Program supervisor Jobs in North York, ON

Our client, a leading financial services institution, is seeking a seasoned Program Manager to lead the delivery of complex technology initiatives across their Canada Markets division. In this role, you will partner closely with business leaders, risk and compliance teams, engineering groups, and external vendors to drive end-to-end execution of critical programs, including platform modernizations, regulatory commitments, and infrastructure upgrades.

This highly visible position requires an execution-focused leader who can bring structure, transparency, and robust governance to multi-stream environments, ensuring alignment with enterprise standards while managing delivery risk in a highly regulated ecosystem.

Location: Toronto, ON (Hybrid - 4 days per week onsite)

Position Type: Full-time / Contract

Advantages
High-Impact Portfolio: Lead high-visibility, enterprise-level initiatives spanning platform modernization, legacy upgrades, and cloud adoption.

Collaborative Onsite Culture: Work closely with senior leadership and key decision-makers through a collaborative 4-day onsite hybrid schedule.

Vendor Governance Ownership: Drive strategic external partnership frameworks, optimize engagement models, and shape critical delivery pipelines.

Innovative Ecosystem: Work in an environment exploring cutting-edge tools, including AI-enabled planning and automated project reporting.

Responsibilities
End-to-End Delivery: Lead the planning, execution, and tracking of complex, multi-million dollar technology initiatives across infrastructure, applications, and business transformations.

Vendor & Partner Management: Manage external vendors and delivery partners; drive accountability against statements of work (SOWs), manage costs/scope changes, and monitor overall delivery performance.

Governance & Compliance: Establish structured delivery practices and clear milestones; proactively identify, track, and mitigate risks and issues in alignment with strict regulatory, audit, and compliance standards.

Stakeholder Engagement: Act as the central point of contact, providing transparent, executive-level status reporting and facilitating alignment across engineering, business, and risk teams.

Execution Discipline: Standardize delivery models (both Agile and structured), reduce operational friction, and optimize resource allocation across competing priorities.

Qualifications
Must-Have Qualifications:
- Project / Program Management: 5 to 8+ years of experience leading complex, large-scale technology programs within enterprise environments.

- Compliance Domain Expertise: 3 to 5 years of experience managing technology deliveries within highly regulated environments (e.g., Risk, Compliance, Audit, or Regulatory commitments).

- Vendor Management: Strong, hands-on experience managing external vendors, negotiating SOWs, and governing time-and-materials or fixed-price contracts.

Desired Skills & Experience:
- Capital Markets Knowledge: Direct experience working with trading platforms, Equities, Fixed Income, or regulatory-driven financial systems.

- Modernization & Migrations: Proven track record delivering platform modernization projects, large-scale data/infrastructure migrations, or cloud adoption programs.

- Delivery Methodology: Deep familiarity with Jira, Confluence, and interactive project dashboards using both Agile and structured waterfall frameworks.

- Optimization Skills: Ability to analyze current delivery practices, establish KPIs, and leverage reporting automation tools (or AI-enabled tools) to streamline program governance.

Summary
This is an exceptional opportunity for a senior Program Manager with a background in financial compliance and capital markets to spearhead critical technology initiatives for a premier institution. If you possess a disciplined approach to execution, outstanding vendor management capabilities, and thrive in dynamic, high-exposure onsite environments, we encourage you to apply.

Randstad Canada is committed to fostering a workforce reflective of all peoples of Canada. As a result, we are committed to developing and implementing strategies to increase the equity, diversity and inclusion within the workplace by examining our internal policies, practices, and systems throughout the entire lifecycle of our workforce, including its recruitment, retention and advancement for all employees. In addition to our deep commitment to respecting human rights, we are dedicated to positive actions to affect change to ensure everyone has full participation in the workforce free from any barriers, systemic or otherwise, especially equity-seeking groups who are usually underrepresented in Canada's workforce, including those who identify as women or non-binary/gender non-conforming; Indigenous or Aboriginal Peoples; persons with disabilities (visible or invisible) and; members of visible minorities, racialized groups and the LGBTQ2+ community.

Randstad Canada is committed to creating and maintaining an inclusive and accessible workplace for all its candidates and employees by supporting their accessibility and accommodation needs throughout the employment lifecycle. We ask that all job applications please identify any accommodation requirements by sending an email to accessibility@randstad.ca to ensure their ability to fully participate in the interview process.