Sr Project Manager - AI/Application Development (Independent Contractor)

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 CIRO

As 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 Opportunity

This is a business to business contract opportunity 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 setting. 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 Services The 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 Requirements To 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

📌 Senior Project Manager (Toronto)
🏢 CIRO / OCRI
📍 Toronto