Oct 2, 2026 58 min
The Shared Services Paradox: AI, BPOs, and Owning the Outcome with Bo Senu-Hodo
For twenty years, shared services and BPO were built to scale people. Now AI can do much of the transactional work those models were designed around. So what happens next? Ravit Gutman,...
Sep 3, 2026 42 min
The 2027 E-Invoicing Wave: A Country-by-Country Guide for Global AP/AR Teams
France's e-invoicing mandate went live on September 1, 2026, and it's just the first wave. Slovakia, Norway, Germany, Portugal, Spain, the UAE, and the UK all have mandates landing in 2027 and...
Aug 12, 2026 23 min
Stop Logging Into 14 Portals a Day: Inside SmartFetch
Somewhere right now, someone in finance is logging into their 14th vendor portal of the day, copying passwords out of a spreadsheet, downloading invoices one by one, and racing a shutoff deadline...
Jul 14, 2026 22 min
Halfway Through 2026: What Actually Happened to AI in Finance
Extropy CEO Ravit Gutman and VP Mike Jasper hit pause at the midpoint of 2026 to grade what they got right (and wrong) back in January. Agents went from trade show demos...
May 28, 2026 21 min
The Execution Gap: Why Great Strategies Fall Apart Before They Begin
Most strategies don't fail because they're wrong. They fail because organizations can't execute them. In this episode, Mike Jasper sits down with Extropy Project Manager Cecile Brown-Smith to unpack the systematic forces...
May 14, 2026 16 min
The Speed Trap: How Growth Without Structure Accelerates Decay
Growth is supposed to be a good thing, so why does it make everything harder? In this episode, Kevin Zirkle and Mike Jasper unpack the tension between speed and structure, and why...
May 7, 2026 43 min
Why AP Is the Hidden Risk in Your SAP Migration
(with Jason Kurtz, CEO of Basware)
Most SAP Cloud ERP migrations treat Accounts Payable as an afterthought. That's a mistake that costs organizations years of lost value, compliance fines, and a core that's anything but clean. In this...
Apr 29, 2026 14 min
Fragmentation, Silos, and Drift: Where Entropy Comes From
In this episode, Kevin Zirkle sits down with Steve Ramirez, a senior manager at Extropy who lived these challenges firsthand on the client side before joining the team. Together, they dig into...
Apr 21, 2026 19 min
Is Your System Breaking Down?
5 Signals You Can't Afford to Miss
Most organizations don't know their systems are failing until something very visible and very costly goes wrong. In this episode of Extropy On AIr, Kevin Zirkle and Mike Jasper break down the...
Apr 16, 2026 12 min
The Extropy Think Tank:
Where Finance Leaders Talk Honestly
In this preview episode, Ravit Gutman and Mike Jasper introduce the Extropy Think Tank, a members-only community built for finance transformation practitioners who are tired of vendor pitches and ready for real...
Apr 15, 2026 7 min
Extropy Think Tank Teaser:
What We're Building and Why
Before the official launch, Ravit Gutman and Mike Jasper sit down to pull back the curtain on the Extropy Think Tank, what it is, why Extropy is the right place to host...
Apr 9, 2026 17 min
The Digital Transformation Myth: Why Technology Is the Least Important Part
Most enterprises believe digital transformation is a technology problem. They're wrong, and it's costing them millions. In this episode of Extropy on AIr, Kevin Zirkle sits down with Mike Jasper, Vice President...
Mar 23, 2026 31 min
AI in Finance Transformation: What Companies Are Missing | SSON Recap & the Dexcom Win
AI is everywhere right now. But most organizations are still asking the same question: Where do we even start? In this episode of Extropy on Air, Mike Jasper sits down with Extropy's...
Mar 16, 2026 18 min
Execution Beats Experimentation: How Agentic AI Is Delivering Real ROI in Finance
Most AI pilots never deliver real financial impact. In fact, research from MIT suggests that 95% of AI pilots fail to accelerate revenue. So what separates organizations experimenting with AI from the...
Mar 10, 2026 55 min
Extropy on Air | International Women’s Month Spotlight: Bo Senu-Hodo
As part of our International Women’s Month series, we’re bringing this powerful conversation back into the spotlight. In this episode of Extropy on Air, Ravit Gutman sits down with Bo Senu Hodo...
Feb 25, 2026 16 min
Entropy vs. Extropy:
Why Digital Transformations Fail
Most digital transformations do not fail because the technology is wrong. They fail because entropy wins. In this episode of Extropy On Air, Kevin Zirkle and Mike Jasper explore the concept of...
Feb 12, 2026 55 min
Leadership, Empathy, and the Future of Women in Finance
What does it truly mean to lead in modern finance? It means rising higher, thinking deeper, and choosing to be more. In this episode of Extropy On Air, Extropy Founder and CEO...
Feb 4, 2026 18 min
The Hidden Cost of
Organizational Entropy
Digital transformations rarely fail because of bad technology. They fail because the organization underneath the technology starts to break down. In this episode of Extropy on Air, Kevin Zirkle and Mike Jasper...
Jan 28, 2026 32 min
Leading Digital Transformation with Confidence
Digital transformation works when people are brought along, not pushed through. In this episode of Extropy On Air, Extropy's Director of Digital Transformation and Client Success, Mike Jasper, and Project Manager Maira...
Jan 13, 2026 15 min
Unlocking Intelligent Invoice Lifecycle Management with Basware
Many finance teams believe their ERP system is “automation.” In reality, it often just digitizes manual work. In this episode of Extropy on Air, Kevin Zirkle sits down with Kevin Farrell, BD&A...
Jan 7, 2026 31 min
From AI Hype to Real Impact: How Leaders Create Value
2026 is here, and the AI conversation is changing. In the first episode of the year, Ravit Gutman and Mike Jasper unpack what organizations learned from AI adoption in 2025 and what...
Dec 29, 2025 24 min
2025 in Review, 2026 in Focus: Leading with Intention
As 2025 comes to a close, Ravit Gutman and Mike Jasper sat down at Extropy's headquarters in Florida for an honest, forward-looking conversation about what this year taught us, and how those...
Dec 17, 2025 27 min
The CFO’s 10 Resolutions for 2026: From Strategy to Execution
As finance leaders look ahead to 2026, one question keeps coming up: What resolutions will actually change how finance operates, not just how it talks? In this episode of Extropy On AIR,...
Dec 4, 2025 20 min
Inside Raindrop: The Next Era of AI-Driven Procurement
In this final episode of our Raindrop x Extropy series, host Kevin Zirkle sits down with Ward Karson, COO of Raindrop, for a forward-looking conversation about how AI is reshaping sourcing, procurement,...
Dec 2, 2025 15 min
AI, Insight & the Future of Finance with Esker
In the final episode of our six-part Esker x Extropy series, host Kevin Zirkle sits down with Jim Dougherty to look beyond automation and into the future of intelligent finance operations. This...
Nov 20, 2025 16 min
Compliance, Visibility, and Control with Raindrop
In this episode of our Raindrop + Extropy on AIR series, host Kevin Zirkle sits down with Raindrop COO Ward Karson to explore how modern eProcurement transforms the Office of the CFO....
Nov 18, 2025 14 min
Paying It Forward with Esker: Intelligent AP That Works for People
Accounts Payable is not always seen as strategic, but when it breaks, the consequences ripple across the entire business. In this episode of Extropy on AIR, Kevin Zirkle talks with Shelly-Ann Campbell...
Nov 13, 2025 18 min
Smarter Sourcing Starts Here: How Raindrop Cuts Cost Without Cutting Corners
In this episode of Extropy on AIR, host Kevin Zirkle of Extropy Advisors welcomes back Ward Karson, COO of Raindrop, to explore how AI is redefining strategic sourcing. From automating event creation...
Nov 13, 2025 27 min
IOFM 2025 Unplugged: Ravit & Mike on The Future of Finance
It’s not your typical finance podcast. This special bonus episode takes you behind the scenes of IOFM 2025 in Las Vegas! Extropy CEO Ravit Gutman and Director of Digital Transformation & Client...
Nov 13, 2025 14 min
Redefining Source-to-Pay with Esker: Visibility, Control, and Connection
Source-to-Pay (S2P) isn’t just about procurement. It’s about empowering finance and operations teams with connected visibility and control. In this episode of Extropy on AIr, Extropy’s Kevin Zirkle and Esker's John Purcell...
Nov 6, 2025 16 min
Know Your Suppliers: Streamlined, Smart, and Secure with Raindrop + Extropy
Supplier management isn’t just about collecting tax IDs. It’s about protecting your business from risk, ensuring compliance, and building resilience. In this episode of Extropy on AIr, host Kevin Zirkle of Extropy...
Nov 4, 2025 23 min
Collect Smarter, Not Harder: Human-Centric AR Automation with Esker
In this episode of Extropy on AIr, host Kevin Zirkle sits down with Aaron LeHew from Esker to explore how automation can empower Accounts Receivable teams without losing the human touch. AR...
Oct 30, 2025 15 min
Contract Control, Without the Chaos - Smarter CLM with RainSign
In this episode of Extropy on AIr, host Kevin Zirkle from Extropy Advisors sits down with Ward Karson, COO of Raindrop, to explore how Contract Lifecycle Management (CLM) is reshaping the way...
Oct 29, 2025 17 min
Bonus Episode: The Future of Finance with Ravit Gutman, CEO of Extropy Advisors
In this special bonus episode of Extropy on Air, host Kevin Zirkle sits down with Ravit Gutman, CEO of Extropy Advisors, for an inside look at her upcoming sessions at the IOFM...
Oct 28, 2025 21 min
Order Chaos to Confidence: Extropy + Esker on Intelligent Order Management
In this episode of Extropy on AIR: Strategic Partnerships Driving Financial Transformation, Kevin Zirkle from Extropy Advisors sits down with Nick Carpenter, Principal of Customer Services at Esker, to tackle one of...
Oct 22, 2025 12 min
Raindrop + Extropy: Strategic Partnership Driving Financial Transformation
In this episode of Extropy on AIR: Strategic Partnerships Driving Financial Transformation, Kevin Zirkle sits down with Ward Karson, COO of Raindrop, to explore how flexibility, modular design, and embedded AI are...
Oct 21, 2025 11 min
The Human Advantage: Introducing Esker + Extropy
In this debut episode of Extropy on AIR’s Partner Series, Kevin Zirkle from Extropy Advisors sits down with Kyle Young of Esker to explore what makes automation truly human-centered. Together, they dive...
Oct 19, 2025 16 min
Extropy on AIR Intro Episode
Welcome to Extropy on AIR This is the official podcast of Extropy Advisors, where transformation meets possibility. Join us as we explore the future of finance, technology, and leadership through candid conversations...