Director, AI Enablement & Delivery
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 strength.
All applicants are expected to:
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.
Additional Expectations for AI-Forward Roles
Applicants in AI-forward roles are also expected to:
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.
Core Competencies
People or Process Leader
Cultivates Innovation - Fosters innovation by taking calculated risks; Work cooperatively with others to produce innovative solutions.
Ensures Accountability - Holds self and others accountable to meet commitments and performance goals.
Directs Work - Provides direction, delegates, and removes obstacles to get work done.
Demonstrates Emotional Intelligence - Exhibits the ability to recognize, understand, and manage emotions and how emotions can influence others; Uses a combination of feedback and reflection to gain productive insight into personal strengths and opportunities.
Exhibits Critical and Creative Thinking - Engaging thinking skills that focus on logic and reasoning to make decisions (critical) and innovative solutions to solve problems (creative).
Leads Change - Facilitates change and transition at the individual and team level; Develops strategic goals for aligning with change.
Develops Talent - Builds team(s) equipped for the future by applying coaching techniques for developing team members to meet their professional/personal goals and the organizational goals; Listens and responds with empathy; Asks thought provoking questions.
Inspires Others - Motivates and influences others by creating an environment where teams can do their best work; Partners across the organization to achieve results.
Benefits
Your benefits start day one and are flexible and customizable to your and your family’s specific needs. Check out the BENEFITS of a Career at National Life !
Base Pay Range . The base pay range for this position is the range National Life reasonably and in good faith expects to pay for the position taking into account the wide variety of factors, including: prior experience and job-related knowledge; education, training and certificates; current business needs; and market factors. The final salary or hourly wages offered may be outside of this range based on other reasons and individual circumstances.
Additional Compensation and Benefits . The total compensation package for this position may also include a full range of medical, financial, and/or other benefits (including 401(k) eligibility and various paid time off benefits, such as vacation, sick time, and parental leave), dependent on the position offered. The successful candidate may also be eligible to participate in National Life’s discretionary annual incentive programs, subject to the rules governing such programs. If hired, the employee will be in an "at-will position" and National Life reserves the right to modify base salary (as well as any other discretionary payment or compensation or benefit program) at any time, including for reasons related to individual performance, company or individual department/team performance, and market factors.
National Life is accepting applications for this role on an ongoing basis and the role remains open until filled.
Salary Pay Range $157,500 — $231,000 USD
National Life Group® is a trade name of National Life Insurance Company, Montpelier, VT – founded in 1848, Life Insurance Company of the Southwest, Addison, TX – chartered in 1955, and their affiliates. Each company of National Life Group is solely responsible for its own financial condition and contractual obligations. Life Insurance Company of the Southwest is not an authorized insurer in New York and does not conduct insurance business in New York. Equity Services, Inc., Member FINRA/SIPC, is a Broker/Dealer and Registered Investment Adviser affiliate of National Life Insurance Company. All other entities are independent of the companies of National Life Group.
Fortune 1000 status is based on the consolidated financial results of all National Life Group companies.
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National Life Group
1 National Life Dr
Montpelier, VT 05604