Senior Context and Semantics Engineering Director

Who you are

• 10+ years of progressive software engineering experience with a strong background in distributed systems, search architectures, data platforms, or AI infrastructure
• 5+ years of senior engineering leadership experience (Director level or above), with a proven track record of managing managers, scaling organizations (50+ engineers), and delivering mission-critical enterprise systems
• 3+ years of direct experience leading teams that build AI/ML infrastructure, semantic search engines, LLM orchestration layers, vector databases, or Knowledge Graphs
• Bachelor's or Master's degree in Computer Science, Engineering, Mathematics, or a related field (Ph.D. is a plus)
• Deep architectural understanding of how to bridge structured enterprise data with unstructured AI models (RAG architectures, embedding generation, chunking strategies, and semantic routing)
• Experience building and scaling Semantic Layers, Ontologies, or enterprise-scale Search/Retrieval systems (e.g., Elasticsearch, Pinecone, Milvus, Neo4j)
• Strong executive presence and communication skills, with the ability to translate complex AI and data concepts into clear business value for non-technical stakeholders
• Product-first mindset with a relentless focus on delivering high-reliability, low-latency infrastructure that powers real-time AI user experiences
• Experience operating within highly regulated data environments (Finance/HR) and implementing AI guardrails for enterprise-grade security
• Experience with the Workday platform and architecture is a strong plus

What the job involves

• The Data Cloud organization is at the forefront of Workday’s next major wave of innovation, driven by a bold mandate to build the industry’s first true Platform for Agents
• We are a high-energy, ambitious team that balances Workday's deep foundational expertise with fresh, forward-thinking perspectives to accelerate our pace of delivery and unlock massive new commercial value
• By leveraging Workday’s unique business context, trusted data, and identity guardrails, we are building the critical engine that will power the future of AI and agentic workflows across the enterprise
• As a team, we value organizational clarity, deep cross-functional collaboration, and rapid execution, working together to evolve our architecture and aggressively scale our impact in the market
• Join the Data Cloud organization, where we are building the intelligent foundation for Workday's next generation of AI Agents
• The Context and Semantics Engineering team is the brain trust responsible for making our AI "enterprise-aware
• " We build the semantic layers, knowledge graphs, and dynamic context engines that ground generative AI in real-world HR and Finance data
• By bridging the gap between raw enterprise data and large language models (LLMs), our team ensures that Workday’s autonomous agents can reason accurately, securely, and with deep contextual awareness at a global scale
• As the Senior Director of Context and Semantics Engineering, you will be a key engineering executive driving the vision, architecture, and delivery of the intelligence layer powering Workday’s AI Agents
• You will lead and scale an engineering organization to build highly scalable semantic engines, advanced RAG (Retrieval-Augmented Generation) pipelines, vector search infrastructure, and dynamic context-management systems
• Sitting at the critical intersection of data architecture and applied AI, you will ensure that our foundational models seamlessly understand and reason over complex, highly regulated enterprise workflows
• This is a high-visibility, high-impact role requiring a visionary leader who can scale organizations, navigate technical ambiguity, and deliver production-grade AI infrastructure that sets the industry standard for Enterprise AI
• Organizational Leadership: Build, scale, and mentor a world-class engineering organization dedicated to AI context, semantic architecture, and data orchestration
• Strategic Technical Vision: Define and execute the technical roadmap for Workday’s AI semantic layer, encompassing vector databases, knowledge graphs, enterprise ontologies, and semantic search capabilities
• AI & RAG Infrastructure: Lead the development of enterprise-grade RAG pipelines, ensuring LLMs are grounded in real-time, accurate, and tenant-isolated HR and Finance data to eliminate hallucinations and drive agentic reasoning
• Cross-Functional Executive Partnership: Collaborate tightly with VP/C-level stakeholders across AI/ML Engineering, Product Management, and Platform Architecture to seamlessly integrate context engines into the broader AI Agent Factory and Sana experiences
• Context & Memory Management: Drive the engineering design for agentic memory, state management, and conversational context, allowing our AI agents to seamlessly handle multi-turn, complex user workflows
• Responsible & Governed AI: Enforce rigorous technical standards for data privacy, RBAC (Role-Based Access Control), and compliance, ensuring that context fed to AI models strictly adheres to enterprise security boundaries
• Innovation & Scale: Evaluate and integrate cutting-edge AI data technologies and orchestration frameworks (e.g., advanced embedding models, GraphRAG, LlamaIndex, LangChain) to future-proof Workday's AI platform at massive scale