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.
About You
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.
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.
Workday prohibits taking adverse action against any candidate or employee for reporting a possible violation of this policy, requesting one or more work accommodations, exercising a privacy right, or cooperating in an investigation in accordance with applicable law. Any employee who retaliates against a candidate or employee for doing so may be subject to disciplinary action, up to and including termination of employment, to the fullest extent allowable under applicable law.
If you require a reasonable accommodation, you may email accommodations@workday.com, as far in advance as possible.
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