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Women Of The C-Suite: “Fear is a liar; Fear will tell you the craziest things” With Melissa Wong CEO of Retail Zipline

Fear is a liar: Fear will tell you the craziest things. When I first started, I legitimately feared our company would fail and that I would end up eating cat food. What happened is nothing further from the truth. When you’re in the moment, don’t let feelings of fear lead your actions or choices. I […]

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Fear is a liar: Fear will tell you the craziest things. When I first started, I legitimately feared our company would fail and that I would end up eating cat food. What happened is nothing further from the truth. When you’re in the moment, don’t let feelings of fear lead your actions or choices.


I had the pleasure to interview Melissa Wong. Melissa is the co-founder and CEO of Retail Zipline, the leading communication and execution platform for retailers who believe in the power of the store experience. Melissa is passionate about retail communications, having served as a corporate communications manager at Old Navy for more than 10 years. Melissa studied at Bates College and currently lives in San Francisco.


Thank you so much for joining us Melissa. Can you tell us a story about what brought you to this specific career path?

You could say I’m an accidental entrepreneur. I spent my career in communications, first in PR and then in Operational Communications for Old Navy. I was at Old Navy for over ten years, where I always focused on driving better behavior, understanding, and execution with our more than 50,000 store teams. Over the years, different CEOs and Heads of Stores would always express the same pain-point: that stores weren’t doing what we were telling them to do. When I dug in, it always came down to a breakdown in communication. Eventually, after creating a duct-taped solution that brought together different pieces of various systems and implementing a best-in-class task management solution for millions of dollars, I decided there had to be a better way. A friend connected me to my co-founder, Jeremy Baker, and we started building a better solution for store execution and engagement.

Can you share the most interesting story that happened to you since you began leading your company?

One of the more notable things I experienced when starting Retail Zipline was the sheer amount of female support from other entrepreneurs and our customers. When we first started the company, my co-founder moved out of the Bay Area to Vancouver. Through our accelerator and network of female leaders that wanted to help support our growth, I was pleasantly surprised to find I wasn’t on my own. I’ve found women leaders to be truly supportive, candid, and authentic, and have been appreciative of all of the insights they’ve given throughout our growth. Our customers also feel connected to our success and goal to empower others. Retail is the most populous job in America, and the majority of employees are women. It’s been an honor to serve these iconic retail brands, like Lush Cosmetics and The Lego Group, and also know we’re promoting the growth and development of women.

Serena’s investment in Retail Zipline was such an exciting moment for us as a company, but also me personally. I’ve looked up to her for years and for her to give us her vote of confidence and support our growth was a milestone moment. It’s been incredible to witness strong female leaders rallying together to support each other and encourage each other to win.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I almost didn’t start Retail Zipline at all for fear of failure. However, I had a conversation with my mother that changed everything. I was talking to her about the problems in the retail industry, namely that stores don’t have the tools they need to execute, but also that it was such a huge risk to leave ten years of what I knew to start a company. She said to me, “What’s the worst that can happen? You can always come back and live with your dad and me.” At that time, I was 35. But, I took her words of advice to heart, realized I didn’t have that much to lose, and decided to follow my passion to create an easier way for others to work. Remembering that conversation in the first couple of years of this journey helped me keep going through the downs and ups of launching a startup and still does!

What do you think makes your company stand out? Can you share a story?

When we talk with our customers, whether it’s a store manager or an HQ employee, I’m always surprised by the amount of joy they get from the enterprise technology we’ve built. Who giggles when talking about enterprise technology? Whether it’s a store manager at Lush Cosmetics talking about us making their lives easier and giving them time back to speak with a customer on the floor, or an operations manager in HQ saying that the visibility into what’s been done in stores is game-changing, we’ve amassed a cult-like following of people that love our product. I think people can tell that the reason we started this company was to fundamentally improve the lives of retail employees, and it’s working. Unlike other tools that approach the store execution problem through simple tasking or workload planning, we approach it through a communications lens. We believe that if you combine tools that balance brand storytelling with accountable ways to keep track of the work, people will be engaged behind the brand, know what to do and when to do it, and better understand priorities.

Are you working on any exciting new projects now? How do you think that will help people?

We are currently beta testing our Associate Experience solution, which helps bridge the knowledge gap between HQ and associates on the floor. We know that seasonal or part-time store associates are a special use case and have developed a solution that will enable these folks to not only feel connected to the brand and be engaged behind all promotions and product launches, but also help them receive information in a more streamlined way from their store leadership team. We’ve often heard that this associate group feels disconnected from what’s happening in the company, but they are the most important face of the brand to customers. Our solution will help keep them in the know and enable them to be the best ambassadors of the brand.

What advice would you give to other female leaders to help their team to thrive?

Create ongoing rituals and moments of recognition for the team. At Retail Zipline, we have a very strong company culture because of some of the rituals we create throughout the week. I like to say we created a retail culture at a tech company. We talk about what’s working and give thanks, as well as discuss what’s blocking us or potential opportunities on a daily basis. At the end of the week, we celebrate with a virtual wave. These small things lead points of connection and community — they’re something everyone participates in and help us feel like a family.

What advice would you give to other female leaders about the best way to manage a large team?

Lead from a place of authenticity. Your team can tell when things are going well or going poorly; they know when you’re saying something from an ego-driven place or from a heartfelt one. Address the ‘why’ instead of avoiding it and give your team the context to understand the direction. Often times I’ve felt like I’m repeating myself too much, but have come to understand that explaining the context and why it matters, as well as reiterating direction helps others get a more global understanding of what we’re trying to solve for and enables everyone to contribute in a more meaningful way.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

There are two main people that I’m grateful for.

The head of our accelerator program, Ravi Belani, was incredible in helping me see what was possible. Coming from over a decade working within retail, I knew nothing about fundraising, building a company or SaaS. He guided me through the fear and helped me develop a plan so I could see what was possible. In some ways, he saw more in me than I did in myself in those early days.

My cofounder Jeremy is my partner in crime in building this business. He has an incredible product vision and a way of bringing ideas to life that leapfrog what’s out there. As cofounders throughout the years, we’ve both worked on our communication and leadership styles during different phases of growth and it’s been an honor to grow this company with him.

How have you used your success to bring goodness to the world?

Similar to how other women have helped me during times of uncertainty or inflection points of growth, I always talk with other women who are making the leap. We are at an incredible time of opportunity, and sometimes I feel like we are the ones holding ourselves back. Only 2.2% of VC money goes to female founders, and the time is now to change the tide on that.

What are your “5 Things I Wish Someone Told Me Before I Started” and why?

  1. Fear is a liar: Fear will tell you the craziest things. When I first started, I legitimately feared our company would fail and that I would end up eating cat food. What happened is nothing further from the truth. When you’re in the moment, don’t let feelings of fear lead your actions or choices.
  2. Remember what recharges you: It’s so easy to go down the rabbit hole of working too much to drive the business forward. However, when you’re depleted, you have to know how to reset yourself and re-charge. I wish I had made a list of things that I do to re-charge before I started Retail Zipline. When you’re in the troughs of work, it can be hard to remember.
  3. Resilience is the best competency: Regardless of whether you have the most amazing product, the best customers, or a fantastic team, something will always go wrong. Business never goes as planned and it’s the ability to get back up and begin again that makes us be better at what we do and how we do it.
  4. It will be hard but worth it: Starting a company is undoubtedly difficult, but also incredibly rewarding. Staying the course and seeing the direct results of your work can be empowering and gives so much more purpose to what you do.
  5. Just keep going: In moments of doubt, just keep going and the work will pay off.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

Giving everyone the opportunity to succeed. The disparity between rich and poor is more evident than ever and everyone should have equal rights to opportunities despite their race, socio-economic background, gender, or history. Providing better education and resources for those who are underserved or marginalized would be the movement I would want to inspire.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

My favorite life lesson quote is the first of the five things I wish someone told me before I started — that “fear is a liar”.

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

I deeply admire Ruth Bader Ginsberg for paving the way for gender equality and women’s rights. She is tenacious, incredibly smart, hilarious, and can probably do more pushups than I can. If I ever meet her, it will be an honor.

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