Technical Program Manager - GRS Technology

Program Delivery & Delivery Management Drive and monitor end-to-end program technical execution: develop and maintain multi-year, multi-domain delivery plans that sequence technical work, integrations, and program increments. Serve as technology program manager: provide consistent, accurate, and timely program status, decisions, and delivery logistics to stakeholders and leadership. Run delivery operations: coordinate cutovers, command-center execution, hypercare, and handoffs to BAU/operations. Establish and run program governance (Steer Co, decision logs, RACI/RASCI matrices, stage gates) and ensure timely escalation and clear accountability for decisions OR support program governance and visibility in programs with an overall program leader from outside the technology organization. Apply AI-powered analytics to program data to surface leading risk indicators, predict schedule variances, and enable earlier, better-informed interventions. Guide teams through the AI-augmented SDLC: understand how AI coding assistants, spec-driven development, and automated testing change delivery cadence, estimation, quality signals, and team composition. Apply responsible-AI judgment: ensure AI usage within the program aligns with enterprise standards for security, data privacy, explainability, and ethics. Build and maintain stakeholder management plans for technical execution; communicate trade-offs clearly; eliminate friction that impedes delivery. Operate independently: lead complex program workstreams with limited direction while escalating appropriately. 10+ years' experience delivering software solutions in an agile environment; experience leading large, complex, multi-year programs. Deep knowledge of Agile scaling practices and the ability to mobilize multiple agile teams across domains toward a shared mission. Strong technical fluency — able to engage credibly on architecture, integrations, cloud platforms, data/AI pipelines, and NFRs. Demonstrated AI proficiency: hands-on experience using generative AI tools (e.g., AI assistants, agents, copilots) to improve program execution, plus a working understanding of AI concepts sufficient to evaluate use cases and guide adoption. Experience with JIRA, Confluence, and SPM/portfolio tools; comfortable defining and enforcing tooling and automation standards. Demonstrated strength in governance, risk management, dependency mapping, and financial reporting (burn vs. plan). Data-driven decision-making: able to define metrics, interpret analytics, and use AI-generated insights while applying sound human judgment. Exceptional negotiation, facilitation, and consensus-building skills with cross-functional stakeholders. Highly developed interpersonal skills and executive presence; proven ability to influence without direct authority. Proven ability to operate with limited guidance and manage ambiguity in fast-evolving environments. Bachelor's or Master's degree in a technical or business discipline (or equivalent experience). Experience in property & casualty insurance or other regulated industries, including familiarity with responsible-AI, compliance, and data-governance considerations. Experience delivering AI/ML or data-platform programs, or embedding AI into the SDLC (AI-assisted development, testing, or operations). Background in DevOps, release orchestration, or technical delivery leadership. Relevant certifications: PMP, SAFe POPM/SPC, or equivalent; AI credentials such as Google Generative AI Leader, AWS Certified Cloud Practitioner / AWS AI Practitioner, or Microsoft AI Fundamentals are a plus.