Originally aired December 2, 2025 on Extropy On AIr.
AI in finance works best when it gives people superpowers, not when it replaces their judgment. In the final episode of our six-part Esker partner series, Kevin Zirkle of Extropy Advisors and Jim Dougherty of Esker look at Esker’s practical, explainable approach to AI, analytics that drive action rather than just reporting, a manufacturer that reached 80%+ automatic cash matching, and four trends shaping the future of finance.
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Key takeaways
- Esker uses AI to enhance human decisions, not override them, and every AI decision is explainable and auditable.
- Analytics should go beyond dashboards to predictive KPIs, root cause analysis, behavioral insights and scenario modeling.
- Because Esker covers both order-to-cash and procure-to-pay, it connects insight across cash in and cash out.
- A global manufacturer reached 80%+ automatic cash matching, a faster month-end close and better forecasting.
- The future is unified cash intelligence, predictive process management, personalized automation and sustainability tracking.
How does Esker approach AI in finance?
Kevin notes that AI is in every headline and strategy deck, but for many finance leaders it still feels like a black box. Jim says Esker takes a practical and ethical approach: AI is embedded to enhance human decision making, not override it. It handles pattern recognition, prioritization and anomaly detection, and every AI decision is explainable and auditable. Users can override or tune any suggestion, which is what lets people trust it. Kevin adds that this philosophy should give companies more confidence in how to govern AI as they move forward.
What makes analytics actionable?
Many platforms stop at the dashboard. Jim says Esker goes further with:
- Predictive KPIs, like anticipated payment delays or invoice approval risks
- Root cause analysis of recurring issues in workflows or vendor behavior
- Behavioral insights that highlight user training gaps or system issues
- Scenario modeling to help finance teams plan proactively
Because Esker covers both order-to-cash and procure-to-pay, it can connect insights across cash coming in and cash going out, which Kevin says gives CFOs real control over their cash strategy. Jim adds that Esker shows business users the logic behind its AI, keeps analytics configurable without code, and focuses on guiding users to take action. That agility matters especially for mid-market and lower enterprise companies without large IT teams.
What does “people first” mean for Esker’s roadmap?
Jim’s core belief is simple: technology should serve humans. That means designing experiences that are intuitive and engaging, and empowering users to make better decisions instead of just automating tasks. Finance teams have a job to do, and it isn’t learning how the AI works. It is getting the numbers they need to make decisions. In Jim’s experience, platforms designed with empathy are adopted faster, perform better and help retain employees, and Esker is doubling down on that mindset.
What results can AI-driven cash application deliver?
Jim shared the story of a large manufacturer receiving high volumes of customer payments across Europe, South America and the United States. Finance teams spent hours manually matching checks, wires and remittances to open invoices, which slowed cash application and limited visibility into customer payment behavior. Esker helped in three ways:
- AI-driven capture extracted payment and remittance details from emails, PDFs and EDI 820 files, improving accuracy over time through machine learning.
- Analytics dashboards gave finance leaders real-time insight into unapplied cash, customer payment trends and DSO.
- Workflow automation routed exceptions to the right team member, cutting the back and forth over email.
The company reached automatic cash matching rates of about 80% and higher, closed the month faster with less unapplied cash, and improved forecasting, with analytics that flagged late-paying and high-risk accounts. Jim’s key point: the AI didn’t automate everything. It kept learning from user corrections, while analytics gave leaders visibility they never had before. Kevin calls it going from friction to foresight.
How does Extropy help Esker customers with AI and analytics?
Jim sees Extropy helping clients define what success looks like, build AI governance into decision making, identify training needs from behavioral data and adjust workflows based on performance insights. The result isn’t just a platform implementation but a smarter operating model that scales, adapts and supports people. Kevin adds that making transformation stick means aligning culture, policy and process, not just configuring screens.
What is the future of intelligent finance automation?
Jim isn’t a fan of the word automation. He sees AI working alongside teams and giving them superpowers, and he points to four trends:
- Unified cash intelligence connecting order-to-cash, procure-to-pay and treasury for real-time, AI-driven decisions.
- Predictive process management that flags bottlenecks and resolves them in record time.
- Hyper-personalized automation where systems adapt to how each user behaves, learns and improves.
- Sustainability integration that uses finance data to track ESG, supplier ethics and waste.
All of it, he says, will require partners who can bridge the gap between platform and purpose.
The Esker series in review
This episode closes our six-part series with Esker. Catch up on the full set:
- The Human Advantage: Introducing Esker + Extropy
- Order Chaos to Confidence: Intelligent Order Management
- Collect Smarter, Not Harder: Human-Centric AR Automation
- Redefining Source-to-Pay: Visibility, Control, and Connection
- Paying It Forward: Intelligent AP That Works for People
- AI, Insight & the Future of Finance (this episode)
In their words
I think it’s more of AI working with your team and giving them basically superpowers.
Jim Dougherty, Esker
We’re giving finance teams confidence, not complexity.
Jim Dougherty, Esker
About the speakers
Kevin Zirkle is Director of Business Development at Extropy Advisors, where he works across Extropy’s partner ecosystem, matching organizations with the right technology and the right people to move transformation from the whiteboard into production.
Jim Dougherty is Technology Evangelist at Esker, where he works with organizations on AI and analytics across order-to-cash and source-to-pay.
FAQ
What does responsible AI look like in finance automation?
It means using AI to enhance human decisions rather than override them. In Esker’s approach, AI handles pattern recognition, prioritization and anomaly detection, every decision is explainable and auditable, and users can override or tune any suggestion.
How is actionable analytics different from a dashboard?
A dashboard shows what happened. Actionable analytics adds predictive KPIs like expected payment delays and approval risks, root cause analysis of recurring issues, behavioral insights that reveal training gaps, and scenario modeling so finance teams can plan ahead. Covering both order-to-cash and procure-to-pay connects insight across cash in and cash out.
What trends will shape the future of finance automation?
Jim Dougherty points to four: unified cash intelligence connecting order-to-cash, procure-to-pay and treasury; predictive process management that flags and resolves bottlenecks; hyper-personalized automation that adapts to how each user works; and sustainability integration that uses finance data to track ESG, supplier ethics and waste.
Keep exploring
- More from our partner series on Extropy On AIr
- Previous in the Esker series: Paying It Forward with Esker: Intelligent AP That Works for People
- Related: Beyond the Demo: Esker All Access
- Why Extropy
Ready to put AI to work for your finance team, with people at the center? Book a discovery call with our team.
