Taxed by Surprise: What Every SaaS Company Should Know

In this episode of Beyond the Ledger, host Shardae Layfield sits down with Stephen Bradshaw, Partner in Bennett Thrasher’s State & Local Tax practice, and Stephan Jiminez, Domestic Indirect Tax Lead at Anrok, to explore one of the most underestimated risks in the software industry- sales tax and compliance for SaaS businesses.

Together, they reveal how unnoticed sales tax exposure can quietly reduce valuation, stall deals during due diligence, and lead to costly surprises for founders and CFOs. From automation and audit readiness to voluntary disclosure agreements and partnership best practices, the conversation offers a clear roadmap for scaling software companies to stay compliant and protect enterprise value.

Listeners will learn:

• Why buyers prioritize sales tax in due diligence
• How exposure impacts cash flow and deal proceeds
• When to consider voluntary disclosure agreements (VDAs)
• Common pitfalls in tax automation and implementation
• How collaboration between firms like Bennett Thrasher and Anrok drives better compliance outcomes

Whether your SaaS company is preparing for growth, raising capital, or planning an exit, this episode offers practical insights to help leaders get compliance right before it’s too late.

Learn more: btcpa.net | Follow Bennett Thrasher for more conversations that move business forward.

Takeaways

• Sales tax exposure can directly reduce sale proceeds and company valuation.
• Buyers’ due diligence teams will always uncover compliance gaps.
• Many SaaS companies delay sales tax readiness until it’s too late.
• Automation is critical for scalable, multi-state compliance management.
• Incorrect product or service tax mapping can create six- or seven-figure liabilities.
• Voluntary Disclosure Agreements (VDAs) can reduce penalties and shorten lookback periods.
• Unfiled or late sales tax returns keep liabilities open indefinitely.
• Strategic partnerships between tax advisors and technology providers strengthen compliance posture.
• Under-collecting and over-collecting both create financial and reputational risk — accuracy is key.
• Proactive compliance improves valuation, investor confidence, and deal execution readiness.

Chapters:

00:00 Understanding Sales Tax for Software Businesses
07:39 The Importance of Automation in Sales Tax Compliance
11:27 Collaboration Between Tax Advisors and Software Solutions
14:23 Navigating Tax Liabilities and Cash Flow Management
21:34 Responsibility for Sales Tax Liabilities
23:32 Common Pitfalls in Sales Tax Software Implementation
30:43 Overlooked Issues in Sales Tax Compliance