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

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.

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 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.

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 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!

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.