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 left out of the rooms where decisions get made.

From tribal knowledge to missing legal sign-off, the execution gap is rarely dramatic. It's dozens of small breakdowns that pile up until the project is already off course.

Tune in for a practical conversation on what it actually takes to convert strategic intent into daily behavior, and why structure, clarity, and the right people in the room make all the difference.

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 what it actually takes to design for sustainable velocity.

If your organization is growing but things feel increasingly chaotic, this one is for you.

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 performs for the next decade.

They get into the real reasons nearly 60% of SAP migrations run over budget or behind schedule, why a specialist AP layer actually protects your clean core instead of adding complexity, how Basware's AI is built on 2.5 billion processed invoices and what that means for touchless processing, what compliance-as-a-service looks like when over 100 global mandates are actively shifting, and why "we'll deal with AP later" is the phrase finance leaders come to regret most.

If you're a CFO, CIO, Controller, or transformation lead anywhere near an SAP program right now, this one is worth your full attention.

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.

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.

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!

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!

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 coherence
• The concept of "visible progress with invisible stagnation" and how executive reporting can reinforce the illusion
• The 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 it
• Four concrete actions leaders can take right now if their transformation feels harder than it should

Building 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

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 them
• The gap between technology, people, and process
• What “Monday morning” actually looks like after a conference like SSON
• Key takeaways from International Women’s Day and evolving leadership expectations

And 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.

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 AI

One 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.

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 leadership
• Confidence, visibility, and finding your voice
• Mentorship, empathy, and modern leadership
• Finance transformation and process excellence
• Building strong teams and creating opportunity for others
• Why women need to stop shrinking and start being more

Bo’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

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 tomorrow

Transformation 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.

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 intentionally

Bo’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.

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 flag
• How unmanaged complexity and turnover erode trust and adoption
• The warning signs leaders often miss until it’s too late
• Why stacking tools increases entropy instead of reducing it
• What it actually takes to design for sustained success after go live

If 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.

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.

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 workflows
• The hidden cost of manual AP processes, late payments, and approval bottlenecks
• How organizations achieve 80%+ touchless invoice rates without re-engineering their ERP
• Real examples of recovered value, faster cycle times, and improved control
• Why successful automation requires both the right platform and the right partner

If your AP team is still chasing approvals or fixing preventable errors, this episode offers a clear path forward.

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.

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 intentional growth looks like as we head into 2026

This isn’t a highlight reel. It’s a grounded conversation about focus, people, and building systems — and cultures — that last.

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 operations
• Reduce manual work by 25–40 percent
• Eliminate risky spreadsheet dependency
• Modernize cash forecasting and Source-to-Pay controls
• Drive touchless transactions at scale
• Upskill finance teams for an AI-enabled future
• Shift finance from historical reporting to true business advisory

If 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.

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 curve
• How AI is already transforming sourcing, contract management, supplier intelligence, and spend analytics
• The rise of natural-language insights for finance and procurement
• Why autonomous sourcing is closer than people think
• The essential role of governance, transparency, and human oversight
• How Raindrop’s graph-based AI model drives smarter, faster, more strategic decisions
• What CFOs should consider as they plan AI investments for the next 3–5 years

Ward 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.

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 design

You’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.

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 CFOs

If 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.

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.

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 2025
• Their 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!

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.

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

You’ll hear about:

• Esker’s approach to human-centered automation
• How Extropy and Esker collaborate to drive real-world transformation
• Why culture is the key to making technology stick

Tune in to learn how innovation and empathy are redefining what’s possible in finance and operations.

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.

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.

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 strategic

• How Esker’s people-first approach transforms collections into collaboration

• The critical differences between Esker, HighRadius, and SideTrade

• How AI enhances, not replaces, human decision-making

• A real-world example of a global manufacturer that cut DSO by six days and tripled collector efficiency

• How Extropy helps organizations configure AR for adoption, accuracy, and long-term value

Whether you’re a CFO, controller, or AR leader, this conversation will change how you think about collections, cash flow, and customer experience.

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.

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 errors

• Improve visibility across the entire order lifecycle

• Reclaim time for customer service teams to focus on relationships, not retyping

• Strengthen cross-functional collaboration between finance, sales, and operations

• Turn order management into a growth engine for the business

This 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