Tax Technology Lead (Sr. Manager)

OpenAI•San Francisco, CA

2d•Hybrid

About The Position

About the Team OpenAI Finance is responsible for ensuring the organization is set up for success in pursuit of its mission. OpenAI’s Tax and Trade team sits at the center of OpenAI’s global growth—shaping how cutting-edge AI products, partnerships, and infrastructure scale across borders while navigating complex tax, trade, and regulatory regimes. We operate as strategic operators, not just compliance experts, embedding early in product, finance, policy, and infrastructure decisions to manage risk, unlock incentives, and enable OpenAI to grow responsibly and competitively worldwide. As OpenAI’s products, monetization models, and global infrastructure expand, our tax systems must scale with the same rigor and reliability as our product architecture. The team partners deeply with Financial Engineering, Product Engineering, and Finance Systems to build a modern tax technology stack that enables accurate, real-time tax determination across OpenAI’s global business. About the Role We’re hiring a Tax Technology Lead (Vertex) to own the design, configuration, and long-term evolution of OpenAI’s tax engine architecture. You will play a foundational role in building one of the most advanced tax technology platforms in the industry - supporting global digital products, high-volume real-time checkout flows, and rapidly evolving monetization models across dozens of jurisdictions. This role is not simply maintaining a tax engine; it is designing the architecture that ensures tax determination is reliable, scalable, and deeply integrated into OpenAI’s product infrastructure. The person in this role will help define how tax operates as a production system across billing, payments, and financial reporting as OpenAI scales globally. In this role, you will lead the implementation and ongoing operation of Vertex as the core tax determination platform integrated into OpenAI’s checkout, billing, and financial systems. You will sit at the intersection of Tax, Financial Engineering, Product Engineering, and Finance Systems, ensuring that tax logic is accurate, scalable, auditable, and production-grade across OpenAI’s rapidly evolving global products and monetization models. This role is based in San Francisco, CA, and we use a hybrid work model of 3 days in the office per week.

Requirements

8+ years of relevant experience, including tax engine implementation or enterprise tax systems architecture.
Strong experience implementing or managing enterprise tax engines such as Verte or OneSource.
Deep familiarity with billing and ERP systems such as Oracle/ASP or NetSuite, and how tax data flows into financial reporting.
Comfort working directly with tax engine request and response data (XML / JSON).
Experience diagnosing tax engine errors, interpreting logs, and validating system data mappings across platforms.
Ability to operate within SDLC and change management frameworks with strong documentation and testing discipline.
Exceptional analytical and problem-solving skills, with the ability to diagnose complex systems issues and implement scalable solutions.
Strong communication skills and the ability to work effectively with engineers, tax professionals, finance leaders, and auditors.
Ability to partner with SaaS vendors (e.g., Vertex) to triage issues, escalate defects, and manage releases.
Strong analytical mindset with attention to detail; able to diagnose complex system issues and recommend scalable solutions.
Clear communicator who can work effectively with engineers, tax professionals, finance leaders, and auditors.

Nice To Haves

Experience working with different payment platforms, including checkout flows and marketplace models is a plus.
Experience working within SDLC / change-management frameworks, including documentation, approvals, and production support.

Responsibilities

Lead the end-to-end configuration and lifecycle management of the Vertex platform, including Vertex O Series, Vertex Edge, and future modules as OpenAI’s product footprint expands.
Design and maintain tax determination logic across real-time checkout flows, invoicing systems, and downstream financial reporting environments.
Ensure consistent tax engine behavior across environments (sandbox, staging, production) and aligned with product and billing architectures.
Custom Rule Development: Design and implement custom taxability drivers, material group logic, and Pre/Post-Tax Assist rules to handle complex business scenarios.
Entity Management: Create and customize new taxpayers (company codes) within the system for new business projects and acquisitions.
Work closely with Financial Engineering, Product Engineering, and Business Systems teams to define tax engine requirements, APIs, data contracts, and integration patterns.
Support checkout flows, including e-commerce scenarios, ensuring correct tax sourcing and liability determination.
Integrate Vertex outputs into billing and ERP environments, including GL mapping, jurisdictional reporting, reconciliation logic, e-invoicing requirements.
Manage tax engine configuration updates including taxability rules, product mappings, jurisdiction logic and exemptions.
Develop and execute robust testing frameworks including unit, integration, and regression testing to validate tax outcomes prior to deployment.
Participate in projects from early design through production deployment with a strong focus on accuracy, observability, and system reliability.
Design and maintain internal controls over tax systems to ensure data integrity and regulatory compliance.
Support tax audits by providing traceable tax data, reconciliations to ERP, and transaction-level documentation.
Monitor tax engine performance, identify anomalies, and proactively remediate system issues.
Build documentation and operational playbooks that make tax systems understandable, maintainable, and scalable across teams.
Serve as OpenAI’s internal subject-matter expert on tax technology architecture and systems behavior.