In payments, the complexity often lies in the product itself. The systems that move money between banks, networks, processors and merchants have been built over decades, and while new entrants often portray legacy infrastructure as outdated baggage, Spreedly CEO Justin Benson argues the reality is much more nuanced.
In a PYMNTS “What’s Next in Payments” interview focused on infrastructure, Benson said the industry too often frames legacy technologies as something to escape from, rather than something that helped build modern commerce in the first place.
“I think legacy infrastructure is almost always an advantage,” Benson says.
This perspective runs counter to the common fintech narrative that outdated payment systems automatically stifle innovation. Benson instead argued that many incumbent providers have survived precisely because they have solved some of the toughest problems in payments.
“When you think about payments, you think about things like security,” Benson said. “You think about things like availability of scale. You think about things like data and insights.”
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The real tension, he suggested, comes not from the infrastructure itself, but from the business models built around it.
control and simplicity
Benson explained that payments are a constant struggle between control and simplicity. Merchants want easy-to-use payment systems, but they also want more control over how their payment stacks operate.
This tension helped shape the payments orchestration market. There, platforms like Spreedly sit between merchants and multiple payment providers, helping businesses route, optimize, and manage transactions without forcing them into a single ecosystem.
“The core of Orchestrator really challenged the premise that simplicity is a tradeoff for control,” Benson told PYMNTS.
He pointed to the rise of companies like Stripe, Square, and Braintree, which initially gained traction by simplifying payments into streamlined one-stop-shop services. However, as merchants grow globally and become more sophisticated, many want greater flexibility in routing, providers, and economics.
This change has created room for orchestration providers that promise both simplicity and optionality for sellers. Benson argued that orchestration works with traditional infrastructure rather than replacing it, abstracting complexity while giving merchants more direct control over their payment operations.
Why startups compete differently
Benson also pointed out that startups often have an advantage because they are not burdened by traditional commercial expectations.
He said legacy providers often operate on the defensive because they already have established revenue streams, profitability targets and investor expectations to protect.
In contrast, startups are not constrained by old operating models and can therefore price aggressively and simplify their products.
“There’s a running joke that some of the highest paid engineers work on COBOL systems,” he said. “These systems are resilient, tested and reliable.”
This dynamic means that so-called “legacy issues” are often less about technology and more about competing priorities within the executive team, he said.
“It really could be a CRO issue, a CFO issue, or a CEO issue,” Benson says.
How AI impacts legacy infrastructure
Artificial intelligence (AI) has the potential to further reshape that debate.
Benson said AI has the potential to undermine one of new fintech’s biggest historical advantages: easier integration and a cleaner developer experience. AI tools could help merchants avoid the outdated interfaces and documentation that once made older providers difficult to use.
“Legacy providers may come back,” Benson said.
At the same time, AI systems rely heavily on large amounts of high-quality data, and incumbent payment companies may hold a significant advantage in this area due to their size and transaction history.
But Benson cautioned that AI will not eliminate commercial tensions around ownership, monetization and risk.
He cited agency transactions as an example. Technically, autonomous agents can already operate on top of existing payment rails, he said. Bigger issues include liability, economics, and transaction control.
“The question is, who owns this deal?” Benson said. “What happens if there is a chargeback? How do I monetize this?”
In the end, Benson argued, incumbents may be underestimating the extent to which innovation relies on commercial reinvention rather than pure technology replacement.
“Perhaps the incumbents are focusing a little too much on the technology gap rather than the commercial relationship gap,” he said.
For an industry obsessed with replacing legacy systems, Benson’s message was markedly different. That means the infrastructure itself may already be good enough. The real challenge is determining how to modernize the underlying business model.
“Legacy infrastructure is very valuable and usually advantageous,” Benson said.
