Project Manager/Leader – Senior
Pay Rate: Flexible
Location: Toronto, Ontario
Contract Length: 6 Months, Hybrid
We at Raise are hiring right now for one of our Clients. If you’re interested, apply below for your chance to join a great place to work.
Responsibilities:
· Post‑secondary education in IT, Computer Science, Engineering, Business Management, or related field, or equivalent relevant experience.
· Strong communication skills to translate technical topics (security, privacy, identity, governance) into delivery decisions and user-facing guidance.
· Demonstrated judgement and accountability in a public‑sector or similar environment.
· Knowledge and understanding of Project Management’s Institute’s Project Management Body of Knowledge.
· Knowledge and understanding of Information Management principles, concepts, policies and practices.
· Knowledge and understanding of Accessibility for Ontarians with Disability Act (AODA) and related regulations and standards.
Experience
· 5+ years delivering complex technology rollouts or digital enablement initiatives in large organizations.
· Experience delivering M365 or enterprise SaaS rollouts involving technical implementation, licensing, onboarding, training, comms, and adoption measurement.
· Experience coordinating delivery gates across security/privacy/compliance stakeholders (e.g., assessments/risk treatment approach).
· Experience with Power Platform / Copilot Studio delivery is a strong asset (agents, environments, governance).
· Ability to handle client relationships to manage expectations, provides updates as required, identifies potential conflicts between project and functional areas.
Technical Capabilities
· Working knowledge of how M365 Copilot uses Microsoft Graph and operates within user permissions and compliance boundaries (sensitivity labels, security trimming
· Familiarity with M365 rollout prerequisites and operational dependencies (identity, access patterns, end-user readiness steps documented for pilots).
· Ability to coordinate Copilot Studio governance controls, including Power Platform admin center data policies/DLP and security/governance concepts for agents.
· Demonstrated experience working with cloud security and compliance controls in an enterprise environment, including coordination with security and risk teams on topics such as identity and access management, data protection, compliance requirements, risk assessments, and implementation of required security controls for cloud‑based services (e.g., Purview).
· Comfortable working with network/security teams on technical constraints, configuration dependencies, and risk mitigations reflected in Copilot risk documentation.
· (Preferred) Ability to build basic Copilot Studio agents (prototype level) to validate patterns and accelerate delivery.
M365 Copilot + Microsoft Chat rollout delivery
· Support the delivery of the Copilot pilot/rollout workplan including licensing activation, onboarding, communications, training coordination, and support pathways.
· Lead technical prerequisites and readiness steps for enterprise roll-out and user access.
· Manage delivery of the approved use case approach and adoption measurement mechanisms that support phased rollout.
Copilot Studio agents (agentic AI) delivery + governance coordination
· Plan and coordinate development of Copilot Studio agents, including environment setup, release sequencing (dev/test/prod), and access controls consistent with Power Platform governance practices described in City materials.
· Coordinate required governance controls for agents (e.g., data policies/DLP via Power Platform admin center) and ensure these are incorporated into delivery plans and release gates.
· Where required, build or co-build basic Copilot Studio agent prototypes to validate patterns, connectors/knowledge sources, and operational readiness.
GitHub Copilot rollout
· Lead the technical aspects of the enterprise roll-out for GitHub Copilot as part of the broader AI enablement portfolio (planning, onboarding, training, adoption tracking), consistent with prior City roadmap references to Copilot for GitHub.
· Work with engineering/security stakeholders to ensure enterprise governance aligns with documented enterprise policy controls for GitHub Copilot.
Security, privacy, IM, and compliance delivery gates
· Maintain and drive completion of required assessments like SAR, TRA, IM, IAM, PIA and risk treatments tied to Copilot and Copilot Studio enablement and related services, ensuring delivery sequencing reflects governance gates.
· Coordinate with security and compliance stakeholders on controls such as plugin posture and governance expectations noted in risk documentation.
· Coordinate with TCS/CISO in establishment and execution of a Purview compliance ownership/operating model referenced as a Copilot implementation deliverable.
Reporting, stakeholder management, and delivery transparency
· Produce concise delivery reporting (status, risks, dependencies, decisions) to program leadership and senior stakeholders and manage escalations through structured options.
· Grounded in the City’s existing rollout/operating model approach across AI enablement.
· Ensures project deliverables meet clients’ business requirements on time, scope and budget, with a focus on cost-effectiveness, efficiencies and compliance with OPS project management methodologies and frameworks.
· Resolves resourcing and inter-personal conflicts, negotiates changes to resourcing, ensures knowledge is shared among team members such as project objectives and deliverables are met.
· Proactively identifies potential risk events and issues before they occur so that proper mitigating strategies can be developed.
· Uses appropriate strategies and actions to overcome resistance to change and capitalize on forces in support of change during all stages of projects – concept, definition, planning, implementation and close-out.
Articulates and prioritizes issues and risks at senior executive levels and recommends mitigation strategies for decision makers
Deliverables
· Integrated technical rollout plan for Microsoft Chat + M365 Copilot (including milestones, training, comms, activation, support).
· Operational rollout assets: onboarding steps, training schedule/material alignment, support and troubleshooting guidance packaged for users.
· Governance + compliance deliverables: completed security assessment/risk artifacts and action tracking; documented approvals and release gates.
· Copilot Studio agent delivery pack: environment plan, DLP/data policy configuration approach, and at least one working prototype/pilot agent where assigned.
· GitHub Copilot rollout plan and controls alignment (policy approach and enablement steps), aligned to enterprise policy management capabilities.
· Adoption and feedback reporting (pilot learnings, issues/themes, recommendations for scale).
· Completed production readiness and operational hand‑off artifacts.
· Maintained audit‑ready documentation, including decisions, approvals, and risk treatments.
· Regular project status reporting, delivery dashboards, and escalation summaries for Program Leads.
· Facilitated delivery forums, working sessions, and cross‑team coordination meetings.
Must Haves:
· This role requires hands-on technical fluency with Microsoft 365 Copilot/Microsoft Chat and Copilot Studio and is not intended for generalist project management profiles
· Experience delivering M365 or enterprise SaaS rollouts involving technical implementation, licensing, onboarding, training, comms, and adoption measurement.
· Experience with Power Platform / Copilot Studio delivery is a strong asset (agents, environments, governance).
· Experience coordinating delivery gates across security/privacy/compliance stakeholders (e.g., assessments/risk treatment approach).
· Familiarity with M365 rollout prerequisites and operational dependencies (identity, access patterns, end-user readiness steps documented for pilots).
· Lead technical prerequisites and readiness steps for enterprise roll-out and user access.
Looking for meaningful work? We can help!
Raise is an established hiring firm with over 65 years of experience. We believe strongly in making the world a better place through work, which is why we’re a certified B Corporation and donate 10% of our profits to charity.
We strive to build teams that reflect the diversity of the communities we work in. We encourage all qualified applicants to apply, including people from traditionally underrepresented groups such as women, visible minorities, Indigenous peoples, people identifying as LGBTQ2SI, veterans, and people with visible/nonvisible disabilities.
We have a dedicated webpage for accommodations where you can learn more about what we offer, and request accommodation: https://raise.jobs/accommodations/
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