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The Importance of Following Your Instinct and Working with Conviction

Lessons on leadership from Retail Zipline CEO Melissa Wong

When Melissa Wong worked in communications at Old Navy, she witnessed a massive disconnect between what was said by headquarters and what was heard by store workers. She realized that retail communications tools were built for workers sitting stationary at desks, not deskless workers moving constantly to manage inventory and service customers. She and her co-founder Jeremy Baker launched Retail Zipline to streamline communications across the entire retail footprint. They had a clear vision and the conviction to address a real need, but as a first-time CEO, Melissa needed to learn to recognize her unique leadership style and, as part of that, become comfortable leaning into her strengths. She has been recognized as a top female executive trailblazer driving innovation in the rapidly changing retail industry, a Forbes thought leader and Retail Zipline continues to be awarded Best Tech Places to Work in the Bay Area and is one of the Most Innovative B2B Retail Startups by CB Insights.

At Emergence, we’re privileged to work with many incredible leaders like Melissa who make our jobs an utter joy. Melissa has been kind enough to share some of the most significant leadership lessons she’s learned thus far during her incredible entrepreneurial journey.

It’s intimidating at times to be a leader, especially a female leader in the still male-dominated tech sector. I’ve often had to push myself through challenging decisions despite not always feeling confident about the outcomes. What I’ve learned over the past six years of growing my business is that our strengths as leaders come from our differences and are often borne of our vulnerabilities. I’m excited to share some of what I’ve learned and hope these lessons help pave the path to success for the next generation of female SaaS founders.

We as female CEOs should never shy away from our unique superpowers.

When raising my initial seed round, I often had this feeling that I needed to approach things from a male perspective. I realized I would never reach my full-potential playing a part, and it was only then that I came to the empowering decision that I would no longer change myself to cater to anyone’s perspectives—male or female. Ultimately, what matters most to me and to my company, is our customers’ perspective. I keep them in mind with everything I do.

My best advice is that as female CEOs we often do things differently, and that can create some pretty incredible superpowers. Our strength comes from using our perspectives to our advantage and in gaining comfort for standing up for our experiences. 

Stay focused on your vision, not someone else’s version of your vision.

My co-founder and I have always had a pretty unique vision for a startup, but my approach was not always well received by investors and the so-called experts. There were many times I was compared to others, especially since investors rely on pattern recognition and there weren’t many others that had similar backgrounds as a comparison. For me, there was no template for success and because of that, it took me a while to truly believe in myself enough to push forward with my vision. 

Today, I am incredibly thankful to have stuck to my gut and turned Retail Zipline into the type of company I’m proud to lead. I’ve stood my ground on what I established to be important, and I’ve stuck to my product vision and priorities. It has been following that path—not someone else’s version of it—that has led us to the success we’ve achieved thus far.

Don’t hesitate to go all-in on your customers and their success.

At Retail Zipline, we believe that our customers are our greatest salespeople and our most ardent evangelists. From the beginning, I wanted to invest heavily in customer success; I wanted to build a community and connect customers. And above all, I wanted customer-centricity, not numbers, to guide all of our key decisions. In some cases, this meant placing big bets on customers early in the relationship. We maintained a “make or break it” mentality, going all-in with conviction and treating our customers as our most valued partners.

With so much uncertainty across the retail industry this year, our emphasis on our customers had never been more important. And because of this, we were able to maintain the strong relationships we had already built. 

My advice to entrepreneurs is to focus on your customers. They are the bedrock of your company. Be a compassionate listener and find ways to bring people together around a common goal. 

Embrace the beauty of delegation.

Like most people, whether a CEO or not, this year has been challenging for many reasons. For me, it was balancing being a new parent while running a company and managing the uncertainty. I’ve often been asked how do I ‘juggle’ it all, but I have come to reject this notion. It’s much more nuanced. First of all, we are humans and we all have the same amount of time in a day. The best advice I live by is to not focus on keeping all of the balls in the air at the same time. Rather, it’s about figuring out which balls are glass and which are rubber and being okay with letting the rubber ones drop—at least until you can reach down to pick them up again. 

Prioritizing as a leader is one of the hardest things to do. I cannot say there is an easy way to help you figure out what that right balance is, but in my personal experience, I can say that I’ve come to appreciate the power of delegation. It took me time, but I have come to the realization that I cannot control everything anymore. What I can do is control the things that matter most and surround myself with an incredible team—both at home and at work.