In January 2026, Kim Kardashian's Skims paid $200,000 to settle with New Jersey for charging customers sales tax on clothing, which is exempt in the state. Skims has accountants, lawyers, and finance teams. They still got it wrong.

This isn't a story about one brand's mistake. It's about a structural challenge that every direct-to-consumer brand faces as it scales. Sales tax obligations don't grow gradually. They tend to appear suddenly as spikes in filing requirements, registration obligations, and compliance complexity. And these spikes are usually tied to specific revenue milestones. Our analysis of over 1,000 scaling brands shows a dramatic pattern. Between $1M and $5M in revenue, annual filings jump from 2 to 39. That's not a gradual increase. It's a cliff.

This guide breaks down the four areas where scaling brands get caught off guard and what to do at each stage of growth:

• The cliffs: The specific revenue milestones where sales tax obligations spike, with data on what to expect from $100K to $50M+
• The gaps: What platforms like Shopify and WooCommerce actually handle versus what's still on you (it's more than you think)
• The traps: The hidden obligations that catch even well-run brands, from 3PL-created nexus to taxability errors to unlimited lookback periods‍
• The playbook: A stage-by-stage action plan for brands approaching $1M, scaling through $5M, and operating at $5M+

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