Sales tax doesn’t have to be this hard
Greg Chapman leads Avalara’s AvaTax business and international operations, including Europe and Brazil. He has deep expertise in helping business partners grow their operations through SaaS partnerships and a proven track record in accelerating growth while leading business development efforts and partner management operations.
Q Where do businesses most commonly get sales tax wrong, and are those patterns consistent regardless of business size?
A The most persistent issues involve nexus monitoring, product taxability, exemption documentation, and sourcing. Teams miss new economic nexus or marketplace facilitator shifts, misclassify SKUs and bundles, let certificates lapse, or use poor address data that breaks destination sourcing. These patterns appear across company sizes: Smaller businesses often lack capacity and controls while larger organizations more often contend with fragmented platforms and policy drift. In both cases, inconsistent data and decentralized tax logic undermine accuracy, timeliness, and audit readiness.
Q How does the complexity of sales tax compliance change when a business sells across multiple channels?
A Omnichannel selling expands the range of edge cases and increases coordination burdens. Marketplaces may collect tax on a seller’s behalf, yet liability typically remains for direct web, point-of-sale, wholesale, and subscription channels, all of which require promotions, partial shipments, returns, and credits to preserve the original tax context. Variations in fulfillment locations alter sourcing rules and rates. Complexity declines when a single policy and authoritative content source govern every channel, standardized data contracts are enforced, one tax engine is reused, and end-to-end transaction lineage ensures that quotes, invoices, and returns reconcile.
Q Many of your clients’ businesses run on platforms like QuickBooks, Shopify, NetSuite, and Salesforce. How should practitioners think about where tax determination happens in the transaction workflow, and why does it matter?
A Practitioners should calculate at the quote or cart stage to set expectations and then finalize at invoice in the system of record, using a central determination service that receives normalized data such as classification, ship-to and bill-to, nexus, exemptions, marketplace indicators, and timing. Replicating rate tables inside each platform leads to drift and reconciliation gaps. Centralized policy, surfaced through platform adapters, delivers accuracy, consistency, and durable controls across the order-to-cash life cycle.
Q AI is being applied to nearly every corner of financial services. What role is it playing in sales tax compliance, and what should practitioners be watching for?
A AI now assists with product classification to tax categories, certificate capture and validation, address cleansing, monitoring statute and rule changes, anomaly detection, notice triage, and forecasting nexus risk, which reduces manual effort and cycle time while improving consistency. Practitioners should require explainability and audit trails, human oversight for determinations, measurable accuracy benchmarks, versioned models and content, and strong privacy and security controls. Vigilance is warranted for hallucinations, biased training data, and model drift so that AI augments authoritative content and governance rather than replacing them.
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