About Us 

We’re not like other insurance companies. From our specialty products to our business model, our culture to our results — we’re different. Different is who we are, and how we work, interact, deliver and succeed together. Creating a different and better insurance experience doesn’t just happen. It takes focus and a shared passion for going beyond the expected to forge relationships and deliver care that makes a difference. This approach rises from and is supported by our talented, ethical and smart team of employee owners united around a single purpose: to work alongside our customers and partners when they need us, in unexpected ways, with exceptional results. Apply today to make a difference with us. 

RLI is a Glassdoor Best Places to Work company with a strong, successful background. For decades, our financial track record has been stellar — a testament to our culture and validation of our reputation as an excellent underwriting company.

Position Purpose

Under general direction, leads the strategy, governance, operating model, and enterprise adoption of artificial intelligence, partnering with Business and Technology leaders to identify and deliver responsible AI solutions that create measurable value. Serves as a key liaison across business, technical, risk, and external partners, providing the expertise needed to evaluate emerging capabilities, communicate opportunities and limitations, and guide implementation across the organization.

The Director, IT - AI is accountable for developing the enterprise AI roadmap, strengthening engagement with business areas, increasing adoption and effective use of AI solutions, and establishing appropriate measures of value, risk, and performance. The scope will include leading AI engineers and other technical professionals directly or through influence, delivering complex technical initiatives, building cross-functional alignment, and influencing senior stakeholders.

Principal Duties & Responsibilities

• Works with Business and Technology partners to develop, communicate, and execute the enterprise AI vision, strategy, roadmap, governance framework, and operating model.
• Builds trusted relationships across the organization to understand business needs, identify meaningful AI opportunities, and prioritize use cases based on value, feasibility, scalability, risk, and strategic alignment.
• Establishes goals, metrics, and reporting practices to measure AI adoption, solution performance, business outcomes, risk, and return on investment.
• Communicates complex AI concepts, opportunities, risks, and limitations clearly to technical and nontechnical audiences, helping leaders make informed decisions about which initiatives to pursue, modify, delay, or decline.
• Partners with architecture, data, cybersecurity, legal, compliance, and other control functions to ensure AI solutions are secure, responsible, sustainable, and aligned with enterprise standards.
• Evaluates emerging AI technologies, vendors, platforms, and approaches while promoting consistency, reuse, scalability, and appropriate strategic control.
• Provides leadership across a portfolio of AI initiatives by helping teams prioritize work, resolve barriers, manage dependencies, and maintain focus on measurable enterprise value.
• Leads technical professionals directly or through influence and supports staffing, talent development, performance management, and succession planning as the AI function grows.
• Promotes a culture of continuous learning and development by remaining up to date of education and learning across IT, AI, and the broader enterprise, including awareness of emerging capabilities, responsible use, governance expectations, practical applications, and evolving risks.

Education & Experience

• Typically requires a bachelor’s degree in Computer Science, Information Technology, Engineering, Data Science, Business, or a related field.
• 7+ years of progressively responsible experience in technology, artificial intelligence, enterprise architecture, data, digital transformation, or a related discipline.
• Demonstrated experience developing or leading an enterprise AI strategy, AI adoption program, or portfolio of AI-enabled solutions.
• Experience with generative AI, large language models, cloud-based AI platforms, machine learning, intelligent automation, or related technologies.
• Experience leading technical professionals directly or through influence.
• Formal people-management experience is preferred but not required when the candidate has demonstrated leadership of teams, programs, or technical communities.
• Experience in insurance, financial services, or another regulated industry is preferred but not required.
• [OR] equivalent level of education and experience.

Knowledge, Skills, & Competencies

Must Have

• Strong knowledge of artificial intelligence concepts, including generative AI, large language models, AI-enabled applications, and enterprise integration considerations.
• Ability to develop and execute an enterprise AI strategy that connects technical capabilities to business needs and measurable outcomes.
• Strong understanding of the opportunities, limitations, risks, and operational requirements associated with implementing AI in a complex enterprise environment.
• Ability to evaluate and prioritize AI use cases based on business value, feasibility, scalability, risk, and strategic alignment.
• Demonstrated ability to build trusted relationships with senior executives, business leaders, architects, engineers, and subject-matter experts.
• Ability to translate complex technical concepts into clear business language.
• Strong strategic planning, prioritization, analytical judgment, and portfolio-management skills.
• Ability to lead through ambiguity and adapt strategy as technologies, regulations, market conditions, and organizational needs evolve.
• Strong presentation, facilitation, communication, and stakeholder-management skills.
• Ability to motivate and guide highly technical, independent professionals.

Nice to Have

• Knowledge of AI governance, responsible AI, data privacy, cybersecurity, regulatory considerations, model risk, and human oversight.
• Understanding of software development, enterprise architecture, cloud platforms, data ecosystems, and technology delivery practices.
• Experience in insurance, financial services, or another regulated industry.
• Formal people-management experience.
• Experience with machine learning, intelligent automation, prompt-based solutions, or multiple enterprise AI platforms.

Compensation Overview

The base salary range for the position is listed below. Please note that the base salary is only one component of our robust total rewards package at RLI. The salary offered will take into account a number of factors including, but not limited to, geographic location, experience, scope & responsibilities of the role, qualifications/credentials, talent availability & specialization, as well as business needs. The below range may be modified in the future.

Base Pay Range

Total Rewards

At RLI, we're all owners. We hire the best and the brightest employees and allow them to share in the company's success through our Total Rewards. With the Employee Stock Ownership plan at its core, the Total Rewards program includes all compensation, benefits and perks that come with being an RLI employee.

Financial Incentives

• Annual bonus plans

• Employee stock ownership plan (ESOP)

• 401(k) — automatic 3% company contribution

• Annual 401k and ESOP profit-sharing contributions (Up to 15% of eligible earnings)

Work & Life

• Paid time off (PTO) and holidays

• Paid volunteer time off (VTO) to support our communities

• Parental and family care leave

• Flexible & hybrid work arrangements

• Fitness center discounts and free virtual fitness platform

• Employee assistance program

Health & Wellness

• Comprehensive medical, dental and vision benefits

• Flexible spending and health savings accounts

• 2x base salary for group life and AD&D insurance

• Voluntary life, critical illness, & accident insurance for purchase

• Short-term and long-term disability benefits

Personal & Professional Growth

RLI encourages its employees to pursue professional development work in insurance and job-related areas. We make a commitment to employees to provide educational opportunities that help them enhance their skills and further their career advancement. RLI fosters a true learning culture and encourages professional growth through insurance courses, in-house training and other educational programs. RLI covers the cost for most programs and employees typically earn a bonus upon successful completion of approved courses and certifications. Our personal and professional growth benefits include:

• Training & certification opportunities

• Tuition reimbursement

• Education bonuses

Diversity & Inclusion

Our goal is to attract, develop and retain the best employee talent from diverse backgrounds while promoting an environment where all viewpoints are valued and individuals feel respected, are treated fairly, and have an opportunity to excel in their chosen careers. We actively support, and participate in, initiatives led by the American Property Casualty Insurance Association that aim to increase diversity in the insurance industry. Cultivating an exceptional and diverse workforce to deliver excellent customer service reinforces our culture and is a key to achieving superior business results.

RLI is an equal opportunity employer and does not discriminate in hiring or employment on the basis of race, color, religion, national origin, citizenship, gender, marital status, sexual orientation, age, disability, veteran status, or any other characteristic protected by federal, state, or local law.