Senior Director, Context and Semantics Engineering (AI)

Description

Your work days are brighter here.

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.

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.

About the Role

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.

Requirements

• Basic Qualifications:
• 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.
• Other Qualifications:
• 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.
• Workday Pay Transparency Statement
• 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 .
• Primary Location: USA.CA.Pleasanton
• Primary Location Base Pay Range: $281,600 USD - $422,400 USD
• Additional US Location(s) Base Pay Range: $231,800 USD - $422,400 USD
• Our Approach to Flexible Work
• With Flex Work, we’re combining the best of both worlds: in-person time and remote. Our approach enables our teams to deepen connections, maintain a strong community, and do their best work. We know that flexibility can take shape in many ways, so rather than a number of required days in-office each week, we simply spend at least half (50%) of our time each quarter in the office or in the field with our customers, prospects, and partners (depending on role). This means you'll have the freedom to create a flexible schedule that caters to your business, team, and personal needs, while being intentional to make the most of time spent together. Those in our remote "home office" roles also have the opportunity to come together in our offices for important moments that matter.
• Pursuant to applicable Fair Chance law, Workday will consider for employment qualified applicants with arrest and conviction records.
• Workday is an Equal Opportunity Employer including individuals with disabilities and protected veterans.
• Workday is committed to providing reasonable accommodations for qualified individuals during our application process, in order to perform one or more essential functions of their job, as well as regarding the use of AI tools for employment decision-making to any degree. Please see below for more details including how to request an accommodation as a qualified veteran, due to a disability or for religious reasons, or as otherwise provided under applicable law.
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