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

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 across functions, and slow drift that happens between the moments of intentional change. If your organization feels like everything is getting harder without one clear reason why, this one's for you.

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 look like people doing their jobs. That's exactly what makes them so dangerous.If you're a leader trying to get ahead of dysfunction before it becomes a crisis, this episode gives you a practical lens for seeing what's hiding in plain sight, and a simple place to start this week.

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, and the human side of change. Topics are driven by the community, conversations stay in the room, and the goal is simple: connect the people who are living these challenges so they can learn from each other. Stay tuned for more exciting news from Extropy!

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 in automation, AI, and analytics — and still end up with teams working overtime, shadow processes, and dashboards full of green lights that mask real dysfunction. Sound familiar?In this episode, you'll learn:Why technology is the amplifier, not the driver, and what happens when what you're amplifying lacks coherenceThe concept of "visible progress with invisible stagnation" and how executive reporting can reinforce the illusionThe three most common failure patterns in digital transformation (including "fragmentation through success" — where every team wins but the company loses)Why the Structure → System → Technology sequence matters, and what goes wrong when organizations invert itFour concrete actions leaders can take right now if their transformation feels harder than it shouldBuilding on earlier episodes, Kevin and Mike connect the dots between corporate entropy, the concept of extropy, and the deliberate design of organizational coherence — the real center of any lasting transformation.Next episode: How entropy shows up inside finance operating models: AP, AR, procurement, and treasury. Where it hides, how it manifests, and how to start diagnosing it.🔗 Learn more at getextropy.com

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 aren’t lacking tools. They’re lacking clarity.We get into:Why so many companies feel stuck between where they are and where AI is taking themThe gap between technology, people, and processWhat “Monday morning” actually looks like after a conference like SSONKey takeaways from International Women’s Day and evolving leadership expectationsAnd most importantly, we share a real example of what getting it right looks like.Dexcom’s Finance Transformation Award win wasn’t about replacing people with AI, it was about using AI to support them.Reducing overtime.Creating space for higher-value work.Scaling without burning out teams.This is what happens when you focus on the human side of AI.If you're navigating AI, finance transformation, or trying to figure out where to start, this episode brings clarity to the noise.

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 AI adoption accelerates.The conversation highlights an important shift: moving from AI that simply generates insights to AI that actually executes work.Together they discuss:• Why many AI pilots stall before delivering value• How agentic AI is transforming accounts payable operations• Why AP is one of the most successful entry points for AI adoption• The difference between AI that informs work and AI that performs work• How governance enables organizations to scale AI responsibly• The buy vs. build decision many finance leaders face when deploying AIOne theme came up again and again throughout the discussion:Execution beats experimentation.For finance leaders exploring AI, this episode offers a grounded look at what it actually takes to move from pilots to measurable operational impact.

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 to mentoring the next generation to leading with both strength and humanity, Bo shares a perspective that is grounded, practical, and deeply empowering.This conversation touches on:Women in finance and leadershipConfidence, visibility, and finding your voiceMentorship, empathy, and modern leadershipFinance transformation and process excellenceBuilding strong teams and creating opportunity for othersWhy women need to stop shrinking and start being moreBo’s message is clear: you do not have to wait to be chosen. You do not have to lead from limitation. You can be more.If you missed this conversation the first time, we’re proud to share it again as part of our continued celebration of the remarkable women shaping our industry.#InternationalWomensMonth #WomenInFinance #WomenInLeadership #FinanceTransformation #ExtropyOnAir

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 structural problem.From system fragmentation and dashboard illusion to AI amplifying weak architecture, this conversation reframes transformation as intentional system design rather than tool deployment.You will learn:• What entropy really means in a business context• Why scale often increases complexity faster than capability• How AI magnifies existing structural weaknesses• What “coherence velocity” means for leadership• Practical steps CFOs and transformation leaders can take tomorrowTransformation is not a project milestone. It is the continuous application of energy to maintain coherence.If you lead finance, operations, or enterprise systems, this episode is for you.

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 transformation. From building teams across Europe and Asia to mentoring the next generation of leaders, she shares what it truly takes to lead with both strength and empathy in today’s finance landscape.This conversation explores:• Why finance must become a true business partner• The importance of understanding process before investing in technology• How data transforms conversations with leadership• Why mentorship is essential for sustainable growth• How women can stop pouring from an empty cup and start leading intentionallyBo’s message is clear. Be the CEO of your own life. Protect your energy. Audit what no longer serves you. And always strive to be more.As always, we continue to Transform Forward.

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 efforts.They explore:Why “we’re live, but it doesn’t feel like we’re live” is a red flagHow unmanaged complexity and turnover erode trust and adoptionThe warning signs leaders often miss until it’s too lateWhy stacking tools increases entropy instead of reducing itWhat it actually takes to design for sustained success after go liveIf you’re a CFO, transformation leader, or executive navigating digital change, this conversation offers a clear lens for diagnosing issues early and designing systems that scale with intention, not chaos.

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 conversation shows what it looks like to lead change in a way that works for the people doing the work.

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 transactions but don’t automate workflowsThe hidden cost of manual AP processes, late payments, and approval bottlenecksHow organizations achieve 80%+ touchless invoice rates without re-engineering their ERPReal examples of recovered value, faster cycle times, and improved controlWhy successful automation requires both the right platform and the right partnerIf your AP team is still chasing approvals or fixing preventable errors, this episode offers a clear path forward.

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 about buying AI, but about using it intentionally. From measuring ROI and time-to-value, to building trust, mastering prompts, and treating AI like a teammate with a specific skill set, this episode gets practical fast.You’ll also hear real examples of where AI is making the biggest impact today, including customer service, finance operations, healthcare, and contract management and why comfort, curiosity, and iteration matter more than perfection.Whether you’re just getting started or refining your AI strategy for 2026, this conversation will help you think differently about how humans and AI work better together.

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 evolveWhat intentional growth looks like as we head into 2026This isn’t a highlight reel. It’s a grounded conversation about focus, people, and building systems — and cultures — that last.

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 decks.Instead, Kevin and Mike challenge each other on what it really takes to:Move AI from experimentation into everyday finance operationsReduce manual work by 25–40 percentEliminate risky spreadsheet dependencyModernize cash forecasting and Source-to-Pay controlsDrive touchless transactions at scaleUpskill finance teams for an AI-enabled futureShift finance from historical reporting to true business advisoryIf you are a CFO, Controller, or finance leader preparing for planning season, this episode offers a clear, execution-focused lens on what must change next year and where to start.

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? We’re just getting started.In this episode, Kevin and Ward explore:Where most organizations really are on the AI maturity curveHow AI is already transforming sourcing, contract management, supplier intelligence, and spend analyticsThe rise of natural-language insights for finance and procurementWhy autonomous sourcing is closer than people thinkThe essential role of governance, transparency, and human oversightHow Raindrop’s graph-based AI model drives smarter, faster, more strategic decisionsWhat CFOs should consider as they plan AI investments for the next 3–5 yearsWard also shares a real-world story of a global enterprise that has achieved 80% automation in sourcing, freeing teams to focus on strategy, innovation, and value creation.If you’ve been following this six-episode Raindrop series, this finale brings it all together, showing the future of procurement, sourcing, and finance intelligence through the lens of AI.

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 O2C and P2P• Actionable analytics vs. static dashboards• The evolution of cash intelligence, process optimization, and user-centric designYou’ll also hear how Extropy Advisors helps organizations build governance, define success, and implement operating models that scale.If you’re a finance, shared services, or digital transformation leader — this episode will give you clarity on where AI is going, and how to prepare your organization for what’s next.

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 powerful client story where Raindrop helped eliminate maverick spend and create a seamless, intelligent buying experience across catalogs, including Amazon Business.If you're a CFO, procurement leader, or operations executive looking to modernize spend management, this episode is packed with practical insights and real-world impact.Listen now and transform forward with us.

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 today, including manual entry, long cycle times, compliance risks, and late payments. Shelly-Ann explains how Esker uses AI, workflow automation, and real-time visibility to help finance teams gain control, reduce risk, and operate with more confidence.This episode covers:• The biggest pain points in AP today• How AI makes AP faster and more predictable without losing control• Real-world customer results, including 89 percent touchless processing• How Extropy and Esker partner to deliver measurable impact• Why modern AP is becoming a strategic priority for CFOsIf your AP team is overwhelmed or looking for a smarter and more human-friendly way to work, this conversation offers practical insights for every finance organization.

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 chaos.You’ll hear real-world examples of companies like Buckman Chemicals and Western Digital, who cut costs and improved speed-to-value by modernizing their sourcing process.Tune in to learn how smarter sourcing can boost margins, strengthen resilience, and become your CFO’s secret weapon for transformation.

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 what finance leaders are prioritizing in 2025Their favorite meal in Vegas (hint: strategy and steak both made the cut)And the clear winner for best conference swag.Tune in for a mix of insight, inspiration, and Extropy energy, straight from the floor of IOFM!

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 dive into how modern S2P transformation improves compliance, reduces manual effort, and enhances supplier collaboration through guided buying, touchless invoice automation, and AI-powered insights.We unpack how organizations can scale faster, drive ROI, and build better supplier relationships without complex integrations or system overhauls.

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 Advisors sits down again with Ward Karson, COO of Raindrop, to explore how supplier management has evolved into a strategic advantage for finance leaders.Discover how Raindrop’s Supplier Management module uses automation, AI, and seamless integrations to streamline onboarding, monitor risk in real time, and elevate ESG transparency.If you don’t know your suppliers, you don’t truly know your business.#DigitalTransformation #CFOCommunity #ProcurementInnovation

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 is more than chasing invoices; it’s about resilience, relationships, and results. Together, they break down:Why traditional AR processes keep teams reactive instead of strategicHow Esker’s people-first approach transforms collections into collaborationThe critical differences between Esker, HighRadius, and SideTradeHow AI enhances, not replaces, human decision-makingA real-world example of a global manufacturer that cut DSO by six days and tripled collector efficiencyHow Extropy helps organizations configure AR for adoption, accuracy, and long-term valueWhether you’re a CFO, controller, or AR leader, this conversation will change how you think about collections, cash flow, and customer experience.

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 organizations handle risk, compliance, and efficiency.Contracts are the lifeblood of every business, but too often, they’re buried in inboxes, shared drives, and outdated systems. Ward unpacks how Raindrop’s CLM and RainSign bring visibility, automation, and AI-powered intelligence to every stage of the contract process, from intake to signature to renewal.They discuss real-world client examples, CFO-level outcomes, and how CLM delivers not just legal protection, but measurable financial value. Whether you’re a CFO, legal leader, or operations professional, this episode reveals why it’s time to move from manual chaos to digital control.

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 Fall 2025 Conference in Las Vegas.Ravit shares her insights on how finance leaders can prepare for the future, exploring trends, evolving roles, and leadership strategies that balance innovation with human connection. Together, they discuss how automation and analytics are reshaping finance, why collaboration between AP and IT is key to transformation, and how modern leaders can redefine roles to drive lasting impact.If you’re attending IOFM or passionate about the intersection of people, process, and technology, this episode offers a powerful preview of the conversations shaping the next era of finance transformation.

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 the most overlooked pain points in finance and operations: order management chaos.For many organizations, order entry is still surprisingly manual, a patchwork of emails, PDFs, and spreadsheets that drain productivity and erode customer trust. Together, Kevin and Nick explore how Esker’s Intelligent Order Management flips that script through AI-powered automation, exception handling, and real-time collaboration tools.You’ll learn how Esker and Extropy help companies:Eliminate manual order entry and reduce costly errorsImprove visibility across the entire order lifecycleReclaim time for customer service teams to focus on relationships, not retypingStrengthen cross-functional collaboration between finance, sales, and operationsTurn order management into a growth engine for the businessThis episode goes beyond automation; it’s about restoring confidence, speed, and accuracy in one of the most critical touchpoints of the customer journey.Listen now to hear how Extropy and Esker are redefining order management for the digital era.#ExtropyOnAir #Esker #OrderManagement #O2C #FinanceTransformation #Automation #CustomerExperience #DigitalTransformation

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 helping CFOs modernize smarter, not harder

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 into how Esker’s cloud platform and Extropy’s transformation strategy combine to help finance teams modernize with confidence, empathy, and impact.You’ll hear about:Esker’s approach to human-centered automationHow Extropy and Esker collaborate to drive real-world transformationWhy culture is the key to making technology stickTune in to learn how innovation and empathy are redefining what’s possible in finance and operations.

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 with experts, innovators, and changemakers who are redefining what’s possible in the digital era.