“You need a good level of understanding and then you need to hire really smart, great people to run those departments. The trick is to be a great manager, organizer, and motivator – and to know how to push people to be their best while also caring about them as people.”

Meet Rachel Jarrett, President and COO of Zola, an innovative wedding planning and registry platform utilizing modern tools and technology. Before Zola, Rachel held numerous roles in retail merchandising, marketing, and operations at Toys R Us, D.E. Shaw, Barnes & Noble, Gilt Group, and her own company Chocolate Works. We spoke to Rachel about her career path, professional development, and entrepreneurial pursuits.

Tell us a bit about how you grew up.

I was born and raised in Manhattan. I consider myself a true New Yorker and am happiest in the city where I grew up. I am grateful for all of the benefits that NYC provided me growing up (culture, diversity, architecture, the 1986 Mets) and I am raising my two children in the city as well.

Can you tell us about your career path? How did you get to where you are today?

My career path is more of a game of hopscotch than a straight-line path. I majored in international relations as a joint BA/MA student at Johns Hopkins and then went to work for the government from 1996 - 2001 in Washington, DC. In that role, I had the opportunity to travel internationally, learn new languages, and serve my country in a way that made me feel very proud and fulfilled. That said, I knew that I would never be happy away from NYC in the long term and so I made the decision to go to business school at Northwestern’s Kellogg as a means towards getting back to the city I love most.

After Kellogg, I ended up at Toys R Us in their post-MBA leadership rotational program. I randomly and luckily ended up in buying during my second rotation and just fell in love with this field instantly. I ended up staying on as a buyer at Toys R Us for about 6 years. After that, I found my way into e-commerce at companies like Barnes & Noble, Gilt.com, and now Zola!

How did working at Gilt, a company known for having spawned so many great startups (including Zola), influence or change you?

Gilt was a transformative experience. In fact, more than any other job I have had, being at Gilt changed me professionally. It exposed me to what it is like to be at a true start-up filled with incredibly smart and talented people. I fell in love with the fast pace and bias towards action that was evident at Gilt. I definitely caught the “bug” for start-ups there. I also had the privilege to work with some outstanding leaders, including Shan-Lyn Ma (the CEO of Zola) and also Kevin Ryan. Kevin has been a phenomenal mentor to me. It is a relationship that I deeply treasure.

On the business side, watching a company grow to over a $1 billion in value and then crash is a painful but richly valuable experience. We spend a lot of time at Zola thinking about what we learned from that journey and how we can capture all that was great about Gilt, while avoiding making some of the same mistakes as we scale. The Gilt experience is a big part of the DNA of our entire executive team.

You have been President and COO at Zola for almost 3 years now. What inspired you to take this role?

If I had to hand-pick my favorite people from Gilt and the people who I thought were the most talented, I would have picked the leadership team at Zola, particularly Shan and Nobu. I just could not pass up the opportunity to be a part of this team and to help them in their mission to use technology to serve today’s couples from the day they get engaged through the first years of their newlywed life. I also felt strongly that the wedding market was one that was ripe to be disrupted and Zola had exactly the product and team to do it.

As President and COO you run finance, operations, merchandising, growth, human resources, and legal! How do you possibly run all those areas? What skills are needed to run such a wide variety of departments?

Being a buyer early on in my career was one of the best training grounds for general management. Many people who are not familiar with buying as a profession think it has to do with picking out stylish items but it is so much more than that. A buyer has to manage the entire P&L of a mini-business within a larger business. I learned so much during my years in merchandising that helped me as a General Manager and now as a President & COO. That said, being a great President & COO does not mean you have to be an expert in all the areas that you oversee.

You need a good level of understanding and then you need to hire really smart, great people to run those departments. The trick is to be a great manager, organizer, and motivator – and to know how to push people to be their best while also caring about them as people.

I think that is the ultimate key to success in a role like this.

Did we see on your LinkedIn that between Gilt and Zola you opened a chocolate shop in New York? What inspired you to run this completely different type of business? What did it teach you?

After years of being in bigger retailers and the hectic pace of Gilt, I decided that I wanted to try going into business for myself and do something completely different. I contacted a small business broker and ended up opening a franchise location of a concept called “Chocolate Works.” It was an incredible experience. I learned what it feels like to be a small business owner and the challenges they face. Ultimately, the financial picture did not make sense for me. The amount of hours that I needed to work in order to make a living was just not sustainable. I ended up selling the store which was a bit sad. It felt like a third child. But then I ended up at Zola and I could not be happier with that outcome!

Despite being a $100B+ industry, the wedding space is only starting to be disrupted now. Why is now the time? Why did it take so long?

The issue with this industry is that no player other than Zola has found the right monetization model and this has prevented lasting and meaningful innovation. Most of the businesses have either been advertising models or service fee model (i.e., pay for this service) and the issue is that neither of these models put the customer’s needs first. We started with wedding registry, which is a phenomenal business model, and this allowed us to solve real pain points for today’s couples. With our healthy monetization model in place, we are well positioned to execute our vision of helping today’s couples plan their entire wedding journey from the day they get engaged all the way through the first years of newlywed life.

Can you talk to us about your view of leadership? What from your background informs your style of leadership?

My view on leadership stems from looking back on the leaders and managers who inspired me the most and made me the happiest at work. For me, those were people who pushed me hard but also saw me as a human being. It was also those who were open, honest, and non-hierarchical. I try to embody these qualities in my own leadership.

I am the type of leader who pushes you to the limit to do your absolute best but also deeply cares about you as a person and a professional.

I have found that most talented and smart people actually feel more fulfilled and happier at work when they are being challenged and pushed outside their comfort zones. It is less difficult to be a passive “easy” manager. It takes more work to push people and give them constructive feedback and help them grow into their best selves.

Fire Round

What is your favorite item on Zola?

Classic sheets from Brooklinen. These sheets are amazing!  Crisp and cool and great quality for an amazing price.

What is the most interesting article or book you have read in the past few months?

“The Case for the Subway” by Jonathan Mahler at the New York Times. This is an exceptional piece of journalism about why the subway system is essential to the survival of New York City. One of the best I have actually ever read.

Who is a female entrepreneur or investor you'd most like to meet and chat with?

Katrina Lake from StitchFix. She built an incredible company with almost no funding or meaningful marketing spend.

What is the best piece of advice you have ever received?

Don’t be afraid to fail. “Failure is the foundation of success and the means by which it is achieved.” – Lao Tz

Madeline Keulen