Director, AI Enablement - Remote

CSAA Insurance Group, a AAA Insurer • Indianapolis, IN

1d • Hybrid

About The Position

CSAA Insurance Group (CSAA IG), a AAA insurer, is one of the leading personal lines property and casualty insurance groups in the United States. The Director, AI Enablement is the enterprise leader responsible for defining and scaling how CSAA designs, enables, and adopts AI-powered ways of working. This role leads the AI Enablement team within the AI Strategy & Enablement division and partners closely with Business Units, Business Innovation Owners, and the AI Hub to identify high-value opportunities for workflow redesign and transformation. It is a player-coach role, involving setting the vision, methods, standards, and quality for AI-enabled workflow change, as well as facilitating critical engagements, shaping complex design efforts, and moving priority initiatives from discovery to scalable adoption. The Director coaches direct reports, strengthens team capability, and ensures workflow design, human-AI interaction, operating model design, facilitation, and enablement assets are practical, responsible, and impactful. The role requires strong systems thinking, service design, process design, and applied AI fluency to translate enterprise AI ambition into measurable business value.

Requirements

• 10+ years of experience building systems, workflows, and large-scale digital transformations, with a clear track record of measurable impact
• 5+ years of leadership experience, whether managing direct reports or steering large-scale, high-stakes company initiatives
• Bachelor’s degree or equivalent practical experience in a related field
• Expert in Systems Thinking: You can map out how a business operates today and design a more efficient "future state" from scratch
• Process Mastery: Proven ability to build and refine complex operating models, service blueprints, and workflow maps
• Practical Outputs: You don’t just "design"; you produce clear, actionable maps and recommendations that teams can actually follow
• Human-Centered AI: Deep understanding of how people and AI work together. You know how to design for human oversight, trust, and error handling
• Technical Logic: Familiar with the "nuts and bolts" of AI systems, such as when a human should intervene, how to handle low-confidence AI outputs, and how to make AI decisions explainable
• AI Fluency: You understand what AI can (and cannot) realistically do, allowing you to guide teams toward solutions that are actually buildable
• Facilitation: A pro at leading workshops—especially with executives—moving people past "brainstorming" and toward hard decisions and commitments
• Storytelling: You can take complex data and turn it into a clear, visual narrative that helps senior leaders make informed choices
• Collaboration: Skilled at working with technical, data, and legal teams to get everyone on the same page, even when you aren't their boss
• Mentorship: A passion for coaching other designers and setting high standards for the team’s work
• Design & Strategy Tools: High proficiency in Figma, Miro, Visio, Lucidchart, and PowerPoint
• AI Integration: Experience using AI tools to speed up research, prototyping, and the design process

Nice To Haves

• Regulated Industry Expertise: Previous experience navigating the complexities of insurance or financial services
• Behavioral Change: A background in organizational psychology or change management with a track record of driving large-scale adoption of new ways of working
• Process Excellence: Practical application of Lean Six Sigma, service design, or similar transformation methodologies
• Innovation & Experimentation: Experience managing pilot programs, workflow innovation labs, or decision-support systems
• Scalable Frameworks: A history of building reusable playbooks, design frameworks, or internal enablement assets that serve the broader enterprise
• Community Building: Experience launching or leading professional Communities of Practice to foster knowledge sharing
• Advanced Credentials: Master’s degree in Human-Computer Interaction (HCI), Organizational Psychology, or Design Strategy, or specialized certifications in Systems Thinking and Human-Centered Design

Responsibilities

• Shape the enterprise AI enablement approach
• Define and evolve CSAA's AI enablement operating model, including standards, templates, design principles, and reusable artifacts
• Establish methods and quality standards for AI-enabled workflow redesign, human-AI interaction, service blueprinting, operating model design, and value realization
• Drive a strong point of view on future ways of working, anticipating how AI will reshape roles, workflows, decisioning, controls, and team structures
• Lead AI-enabled workflow, systems, and operating model design
• Partner with Business Units and the AI Hub to identify high-value workflow opportunities and prioritize where redesign can create measurable impact
• Lead current-state assessment and future-state design, mapping workflows, services, decision points, roles, and handoffs across the end-to-end system
• Oversee the creation of service blueprints, workflow maps, process flows, journey maps, operating model designs, and other artifacts that make future-state work tangible and actionable
• Define how humans and AI should work together across workflows, including where AI should automate, augment, or escalate to human judgment
• Set direction for human-in-the-loop patterns such as intervention triggers, confidence thresholds, review paths, exception handling, override mechanisms, explainability, and feedback loops
• Partner with technical, data, product, and governance teams to shape prototypes, pilots, and scalable production solutions
• Establish and lead the enterprise AI Community of Practice
• Define the CoP charter, operating model, and cadence, ensuring it drives outcomes, not just attendance
• Facilitate cross-BU collaboration to reduce duplication, share vendor and tool learnings, and align on common workflows, standards, and integration patterns
• Create a structured learning loop to capture insights from pilots and deployments, convert them into repeatable patterns, and scale them across teams
• Strengthen enterprise capability by creating forums, practices, and assets that help teams design and adopt AI-enabled ways of working
• Measure enterprise AI value and effectiveness
• Establish and own enterprise reporting on AI value, workflow impact, adoption, and enablement effectiveness, translating insights into clear recommendations
• Publish a clear reporting cadence that informs portfolio prioritization, investment decisions, and where enablement should focus next to increase performance lift
• Help define meaningful success measures for workflow redesign, human-AI collaboration, service improvement, and organizational adoption
• Team leadership and capability building
• Lead, coach, and develop talent, including roles focused on systems design, facilitation, workflow transformation, and community of practice development
• Set the quality bar for design craft across the team, including workflow architecture, blueprinting, human-AI interaction design, executive storytelling, and consultative partnership
• Foster a culture of experimentation, practical delivery, and continuous learning

Benefits

• Total compensation package
• Annual bonus eligibility for most roles
• 401(k) with a company match
• Career growth opportunities
• Flexible Workplace (remote-first culture, Home-Flex roles, flexibility to work from various locations including CSAA offices)
• Inclusive and welcoming workplace
• Professional development
• Corporate responsibility
• Diversity
• Wellness

What This Job Offers

• Job Type: Full-time
• Career Level: Director