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Senior AI Project Manager

  • Toronto, ON, Canada
  • Greater Toronto Area, Canada, Canada
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Experience
7+ years of progressive project management experience leading large-scale, complex enterprise technology transformations.
Posting language
English
Posted

Original job description

Position Overview: Senior Project Manager - AI SDLC

We are seeking an experienced Senior Project Manager – AI SDLC to lead the strategic rollout of enterprise-wide, AI-augmented engineering capabilities, developer tooling, and intelligent software engineering workflows. In this role, you will orchestrate the enterprise adoption of AI-driven capabilities - such as GitHub Copilot, specialized coding agents, telemetry/monitoring, and automated CI/CD guardrails. You will operate at the intersection of engineering excellence and institutional risk, aligning technical execution across Software Engineering, Architecture, Information Security, Enterprise Risk, and Product organizations.

Responsibilities

  • Program & Delivery Execution: Drive end-to-end delivery of complex AI SDLC workstreams, establishing milestones, managing critical-path dependencies, and unblocking engineering teams across concurrent projects.
  • AI Tooling & Workflow Enablement: Partner with platform and engineering leads to roll out generative AI developer tools (e.g., GitHub Copilot, custom LLM agents), establishing adoption benchmarks, rollout phases, and enablement strategies.
  • Governance, Compliance & Security: Ensure AI capabilities integrate seamlessly with enterprise risk controls, regulatory requirements, IP protection standards, and model risk governance frameworks.
  • DevOps & Platform Integration: Coordinate delivery across platform teams to embed AI-assisted tools within existing enterprise CI/CD pipelines, automated testing, and developer environments.
  • Operational Readiness: Define transition frameworks to move AI tooling and telemetry from pilot phases to enterprise-wide production and sustained operational support.
  • Financial Management & Forecasting: Manage project financials, vendor allocations, burn rates, and quarterly resource forecasting within the broader program portfolio.
  • Executive Communication & Alignment: Produce data-driven progress dashboards, risk burndown reports, and steering committee briefings for executive leadership.
  • Qualifications

    • 7+ years of progressive project management experience leading large-scale, complex enterprise technology transformations.
    • Technical Fluency: Demonstrated background collaborating directly with software engineers, DevOps specialists, and enterprise architects in a modern cloud-first or platform engineering environment.
    • Delivery Methodologies: Deep expertise in Agile, Scrum, and hybrid frameworks, with a proven track record of maintaining delivery velocity alongside rigorous governance standards.
    • Governance & Risk Acumen: Strong experience navigating corporate risk controls, audit readiness, change management, and security sign-offs.
    • Portfolio & Financial Tracking: Proficiency in managing multi-million-dollar technology budgets, forecasting, and resource capacity planning.
    • Stakeholder Influence: Exceptional executive presence and conflict-resolution skills, capable of bridging conversations between deeply technical developers and business risk executives.

    Preferred Qualifications

    • Hands-on delivery experience with AI/GenAI software engineering initiatives, developer productivity platforms, or emerging tech rollouts (e.g., GitHub Copilot, Cursor, Tabnine, enterprise LLM toolchains).
    • Background in Financial Services or similarly complex, heavily regulated environments (e.g., OSFI, FINRA, or ISO compliance frameworks).
    • Familiarity with modern DevOps ecosystems (Git, automated testing frameworks, containerization, cloud platform engineering).
    • Relevant certifications: PMP, PMI-ACP, CSM, or SAFe Agilist.
    More about this job

    Responsibilities

    Lead enterprise-wide delivery and adoption of AI-augmented software engineering tools and workflows, coordinating engineering, platform, security, risk, architecture, and product teams. Manage governance, operational readiness, budgets, dependencies, and executive reporting as AI capabilities move from pilots into production.

    Requirements

    Requires at least 7 years of project management experience leading complex enterprise technology transformations, along with technical fluency in software engineering, DevOps, and platform environments. Candidates should have strong Agile or hybrid delivery, governance and risk, financial planning, and executive stakeholder skills; AI engineering initiative experience and relevant certifications are preferred.

    Skills

    • Project Management
    • AI SDLC Delivery
    • Generative AI Tooling
    • Agile
    • Scrum
    • Hybrid Delivery Frameworks
    • DevOps
    • CI/CD Integration
    • Enterprise Risk Management
    • Governance and Compliance
    • Security and Audit Readiness
    • Financial Forecasting
    • Resource Planning
    • Executive Communication
    • Stakeholder Management
    • Change Management

    Visa sponsorship

    Not detected in the job text

    Categories

    • Technology
    • Management & Leadership
    • Software
    • Engineering
    • Security & Safety

    Keywords

    • AI SDLC
    • Generative AI
    • GitHub Copilot
    • Custom LLM Agents
    • Cursor
    • Tabnine
    • Developer Productivity Platforms
    • Software Engineering
    • DevOps
    • CI/CD
    • Automated Testing
    • Telemetry
    • Monitoring
    • Cloud Platform Engineering
    • Git
    • Containerization
    • Agile
    • Scrum
    • Hybrid Frameworks
    • Enterprise Risk
    • Model Risk Governance
    • Regulatory Compliance
    • IP Protection
    • Audit Readiness
    • Change Management
    • Financial Services
    • OSFI
    • FINRA
    • ISO Compliance
    • PMP

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