Operational Readiness Lead

Financial Services Regulatory Authority (FSRA) • Toronto, ON

23h • Onsite

About The Position

The Operational Readiness Lead provides accountability for ensuring new and enhanced capabilities—including data collection platforms, regulatory systems, and analytics solutions—are operationally ready, resilient, and sustainable. The Operational Readiness Lead partners with delivery, operations, and senior stakeholders to ensure enterprise‑wide readiness across people, processes, technology, and controls through go‑live and into steady‑state operations.

Requirements

• Postsecondary degree in Information Technology, Business, Engineering, or a related field ((or an equivalent combination of education and professional experience)
• ITIL certification (Foundation or higher); MS D365 certification
• 8+ years of experience in operational readiness, service transition, or technology delivery
• Proven experience with IT service transition and operational readiness frameworks, IT Service Management (ITIL-based environments, Technology and data platforms (applications, integrations, data pipelines)
• Experience supporting data-intensive solutions, including regulatory data collection, reporting, or analytics platforms
• Experience in financial services, government, or regulatory organizations
• Experience with large-scale data or digital transformation programs
• Demonstrated success leading transition-to-operations for large, complex initiatives
• Proven track record of successfully transitioning complex technology and data initiatives into steady-state operations
• Familiarity with cloud and enterprise environments; MS D365 experience
• Familiarity with infrastructure monitoring, DevOps, and ITIL frameworks.
• Strong knowledge of privacy, security, and regulatory compliance requirements
• Exceptional stakeholder relationship management and facilitation skills
• Strong risk management and problem-solving capabilities
• Ability to influence without authority across technical and business teams
• Ability to optimize workflows to speed up deployment without sacrificing stability.
• Highly organized, detail-oriented, and outcomes-focused
• Proven ability to manage stakeholder expectations and translate technical issues for business units.
• Communication and training skills to ensure teams have the skills, training, and support to maintain the new system.
• Proven leadership skills in organization-wide transformation and the ability to translate complex business needs into technical roadmap.

Responsibilities

• Lead end-to-end operational readiness planning for major technology and data initiatives
• Define & execute transition-to-operations strategies, including go-live, hypercare, and handover activities
• Ensure operational requirements are identified early and embedded throughout delivery
• Develop and maintain comprehensive readiness artifacts (e.g., readiness assessments, checklists, cutover plans)
• Coordinate the successful handoff of solutions to IT Operations, Application Support, and business owners
• Ensure support models are clearly defined, including Tiered support and escalation paths, Service Level Agreements (SLAs), Incident, problem, and change management processes
• Lead hyper care periods and confirm operational stability before formal closure
• Ensure operational teams are trained, enabled, and prepared to support new solutions
• Oversee development of operational documentation, including: Runbooks and standard operating procedures (SOPs), Support playbooks and troubleshooting guides
• Identify organizational impacts and support change management activities in partnership with stakeholders
• Partnering closely with Product Owners and delivery teams, IT Operations and Service Management, Data, Analytics, and Governance teams and Business and regulatory stakeholders
• Provide clear, risk-based readiness reporting to leadership and decision forums
• Identify, escalate, and mitigate operational risks and dependencies
• Validate readiness across: Infrastructure, environments, and access controls, Data quality, reconciliation, and monitoring processes, Security, privacy, audit, and regulatory compliance requirements
• Ensure alignment with IT Service Management (ITSM) practices and enterprise standards

Benefits

• Employer-matched defined benefit pension plan
• Comprehensive and competitive benefits plan
• Prioritize learning and development
• Wellbeing
• Diversity, equity, inclusion and belonging
• Community giving

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: Associate degree