From Automation Pioneer to AI Trailblazer: How Ken Virgin, CEO of Aimyable, Is Shaping the Future of AP 

Ken Virgin has always been at the forefront of change in Accounts Payable. From pioneering electronic invoicing to now leading the introduction of AI Digital Coworkers, his vision has consistently anticipated the future of finance operations. With Aimyable, Virgin isn’t just offering another tool, he’s reimagining the very nature of work in AP. For CFOs and finance leaders, the message is unmistakable: the future of accounts payable will be shaped not by systems, but by digital coworkers who work alongside their human peers.  

The CEO: Who is Ken Virgin?  

Ken Virgin, CEO of Aimyable, has spent his career at the crossroads of technology and finance. He began in the 1990s with Andersen Consulting (now Accenture), implementing ERP systems focused on accounts payable (AP) and purchasing. Seeing opportunity in emerging Internet technologies, he founded iPayables, one of the early pioneers in AP automation.  
 
For more than two decades, Virgin served as CEO of iPayables, growing the company to over 100 employees and winning clients such as American Airlines, Delta, and Kroger. Under his leadership, iPayables patented innovative technologies and made electronic invoicing mainstream for global enterprises. In 2022, Virgin sold the company and set his sights on a new frontier: artificial intelligence.  
 
Operating now from Southern California, Virgin leads a distributed team at Aimyable. His leadership philosophy emphasizes three pillars: delivering measurable value to customers, ensuring a culture of attentive service, and breaking down silos between technology and client-facing teams. “Technology only matters if it creates real value for customers,” he explains. “That focus drives everything we do at Aimyable.”  

Why Aimyable? The Inspiration Behind the Company  

The inspiration for Aimyable came from Virgin’s recognition that, despite decades of progress in automation, AP teams still struggled with bottlenecks. Exception handling remained manual, integration challenges slowed adoption, and hiring qualified clerks had become increasingly difficult.  
 
Virgin saw AI as the next paradigm shift, similar to the rise of the Internet in the 1990s. “Instead of building yet another integration-heavy tool, I asked: what if we created a digital coworker? What if we gave finance leaders an intelligent teammate who could work like a clerk and without complex system changes?”  
 
That question became the foundation of Aimyable. By designing an AI Digital Coworker, Virgin aimed to solve long-standing issues in AP: accessibility, speed to value, and the ability to handle not just structured tasks but exceptions and variations in real world workflows.  

Meet Aimy: The AI Digital Coworker for Accounts Payable 

At the heart of Aimyable is Aimy, the first AI Digital Coworker for accounts payable. Unlike traditional tools, Aimy is set up just like a new employee. She is given her own workstation, where she controls the mouse and keyboard, and she is trained directly by AP managers through conversational guidance.  
 
“You talk to Aimy the same way you would train a new clerk,” Virgin explains. “You show her how to separate PO and non-PO invoices, how approvals work, and how exceptions are resolved. She documents every step, enforces the controls you define, and then executes consistently.”  
 
Aimy doesn’t just assist, she works. She can take on repetitive invoice processing, help at month-end close, or absorb overflow when teams are stretched thin. The beauty of an AI Digital Coworker is that they don’t complain, need breaks, or resist taking on the least desirable tasks. In short, she becomes a reliable and valuable member of the team, freeing AP professionals to focus on analysis, forecasting, and other higher-value finance work.  

Aimyable vs. Other AI Tools for AP  

The difference between Aimy and traditional AP automation tools is stark. Most automation platforms require lengthy integrations, rigid configurations, and ongoing reliance on consultants to make changes. By contrast, Aimy requires no integration at all. Training her is as simple as describing the process and approving her steps.  
 
“Aimy is not a chatbot assisting someone else with a product,” Virgin emphasizes. “She is the coworker doing the work.” While other systems use AI to enhance user interfaces or improve OCR, Aimy uses AI to actually perform tasks, respond to suppliers, and adapt processes over time.  
 
This flexibility makes Aimyable especially powerful for midmarket finance teams. It removes barriers to adoption and provides agility that system-based automation can’t match. Aimy doesn’t represent a marginal improvement in tools; she represents a fundamentally new way of working.  

The Advantages of Embracing AI Early  

Virgin is candid about the tradeoffs of adopting new technology early. Early adopters may encounter some imperfections, but the benefits outweigh the risks with AI. “If you wait too long, you risk being seen as a laggard. In finance, that can impact not just your department but your career,” he warns.  
 
He believes AP managers must seize the opportunity to lead. “If accounts payable leaders don’t drive AI adoption, others in the organization will decide how AP should work, and history shows that often leads to inefficiencies.” By experimenting with Aimyable, managers can position themselves as forward-looking leaders, providing valuable counsel to their CFOs and executives.  
 
Virgin’s advice is clear: don’t wait. “AI is here now.  The faster AP managers embrace it, the more they’ll shape how AI is used to benefit their companies.”  

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