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Director, AI Enablement - Remote

May 2, 2026

<h2>Job Title</h2>Director, AI Enablement - Remote<h2>Location</h2>California - Home Teleworkers<h2>Additional Locations</h2>Arizona - Home Teleworkers<h2>Job Information</h2>CSAA Insurance Group (CSAA IG), a AAA insurer, is one of the leading personal lines property and casualty insurance groups in the United States. Here, 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 – RemoteYour 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.Your Work: Shape the enterprise AI enablement approach<ul><li>Define and evolve CSAA's AI enablement operating model, including standards, templates, design principles, and reusable artifacts.</li><li>Establish methods and quality standards for AI-enabled workflow redesign, human-AI interaction, service blueprinting, operating model design, and value realization.</li><li>Drive a strong point of view on future ways of working, anticipating how AI will reshape roles, workflows, decisioning, controls, and team structures</li></ul>Lead AI-enabled workflow, systems, and operating model design<ul><li>Partner with Business Units and the AI Hub to identify high-value workflow opportunities and prioritize where redesign can create measurable impact.</li><li>Lead current-state assessment and future-state design, mapping workflows, services, decision points, roles, and handoffs across the end-to-end system.</li><li>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.</li><li>Define how humans and AI should work together across workflows, including where AI should automate, augment, or escalate to human judgment.</li><li>Set direction for human-in-the-loop patterns such as intervention triggers, confidence thresholds, review paths, exception handling, override mechanisms, explainability, and feedback loops.</li><li>Partner with technical, data, product, and governance teams to shape prototypes, pilots, and scalable production solutions.</li></ul>Establish and lead the enterprise AI Community of Practice<ul><li>Define the CoP charter, operating model, and cadence, ensuring it drives outcomes, not just attendance.</li><li>Facilitate cross-BU collaboration to reduce duplication, share vendor and tool learnings, and align on common workflows, standards, and integration patterns.</li><li>Create a structured learning loop to capture insights from pilots and deployments, convert them into repeatable patterns, and scale them across teams</li><li>Strengthen enterprise capability by creating forums, practices, and assets that help teams design and adopt AI-enabled ways of working.</li></ul>Measure enterprise AI value and effectiveness<ul><li>Establish and own enterprise reporting on AI value, workflow impact, adoption, and enablement effectiveness, translating insights into clear recommendations.</li><li>Publish a clear reporting cadence that informs portfolio prioritization, investment decisions, and where enablement should focus next to increase performance lift.</li><li>Help define meaningful success measures for workflow redesign, human-AI collaboration, service improvement, and organizational adoption.</li></ul>Team leadership and capability building<ul><li>Lead, coach, and develop talent, including roles focused on systems design, facilitation, workflow transformation, and community of practice development.</li><li>Set the quality bar for design craft across the team, including workflow architecture, blueprinting, human-AI interaction design, executive storytelling, and consultative partnership.</li><li>Foster a culture of experimentation, practical delivery, and continuous learning.</li></ul>Required Experience & Skills Leadership & Background<ul><li>10+ years of experience building systems, workflows, and large-scale digital transformations, with a clear track record of measurable impact.</li><li>5+ years of leadership experience, whether managing direct reports or steering large-scale, high-stakes company initiatives.</li><li>Educational Background: Bachelor’s degree or equivalent practical experience in a related field.</li></ul>Design & Systems Architecture<ul><li>Expert in Systems Thinking: You can map out how a business operates today and design a more efficient "future state" from scratch.</li><li>Process Mastery: Proven ability to build and refine complex operating models, service blueprints, and workflow maps.</li><li>Practical Outputs: You don’t just "design"; you produce clear, actionable maps and recommendations that teams can actually follow.</li></ul>AI & Automation Strategy<ul><li>Human-Centered AI: Deep understanding of how people and AI work together. You know how to design for human oversight, trust, and error handling.</li><li>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.</li><li>AI Fluency: You understand what AI can (and cannot) realistically do, allowing you to guide teams toward solutions that are actually buildable.</li></ul>Communication & Influence<ul><li>Facilitation: A pro at leading workshops—especially with executives—moving people past "brainstorming" and toward hard decisions and commitments.</li><li>Storytelling: You can take complex data and turn it into a clear, visual narrative that helps senior leaders make informed choices.</li><li>Collaboration: Skilled at working with technical, data, and legal teams to get everyone on the same page, even when you aren't their boss.</li><li>Mentorship: A passion for coaching other designers and setting high standards for the team’s work.</li></ul>Technical Toolkit<ul><li>Design & Strategy Tools: High proficiency in Figma, Miro, Visio, Lucidchart, and PowerPoint.</li><li>AI Integration: Experience using AI tools to speed up research, prototyping, and the design process.</li></ul>What would make us excited about you?<ul><li>Regulated Industry Expertise: Previous experience navigating the complexities of insurance or financial services.</li><li>Behavioral Change: A background in organizational psychology or change management with a track record of driving large-scale adoption of new ways of working.</li><li>Process Excellence: Practical application of Lean Six Sigma, service design, or similar transformation methodologies.</li><li>Innovation & Experimentation: Experience managing pilot programs, workflow innovation labs, or decision-support systems.</li><li>Scalable Frameworks: A history of building reusable playbooks, design frameworks, or internal enablement assets that serve the broader enterprise.</li><li>Community Building: Experience launching or leading professional Communities of Practice to foster knowledge sharing.</li><li>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.</li></ul>Why Choose a Career at CSAA IG?At CSAA IG, we are a mission-driven organization proudly committed to empowering our members, our employees, and our communities to thrive. Recognition: We offer a total compensation package, annual bonus eligibility for most roles, 401(k) with a company match, and so much more! Read more about what we offer and what it is like to be a part of our dynamic team at <a href="https://careers.csaainsurance.aaa.com/us/en/benefits" target="_blank" rel="noopener noreferrer">https://careers.csaainsurance.aaa.com/us/en/benefits</a>.Career Growth: We believe in growth for everyone. Here at CSAA IG, leaders and mentors partner with employees to align interests, unlock development opportunities, and support long‑term success.Flexible Workplace: We embrace a remote-first culture through our Flexible Workplace. Most employees hold Home-Flex roles, working primarily from home, often with the flexibility to work from various locations including CSAA offices. Our flexible workplace empowers you to balance remote work with intentional in‑person moments that deepen connection and collaboration.Inclusion and Belonging: An inclusive and welcoming workplace is the cornerstone of our success. By fostering an environment where people feel valued and heard, we deepen our ability to understand and meet the unique needs of our members. This strengthens innovation and enhances our products and services, giving us a competitive edge in the market.Sustainability: As climate change leads to more frequent and severe weather events, we are taking bold action to build more resilient communities and reduce our environmental impact. Submit your application to be considered. We communicate via email, so check your inbox and/or your spam folder to ensure you don’t miss important updates from us.CSAA is committed to providing reasonable accommodations to qualified applicants and employees with disabilities or other limitations. If you would like to request an accommodation to participate in the job application or interview process, please contact <a href="mailto:TalentAcquistion@csaa.com" target="_blank" rel="noopener noreferrer">TalentAcquistion@csaa.com</a>If you apply and are selected to continue in the recruiting process, we will schedule a preliminary call with you to discuss the role and will disclose during that call the available salary/hourly rate range based on your location. Factors used to determine the actual salary offered may include location, experience, or education.CSAA does not provide visa sponsorship for this role. 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.).CSAA Insurance Group is an equal opportunity employer..

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...