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Director, AI/ML Engineering

Location: 8116 - Midtown Office - 2220 W. Broad Street, Richmond, Virginia, 23220

CarMax is looking for a Director, AI/ML Engineering to lead and scale our artificial intelligence and ML capabilities. The AI/ML Engineering team powers next-generation AI solutions, including agentic AI systems, generative AI applications, and intelligent automation workflows, as well as core machine learning models such as vehicle pricing, personalized recommender on carmax.com, ad-bidding, and computer vision. This role is critical for our data and AI organization that provides scalable, reliable, and real-time models for best customer and associate experience.

We are looking for highly motivated individuals comfortable in a dynamic environment, with experience leading 50+ member teams (FTEs and contractors) and a solid track record in AI engineering, generative AI, agentic systems, and Machine Learning technology and platform.

The role requires the ability to step into multiple roles ranging from technical product manager, team mentor, and technical architect. This position is ideal for individuals with high accountability, developing future leaders, strong analytical skills, financial skills, a great communication style, a partnership mentality, and comfort turning facts into recommendations. The individual must be able to influence cross-functional business partners and effectively provide the Technology point-of-view on complex business issues to senior management, team members, and partners.

• Establish a technology vision and strategy for AI engineering — spanning agentic AI, generative AI, AI workflow automation, machine learning engineering, platform, and services, focusing on business outcomes tracked via key metrics, including overall financial management
• Define and execute a roadmap for Agentic AI systems — autonomous, multi-step AI agents that take action on behalf of customers and associates — integrating with existing ML and data science platforms
• Lead the adoption of generative AI technologies (including large language models and multimodal AI) to create differentiated customer experiences, associate tools, and internal productivity solutions
• Architect and govern AI workflow and automation pipelines that connect generative AI, agentic components, and traditional ML models into end-to-end intelligent business processes
• Lead and develop a 40+ member team (FTEs and contractors) responsible for feature engineering, agentic AI development, generative AI engineering, ML engineering, automation, and ML Ops for data science models
• Partner with Technology and Product leadership to define, drive, and deliver our AI/ML services to power the brand's omni-channel front-end experiences (website, mobile apps, in-store experience)
• Closely collaborate with data science and leadership to identify solutions, prioritize the roadmap and ensure delivery commitments
• Foster a product engineering culture within the team and establish best practices around discovery, prototyping, continuous and rapid testing, and learning, with a relentless focus on delivering customer value
• Establish responsible AI governance practices, including safety, bias mitigation, explainability, and compliance guardrails for generative and agentic AI systems
• Collaborate with other Product Managers and Architects on the design and integration with other products and/or technology platforms
• Collaborate with other key stakeholders (e.g., legal, security, etc.) to ensure product features meet all security and privacy requirements — with particular attention to data governance and safety requirements for generative AI and agentic systems
• Partner with Reliability Engineering team to ensure proper controls have been implemented for proactive monitoring of critical product features, availability, and stability

• Proven technology leader with experience building and managing highly engaged teams
• Passionate about AI engineering — including agentic AI, generative AI, and AI automation — as well as Data Science and Machine Learning engineering
• Persuasive communicator – able to explain complex or intangible concepts to stakeholders at all levels
• Good listener – weighs input from multiple perspectives when forming opinions and recommendations
• Collaborative and team-oriented work approach
• Experience gaining consensus among a large, diverse group of stakeholders
• Experience managing, training and mentoring others in Engineering methodologies and best practices
• Able to easily motivate and inspire team members, peers, stakeholders and executives
• Innovative; thinks beyond boundaries
• Analytical; solves problems at root cause and prioritizes effectively
• Continuous improvement mentality; never satisfied
• Comfortable speaking to large audiences and executives
• Flexible and open-minded; proactively seeks input from others
• Entrepreneurial drive and spirit; enjoys working in a fast-paced environment
• Handles constructive criticism with ease; adapts easily and efficiently to change

• BA/BS Degree required. Master's Degree a plus.
• 10+ years' experience in AI engineering, generative AI, or Data Science/Machine Learning or related engineering field. Experience with large language models (LLMs), agentic AI frameworks, and AI automation platforms is highly preferred. ML Ops experience is a plus.
• 5+ years' experience managing direct reports
• Experience with lean/agile development processes
• Hands-on familiarity with generative AI tools and platforms (e.g., OpenAI, Anthropic, AWS Bedrock, Azure OpenAI) and agentic frameworks (e.g., LangChain, AutoGen, or similar)
• Experience designing and deploying AI workflow automation solutions integrating LLMs, APIs, and traditional ML models into cohesive business processes

This role will be based out of the CarMax Home Office in Richmond, VA and Associates will work onsite four days per week.

Applicants must be currently authorized to work in the United States on a full-time basis. Sponsorship will not be considered for this specific role.

CarMax disrupted the auto industry by delivering the honest, transparent and high-integrity experience customers want and deserve. This innovative thinking around the way cars are bought and sold has helped us become the nation’s largest retailer of used cars, with over 250 locations nationwide.

Our amazing team of more than 25,000 associates work together to deliver iconic customer experiences. We help every associate grow their career and achieve their best, at work and in their community. We are recognized for our commitment to training and diversity and are one of the FORTUNE 100 Best Companies to Work For®.

CarMax is committed to bringing together people from different backgrounds and perspectives, providing employees with a safe, welcoming, and inclusive work environment.

CarMax is an equal opportunity employer, and all qualified candidates will receive consideration for employment without regard to age, race, color, religion, sex, sexual orientation, gender identity, genetic information, national origin, protected veteran status, disability status, or any other characteristic protected by law.

Upon an applicant's request, CarMax will consider reasonable accommodation to complete the CarMax Job Application.