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Retail is often a balancing act—between innovation and stability, between adopting new technology and preserving tried-and-true methods, and between treating vendors as mere service providers versus true business partners. These themes were at the heart of a recent conversation on the Endless Aisle podcast with Jason Lerman, VP of IT and Systems at UNTUCKit, as he reflected on his career, the role of technology in retail, and the evolving relationship between brands and vendors.
Read below for key takeaways from Jason’s interview, and click here to listen to the full podcast episode.
Jason Lerman’s journey in retail began with a part-time job at a toy store, where he developed an early passion for merchandising and customer experience. His curiosity about consumer behavior led him to experiment with store layouts, ultimately increasing sales and sparking an interest in analytics-driven retail decision-making.
From there, Jason’s career took him through various retail and e-commerce roles, including time at luxury fashion brand Zadig & Voltaire and media powerhouse Barstool Sports, before he made a “boomerang” return to UNTUCKit in 2023. His diverse background—spanning operations, logistics, and technology—has given him a unique perspective on how different functions within a retail business interconnect.
One of the central themes of Jason’s discussion was the distinction between vendors and partners. He noted that many vendors struggle to engage retailers effectively, often approaching them with aggressive sales tactics rather than genuine collaboration.
“Every brand is a fingerprint,” Jason explained. “So many times, vendors come in thinking their product is a perfect fit without really listening to the nuances of the business.”
He emphasized that true partnerships are built on understanding the retailer’s needs and adding consistent value over time. For vendors looking to build meaningful relationships, Jason suggested a more consultative approach—offering insights based on a retailer’s current challenges rather than simply pushing a product.
As retailers seek to build stronger partnerships, technology often plays a pivotal role in driving collaboration and efficiency. However, retail technology has advanced rapidly, but not all innovations are created equal. Jason highlighted the importance of ROI-driven decision-making when implementing new solutions. “Sometimes we get excited about new technology, implement it, and realize it’s just a cost without delivering the expected benefits,” he said.
To ensure tech investments align with business goals, UNTUCKit takes a strategic approach, considering:
One of Jason’s priorities has been consolidating UNTUCKit’s tech stack, auditing vendor relationships, and ensuring that every solution in place provides measurable value. By managing partnerships proactively, the company avoids unnecessary costs and improves efficiency across its operations.
Jason also emphasized the value of industry networking and knowledge sharing, noting how events like Endless Aisle Live facilitate meaningful connections. “Sometimes we’re so focused on our day-to-day work that we don’t take time to step back and learn from others,” he said.
By engaging with peers, UNTUCKit stays ahead of trends, learns from other retailers’ successes (and failures), and gains insights into emerging best practices. This collaborative mindset reinforces the company’s philosophy of continuous improvement.
As UNTUCKit looks ahead, Jason remains committed to fostering a culture of analytical thinking through stronger internal mentorship, ensuring that teams approach challenges with a data-driven mindset. A key priority is enhancing AI-driven inventory planning and allocation, allowing the brand to optimize stock levels and streamline operations. At the same time, Jason is focused on strengthening vendor relationships to maximize efficiency and ensure that every partnership contributes tangible value to the business. With a continued emphasis on maintaining a lean and focused operational strategy post-COVID, UNTUCKit is positioning itself for a year of smart, strategic growth.
Despite the challenges of the past few years, Jason sees a bright future for UNTUCKit. “We finally see the light,” he said. “2025 is going to be a good year—as long as we stay on course and focus on what’s important.”
With a strong commitment to innovation, strategic partnerships, and a deep understanding of customer behavior, UNTUCKit is well-positioned to navigate the evolving retail landscape.
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