Extropy on AIR: Finance Transformation, AP Automation & AI in Finance

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 behind that gap. They explore why entropy quietly erodes even the best-laid plans, how ambiguity stalls teams and kills momentum, and why the people closest to the work are often...

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 scaling faster than your systems can support is one of the fastest paths to corporate entropy. They break down what "scaling before stabilizing" really looks like, why speed is a multiplier for both good and bad, and wha...

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 episode of Extropy On AIr, host Ravit Gutman sits down with Jason Kurtz, CEO of Basware, to break down why the calls you make about AP during your migration window will shape how your finance function...

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 something most transformation conversations skip: where entropy actually originates. Not from bad leadership or poor execution, but from silos that started as solutions, incentives that were never aligned ac...

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 five telltale signals of organizational entropy: exception dependency, shadow systems, decision escalation, metric conflict, and hero dependency. The uncomfortable truth? These don't look like problems. They...

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 conversation. No software providers. No marketing fluff. Just honest peer dialogue about what's actually working (and what isn't) as organizations navigate AI adoption, process automation,...

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 it, and what finance leaders can expect. This isn't another product demo or vendor pitch. It's an honest, people-first space for finance transformation conversations that actually matter. Subscribe so you don't miss what's coming!

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 at Extropy Advisors, to dismantle one of the most expensive myths in business today: that buying better platforms leads to better outcomes. They dig into why organizations invest heavily i...

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 CEO, Ravit Gutman, to unpack what’s really happening in finance transformation after a week at the SSON conference. Because while every solution is “AI-first,” the reality on the ground looks very different. Leaders...

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 ones actually seeing measurable results? In this episode of Extropy on Air , Kevin Zirkle sits down with Adam Lustig from Basware to explore what is really happening inside finance organizations as A...

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 for an honest and energizing discussion about women in finance, leadership, transformation, visibility, empathy, and what it truly takes to grow into your voice. From navigating corporate spaces as a woman...

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 entropy as the slow drift toward disorder inside growing organizations. They unpack why traditional transformation language, like automation, optimization, and modernization, often misses the deeper structur...

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 Ravit Gutman sits down with finance leader Bo Senu-Hodo , whose voice and perspective first captured attention at IOFM last fall. Bo brings decades of global experience across shared services, source to pay, and finance tran...

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 unpack the hidden cost of organizational entropy . The slow, cumulative drift toward complexity, fragmentation, and disorder that quietly undermines even the most well funded transformation...

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 Correia share how clear communication, strong project structure, and hands-on support help teams navigate financial transformation with confidence. From kickoff to go-live, this co...

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 Special Projects at Basware , to break down why ERP-centric thinking holds AP teams back and how intelligent invoice lifecycle management changes the equation. You’ll learn: Why ERP systems manage trans...

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 will truly separate leaders from laggards in the year ahead. They explore why most companies struggled to see value from early AI investments, how to rethink AI strategy beyond buzzwords, and why success is no longer a...

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 lessons are shaping the road ahead. In this episode, they reflect on: What truly moved the needle in 2025 (and what didn’t) How Extropy’s approach to AI, automation, and transformation continues to evolve What...

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 , Kevin Zirkle and Mike Jasper , of Extropy Advisors break down 10 real, executable resolutions CFOs must commit to in 2026 . This is not a conversation about buzzwords, pilot programs, or aspirational strategy dec...

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, and finance decision-making. AI is no longer an abstract concept. It is embedded, accessible, and already delivering measurable value for the modern Office of the CFO. But the most exciting part?...

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 episode dives into Esker’s people-first approach to AI, including: • How AI enhances—not replaces—human decision-making • Why explainability and trust matter in enterprise AI • Predictive insights across O2...

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. From guided buying and budget-aware requisitioning to AI-driven insights, duplicate detection, and supplier recommendations, Raindrop brings simplicity and control to every purchasing decision. Ward also shares a pow...

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 of Esker about how modern AP automation transforms a historically manual and reactive function into a connected, intelligent, and people-centered process. They explore the challenges AP teams face to...

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 to bid normalization and supplier discovery, Raindrop’s sourcing module helps organizations achieve faster cycle times, measurable savings, and risk-aware decision-making without the spreadsheet cha...

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 Success Mike Jasper sit down to unpack the biggest trends shaping finance transformation, Ravit’s three packed sessions, and a few lighter moments from the conference. You’ll hear: Fresh insights on wha...