110. UNTUCKit's VP of IT and Systems, Jason Lerman: “Great retail technology should be invisible.”

UNTUCKit built its brand around a simple idea: shirts designed to be worn untucked. But behind that simple product is a complex technology operation supporting 80+ stores, multiple e-commerce sites, and a growing global business. In this conversation, Paula Macaggi sits down with Jason Lerman, VP of IT & Systems at UNTUCKit, to unpack what really happens behind the scenes of retail technology. They discuss the evolution from “best-in-breed” platforms to what many retailers now recognize as a “Frankenstein tech stack,” the hidden complexity of system integrations, and why the best technology in retail is often the kind customers never notice.

Jason also shares his perspective on vendor relationships, implementation mistakes, legacy technology debt, and how retail leaders should think about building a modern tech stack today. The conversation explores the role of centralized data, the challenges of managing dozens of technology partners, and how emerging technologies like AI and agentic systems could reshape the future of retail operations.

Learn more about UNTUCKit: https://www.untuckit.com
Follow Jason Lerman on LinkedIn: https://www.linkedin.com/in/jason-lerman/