Director, Filings and Compliance

About NumeralHQ

Numeral is building the automation backbone for internet commerce — starting with the painful world of sales tax compliance. We handle everything from registration to remittance, delivering a white-glove service so e-commerce businesses can stay laser-focused on what they do best: growing their products, customers, and teams.

We’re one of the fastest-growing companies from Y Combinator’s W23 batch, backed by top-tier investors including Benchmark Capital. Our team has deep roots from the early days at Stripe, Airbnb, Notion, and other breakout companies — and now we’re bringing that same level of craft, speed, and ambition to a space that’s long overdue for reinvention.

Numeral is small but mighty. Growth is already borderline unmanageable — which means every hire we make now will directly shape the trajectory of the company. If you’re excited about joining as an early team member and want the kind of ownership that defines careers, we want to meet you.

Mission

Running an online business today means wearing a thousand hats — most of them not the reason founders started their company. Our mission is to eliminate the administrative and accounting burdens that distract businesses from doing what they love.

We’ve already helped hundreds of merchants avoid the headache of building giant finance teams just to manage tax compliance. Tomorrow, we’re scaling that impact even further: building the automation layer that lets internet businesses stay nimble, compliant, and future-proof.

About the role:

As the Director, Filings and Compliance, you’ll lead Numeral’s filings operations, overseeing a distributed team responsible for tax filings. You’ll work closely with leadership, the broader Ops team, product, and engineering to ensure accuracy, process discipline, and operational excellence across a team of approx. 50 (and growing!), including offshore contractors.

This role is a blend of operational leader, process architect, and people manager — ideal for someone with domain expertise in tax filings, a strong analytical mindset, and a passion for building scalable processes in a fast-growing startup environment.

Responsibilities:

• Lead and manage the filings team: Provide performance management, mentorship, and support to drive high-quality work and accountability.

• Scale processes: Maximize automation to reduce repetitive tasks so teams can focus on highest leverage opportunities. Develop playbooks, reporting structures, and metrics to improve throughput, quality, and visibility across the distributed team.

• Drive operational excellence: Design, implement, and refine workflows and processes across filings, customer support, and client teams to ensure accuracy, efficiency, and compliance.

• Ensure compliance and accuracy: Troubleshoot discrepancies in accounting or filings, and lead research projects on new regulatory rules.

• Partner cross-functionally: Work closely with product and engineering to communicate business issues, escalate risks, and contribute to operational solutions.

Qualifications:

• 9+ years of demonstrated domain expertise in U.S. tax filings; international experience a plus.

• Proven experience managing distributed teams, ideally in operations-heavy roles, with strong performance management and process implementation skills.

• Experience building scalable processes in a startup, high-growth environment or consulting firm.

• Experience in e-commerce, SaaS of Fintech is highly preferred.

• Familiarity with regulatory reporting systems, tools, or platforms used in finance and filings.

• Strong analytical and Excel/data skills, with the ability to troubleshoot complex discrepancies.

• Excellent communication skills — able to convey complex issues clearly to leadership and cross-functional teams.

• Critical thinker with a proactive problem-solving mindset, comfortable working in a fast-growing startup.

• Proven ability to work cross functionally with product and engineering.

Why Join Us?

• Be a core builder in an ambitious, globally minded startup.

• Learn hands-on how to scale international compliance systems.

• Work across functions and with leadership early in your career.

• Make a visible impact immediately through enablement and operational design.

• Please note that although this role does not require the candidate to be in office daily, we are ideally seeking someone with flexibility to periodically commute/travel to the SF-HQ.