Lead enterprise AI strategy, governance, and adoption; partner with business and technical leaders to prioritize use cases, measure value and risk, and guide secure, responsible implementation of AI solutions while managing and developing AI talent.
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.
- 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.
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.
- 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)
- 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
- 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
- Training & certification opportunities
- Tuition reimbursement
- Education bonuses
RLI Insurance Company Chicago, Illinois, USA Office
Chicago, United States
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