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 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.

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 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.

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 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.

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 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.

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 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.

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 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.