Senior Director, Context and Semantics Engineering (AI)

We’re obsessed with making hard work pay off, for our people, our customers, and the world around us. As a Fortune 500 company and a leading AI platform for managing people, money, and agents, we’re shaping the future of work so teams can reach their potential and focus on what matters most. The minute you join, you’ll feel it. Not just in the products we build, but in how we show up for each other. Our culture is rooted in integrity, empathy, and shared enthusiasm. We’re in this together, tackling big challenges with bold ideas and genuine care. We look for curious minds and courageous collaborators who bring sun-drenched optimism and drive. Whether you're building smarter solutions, supporting customers, or creating a space where everyone belongs, you’ll do meaningful work with Workmates who’ve got your back. In return, we’ll give you the trust to take risks, the tools to grow, the skills to develop and the support of a company invested in you for the long haul. So, if you want to inspire a brighter work day for everyone, including yourself, you’ve found a match in Workday, and we hope to be a match for you too.

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.

Responsibilities:

• 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. 

• 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.

The annualized base salary ranges for the primary location and any additional locations are listed below.  Workday pay ranges vary based on work location. As a part of the total compensation package, this role may be eligible for the Workday Bonus Plan or a role-specific commission/bonus, as well as annual refresh stock grants. Recruiters can share more detail during the hiring process. Each candidate’s compensation offer will be based on multiple factors including, but not limited to, geography, experience, skills, job duties, and business need, among other things. For more information regarding Workday’s comprehensive benefits, please click here.

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