Payroll failures rarely begin in payroll.
They begin upstream—inside disconnected systems, late approvals, inconsistent data, changing regulations and small decisions made across HR, operations and finance. By the time those problems reach payroll, the team has almost no time to fix them and no room to be wrong.
In this episode of The Next Moves, Joe Diubaldo sits down with Oz Khan, who leads Ventures at ADP, to unpack why payroll remains so fragile inside otherwise capable companies.
Oz explains how growing organizations inherit a “Frankenstein stack” of systems that were purchased at different times, by different departments, to solve different problems. Each team believes its platform is the source of truth, but when the information reaches payroll, the numbers do not always reconcile.
Joe and Oz explore what payroll breakdowns reveal about a company’s broader operations, why acquisitions and rapid expansion make the problem worse, and why fixing it often requires unglamorous foundational work before new technology can help.
The conversation then moves beyond payroll into the future of finance and AI-enabled leadership. They discuss why AI cannot simply replace experienced people, how functional experts can begin building their own workflows, and why leaders who have only experimented with AI at a surface level may be dangerously overconfident about what it can do.
If you are a CEO, CFO, finance leader or operator trying to introduce AI into a complex business, this episode will help you understand what needs to be fixed before automation can deliver on its promise.
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Chapters
00:00 Why Payroll Sits at the Bottom of the Funnel
01:00 Why Payroll Is So Fragile
03:39 The Frankenstein Tech Stack
05:23 Where Every Upstream Error Ends Up
08:22 Fixing the Plumbing
12:03 Can Payroll Systems Become Self-Healing?
15:30 M&A, Growth and Broken Systems
20:09 The “Just Use AI” Trap
23:04 The Finance Leader of the Future
26:06 Building With AI, Not Just Using It
28:24 Creating a Culture of Curiosity
32:14 Why Leaders Need to Understand AI
33:19 What Comes Next
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Watch the full interview and subscribe for more conversations with the operators behind the world’s most resilient businesses.
Connect with guest Oz Khan on LinkedIn ➡️ https://www.linkedin.com/in/ozkhan2/
Connect with Host Joe Diubaldo on LinkedIn ➡️ https://www.linkedin.com/in/joediubaldo/
🔔If this conversation resonated with you, like the episode and subscribe to stay up to date on future conversations with founders and operators.
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Joe Diubaldo, host of The Next Moves and founder of Clarity Recruitment, has made it his life to help people build better careers and better companies. Along the way, there’s been one lesson that always stands out. We all get stuck. The Next Moves podcast has been curated to help you get unstuck; to help you plan the next move and then the move after that.
