Location: Hybrid Downtown Toronto (3 days onsite)
Length of project related mandate length: 12 months
Estimated level of effort: 37.5 hours per week
About CIROAs a self-regulatory organization, our mission is to promote healthy capital markets by regulating fairly and effectively so that investors are protected and confident investing in their futures. At the we are committed to setting high regulatory standards for the investment.
The OpportunityThis is a business to business contract chance intended for individuals operating through their own incorporated business. The successful contractor will provide services under the terms of a professional services agreement.
We are seeking a highly experienced
Senior Project Manager
to lead the
delivery of AI, automation, and enterprise technology initiatives
within a dynamic and evolving technology environment. This role is ideal for a senior project leader who thrives in ambiguity, can influence stakeholders at all levels, and has successfully delivered complex technology projects from concept through implementation.
You will partner with business and technology teams to drive strategic initiatives while helping shape the organization's AI and automation journey.
Scope of ServicesThe contractor is expected to perform activities such as:
Lead end-to-end delivery of
AI, automation, and enterprise technology projects .
Manage project scope, timelines, budgets, risks, dependencies, and stakeholder communications.
Collaborate with business leaders, technology teams, and executive stakeholders to ensure successful project outcomes.
Drive process improvement and technology transformation initiatives.
Navigate complex project environments while balancing multiple priorities.
Required skills and experience
10+ years of experience managing business/technology related projects




Led five or more complex
system integration projects
Demonstrated experience delivering
AI, Generative AI, intelligent automation, RPA, machine learning, or
workflow automation initiatives
Experience leading
end-to-end AI solution implementations
from business case through deployment and adoption
Experience managing
AI agent, Copilot, automation workflow, or Power Platform initiatives
Strong understanding of
AI governance, risk management, privacy, security, and responsible AI principles
Experience working with governance forums, risk, compliance, legal, cybersecurity, and architecture teams to obtain approvals for AI solutions
Understanding of AI model risks including bias, explainability, transparency, security, and regulatory compliance
Led projects involving the end-to-end development, implementation, and governance of Microsoft Power Platform solutions (Apps, Automate, Dataverse, BI).
Demonstrated ability to collaborate and lead across a matrix organization on execution of projects and projects that touch multiple functions
Experience conducting project discovery activities
Project Management Professional (PMP)
certification.
Post-secondary degree (computer science/engineering preferred)
Nice to Haves
Previous experience in a Regulatory environment or financial services industry
Experience with Project Management Tools (i.E. MS PPM/Project, Planview Clarizen, other Planview PM tools, Clarity)
Contractor RequirementsTo be considered, contractors should:
Be incorporated and legally authorized to conduct business in Canada
Carry appropriate liability insurance
Be responsible for all applicable taxes, statutory remittances, and business expenses
Be able to enter into a professional services/consulting agreement
Provide professional references upon request
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📌 Senior Project Manager (Winnipeg)
🏢 CIRO / OCRI
📍 Winnipeg