Meet Melissa Wong, co-founder and CEO of Zipline, a leading operations platform for field teams within brick-and-mortar stores (and one of Women in Retail Leadership Circle’s amazing partners). Founded in 2014, Zipline drives better business agility, sales execution, and employee engagement for the world’s most innovative retail brands. Today, tens of thousands of stores and hundreds of thousands of users around the world trust and love Zipline to streamline their operations and improve their businesses. Customers include Gap, Sephora, American Eagle Outfitters, O’Reilly Auto Parts, 7-Eleven, and more. In this exclusive interview, Wong discusses why she founded Zipline, leadership challenges she’s experienced and how she navigated them, and more.

Inner Circle: What inspired you to start Zipline? Was there a particular moment or experience that made you realize the retail industry needed a better communication platform?
Melissa Wong: I like to joke that I’m a reluctant entrepreneur. I was at Old Navy for over 10 years, where I oversaw store communications and constantly struggled to get stores to “do the thing.” I actually worked under four different brand presidents during my time Old Navy, and every “big new strategy” still fell apart on the way to the sales floor. One day our vice president said to me, “Melissa, we need to engage the DMs — they’re the silver bullet.” I knew she was right, but what could I do? Nobody was reading what we were sending. I could go through another “communications evolution” project, but what was the point? I started calling peers across the retail industry, asking if they were dealing with similar challenges — and they were. At that point, I realized we weren’t alone. Everybody was stuck. Zipline was born out of that realization.

IC: Can you share a specific example of a leadership challenge you’ve encountered, and how you successfully navigated that challenge?
MW: Honestly, the biggest challenge for me was starting Zipline. I didn’t come from tech; I wasn’t sure I could raise money or build software. I didn’t think I was smart enough. My workaround was incremental courage: I would pitch just one investor, learn, adjust, pitch the next. Step by step your confidence builds. I learned to question my own self-limiting assumptions and keep moving forward, one step at a time.

IC: In the book you wrote with your co-founder, Jeremy Baker, “Stores Don’t Suck: The 5 Principles of Amazing Retail Execution,” you lay out a framework designed to transform store operations through better communication and actionable practices. Which of the five principles do you believe has the most potential to revolutionize in-store execution, and how can retailers begin to implement it effectively?
MW: It’s a toss-up between “Align the Organization” and “Measure the Execution.” If every layer of the organization isn’t pointed at the same goal, nothing else matters — especially right now because there’s so much going on: tariffs, changing consumer preferences, artificial intelligence innovation. Information, priorities and strategies need to be communicated and executed in real time across the business. There can’t be a delay in the cascade.

At the same time, retailers need to be able to test and learn iteratively, and you can only do that if you have good data. We now have access to so much data: customer data, traffic data, inventory data. Measuring store execution and engagement is so much more critical because now you can bring all that data together to understand how execution and engagement actually impacts your bottom line. The retailers that use that data to inform their strategies are going to pull ahead.

IC: As a leader at Zipline, how do you personally apply these principles to foster a culture of effective communication and high performance within your own team?
MW: I’m particularly passionate about principle four, empower the workforce. When people join Zipline, we want to make sure that they’re aligned to our mission of transforming the industry. We want them to feel like they’re part of something bigger. In every interview I ask, “What drives you?” I want to hear people talk about helping others or making an impact.

IC: Retail environments can be fast-paced and challenging. In your view, what leadership qualities are essential for inspiring frontline teams?
MW: Over the course of my career, I’ve had the privilege of working with (and for) some really inspiring retail leaders. One thing they all had was a clear vision. A retail leader’s job is to show their frontline what good looks like; they need to paint a picture of what’s possible. One leader I worked for always said, “stores are the best manifestation of the brand,” and that stuck with me. That was so inspiring to our frontline teams. I also think empathy and understanding is huge. A good leader has to understand what associates actually live through every shift, day after day. Otherwise that vision will seem too unrealistic and fall flat.

IC: How do you see the role of store associates evolving in the age of AI and automation?
MW: First and foremost, frontline work isn’t going away — we all know that. AI will be an enabler and optimizer. It has the potential to coach every store employee to be their best in a personalized and targeted way. It will help inform better decision-making, connect the dots, personalize content and actions in a way that’s best suited to the associate and the brand, and, ultimately, help provide a totally seamless experience between a brand’s online and in-store experience.

IC: Looking ahead, what changes do you foresee in retail leadership as technology and communication continue to evolve? How should leaders in the industry prepare themselves to meet these future demands?
MW: Previously siloed teams will have to become interconnected, and technology has to enable that. Keeping a close eye on AI is non-negotiable, of course. And, most importantly, I think retail leaders will need to lean on each other — in real communities of practice, like WIRLC — to keep learning. Retail is moving so fast. This is a great opportunity to push ourselves and to challenge our own assumptions about what we can become as individuals, as well as an industry, by trying new things.