Kitty and Steve sit down with Kyle Hatfield from Centsless to unpack why cash rounding, penny shortages, exact-change signs, refunds, split tender, EBT/SNAP, wage risk, and reconciliation are turning the cash drawer into a real payments infrastructure problem for ISVs and POS platforms.

Jul 8th, 2026

Centsless: Making Cash Rounding Defensible

Centsless helps merchants, POS vendors, and financial institutions navigate cash rounding in the post-penny economy with jurisdiction-aware rules, audit trails, refund handling, and compliance infrastructure.

The White House fintech executive order could open new doors for fintech firms, bank partnerships, digital assets, and payment-system access, but more flexibility also means more scrutiny, stronger controls, and clearer accountability.

AI can help payments compliance teams move faster, spot patterns, summarize cases, and prioritize alerts, but it cannot replace human judgment, accountability, governance, or defensible decision-making.

Beneficial ownership reporting has been messy, but the lesson for platforms is clear: compliance workflows need to be flexible, documented, configurable, and built for change.