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

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 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.

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Contracts are the lifeblood of every business, but too often, they’re buried in inboxes, shared drives, and outdated systems.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 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

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 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.

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.