on your support in assessing and devising solutions from a pragmatic and objective perspective.
Having previously delivered transformational Microsoft 365 projects from start to end, you're well equipped to work with managers to shape and define projects through the development of time artifacts, including the preparation of planning materials, work plans, reports, briefing notes, and presentations. You're equally prepared to conduct research and analysis, bringing conclusions forward to the client/stakeholders for strategic discussion, or to contribute to the development and implementation of technology solutions.
You will provide hands-on expertise in the areas of:Microsoft 365 SaaS Solution Implementation:- Support and build the Microsoft 365 roadmap within City of Toronto.
- Lead the design, implementation, rollout, and optimization of Microsoft 365 Toolset and solutions, with an initial focus on tools such as Intune and Purview.
- Collaborate with business stakeholders to understand their needs and requirements for enterprise solutions, translating them into technical designs and architecture.
- Drive the evaluation, selection, and integration of tools and services to support business processes and workflows effectively.
- Drive the adoption and utilization of M365 tools across the organization through user training, change management initiatives, and ongoing support.
- Provide technical leadership and guidance to project teams throughout the implementation lifecycle, including solution design, configuration, testing, deployment, and support.
- Develop comprehensive solution architectures and design documents for solutions, ensuring alignment with best practices and organizational standards.
- Collaborate with cross-functional teams, to ensure alignment of enterprise solutions with overall business objectives and strategies.
- Leverage knowledge of business systems technologies to provide leadership in the identification and evaluation of technology options for business areas.
- Analyze and troubleshoot complex issues within applications, providing recommendations for long-term improvements.
- Evaluate business and technical design alternatives.
- Propose cost-effective solutions that improve program/service delivery.
- Develop feedback loop cycles and collaborate with users and stakeholders to understand requirements and objectives, translating them into comprehensive technical solutions and architectures.
- Establish use cases and traceability matrices based on interviews and requirements.
- Build metrics and reporting in support of CMO and FMO KPIs.
- Act as a subject matter expert on M365 technologies, providing guidance and support to stakeholders, Technology teams, and end-users on technical issues, best practices, and troubleshooting.
- Act as the bridge between Technology, Users, and Stakeholders, leading meetings and workshops as required to ensure technology solutions are meeting requirements.
- Lead discussions with other Technology teams and delivery partners.
- Deliver presentations to development teams and client audiences as required.
- Convey recommendations in clear non-technical terms.
- Create project reports, presentations, business cases, and systems documentation as required.
- Develop and maintain technical documentation, standards, and best practices for Microsoft solutions, including architectural diagrams, configuration guides, and troubleshooting procedures.
- Provide input into RFC/RFI/RFP and negotiation of contracts.
- Develop and maintain documentation for configurations, processes, and procedures to support knowledge sharing and training initiatives.
- Quick to gain knowledge in new areas and become a productive contributor.
Partnership, Vendor & Relationship Management:- Develop ongoing positive working relationships within Technology Services, as well as with client and partner Divisions. Foster collaboration and service excellence in cross-functional teams, and act as a trusted advisor to senior leadership across the organization.
- Build collaborative relationships with City stakeholders and senior management and assists them in recognizing where Technology Services can add value to, transform or support program operations.
- Foster and manage external partner relationships and manage large, complex contracts to deliver transformation programs and value for the City investments.
Culture and Team Leadership:- Cultivate a sense of unity where each member understands their purpose and impact with focus on excellent customer service and experience.
- Build high performance and resiliency through trust, transparency, and respect.
- Encourage creativity and innovation by welcoming diverse perspectives, promoting healthy debate, and questioning the status quo.
- Respect others' ideas and create a sense of independence and ownership.
Key Qualifications:- Extensive experience in enterprise solutions architecture, technical leadership, and implementation, with a customer-first approach.
- Extensive experience with implementation of Microsoft 365 including design, configuration, deployment, and optimization.
- Experience in Agile delivery, with successful large-scale rollouts of Microsoft365 SaaS solutions, including data ingestion, integration, role-based permissions, security, and change management.
- Certifications such as Microsoft Certified Microsoft Certified: Administrator, Security, Compliance, and Identity Fundamentals, or ITIL Foundation are an asset.
- Strong understanding of SaaS and specifically Microsoft 365.
- Strong understanding of enterprise IT delivery and cybersecurity principles.
- Keen focus on Customer Experience and Useability in all solutions.
- Strong change management skills, including the ability to create concise & clear user guides, iterated on based on feedback loop.
