[Hiring] Director, AI Enablement @CSAA Insurance Group, a AAA Insurer

Role Description

The Director, AI Enablement is the enterprise leader responsible for defining and scaling how CSAA designs, enables, and adopts AI-powered ways of working. Leading the AI Enablement team within the AI Strategy & Enablement division, this role partners closely with Business Units, Business Innovation Owners, and the AI Hub to identify high-value opportunities for workflow redesign and transformation.

This is a player-coach role: a senior design and enablement leader who not only sets the vision, methods, standards, and quality bar for AI-enabled workflow change, but also stays close to the work by facilitating critical engagements, shaping complex design efforts, and helping move priority initiatives from discovery to pilot 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 built for impact. With strong systems thinking, service design, process design, and applied AI fluency, the Director translates enterprise AI ambition into measurable business value.

Qualifications

• 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.

Requirements

• Expert in Systems Thinking: Ability to map out how a business operates today and design a more efficient "future state" from scratch.
• Proven ability to build and refine complex operating models, service blueprints, and workflow maps.
• Deep understanding of how people and AI work together, designing for human oversight, trust, and error handling.
• Familiar with the "nuts and bolts" of AI systems, including intervention points and explainability.
• High proficiency in Figma, Miro, Visio, Lucidchart, and PowerPoint.
• Experience using AI tools to speed up research, prototyping, and the design process.

Benefits

• Total compensation package, annual bonus eligibility for most roles, 401(k) with a company match.
• Growth opportunities through partnerships with leaders and mentors.
• Remote-first culture with flexible workplace options.
• Inclusive and welcoming workplace environment.
• Commitment to sustainability and building resilient communities.