E64: Numeral CEO Sam Ross: Why I Abandoned My Profitable Business to Raise $50M for Something "Boring"
About this episode
Sasha Orloff interviews Sam Ross about his decision to raise $50M for an AI-driven sales tax automation platform.
In this episode, Sasha Orloff sits down with Sam Ross, co-founder and CEO of Numeral and former product leader at Teespring and Airbnb, about raising Series B funding from Mayfield (following Benchmark's Series A and Uncork's seed) to build what he calls "the most boring AI company"—an end-to-end sales tax automation platform that uses AI to eliminate the manual burden of multi-state and international tax compliance for e-commerce and SaaS businesses, transforming a traditionally services-heavy industry into a fully automated solution that handles everything from nexus analysis and registration to filings and government correspondence. -- SPONSORS: Notion Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at https://notion.com/startups/puzzle Puzzle 📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an…
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