AI use among tax examiners and collectors, and revenue agents is little observed so far. Measured exposure for tax examiners and collectors, and revenue agents: 3% (little observed).

Share of this job’s tasks that AI is already used for at work, from real usage. It is not a forecast of job loss, and a low number means no use seen yet. Source: Anthropic Economic Index.

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About the job

US INDIRECT TAX LEAD

Location: Palo Alto, CA

Department: Finance (Tax)

Employment Type: Full time

Location Type: On-site

THE MISSION

Whop is on a mission to deliver everyone a sustainable income. Today, 50,000 people make money on Whop every month, and Whop users are on track to earn more than $5 billion this year. We are building the infrastructure for the next generation of internet entrepreneurs, and we will keep going until one billion people earn money on Whop every month.

THE ROLE

We are seeking a Senior Manager of US Sales and Use Tax to own Whop's US indirect tax function end to end and build it to scale.

This leader will own taxability, compliance, tax engine integration, tax positions, and audit defense across every US state and local jurisdiction where Whop operates as a marketplace facilitator, merchant of record, or direct seller of digital products and services. You will report to the Director of Tax and work closely with Engineering, Data, Legal, Product, and Finance.

WHAT YOU'LL OWN

- Own US sales and use tax compliance across all states and local jurisdictions, leveraging tax engines to monitor economic nexus and manage registrations, returns, remittances, exemption certificates, and reconciliations to the general ledger.

- Lead taxability studies for new products, and manage communications with tax engine providers and outside advisors to deliver well-supported tax analysis and positions.

- Own the integration of our tax engine with Whop's checkout and payments stack: product tax code mapping, sourcing and situs logic, exemption handling, and testing and validation of calculation results.

- Research, conclude on, and document tax positions, including Whop's tax role in each transaction flow, sourcing, bundling, and exposure analysis, in memos that withstand auditor and diligence scrutiny.

- Lead audit support and defense end to end: information document requests, sampling, workpapers, managed audit and VDA negotiations, and appeals where warranted.

- Quantify, reserve for, and remediate historical exposure through voluntary disclosure agreements and amnesty programs, and support ASC 450 reserve analysis.

- Partner with Engineering, Data, Legal, Product, and Finance so indirect tax implications are identified before products, pricing, or payment flows ship.

- Implement AI into individual steps of tax workflows, with appropriate controls, review, and documentation around each use.

- Build and maintain the policies, process narratives, controls, tools, and documentation that make the function repeatable and audit-ready.

WHAT WE'RE LOOKING FOR

- 12+ years of progressive US sales and use tax experience, with hands-on ownership of multistate compliance for a high-volume business; marketplace, payments, fintech, SaaS, or digital goods environment preferred.

- Extensive hands-on experience integrating a tax engine (such as Avalara, Vertex, Numeral, or similar) with checkout, billing, or ERP systems, including product tax code mapping, sourcing logic, and testing.

- Demonstrated experience leading taxability studies across digital products, SaaS, and services, and translating conclusions into system rules.

- A track record drafting tax position memos and exposure analyses, and defending them with state auditors, external advisors, and financial-statement auditors.

- Direct experience leading state sales and use tax audits from opening conference through close, including sampling negotiations, VDAs, and appeals.

- Big Four, in-house industry, or state tax authority auditor experience preferred.

- A track record of proactively using AI tools to refine or create new processes with demonstrated, significant gains in speed. Comfort working with SQL or large transaction datasets is a nice to have.

- The judgment to distinguish routine compliance decisions from positions requiring technical analysis, escalation, or outside counsel.

NICE-TO-HAVE EXPERIENCE

- JD, LLM in Taxation, or other law background.

- CPA or CMI (Certified Member of the Institute for Professionals in Taxation).

- Marketplace facilitator law, digital products taxation, or telecom and communications taxes.

HOW WE WORK

Whop is an in office company of about 100 people. Most of the team are former founders and entrepreneurs. We give people real agency, meaningful resources, and ownership of hard problems. We expect everyone to move fast, tell the truth, and improve every surface they touch.

- Be technical. Your work should be correct, grounded in fact, and able to withstand scrutiny

- Force function. Solve the root cause and make the system materially better

- Disagree then commit. Debate hard before a decision, then execute together

WHAT WHOP OFFERS

- Best in class cash compensation and meaningful equity

- A high trust environment with real ownership and direct access to company leaders

- Meals, wellness support, and office benefits designed for an in-person team

EQUAL OPPORTUNITY

Whop is an equal opportunity employer. We consider qualified applicants without regard to race, color, religion, sex, national origin, age, disability, veteran status, sexual orientation, gender identity, or any other status protected by law. If you need a reasonable accommodation during the hiring process, let us know.