Director, AI Enablement & Delivery

National Life Insurance Company • Montpelier, VT

1d • $157,500 - $231,000 • Onsite

About The Position

National Life Group is building enterprise AI capabilities that improve how work gets done, strengthen the client and advisor experience, and support responsible innovation in a regulated financial services environment. The Director, AI Enablement & Delivery leads a significant AI delivery and enablement function, program, or area of accountability and translates enterprise AI priorities into short-term objectives, operating plans, and measurable outcomes.

This role serves as a field expert and principal advisor on AI delivery, adoption, governance, and business transformation. It leads large, complex initiatives across multiple business and functional areas, shapes policies and practices affecting AI-enabled operations, and provides recommendations on critical issues that may lack clear precedent or strategic direction.

The ideal candidate is a recognized AI and transformation leader who can influence senior decision-makers, navigate multifaceted business and risk considerations, and drive results across departments through expertise, judgment, and strong stakeholder leadership.

Requirements

• Bachelor's degree in Business, Finance, Computer Science, Information Systems, Data and Analytics, Operations, or a related field and fourteen or more years of related work experience; advanced degree and eleven or more years of related experience; or eighteen or more years of equivalent combined education and work experience.
• Extensive experience leading large, complex, cross-functional AI, data, technology, automation, digital transformation, product, program, or enterprise change initiatives.
• Demonstrated experience leading a department, major program, team, or area of accountability with significant company impact.
• Recognized expertise in AI delivery, enablement, adoption, governance, business transformation, or a related discipline.
• Experience translating strategic objectives into short-term goals, operating plans, policies, and measurable outcomes.
• Demonstrated ability to resolve critical issues that are not clearly defined and may lack established direction or precedent.
• Experience influencing senior leaders, governance bodies, and key decision-makers across departments.
• Strong business acumen, executive communication, negotiation, facilitation, and stakeholder management skills.
• Experience leading and developing teams, managers, program leaders, or senior professionals.
• Leverage approved AI tools, where appropriate, to improve the efficiency, quality, and impact of their work.
• Stay curious and open to new AI-enabled ways of working.
• Exercise sound judgment by reviewing and validating AI-generated content.
• Maintain accountability for the accuracy, quality, fairness, and integrity of work products by adhering to National Life's AI guiding principles.
• Use AI responsibly and in accordance with company policies related to confidentiality, data privacy, security, compliance, retention, and intellectual property.
• Identify practical opportunities to apply AI to improve workflows, productivity, analysis, and business outcomes.
• Create effective prompts, workflows, controls, and human-in-the-loop (HITL) review processes that support responsible AI use.
• Critically evaluate AI-generated outputs for accuracy, quality, bias, fairness, confidentiality, compliance, security, and business relevance.
• Partner appropriately with Legal, Compliance, Risk, Security, Data/Technology, and business stakeholders to move AI ideas from experimentation to responsible adoption.
• Help model responsible, human-centered AI adoption across the organization.

Nice To Haves

• Leadership experience in insurance, financial services, or another highly regulated industry.
• Deep experience with generative AI, machine learning, agentic systems, enterprise automation, AI platforms, or AI-enabled operating model transformation.
• Experience designing or implementing responsible AI governance, model risk, privacy, security, compliance, legal, or technology control frameworks.
• Experience managing AI investment portfolios, roadmaps, business cases, operating models, performance measures, and value-realization programs.
• Experience with enterprise product management, transformation offices, design thinking, process engineering, change leadership, or workforce enablement.

Responsibilities

• Lead an enterprise AI delivery and enablement program, department, or significant area of accountability.
• Translate enterprise AI strategy into short-term objectives, operating plans, portfolio priorities, delivery standards, and adoption goals.
• Direct large, complex AI initiatives spanning multiple business areas, technologies, data domains, risk functions, and operational processes.
• Serve as a principal advisor to senior leaders, governance bodies, and business partners on AI opportunities, delivery feasibility, adoption readiness, business value, risk, and operating model implications.
• Shape policies, methods, standards, and governance practices that affect AI delivery and AI-enabled operations across departments or the division.
• Resolve critical, undefined, or multifaceted delivery issues by considering business, technology, data, regulatory, financial, operational, and human impacts.
• Lead the development and management of AI portfolios and roadmaps for assigned areas, ensuring alignment with enterprise strategy, risk appetite, business priorities, and delivery capacity.
• Establish performance measures and review mechanisms for AI initiatives, adoption programs, operational outcomes, and value realization.
• Direct development of business cases, investment recommendations, prioritization frameworks, and executive decision materials.
• Partner with legal, compliance, risk, privacy, security, technology, data, architecture, and audit stakeholders to ensure responsible AI requirements are integrated into operating plans and delivery practices.
• Guide implementation of risk tiering, controls, validation, monitoring, documentation, human oversight, data-use requirements, and governance evidence.
• Lead enterprise or multi-department adoption strategies, including operating model redesign, workforce readiness, leadership engagement, training, communications, support models, and adoption measurement.
• Establish repeatable enterprise implementation patterns, delivery playbooks, governance procedures, enablement resources, and human-in-the-loop practices.
• Build formal networks with key decision-makers and external partners to accelerate delivery, resolve dependencies, and improve organizational AI capability.
• Present results, recommendations, risks, and strategic tradeoffs to senior leaders and governance bodies.
• Influence stakeholders toward desired departmental and enterprise outcomes in sensitive, high-impact situations.
• Lead, coach, and develop teams, program leads, or senior individual contributors, or guide the work of peers and junior colleagues across a significant area of accountability.
• Model NLG values, responsible AI practices, and human-centered change leadership.
• All other duties as assigned.

Benefits

• Benefits start day one and are flexible and customizable to your and your family’s specific needs.
• 401(k) eligibility
• Various paid time off benefits, such as vacation, sick time, and parental leave
• Discretionary annual incentive programs

What This Job Offers

• Job Type: Full-time
• Career Level: Director