Director, AI Delivery Squad Lead, Underwriting

The Director of AI, Delivery Squad Lead is accountable for the end-to-end execution of AI powered underwriting initiatives (i.e., Life Insurance Underwriting, Automated Underwriting, Underwriting Decision Support, Advisor Underwriting Experience, and Underwriting Transformation). The role translates Solutioning-defined priorities into delivered AI solutions, ensuring execution with speed, quality, and measurable business impact.
This role requires a deep understanding of life insurance risk assessment and underwriting decision-making to ensure AI solutions appropriately balance growth, customer experience, risk selection, and operational efficiency.
This role is the single point of accountability for delivery execution, ensuring initiatives are effectively scoped, sequenced, executed, and aligned to timelines, capacity, and governance requirements.
The role also provides financial oversight of the delivery portfolio, coordinates dependencies across IT, data, architecture, and business stakeholders, and ensures delivery teams have clear scope, sequencing, and execution expectations.
Position Responsibilities:
End-to-End Delivery Execution
Own the full lifecycle delivery of assigned AI initiatives, from execution planning and backlog readiness through production deployment, adoption, and value realization.
Translate prioritized initiatives into clear work packages, defined scope, team tasks, sequencing, and delivery timelines; ensure the squad understands priorities, responsibilities, and expected outcomes.
Lead the day-to-day execution of data scientists and cross-functional squad members by setting clear accountabilities, monitoring commitments, and maintaining delivery momentum and discipline.
Proactively identify risks, remove blockers, and resolve delivery issues to maintain pace and quality.
Establish and maintain the squad’s delivery operating rhythm, including sprint planning, backlog management, quality controls, and performance reviews.
Translation of Strategy to Execution
Apply deep domain expertise in life insurance risk assessment, underwriting philosophy, and risk selection to guide solution design, prioritize opportunities, and ensure AI capabilities address meaningful underwriting challenges.
Convert Solutioning priorities into execution-ready plans
Leverage deep domain expertise to tailor execution plans to operational, regulatory, and market context, driving measurable business impact
Actively bridge business strategy and technical delivery by contextualizing priorities with industry trends, stakeholder needs, and organizational objectives to ensure alignment and value realization.
Align delivery to business strategy and defined scope
Execute approved priorities within established intake and governance frameworks; provide delivery feasibility, capacity, dependency, and sequencing input without owning intake or portfolio prioritization decisions.
Underwriting AI Delivery Leadership
Lead execution of the underwriting AI portfolio, ensuring each approved initiative progresses through planning, build, validation, production deployment, adoption, and outcome measurement.
Translate underwriting priorities into executable roadmaps and delivery plans.
Partner with underwriting leaders to modernize underwriting operations through AI.
Partner with underwriting leaders to plan and execute change, training, communications, and operating-process updates required for adoption of AI-enabled underwriting capabilities.
Lead the translation of complex underwriting challenges into data-driven and AI-enabled solutions through close collaboration with data scientists, engineers, and business stakeholders.
Identify opportunities to standardize and reuse underwriting data, models, components, controls, and delivery patterns across products and business units, and coordinate their implementation with platform owners.
Balance growth, risk, operational efficiency, and customer experience objectives.
Cross-Functional Delivery Orchestration
Lead cross-functional delivery across data science, engineering, product, business teams, and shared services.
Orchestrate delivery across underwriting, actuarial, product, distribution, data science, engineering, risk, compliance, technology, architecture, and other shared-service partners.
Maintain an integrated dependency plan across systems, data, architecture, controls, operating processes, and delivery partners; resolve or escalate constraints before they affect committed milestones.
Confirm stakeholder decisions, control requirements, operating readiness, and handoffs at each stage of the delivery lifecycle.
Portfolio Management & Delivery Orchestration
Maintain the integrated delivery portfolio view for approved underwriting AI initiatives, showing alignment to segment priorities, OKRs, AI strategy, dependencies, milestones, capacity, risks, and expected outcomes.
The portfolio may include automated underwriting platforms, underwriting requirement optimization, advisor-facing underwriting assistants, underwriting knowledge and decision-support capabilities, fraud detection, and future-state underwriting transformation initiatives.
Translate the approved roadmap into sequenced, executable portfolio plans with defined milestones, dependencies, resource requirements, and capacity constraints.
Coordinate delivery across initiatives by identifying cross-portfolio dependencies, assessing execution trade-offs, and escalating decisions that require Product, Solutioning, or stakeholder prioritization.
Maintain disciplined execution through project controls, risk management, performance reporting, and transparent escalation; recommend re-baselining when assumptions or commitments change and drive approved corrective actions.
Resource & Budget Management
Own resource and financial planning for the approved delivery portfolio, aligning squad capacity, external spend, and funding requirements to committed outcomes and delivery milestones.
Monitor actual and forecast spend, explain variances, and identify emerging resource or funding constraints early enough to support corrective action.
Provide leadership with decision-ready budget updates, including actuals, forecasts, variance drivers, funding risks, and cost estimates for approved or emerging opportunities..
Delivery Governance & Reporting
Operate within established intake, delivery governance, risk, compliance, architecture, and responsible AI frameworks, ensuring required approvals and evidence are completed before key delivery gates.
Contribute delivery estimates, dependency assessments, resource requirements, acceptance criteria, and technical feasibility input so approved initiatives are ready for squad execution.
Provide timely, decision-oriented reporting on progress, milestones, capacity, financial performance, risks, dependencies, outcomes, and required leadership actions.
Value Realization
Ensure each initiative has approved KPIs, baseline measures, target outcomes, accountable business owners, and an agreed measurement approach before delivery begins.
Track delivery, adoption, operational, customer, risk, and financial measures through implementation and value realization.
Collaborate with Finance stakeholders to validate assumptions, estimates and realized value, and support reporting aligned to business expectations
Measure and report underwriting outcomes, including increased capacity and new-business throughput; reduced cycle times, unnecessary requirements, and operating costs; higher straight-through processing rates; improved underwriting consistency; and a better advisor experience.
People Leadership
Build squad delivery capability by coaching cross-functional teams, strengthening delivery practices, and reinforcing predictable, high-quality execution.
Required Qualifications:
Life insurance underwriting, risk assessment, and risk selection principles, including understanding mortality and morbidity drivers, underwriting decision frameworks and AI-enabled decision support.
Experience with insurance product manufacturing and distribution, including advisor and customer experience.
Experience operating in regulated insurance and compliance environments.
Enterprise AI product and solution delivery experience, including cross-functional execution from planning through production deployment and value realization.
Understanding of agentic AI patterns and safeguards, including orchestration, planning, memory, tool use, permissions, auditability, failure handling, and human escalation.
Experience with grounding, retrieval-augmented generation, prompt design, evaluation, observability, and responsible AI controls for accurate, reliable, and compliant GenAI solutions.
Experience delivering enterprise GenAI solutions, with knowledge of foundation models, orchestration, APIs, vector retrieval, data integration, deployment, adoption, and value realization.
Experience applying advance analytics, machine learning, AI, or decision science to solve complex underwriting, risk management, or insurance business challenges.
Demonstrated ability to manage delivery risks, dependencies, resources, budgets, governance, and executive-level portfolio reporting.
Strong stakeholder leadership and ability to bridge underwri