AI is reshaping finance faster than most teams can keep up, and tax compliance is one of the first places it’s making a real impact.

In this episode of Beyond Death & Taxes, Matt and Clay explore the rapidly evolving role of AI in finance, featuring insights from Avalara’s popular webinar, Reinventing Tax Compliance: The AI Boom and How to Put It to Work. They walk through findings from a global study of finance leaders, revealing how teams are adopting AI, where they’re still hesitant, and which compliance tasks are most primed for automation.

From the rise of e-invoicing mandates to AI-powered research, reporting, and “agentic” workflows, this episode breaks down what’s actually happening inside modern finance departments and what’s coming next. You’ll also hear how Avalara is integrating AI directly into tax research, reporting dashboards, ERPs, and even email tools to reduce risk, speed up decision-making, and cut manual work.

And before diving in, the hosts pay their respects in the Compliance Graveyard to one of the oldest inefficiencies in the book: manual data entry — and why it’s finally time to lay it to rest.

Key Takeaways

• How AI adoption is accelerating across finance and what’s driving the momentum.
• Why global e-invoicing mandates are reshaping compliance, and what teams need to prepare for now.
• Where manual processes create the biggest risks and how AI can close those gaps.
• What “agentic AI” really means and why it’s poised to change tax workflows entirely.
• Why human oversight remains essential — especially when it comes to privacy, accuracy, and trust.

Whether you’re experimenting with AI or still figuring out where it fits, this conversation offers a grounded look at how automation is reshaping compliance today and where it’s headed next.

Related Links

1. Watch the full webinar: Reinventing Tax Compliance — The AI Boom and How to Put It to Work.
2. Explore more articles, reports, and insights on how AI is reshaping tax workflows in the Avalara Resource Center

Some states make sales tax filing straightforward — and then there are the ones that keep even seasoned pros on their toes.

In this episode of Beyond Death & Taxes, Matt and Clay dig into one of Avalara’s most downloaded webinars: the 10 trickiest states for sales tax returns. From inconsistent deadlines to confusing location reporting and “alphabet soup” schedules, they walk through the quirks and complexities that make filing in certain states uniquely challenging.

You’ll hear expert insights from Avalara’s tax pros as they break down what makes states like California, Colorado, Illinois, New York, Louisiana, Texas, and more so difficult — and what finance teams should be watching out for as rules, thresholds, and interpretations continue to shift.

And before diving in, the hosts pay their respects in the Compliance Graveyard to one of the most persistent myths in the industry: the idea that all states handle sales tax the same way. (Spoiler: they do not.)

Key Takeaways

• States vary widely: Sales tax rules, deadlines, and formats differ dramatically from state to state.
• Nexus keeps evolving: Physical, economic, and marketplace nexus rules continue to shift — and vary by jurisdiction.
• Some states are especially tough: Places like California, Colorado, Illinois, New York, and Louisiana come with added complexity.
• Accurate data matters: Clean, consistent tax data is essential for timely and accurate returns.
• Deadlines can get messy: Filing frequencies and prepayment requirements change as you hit new thresholds.

Whether you file in two states or twenty, this episode will help you better understand the pitfalls, patterns, and prep work needed to stay compliant across the country.

The foundation of compliance starts here!

In this episode of Beyond Death & Taxes, Matt and Clay dust off the fundamentals of compliance with highlights from Avalara’s popular “Sales Tax 101” webinar. They uncover why sales tax matters, how nexus really works, and the five essential steps every finance team should follow to stay compliant.

Along the way, we make a pitstop in the Compliance Graveyard, burying one of compliance’s longest-lived myths: the assumption that sales tax is always somebody else’s problem.

Key Takeaways

• The old “someone else handles sales tax” mindset is officially dead.
• Why sales tax is critical to state budgets — and why it should matter to you.
• The three basics of taxability (Where, Who & What) and how they drive your obligations.
• The five core steps to staying compliant — from registering to remitting.
• Common nexus triggers that could create unexpected tax liabilities for your business.

Even the “basics” of sales tax can trip up the best finance teams. Learn how to spot the risks and streamline compliance before it becomes a headache.