Director, AI Enablement & Delivery

National Life Group; Montpelier (VT); On-site; USD 180,000 - 260,000; Full time

Job summary

National Life Group is seeking a Director of AI Enablement & Delivery to drive enterprise AI delivery, governance, and transformation across multiple functions. You will translate AI priorities into actionable plans, collaborating with legal, risk, privacy, and technology stakeholders, and guide senior leaders through complex, regulatory initiatives.

The role requires deep AI leadership, stakeholder management, and the ability to influence decision-makers.

Qualifications

• Bachelor's degree required with 14+ years of related work experience; advanced degree with 11+; or 18+ years total experience.
• Experience leading large, cross-functional AI, data, technology, or enterprise-change initiatives.
• Proven ability to influence senior leaders and drive results across departments.

Responsibilities

• Lead an enterprise AI delivery and enablement program or major area of accountability.
• Translate AI strategy into short-term objectives, operating plans, and priorities.
• Direct large AI initiatives spanning multiple business areas, data domains, and risk functions.
• Advise senior leaders on AI opportunities, feasibility, adoption readiness, and business value.
• Shape governance practices, standards, and operating models for AI delivery across departments.
• Resolve critical delivery issues considering business, tech, data, regulatory, and financial impacts.
• Lead AI portfolios and roadmaps aligned with enterprise strategy and capacity.
• Establish performance measures for AI initiatives and adoption programs.

Skills

AI delivery leadership

Stakeholder management

Change leadership

Executive communication

Cross-functional coordination

Regulated industry expertise

Education

Bachelor's degree in Business, Finance, Computer Science, Information Systems, Data and Analytics, Operations, or a related field

Job description

Come join one of America’s fastest-growing insurance companies. Since 1848, National Life Group has aimed to keep our promises, providing families with stability in good times and in bad. Throughout that history, we have provided peace of mind to those families as they plan their futures.

Our mission extends beyond the insurance and annuities policies that we offer. We strive to make the world a better place through our grants from our charitable foundation, paid volunteer time for our employees, environmentally sustainable and healthy workplaces, and events that promote the work of nonprofits in our own backyard.

We foster a collaborative environment with opportunities for growth and encourage our associates to live our values: Do good. Be good. Make good.

Please note that we do not offer visa sponsorship for this position.

Role Summary

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.

This position currently offers an onsite work schedule, with the expectation that you will be in the office four (4) days per week during onsite core days. Our current onsite core days are Monday, Tuesday, Wednesday, and Thursday. The work schedule type and core days are subject to change with advance notification and manager discretion.

Essential Duties And 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.

Minimum Qualifications

• 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.

Preferred Qualifications

• 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.

AI Proficiency Expectations (All Roles)

At National Life Group, we view AI as an enabler of human potential. We use AI to help us work smarter, serve more clients, and keep our promises, while remaining a relationship-driven business where our people are our greatest