Sam Ross, co-founder and CEO of Numeral, turned his frustrations with sales tax compliance into one of the fastest-growing startups in fintech. On September 18, 2025, the company announced Numeral raises $35M to automate sales tax with AI, bringing its valuation to $350 million.
Image Credits:Numeral
This new funding round, just six months after an $18M Series A, was led by Mayfield with support from Benchmark, Uncork Capital, Y Combinator, and Mantis—the venture firm co-founded by The Chainsmokers.
The pain point that sparked Numeral
Ross first came up with the idea while traveling the world after working as a product manager at Airbnb. To fund his travels, he launched small e-commerce brands, including an online jewelry store and a vitamin DTC site.
While he enjoyed the flexibility, he was constantly frustrated by the complexity of handling sales tax. The rules became even tougher in 2018, when the Supreme Court ruled that online businesses must collect and pay taxes in every state where customers are located—not just where the business had a physical presence.
Suddenly, Ross had to manage taxes across 40+ states. “That was painful,” he recalled.
From Y Combinator to a $350M valuation
In 2023, Ross joined Y Combinator, encouraged by his former Airbnb boss Gustaf Alstromer. His goal: build an AI-powered solution that automates every step of sales tax compliance.
Just two years later, Numeral has become a trusted platform for e-commerce and SaaS companies navigating tax rules across more than 11,000 jurisdictions. The software handles everything—tracking new laws, organizing tax documents, filing returns, and even making payments.
Why AI is a game-changer for sales tax
Unlike traditional software, Numeral’s AI is designed to act like a human tax accountant, learning and adapting to changing regulations. This reduces the need for manual oversight and helps businesses stay compliant without drowning in paperwork.
With Numeral raises $35M to automate sales tax with AI, the company plans to scale its technology, expand its customer base, and push further into automating global tax compliance.
What’s next for Numeral
Ross and his team are betting big that AI will transform how businesses manage taxes worldwide. With $35M in fresh capital, Numeral is positioned to become the go-to solution for companies tired of navigating complex tax codes.
For startups, DTC brands, and SaaS businesses, this could be the end of tax compliance headaches—and the start of smarter, AI-driven automation.
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