Episode #8
Andrew Rea & Aman Samra Speak C-Suite
In this episode of Speaking C-Suite, hosts Johnnie Walker (Rooled) and David Hemenway (The Angel Nest) sit down with Andrew Rea, founder and CEO of Taxwire, and Aman Samra, VP of Finance at Spellbook, to talk through how growing companies handle sales tax compliance across thousands of jurisdictions. Andrew traces the shift back to the 2018 Supreme Court ruling that removed the physical presence requirement for sales tax, combined with remote hiring creating nexus in new states and software increasingly becoming taxable. California will start taxing software for the first time starting January 1. Taxwire now files and remits around $100 million a year in sales tax for its customers, pairing a tax engine with an in-house research team of four people covering roughly a dozen industries. Aman shares how he evaluates compliance vendors as Spellbook scaled from the Canadian and US markets to over 100 countries in three years. He set a $10 million ARR threshold for bringing in a dedicated sales tax platform, and explains why he passed on vendors charging a percentage of revenue in favor of a flat, predictable cost. The conversation also covers Taxwire's free nexus exposure tool for accounting firm partners like Rooled, letting controllers flag a client's exposure before it becomes a problem. Key topics include: The 2018 Supreme Court ruling that changed how sales tax nexus works Why software taxability is expanding state by state Setting a revenue threshold for when to bring in a compliance platform Evaluating vendors on service model instead of percentage-of-revenue pricing How large language models are used to structure tax law into a rules engine Building a tax research team that supports a dozen industries Using a free nexus tool to catch exposure before it becomes historical liability Andrew Rea's path from Columbus, Ohio to founding Taxwire Speaking C-Suite is supported by Aleph, Rillet, Tabs, and Taxwire. This episode also features Taxwire's own founder as a guest. Thank you for helping make this series possible. Subscribe on YouTube and follow Speaking C-Suite for conversations with operators shaping the future of finance and growth.


