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 She closes with a forward-looking case for reimagining sales tax altogether—moving away from outdated definitions and toward a clearer, supply-based framework.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 anticipate where rules are heading.
● Pass-through entity structures can create hidden exposure. Layered LLCs may multiply compliance obligations across income, sales, property, and local business taxes, and form-over-substance questions can become harder to defend.
● Moving to a no-income-tax state rarely solves business tax. Source income can still trigger non-resident filing obligations, and aggressive residency rules in some jurisdictions may count a single arrival as a taxable day.
● Defining and documenting risk can protect everyone. Laying out the continuum of options and consequences in writing may help clients make informed choices and may support their position if a matter later moves to controversy.
● Proactive SALT advice is available. If companies cannot justify a full-time in-house specialist, outside SALT advisors can help companies mitigate risk.
Guest:Stephanie Lipinski Galland, Principal, Miles & Stockbridge
LinkedIn: https://www.linkedin.com/in/stephanie-lipinski-galland-1205a991/
Stephanie Lipinski Galland is a Principal at Miles & Stockbridge with more than 30 years representing businesses before state and local taxing authorities on income, franchise, sales, use, and unclaimed property matters, as well as M&A due diligence and administrative appeals. She previously served as Director of Taxation at Gap Inc. and worked at the Virginia Department of Taxation, and she teaches state and local tax as an Adjunct Professor at Georgetown University Law Center. A Fellow of the American College of Tax Counsel and a former Chair of the ABA's State and Local Tax Committee, she was named Best Lawyers' 2026 "Lawyer of the Year" for Litigation and Controversy (Tax) in Richmond.
Connect:
● Website: https://www.aprio.com/business-tax/state-local-tax-salt-consulting/
● Meredith Smith on LinkedIn: https://www.linkedin.com/in/meredith-smith-047aa13/
● Judy Vorndran on LinkedIn: https://www.linkedin.com/in/judyvorndran/
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Disclaimer: The views, thoughts, and opinions expressed on the SALTovation podcast, including that of all participants, are the speaker’s own and do not represent the views, thoughts, and opinions of Aprio or any of its affiliates. The material and information presented on the podcast is for general information purposes only. The “Aprio” name and all forms and abbreviations are the property of its owner and its use does not imply endorsement of or opposition to any specific product or service.
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