THE EXTROPY PODCAST

Extropy On AIr

Real talk about finance transformation, AI and the people making it work. Hosted by Ravit Gutman and Mike Jasper, with finance leaders and partners who’ve been in the trenches.

LATEST EPISODE 10 min

Extropy On AIr: Find Your Community, Live from Basware Dublin

Ravit Gutman, Founder & CEO of Extropy Advisors, and Mike Jasper, VP of Extropy Advisors, recorded this one between sessions at Basware’s VIP and NextGen customer event in Dublin. Both...

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All episodes

Every conversation, in one place

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,...

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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...

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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...

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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...

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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...

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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...

Partner series

Conversations with the partners we build with

Multi-part series with the technology partners behind our client work. Straight talk on AP, AR, procurement and what actually makes automation stick.

4-PART PARTNER CONVERSATIONS

Basware x Extropy

Conversations with Basware leaders on invoice lifecycle management, ERP migrations and where agentic AI is paying off in AP.

FEATURINGJason Kurtz (CEO), Kevin Farrell and Adam Lustig of Basware
Play the series from Part 1
  1. Part 1 | Jan 13, 2026 | 15 min Unlocking Intelligent Invoice Lifecycle Management with Basware
  2. Part 2 | Mar 16, 2026 | 18 min Execution Beats Experimentation: How Agentic AI Is Delivering Real ROI in Finance
About the show

Extropy On AIr, in brief

What is Extropy On AIr?

Extropy On AIr is the podcast from Extropy Advisors about finance transformation. Episodes cover AP and AR automation, AI in finance, ERP and procure-to-pay change, and the people side of making new technology stick.

Who hosts Extropy On AIr?

Extropy CEO Ravit Gutman and Mike Jasper, VP of Finance Transformation, host most episodes, joined by finance leaders, practitioners and technology partners.

Where can I listen to Extropy On AIr?

Every episode plays right on this page. You can also follow the show on Spotify, Apple Podcasts and Audible.

What are the partner series?

The partner series are multi-part conversations with the technology partners behind Extropy's client work, including Basware, Esker and Raindrop. They cover invoice lifecycle management, AR and order management, procurement and how AI is changing each one.

How can I be a guest or suggest a topic?

Use the "Pitch an episode" form on this page to pitch yourself, recommend a guest or suggest a topic. The podcast team reviews every pitch and reaches out if it is a fit.

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