OFFBounds Retail

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/

Creators and Guests

Host
Paula Macaggi
Informing Commerce Leaders | Founder of OFFBounds - #1 Podcast for Commerce Leaders | Speaker | Reta Awards Judge | Top Retail Expert 2024
Editor
Bicho de Goiaba Podcasts
A Brazilian podcast producer. Main clients: Coca-Cola, PepsiCo, Grant Thornton, SKF and Alelo.

What is OFFBounds Retail?

OFFBounds is a podcast where commerce executives share their perspectives, successes, and lessons learned in their careers to inspire other global leaders in their journey and decision-making.

Every week, the host Paula Macaggi meets industry leaders to discuss business strategies, careers, and leadership in one-on-one conversations challenging the limits of borders and boundaries.

Paula unveils the person behind the leader and brings to her audience of commerce executives experiences to relate, motivate, and reflect on decisions that are shaping commerce.

OFFBounds is the first podcast recorded in person with audio and video featuring executives in commerce from around the world.