Portfolio Delivery Director - AI Native Engineering & Hyperfactory Transformation We are seeking a highly accomplished Portfolio Delivery Director - AI Native Engineering & Hyperfactory Transformation to lead one of the strategic business portfolios within a large-scale transformation engagement for a leading insurance provider. This leader will own end-to-end accountability for portfolio delivery across multiple programs, projects, products, and managed services teams. The role is responsible for successful transition from incumbent vendors, knowledge transfer, stabilization, technology transformation, operational excellence, SLA achievement, customer satisfaction, and business outcomes. A key expectation of this role is to establish and operationalize an AI-Native Delivery Organization from Day One by implementing an AI Hyperfactory operating model, transforming traditional engineering teams into AI-augmented, high-performing delivery organizations that deliver measurable gains in productivity, quality, speed, and business value. Responsibilities Own end-to-end delivery of a strategic portfolio consisting of multiple programs, projects, products, and managed services engagements Serve as the single point of accountability for portfolio performance, delivery excellence, customer satisfaction, and business outcomes Drive operational excellence, continuous improvement, and delivery predictability across the portfolio Lead transition activities from incumbent vendors and legacy delivery organizations, including migration, stabilization, and Knowledge Transfer (KT) plans with minimal business disruption Establish transition governance, risk management, and executive reporting mechanisms Successfully transition services into steady-state operations while meeting agreed stabilization targets Establish and operationalize an AI Hyperfactory delivery model and define the portfolio's AI-native transformation roadmap Drive adoption of AI across software engineering, quality engineering, testing, release management, operations, support, and delivery governance Implement AI-enabled engineering practices including code generation, code reviews, automated testing, intelligent operations, knowledge management, and delivery analytics Build reusable AI accelerators, frameworks, playbooks, and best practices that can be scaled across the portfolio Drive measurable improvements in engineering productivity, delivery velocity, quality, and operational efficiency through AI adoption Lead organizational change and transformation of traditional teams into AI-first engineering organizations Monitor portfolio health, dependencies, risks, issues, and mitigation plans Own achievement of all SLAs, KPIs, OLAs, and contractual service commitments Lead executive escalations and resolution of critical delivery issues Build trusted relationships with client executives, business leaders, and technology stakeholders Lead steering committees, governance reviews, and executive business reviews Partner with client leadership to align delivery priorities with strategic business goals and transformation initiatives Own portfolio financial performance, including revenue, margin, utilization, forecasting, and cost optimization Support account growth, renewals, transformation opportunities, and strategic initiatives Build, lead, and scale high-performing global delivery teams, driving talent development, succession planning, and leadership growth Foster a culture of accountability, innovation, collaboration, and continuous learning Requirements Bachelor's degree in Engineering, Computer Science, Information Systems, Business, or a related field 15+ years of experience in technology delivery, program management, managed services, or digital transformation leadership 8+ years of experience leading large-scale portfolios, programs, or enterprise client engagements Proven experience managing multi-million-dollar portfolios with accountability for delivery, customer outcomes, and financial performance Demonstrated success leading complex transitions from incumbent vendors, including knowledge transfer, stabilization, and operational transformation Strong experience operating within outcome-based, SLA-driven, or managed services delivery environments Experience leading globally distributed teams across onshore, nearshore, and offshore delivery models Deep understanding of Agile, DevOps, Product Engineering, Cloud, and modern software delivery practices Strong executive stakeholder management, governance, and communication skills Proven experience leading enterprise-scale AI Native Engineering transformations Demonstrated experience establishing and operationalizing AI Hyperfactory or AI-powered delivery operating models Experience implementing AI-enabled software engineering, testing, operations, service management, and delivery governance practices Track record of driving AI adoption and achieving measurable improvements in productivity, quality, speed-to-market, and operational efficiency Strong understanding of Generative AI, AI agents, intelligent automation, responsible AI, governance, and enterprise AI operating models Nice to have Experience within Insurance, Financial Services, Banking, or other highly regulated industries Experience leading large-scale application modernization, digital transformation, cloud transformation, and managed services programs PMP, SAFe, PMI-ACP, Scrum, ITIL, or equivalent certifications Experience with Microsoft Copilot, Azure AI, GenAI platforms, Agentic AI frameworks, and modern AI-enabled engineering ecosystems