(Hybrid – Toronto) The Delivery Lead is accountable for the end-to-end delivery of insurance technology initiatives, spanning legacy mainframe/AS400 platforms and modern cloud-based and data-enabled solutions. This role focuses on delivery execution, coordination, and oversight rather than people management or hands-on development. The successful candidate brings deep experience delivering insurance core systems (policy, billing, claims), understands legacy COBOL/AS400 environments, and is comfortable overseeing projects working with Python-based services and cloud platforms to modernize and integrate insurance systems.Key ResponsibilitiesDelivery Ownership (No Direct Reports)Own and manage end-to-end delivery for insurance application initiatives, from initiation through release and stabilization.Translate insurance business requirements into delivery plans, milestones, dependencies, and outcomes.Manage scope, schedule, and delivery risks across multiple concurrent initiatives.Ensure alignment with enterprise architecture, security standards, and regulatory expectations.Operate in a matrixed environment with no direct reports, influencing delivery outcomes through collaboration and governance.Insurance Domain FocusServe as a delivery expert for insurance core systems, including policy administration, rating, underwriting, billing, and claims platforms.Ensure solutions meet insurance-specific needs such as regulatory compliance, data integrity, auditability, and financial controls.Partner with business and actuarial stakeholders to ensure technology solutions support product and operational objectives.Technical Oversight (Non–Hands-On)Provide technical delivery oversight for solutions spanning:Mainframe / AS400 (COBOL,



CLP-based systems)Python-based applications and servicesCloud platforms (AWS, Azure, or GCP)Review solution designs, architecture artifacts, estimates, and delivery approaches.Assess design and delivery impacts related to performance, resilience, data security, and integration.Ensure legacy systems are effectively integrated with up-to-date platforms using APIs, messaging, or middleware.Cloud & Modernization DeliveryOversee delivery of cloud migration, modernization, and data initiatives within an insurance ecosystem.Ensure cloud solutions align with organizational standards for security, cost management, observability, and scalability.Support hybrid architectures where on-prem/mainframe systems interact with cloud-native and Python-driven services.Testing, Quality & Production ReadinessOversee test strategy, planning, and execution (unit, integration, regression, UAT) without hands-on testing.Ensure production readiness, including release coordination, operational documentation, and support models.Coordinate resolution of production issues, including root-cause analysis and remediation planning.Support internal and external audits by ensuring delivery artifacts and controls are in place.Stakeholder & Governance ManagementAct as a single delivery point of accountability for business, IT,



and vendor stakeholders.Provide clear and proactive status reporting, risk management, and decision support.Facilitate governance forums and delivery checkpoints as required.Continuous ImprovementIdentify opportunities to improve delivery efficiency, tooling, and governance.Recommend automation and process improvements across legacy and cloud environments.Contribute to delivery standards, templates, and best practices across insurance technology teams.QualificationsRequired Experience7–10+ years delivering technology solutions in the insurance industry.Strong experience with mainframe / AS400 (COBOL-based) insurance systems.Proven experience in a Delivery Lead, Technical Delivery Manager, or Program Delivery role with no direct reports.Experience overseeing Python-based applications or data solutions.Hands‑on knowledge (oversight-level) of cloud platforms such as AWS, Azure, or GCP.Experience integrating legacy insurance platforms with modern, API‑driven architectures.Knowledge & SkillsStrong understanding of SDLC, release management, testing practices, and production support.Familiarity with JIRA and Confluence for delivery tracking and documentation.Ability to review and guide test plans and execution without performing testing.Understanding of security, compliance, and audit requirements in regulated insurance environments.Excellent analytical, organizational, and problem‑solving abilities.Communication & CollaborationStrong verbal and written communication skills.Comfortable working in highly collaborative, matrixed environments.Proven ability to influence outcomes without formal authority.Salary$75,900.00 - $141,900.00Pay TypeSalaried#J-18808-Ljbffr

📌 It Delivery Lead – Insurance Platforms - $75,900 - $141,900 A Year (Winnipeg)
🏢 BMO
📍 Winnipeg