Masterpiece Domain Lead
About The Position
We are executing a multi-year, enterprise-scale transformation of its Personal Risk Services (PRS) technology estate—transitioning from monolithic, mainframe-based systems to a cloud-native, API-first, composable architecture on AWS/Azure. As our Domain Leader – Core Modernization, you will architect and drive this transformation, establishing a Center of Excellence to deliver reusable modernization patterns, leveraging AI/ML for code analysis and migration acceleration, and replacing legacy batch and MQ interfaces with REST APIs and event streaming. You will ensure all modernization investments align with Chubb’s regulatory, operational resilience, and long-term technology strategies, while orchestrating multi-year roadmaps, standing up modernization squads, and aligning business, risk, compliance, and technology stakeholders. In this role, you will: Architect and govern the target-state technology stack, including API gateways, microservices, containerized workloads, and automated CI/CD pipelines Decompose and re-platform core PRS systems (policy admin, rating, billing, claims orchestration) from legacy mainframe to cloud-native services Implement strangler-fig and parallel-run migration strategies to de-risk transformation and maintain production stability for over 1M in-force policies Deploy AI/ML tooling for automated code analysis, dead-code identification, dependency mapping, and mainframe-to-modern language translation Leverage generative AI to accelerate requirements documentation, interface specifications, test case generation, and knowledge extraction from legacy codebases Build AI-enabled observability and predictive analytics to monitor migration health, detect anomalies, and proactively manage SLA risks during cutover Establish AI-powered governance dashboards for real-time visibility into modernization progress, technical debt reduction, and business value realization Serve as primary modernization liaison to senior leadership, Enterprise Architecture Review Board, and Risk/Compliance, presenting investment cases and risk dashboards Implement Scaled Agile (SAFe) delivery practices, building and leading a high-performing organization of 40–60 engineers, architects, and delivery leads across global teams Drive migration of downstream integrations (agents, reinsurers, regulators, third-party providers) to modern APIs and event-driven interfaces, prioritizing workstreams by business impact through data analytics and stakeholder feedback
Requirements
- 15+ years of progressive enterprise technology experience, including 5+ years leading large-scale platform modernization or legacy transformation programs; direct experience with Tier-1 P&C carrier technology environments (e.g., Chubb, AIG, Travelers) preferred
- Bachelor’s degree in Computer Science, Engineering, or related field required; Master’s degree preferred
- Deep expertise in cloud-native architectures (AWS/Azure/GCP), microservices, API-first design, containerization (Kubernetes/Docker), and event-driven integration (Kafka, MQ)
- Proven track record of modernizing mainframe or legacy policy administration systems in insurance or financial services; knowledge of insurance platforms such as Guidewire, Duck Creek, Majesco, or proprietary mainframe systems
- Strong command of AI/ML applications in software modernization, including code analysis, automated testing, and migration acceleration tooling
- Experience managing $15M+ technology program budgets with accountability for ROI, timeline, and risk governance; experience with COTS-vs-build evaluation frameworks and vendor due diligence for core system replacement preferred
- Demonstrated ability to build and lead organizations of 40+ across onshore/offshore delivery models
- Executive presence with a track record of influencing C-suite stakeholders, board-level committees, and cross-functional governance forums
- Familiarity with ISO 20022, ACORD data standards, and regulatory reporting requirements (state filings, NAIC) preferred
- SAFe Program Consultant (SPC), PMP, or equivalent Agile/delivery certifications preferred
Nice To Haves
- direct experience with Tier-1 P&C carrier technology environments (e.g., Chubb, AIG, Travelers) preferred
- Master’s degree preferred
- Familiarity with ISO 20022, ACORD data standards, and regulatory reporting requirements (state filings, NAIC) preferred
- SAFe Program Consultant (SPC), PMP, or equivalent Agile/delivery certifications preferred
Responsibilities
- Architect and govern the target-state technology stack, including API gateways, microservices, containerized workloads, and automated CI/CD pipelines
- Decompose and re-platform core PRS systems (policy admin, rating, billing, claims orchestration) from legacy mainframe to cloud-native services
- Implement strangler-fig and parallel-run migration strategies to de-risk transformation and maintain production stability for over 1M in-force policies
- Deploy AI/ML tooling for automated code analysis, dead-code identification, dependency mapping, and mainframe-to-modern language translation
- Leverage generative AI to accelerate requirements documentation, interface specifications, test case generation, and knowledge extraction from legacy codebases
- Build AI-enabled observability and predictive analytics to monitor migration health, detect anomalies, and proactively manage SLA risks during cutover
- Establish AI-powered governance dashboards for real-time visibility into modernization progress, technical debt reduction, and business value realization
- Serve as primary modernization liaison to senior leadership, Enterprise Architecture Review Board, and Risk/Compliance, presenting investment cases and risk dashboards
- Implement Scaled Agile (SAFe) delivery practices, building and leading a high-performing organization of 40–60 engineers, architects, and delivery leads across global teams
- Drive migration of downstream integrations (agents, reinsurers, regulators, third-party providers) to modern APIs and event-driven interfaces, prioritizing workstreams by business impact through data analytics and stakeholder feedback
Benefits
- Chubb offers a comprehensive benefits package, more details on which can be found on our careers website.
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What This Job Offers
Job Type
Full-time
Career Level
Mid Level
