High-Stakes Global Transaction Tax Software: Multi-Trillion-Dollar Industry

Sales tax and global VAT compliance is no longer just an administrative nuisance—it’s a trillion-dollar problem. The 2018 Wayfair decision and economic nexus provisions have unleashed an unprecedented compliance burden, while AI-driven growth accelerates the scale and urgency of the issue.

The Complexity of Sales Tax and Global VAT Compliance

U.S. Sales Tax Revenue: A Detailed Breakdown

In the U.S., businesses selling taxable goods or services must register, file, and remit sales tax if they meet nexus criteria—not just to states but also to counties, cities, and local jurisdictions, each with distinct rules. While large enterprises historically managed this complexity, it often overwhelms small to midsize firms.

The Census Bureau’s data for 2023, aggregated across all quarters, showed total state and local tax revenue of approximately $1.4 trillion. The Tax Foundation indicates that sales taxes account for 15.7% of combined state and local tax collections, leading to an estimated sales tax revenue of $219 billion for 2023.

Global VAT Revenue: Estimating the Worldwide Total

The World Bank estimates 2023 global GDP at $106 trillion, and the IMF’s 2021 data suggests tax revenue averages 17.1% of GDP, totaling $18.1 trillion. With VAT contributing over 27% of this in VAT-implementing countries, global VAT revenue is approximately $5 trillion annually, underscoring the vast compliance landscape for international businesses.

The Growing Need for Sales Tax Compliance Software

Brick-and-mortar businesses once grappled with varying local tax rates and rules, a challenge that birthed startups like Davo. Acquired by Avalara, Davo automated tax calculations and remittance from point-of-sale systems for small restaurants, easing manual compliance burdens.

The e-commerce era intensified this issue after the U.S. Supreme Court’s 2018 Wayfair ruling allowed states to mandate sales tax collection from out-of-state online sellers, thrusting businesses into nationwide obligations. Avalara emerged as a leader, streamlining duties for small to midsize and midmarket firms. TaxJar challenged its dominance before its 2021 acquisition by Stripe for a reported $900 million, followed by Avalara’s 2022 purchase by Vista Equity Partners for $8.4 billion.

Why Global Sales Tax Compliance Matters More Than Ever

Sales tax and VAT tie directly to revenue, and compliance demands have surged as AI startups—such as Bolt, Cursor, Gamma, Icon, and Lovable—achieve rapid growth. Unlike traditional software firms, which took years to reach $100 million in annual recurring revenue, these companies hit economic nexus thresholds faster amplifying tax obligations.

Globally, new regulations add complexity. The EU’s recent CESOP directive, effective January 2024, mandates payment service providers to share cross-border transaction data with regulators, tightening VAT and GST enforcement on foreign sellers of physical and digital goods.

AI firms face unique challenges compared to traditional SaaS companies. Pre-generative AI, B2B SaaS enjoyed predictable scalability with flat costs, enabling product-led growth in low-interest-rate environments. Companies like Cal.com forecasted margins easily. But generative AI introduces volatile incremental costs—compute usage, dynamic pricing, and licensing fees from providers like OpenAI or Anthropic—creating cash-flow volatility akin to physical goods industries, yet amplified by rapidly evolving tax rules and exponential competition.

Developers, users, and suppliers of these AI technologies now face a financial reality that software cost is now incremental and direct, but with a modern twist: the rules are evolving faster than ever and competition is exponential.

Modern Solutions for a Modern Problem

“Startup CFOs and controllers now question basis-point models—0.3% to 0.5% of revenue for tax calculations alone is steep, especially for larger contracts.”

Taxwire, a venture-backed startup, recently emerged from stealth to address this challenge. Its team, with experience from Taxjar, Stripe Tax, Amazon’s tax technology group, Fonoa, and Avalara, targets high-growth companies and their accounting teams. CEO Andrew Rea critiques traditional pricing: “Startup CFOs and controllers now question basis-point models—0.3% to 0.5% of revenue for tax calculations alone is steep, especially for larger contracts.”

Rea argues the scale and speed of AI product adoption, where business-facing software providers meet consumer-like demand, require end-to-end, global solutions without the time and money required by traditional sales tax software implementations at a cost that is scalable for young companies.

Taxwire leverages AI to audit historical noncompliance—a complex, manual task typically handled by large CPA firms—and automates ongoing tax calculations, filings, and remittances globally with precision. They bundle these productized services with their core sales tax engine that automates ongoing tax calculation, filings, and remittance globally. Its proprietary technology, Rea claims, avoids incremental costs, offering scalable pricing for young firms facing unpredictable revenue growth across jurisdictions and price its offering more competitively to other solutions in the market.

Though funding details remain unannounced, Rea confirms millions raised from Vinyl Capital (early Klaviyo), Recall Capital (early operators at Gusto, Plaid, and Scale AI), J Ventures (early Ramp investors), NOMO Ventures (early Expensify investors), Expansion Venture Capital (early Carta investors), 1121.vc, Siqi Chen (Runway Financial founder), and angel investors, including startup CEOs, CPAs, and CFOs.

Vendor Evolution: Three Waves of Solutions

Sales tax software has evolved in waves. Mainframe-era solutions like Vertex and Thomson Reuters ONESOURCE persist, followed by cloud-era players Avalara and Taxjar. Modern entrants—Anrok, Zamp, Numeral, and Taxwire—address niche pain points for specific verticals and audiences.

“Neglecting tax compliance is like deferring treatment for an infection—the problem grows, and consequences eventually demand action. Vendor choice depends on industry, activities, risk tolerance, and resources.”

Graham Martin, Taxwire’s head of tax, offers an analogy: “Neglecting tax compliance is like deferring treatment for an infection—the problem grows, and consequences eventually demand action. Vendor choice depends on industry, activities, risk tolerance, and resources.”

Prior joining Taxwire, Martin previously served as the first tax hire at Taxjar, tax lead at Stripe, and vice-president of indirect tax at Zamp.

Who Needs These Solutions—and When?

Rea, who tackled this issue at Ordo (an Accel-backed platform linking schools with food suppliers), recommends startups conduct a nexus study post-product-market fit or nearing $500,000 to $1 million in annual revenue, when noncompliance costs become material. At Ordo, Capital (acquired by Rho in 2023), and On Deck (which raised over $20 million from Founders Fund), he found existing solutions lacking for fast-growing, complex firms. “No one else was building the right product, the right way,” he says.

Outside of the Finance, Accounting, and Tax Departments, Rea observed that startup founders, fractional CFOs, CPAs, bookkeepers, and biz ops teams also deal with Sales Tax and global VAT issue, depending on industry and company stage.