Outdated by Design: The Case for Reimagining Sales Tax

Outdated by Design: The Case for Reimagining Sales Tax

July 1, 2026 · 38 min · Episode 139

About this episode

The episode discusses the complexities of sales tax compliance and the need for a reimagined approach to the system.

Aprio's Meredith Smith and Judy Vorndran continue their conversation with Stephanie Lipinski Galland, Principal at Miles & Stockbridge, on why sales tax compliance remains so difficult six years after Wayfair—and why the system itself may be overdue for a rethink. Together they explore the human cost of navigating thousands of jurisdictions and constant change, and what it really takes to help clients stay compliant. Stephanie shares the recurring challenges she sees with clients and her consistent message: an advisor's job is to lay out the options and consequences, even though it may not be what clients want to hear. She closes with a forward-looking case for reimagining sales tax altogether—moving away from outdated definitions and toward a clearer, supply-based framework. Key Takeaways: ● Sales tax complexity may inhibit compliance. With thousands of jurisdictions and frequently changing rates, some businesses struggle to justify the resources required, and a few simply throw up their hands. ● Thresholds can change with the budget. As state needs shift, the assumptions practitioners once treated as settled can erode, so tracking legislatures and budgets may help…

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