Mid-Market & Scaling

How do I build a sales tax compliance roadmap for the next 12 months?

A 12-month compliance roadmap starts with a nexus audit, quantifies historical exposure, selects the right software stack, assigns internal ownership, and schedules the ongoing compliance calendar. Here's how to build it.

How do I handle historical nexus exposure across 10+ states discovered late?

Discovering you have unregistered nexus in 10+ states is a manageable problem, if you act quickly. The right path is a coordinated multi-state VDA program, which compresses lookback periods and waives penalties. Here's how the process works at scale.

How do I manage sales tax compliance across 30–45 states as a mid-market brand?

Managing compliance across 30–45 states requires a structured stack: SST registration for the 24-state block, AutoFile for the remainder, a dedicated exemption certificate program, and a named internal owner with monthly calendar time. Here's the operational model.

How do I reconcile Amazon 1099-K data with my state sales tax filings at scale?

The Amazon 1099-K doesn't reconcile directly to state sales tax returns, it's a gross receipts document, not a jurisdiction-level report. Reconciliation requires pulling Amazon's transaction-level data by state and matching it against your state returns. Here's how.

How do sales tax obligations change during rapid growth — doubling GMV year over year?

Doubling GMV year over year means crossing new economic nexus thresholds in rapid succession, filing frequency upgrades in existing states, and physical presence expansion that creates new obligations. Compliance infrastructure that worked at $5M fails at $10M. Here's what changes and when.

How do US sales tax obligations change when I expand to Canada, the EU, or the UK?

International expansion adds VAT, GST/HST/PST, and customs obligations on top of US state sales tax, it doesn't replace them. US sales tax obligations continue for US-sourced transactions regardless of where the customer is located. Here's what actually changes.

What are the biggest sales tax mistakes scaling ecommerce brands make?

The most expensive sales tax mistakes at mid-market scale aren't about rate errors, they're structural: assuming marketplace collection eliminates all obligations, not tracking nexus as the business scales, and treating exemption certificates as a checkbox rather than an audit asset.

What does sales tax compliance actually cost a $5M–$20M ecommerce brand?

For a $5M–$20M ecommerce brand, total sales tax compliance cost runs $8,000–$60,000+ per year depending on software, nexus footprint, exemption complexity, and whether you use a managed service or AutoFile software. Here's what each cost layer actually looks like.

What is the right software stack for a $20M ecommerce brand managing multi-state compliance?

A $20M ecommerce brand needs jurisdiction-level calculation, multi-state AutoFile, and SST enrollment, not an enterprise platform with enterprise pricing. The right stack costs $5,000–$12,000/year and handles 25–40 states reliably. Here's what it looks like.

What questions should I ask a CPA or sales tax consultant before hiring them?

The key questions to ask before hiring a sales tax CPA or consultant: their multi-state ecommerce experience, VDA track record, audit representation background, fee structure, and whether they'll actually know your account or hand it to a junior associate.

When does it make sense to use a managed filing service vs. AutoFile software?

Managed filing services handle compliance on your behalf at $2,500–$10,000/month. AutoFile software handles the same filing mechanics for $200–$600/month and lets you retain control. The decision hinges on your internal bandwidth and risk tolerance, not filing complexity.

When should a growing ecommerce brand hire a dedicated sales tax resource?

Most ecommerce brands don't need a dedicated sales tax hire until $30M–$50M GMV with 25+ nexus states. Before that point, the right combination is strong AutoFile software plus a fractional tax advisor on retainer. Here's how to read the signals.