Director, AI/ML Engineering

CarMax is looking for a Director, AI/ML Engineering to lead and scale our artificial intelligence, and ML capabilities. The AI/ML Engineering team is the engineering arm powering 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, experience leading 50+ member teams (comprised of FTEs & contractors), and with a solid track record in AI engineering, generative AI, agentic systems, and Machine Learning technology and platform.

The role requires 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, 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.

Key Role Responsibilities

As a Director for AI/ML Engineering, you will:
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 & 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

Qualifications and Requirements
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

Education and/or Experience
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

Work Location and Arrangement: This role will be based out of the CarMax Home Office in Richmond, VA and Associates will work onsite 4 days per week.

Work Authorization: Applicants must