IT Director - AI at RLI in Chicago, IL

Job description

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