If the U.S. midmarket were its own country, it would be one of the largest economies in the world. Yet many of these businesses still rely on outdated, manual processes to manage something as fundamental as getting paid.
That topic set the tone for an invigorating conversation between Alta Vista Technology CEO Scott Jackson, VP of Sales & Marketing Mike Petroskey, and special guest, Carey Kolaja, CEO of Versapay .
Rather than a generic product walkthrough or finance lecture, they had an unscripted chat about leadership, trust, technology, and why accounts receivable still feels harder than it should.
Moving money should be a right
Carey didn’t start her career in B2B finance. With nearly 30 years of fintech and early experience at PayPal, she has spent much of her career thinking about how money moves, and why it so often doesn’t.
“Moving money, and accessing money you’ve already earned, shouldn’t be hard. It should be a right.”
That belief shapes how she thinks about B2B payments today. In a world where consumers can pay with a tap of their phone or ride in a self-driving car, businesses still jump through hoops to collect invoices for money they have already earned.
The result is slower cash flow, strained customer relationships, and finance teams spending time chasing payments instead of moving the business forward.
The real moat isn’t technology
As the conversation shifted, Carey challenged a common assumption that technology alone creates a competitive advantage.
“Technology will be commoditized. The real moat is people.”
With AI evolving rapidly, Carey believes the differentiator, especially in the midmarket, will be talent, creativity, and the ability to experiment. Tools matter, but only when paired with teams empowered to use them to their full advantage.
Scott echoed that sentiment from a leadership perspective, calling out a phrase that may be overused, but still rings true.
“It’s cliché, but you really do have to get comfortable being uncomfortable.”
The discussion touched on how quickly roles are changing, with careers evolving every 12 to 18 months, and what leaders increasingly expect from their teams: adaptability, ownership, and the willingness to try, learn, and adjust.
Trust, AI, and the delicate dance of AR
Carey, Scott, and Mike dove into the hot–yet sensitive–topic of the trust between businesses and customers, people and technology, and even humans and AI.
From Uber rides to Waymo self-driving cars, Carey drew parallels between how trust is built in consumer technology and how it must exist in B2B finance.
That balance clearly shows up in accounts receivable.
“Collections are a delicate dance. If you don’t do it right, you can damage the relationship.”
Carey shared how Versapay is working on prediction models that help teams anticipate payment behavior. The goal is to give finance teams better signals on when to automate and when human judgment matters most, so efficiency does not come at the expense of trust.
The moment of challenge accepted
One of the most memorable moments came when Mike playfully challenged Carey with a ChatGPT prompt: “What is your biggest fear would be when sharing openly on LinkedIn”. The answer sparked laughter, reflection, and a deeper conversation.
Watch the full conversation
This blog captures just part of the discussion. The full podcast goes deeper into leadership, trust, AI agents, experimentation, and why accounts receivable is quietly becoming one of the most strategic functions in modern businesses.
Watch the full conversation on Alta Vista’s YouTube channel to hear Carey, Scott, and Mike explore these ideas in their own words.
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