Finance has always been about precision, proof, and trust — qualities now being redefined in the age of AI. According to OneStream’s new AI Pulse Report, three out of four CFOs are leading enterprise AI strategy, yet only a third have managed to scale it successfully. So what happens when the people who once managed numbers begin managing intelligence?
In this episode of The Future of Less Work, host Nirit Cohen sits down with Tom Shea, CEO of OneStream, to explore how AI is transforming finance — and, with it, the future of work. Tom shares why CFOs are uniquely positioned to steer the AI agenda, how finance’s “show-your-work” discipline is shaping enterprise trust, and why solving deterministic problems — where there’s only one right answer — is key to building real confidence in AI.
The conversation delves into what happens when human judgment, context, and mentorship meet machine precision. From the risk of losing early-career learning to the emergence of AI agents as digital teammates, Tom and Nirit unpack what it takes to build systems that don’t just automate, but understand.
If you’ve ever wondered how the rise of AI will reshape not just finance, but how organizations think, decide, and grow, this episode offers a grounded look at the future of intelligent work — where humans and machines learn to trust each other.
Guest Information:
Tom Shea is the co-founder and CEO of OneStream, and one of the original architects of the OneStream platform. His mission is to transform the corporate performance management (CPM) ecosystem with a solution that combines power and flexibility with ease of use, deployment, and maintenance. For more than a decade, Tom has been dedicated to delivering value, success, and support to users – drawing on his deep understanding of finance and technology to drive fully innovative products. Before founding OneStream, he co-founded UpStream Software, where he invented and architected UpStream TB and UpStream WebLink, pioneering the Financial Data Quality Management space.
Chapters:
00:00 — Why CFOs Now Lead AI Strategy
01:35 — Can AI Replace or Redesign Finance Work?
03:33 — Deterministic vs Non-Deterministic AI in Finance
05:39 — How AI Learns Corporate Context
07:42 — Why Deterministic Problems Are the Hardest for AI
09:45 — Will AI Eliminate Entry-Level Finance Roles?
11:42 — Can AI Fix the Spreadsheet Problem?
13:57 — How AI Frees Finance to Become Strategic
15:35 — What Happens When AI Handles the Basics?
17:44 — From Human-in-the-Loop to Trusted AI Agents
20:00 — Why Finance Needs Explainable AI
21:56 — Why So Many AI Pilots Fail
24:15 — Productized AI vs Internal Experiments
25:59 — Unlocking Full AI Value in Finance
27:28 — Why AI Needs Context, Not Just Data
29:02 — Coding Human Judgment Into AI Systems
31:17 — The Real Opportunity: Turning Over Agency to AI
32:55 — Will AI Replace Work or Give Us Superpowers?