Numeral Raises $35M to Automate Sales Tax with AI

Numeral raises $35M to automate sales tax with AI

Sam Ross launched Numeral after a practical frustration: running direct-to-consumer stores while traveling and wrestling with a suddenly complex sales tax landscape. The 2018 Supreme Court decision that required out-of-state businesses to collect sales tax turned a single-state headache into dozens of jurisdictions overnight.

Ross, a former Airbnb product manager, was nudged by Y Combinator partner Gustaf Alstromer to build a company that automates every step of sales tax management. On Thursday Numeral announced a $35 million Series B led by Mayfield, valuing the two-year-old startup at $350 million and coming six months after an $18 million Series A.

Numeral uses AI to handle structured, rule-based work: tracking tax law changes across more than 11,000 jurisdictions, monitoring tax-related mail, filing returns and remitting payments on behalf of clients. Because many tax rules are deterministic, Ross argues AI is well suited to minimize manual burden and reduce errors.

Numeral’s system encodes thousands of idiosyncratic rules (for example: how New York treats bagels depending on preparation) so businesses don’t have to. The company says revenue grew 3.5x over the last year and it now serves over 2,000 software and e-commerce clients, including EightSleep and Graza Olive Oil.

The market is competitive: startups like Anrok and Zamp and legacy incumbent Avalara are all focused on tax automation. Numeral highlights its international footprint—filing in smaller markets such as Tanzania and Kenya—as a key differentiator versus rivals and traditional CPA firms.

Why this matters: as DTC and SaaS businesses scale, tax compliance becomes an operational limiter — one that can trigger audits, late fees and fractured accounting. Automating these workflows turns a cost center into a predictable process, frees finance teams to focus on strategy, and lowers the risk of surprise liabilities.

• What AI handles in practice: tracking law changes, mapping taxes by SKU and jurisdiction, filing returns, paying liabilities, and managing tax notices
• Business benefits: fewer manual reconciliations, faster onboarding to new markets, and clearer audit trails for CPA partners

For technology and finance leaders, Numeral’s raise underscores a broader trend: compliance is becoming a data and automation problem, not just paperwork. That opens opportunities for platforms that can combine regulatory intelligence with reliable operational workflows.

QuarkyByte’s approach to similar challenges is to blend regulatory mapping, scenario simulation and integration design so organizations can measure the impact of compliance automation before they deploy. Whether you’re a fast-growing DTC brand, a SaaS platform expanding internationally, or a public company preparing for scaled audits, this is a space where analytics and pragmatic engineering deliver measurable ROI.