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Interview

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From “Best in Breed” to Frankenstein Stack: The Reality of Retail Technology

📍New York, NY

Retail technology rarely makes headlines when it works well. And that is exactly the point. As Jason Lerman, VP of IT & Systems at UNTUCKit, explains, the best technology in retail should be almost invisible to the customer. When a shopper walks into a store, browses online, or completes a purchase, the experience should feel seamless. Behind that simplicity, however, sits a complex ecosystem of systems, integrations, and decisions that rarely get discussed outside the technology teams responsible for keeping everything running.

UNTUCKit, known for its shirts designed to be worn untucked, operates a growing retail business that includes dozens of stores across the United States and Canada, multiple ecommerce sites, and a fulfillment network supporting its global customers. Supporting that operation requires a sophisticated technology infrastructure. Over time, like many retailers, the company adopted a range of specialized platforms. What began as a strategy to build a “best in breed” technology stack can gradually evolve into something far more complicated to manage. Lerman describes the moment many organizations recognize the problem as the point when every project meeting becomes a conversation about which system is blocking another.

The operational realities behind retail technology decisions go far beyond selecting a platform. Integration challenges, vendor relationships, contract management, and evolving business needs all shape whether a technology investment ultimately delivers value. Lerman highlights the importance of strong discovery during the selection process, alignment between vendors and retailers, and clarity around what success should actually look like once a system is implemented. Without that discipline, retailers risk layering additional tools on top of an already complex environment, increasing the burden on both technology teams and store operations.

Looking ahead, Lerman sees the next phase of retail technology being shaped by artificial intelligence and emerging agent-based systems. These developments could change how platforms communicate, how data flows across systems, and how decisions are made within organizations. Yet the core challenge remains unchanged. Retailers need flexibility, strong data foundations, and technology architectures that allow them to evolve as new capabilities emerge. For leaders navigating the intersection of commerce and technology, the objective is not simply to add more tools. It is to build systems that allow the business to move faster while keeping the customer experience effortless.

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