Deployment Lead / Toronto, ON / Onsite (4 days) / FTE

Job Title: Deployment Lead

Location: Toronto, ON

Work Model: Onsite – Minimum 4 Days/Week

Employment Type: Full-Time

Job Summary

We are seeking an experienced Deployment Lead to manage end-to-end deployment planning and execution for a major product launch and portfolio conversion (TSYS to TSYS). The ideal candidate will have strong experience in deployment management, production cutovers, conversion planning, cross-functional coordination, risk management, and executive reporting.

Key Responsibilities

• Lead end-to-end deployment planning and execution for product launches and portfolio conversion initiatives.
• Own the integrated deployment plan and master activity schedule, including workstream runbooks, dependencies, milestones, cutover activities, and readiness tracking.
• Coordinate internal teams, external vendors, technology teams, and business stakeholders throughout deployment and conversion activities.
• Plan and coordinate all pre-conversion activities, including mock conversions, dress rehearsals, validation, and production readiness activities.
• Lead production cutover execution, ensuring all activities, dependencies, checkpoints, and rollback plans are properly coordinated.
• Coordinate production product launch activities, including pilot implementation and customer rollout.
• Manage and resolve environment collisions and deployment conflicts across Cortez and non-Cortez workstreams.
• Oversee the delivery and deployment of new product features being introduced on the target platform.
• Drive deployment governance, including status tracking, risk and issue management, dependency management, and escalation.
• Identify deployment risks and develop mitigation and contingency plans to ensure successful production implementation.
• Prepare and deliver executive-level deployment status, readiness, risk, and cutover reports.
• Coordinate post-production validation, stabilization, issue resolution, and transition to ongoing support.
• Ensure deployment activities are completed within established timelines and meet production readiness and quality requirements.

Required Skills & Experience

• 8+ years of experience in deployment management, release management, implementation, or technical project delivery.
• Proven experience managing complex enterprise deployments, product launches, portfolio conversions, or platform migrations.
• Strong hands-on experience with cutover planning, mock conversions, dress rehearsals, and production implementation.
• Experience coordinating multiple cross-functional workstreams and external vendor teams.
• Strong knowledge of deployment governance, risk management, dependency management, and readiness tracking.
• Excellent stakeholder management, communication, coordination, and problem-solving skills.
• Experience preparing executive-level status and deployment reports.
• Ability to manage multiple priorities and resolve deployment conflicts in a fast-paced enterprise environment.
• Strong experience with production implementation and post-production stabilization.

Preferred Qualifications

• Experience in banking, payments, financial services, card processing, or transaction processing.
• Experience with TSYS or similar payment processing platforms.
• Experience managing portfolio conversion or product migration initiatives.
• Familiarity with Cortez/non-Cortez environments or similar enterprise deployment ecosystems.