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.
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SPONSORS:
Notion
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Puzzle
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RECOMMENDED IN THIS EPISODE:
https://www.linkedin.com/in/sambross/
https://www.numeral.com
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X/SOCIAL:
@SpamRoss (Sam)
@sashaorloff (Sasha)
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TIMESTAMPS:
(00:00) Preview
(00:49) Intro
(01:22) Guest Introduction: Sam Ross
(01:44) Most boring AI company
(03:54) AI and sales tax
(06:08) Origin story and early challenges
(10:56) Building the business and first customers
(13:14) Sponsors: Notion | Puzzle
(14:36) Sales tax compliance and solutions
(17:12) Automating mail and customer engagement
(18:24) E-commerce and tax compliance challenges
(19:40) Marketplace tax exposure issues
(22:15) Government complexities and physical mail
(23:54) Founding story and funding journey
(30:55) AI innovations in tax compliance
(33:11) Future of AI and browser automation
(34:33) Wrap
