Director, AI Enablement - Remote

CSAA Insurance Group, a AAA Insurer•California - Home Teleworkers, IN

3d•Remote

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. Every employee shapes our mission. We build innovative, human-centered solutions that help AAA members prevent, prepare for, and recover from life's uncertainties. You will join a collaborative, inclusive culture where your strengths have room to grow and your ideas can drive real impact. Step into a role where you can contribute to our shared success through meaningful work. We are actively hiring for a Director, AI Enablement – Remote. Your Role: 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.

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.
High proficiency in Figma, Miro, Visio, Lucidchart, and PowerPoint.
Experience using AI tools to speed up research, prototyping, and the design process.
Applicants must have authorization to work indefinitely in the US. Please do not apply for this role if at any time (now or in the future) you will need immigration support (i.e., H-1B, TN, STEM OPT Training Plans, etc.).

Nice To Haves

Previous experience navigating the complexities of insurance or financial services.
A background in organizational psychology or change management with a track record of driving large-scale adoption of new ways of working.
Practical application of Lean Six Sigma, service design, or similar transformation methodologies.
Experience managing pilot programs, workflow innovation labs, or decision-support systems.
A history of building reusable playbooks, design frameworks, or internal enablement assets that serve the broader enterprise.
Experience launching or leading professional Communities of Practice to foster knowledge sharing.
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.