Senior Enterprise Solutions Technical Lead

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

The City of Toronto is the fourth largest city in North America and the fourth largest government in Canada, with a highly diverse and multicultural population. In addition, the City of Toronto has several agencies and corporations including the Toronto Police Service, Toronto Public Library, and the Toronto Transit Commission, which make up the broader municipal organization.

Consistently ranked one of the world’s most livable cities, Toronto is home to more than 2.9 million people whose diversity and experiences make this great city Canada’s leading economic engine and one of the world’s most diverse and livable cities.

Toronto is a global leader in technology, finance, film, music, culture, and innovation, and consistently places at the top of international rankings due to investments championed by its government, residents, and businesses.

In its pursuit of modernizing City services through strategic investment, digital transformation, and a culture of innovation, the Technology Services Division collaborates with all City Divisions, agencies, boards, and corporations to deliver client centric business solutions and secure, reliable IT infrastructure. Embarking on a transformative journey, the Technology Services Division is reshaping its culture and service delivery approach, focusing on four key priorities:

Build Resilient Foundations: Establish a robust, reliable, and secure technology infrastructure.
Deliver User-Centric Solutions: Provide enterprise-grade modern solutions with a focus on user experience.
Harness Data Power: Utilize data to drive operational processes and informed decision-making Citywide.
Empower Stakeholders: Engage and empower stakeholders to foster a culture of agility and innovation.

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.

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.

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