#automation #businessoperations #workflowmanagement

When Automation Breaks: A Real Billing Disaster

Name: When Automation Breaks: A Real Billing Disaster
Uploaded: 2026-09-21T21:21:24+00:00
Duration: 3 min 2 s
Description: Stephen Yoss shares a cautionary tale about automation failures—from billing errors that spiral into thousands of wrong invoices to API misalignments between systems. The paradox? The faster your setup, the fewer natural checkpoints your team has to catch problems. Learn why keeping a human in the loop isn't just best practice—it's your safeguard for maintaining client trust.

3:02 · A clip from Winning Hearts and Minds: Building Future-Ready Businesses, taught by Stephen Yoss · Watch on YouTube ↗

Stephen Yoss shares a cautionary tale about automation failures—from billing errors that spiral into thousands of wrong invoices to API misalignments between systems. The paradox? The faster your setup, the fewer natural checkpoints your team has to catch problems. Learn why keeping a human in the loop isn't just best practice—it's your safeguard for maintaining client trust. From the course “Winning Hearts and Minds: Building Future-Ready Businesses” (2 CPE credits, Information Technology, Basic): https://www.cpetoday.com/course/winning-hearts-and-minds-building-future-ready-businesses Taught by Stephen Yoss — Speaker & Author, CPE Today. More from Stephen Yoss: https://www.cpetoday.com/instructor/stephen-yoss CPE Today offers live webinars, Live Replays and self-study for CPAs and accounting professionals. NASBA-sponsored (ID 167619) and an IRS-approved CE provider. https://www.cpetoday.com/ #automation #businessoperations #workflowmanagement

More from this course

4:02 The Accounting Shortage Is Real—And It's Permanent

1:26 AI is Here to Stay—Whether You Like It or Not

2:10 Why Clean Data Beats Automation