Senior Director, Data Platform and AI - Oyster

About Oyster

Oyster is a global employment platform that enables companies to hire, pay, and care for brilliant people anywhere in the world. Fully distributed across 60+ countries since 2020, Oyster is a B Corp-certified company recognized for creating a high-performing remote culture.

The Role

This position is fully remote (working within UTC -7 to UTC +3). As the Senior Director, Data Platform and AI, you will own the technical infrastructure and strategic direction to transform Oyster into an AI-native global platform. Part of the Senior Tech Leadership Team, this role unites data platforms, product analytics pipelines, knowledge management, and advanced automation frameworks.

You will lead the organizational and technical shift to transition AI initiatives from isolated experimentation into centralized production systems. You will optimize internal workflows, modernize knowledge architecture, directly enhance the customer-facing product, lower cost-to-serve, and empower teams across Oyster to scale their own AI use productively.

Key Responsibilities

• Drive the Company-Wide AI Agenda: Scale local AI initiatives into centralized production systems that generate measurable business value.
• Execute Cross-Functional Transformations: Transition AI usage from siloed automation projects to broad operational business shifts.
• Cross-Functional Collaboration: Partner with Product, Engineering, and Operations leaders to embed AI into customer-facing products, internal workflows, and core processes.
• Technical Authority: Serve as the ultimate technical authority for data and AI infrastructure, making architectural decisions across MLOps pipelines, LLM orchestration, and distributed data systems.
• Corporate Data Platform: Oversee the development of a scalable data platform serving as the foundation for all AI and machine learning capabilities.
• Knowledge Architecture: Transform internal knowledge structures by converting unstructured data into intelligent, searchable, and actionable assets.
• Optimize Data Pipelines: Re-build and evolve company-wide data structures and connectivity pipelines to support AI models efficiently while reducing cost-to-serve.
• Standards and Governance: Set company-wide tooling standards, technical quality guardrails, and engineering best practices for embedded AI specialists.
• Decentralized Support: Support key local solutions built by business-unit specialists, providing centralized platform support and infrastructure.
• Compliance and Ethics: Ensure global AI initiatives strictly adhere to data privacy, security, and ethical compliance standards.
• Enablement & Training: Educate and empower global teams to scale AI usage safely and productively, partnering with People and Operations to upskill specialists into power-users.
• Change Management: Drive organizational change management efforts to shift company culture from traditional manual processes to AI-assisted operations.

Core Requirements

• Demonstrated passion for AI and concrete experience driving internal organizational change to reshape employee workflows and habits.
• Proven track record operating within a service-delivery or complex operational business model where data strategy directly impacts real-world workflows.
• Heavy background in data engineering, distributed systems development, platform services infrastructure, or system architecture.
• Deep technical track record in distributed data systems, MLOps pipelines, and LLM orchestration frameworks.
• Success building, testing, and scaling complex asynchronous data structures, machine learning routing layers, or high-volume API integrations.
• Holistic architectural perspective across technical platforms, business processes, and human teams to optimize end-to-end workstreams.
• Demonstrated ability to guide non-technical teams through operational transitions and drive adoption of AI-assisted daily workflows.
• Comprehensive familiarity with model validation systems, technical anomaly logging, data pipeline health metrics, and automated governance frameworks.
• Reliable home internet connection and fluency in written and spoken English.

Preferred Qualifications

• Experience architecting semantic search solutions, internal retrieval-augmented generation (RAG) layers, or multi-tenant customer data structures from scratch.

Benefits & Work Culture

• Work from anywhere: Fully remote environment with location flexibility.
• Paid time off: 40 days off per year (including holidays and vacation).
• Mental health support: Access to Plumm mental well-being services.
• Wellbeing allowance: Monthly wallet stipend for wellness expenses via ThanksBen.
• Parental leave: At least 3 months' paid leave for all new parents, with job protection up to 12 months.
• WFH stipend: Financial support for laptop and home office setup.