During Women’s History Month, Women in Retail Leadership Circle (WIRLC) is highlighting women who are making history today in the world of retail. March 25 is National Women in Wine Day, which is why we’re sharing this exclusive interview with Jessica Kogan, chief growth and experience officer at Vintage Wine Estates, a family of wineries and wines. A fast-growing wine producer with a direct-to-consumer platform, Vintage Wine Estates has wineries throughout Napa, Sonoma, California’s central coast, Oregon, and Washington State.

Inner Circle: Let’s start by going through your career journey. How did you end up in the world of e-commerce, and specifically wine?

Jessica Kogan: I ended up in e-commerce after launching Boo.com, a failed but incredible global fashion startup. It was a spectacular concept for 1999: a multi-language, multi-currency, transactional platform featuring multi-brand fashion clothing (Patagonia, Helly Hansen, Puma, etc.), with international dropship fulfillment and a dressing room avatar called Miss Boo. At the time, international fashion shopping was brand new to the internet. The only problem was that it took roughly five minutes to download each page – we were still in the dial-up age and the site was built for a T-1 connected world. I loved marketing the site and was hooked on e-commerce and the brilliant decentralization of shopping. I joined Razorfish to understand everything e-commerce and went on to build systems that facilitated stock market trading from your home; access to lesson rubrics on teaching tolerance in the classrooms of American teachers; and livestream videos of luxury runways available to anyone around the globe with internet access. I eventually left Razorfish to start a wine company in San Francisco. Wine felt perfectly suited for e-commerce because of its opaque distribution, confusing communication and anxiety-provoking misinformation. I cofounded Cameron Hughes Wine and a digital-native wine e-commerce business was born.

IC: Can you tell us a little bit about your latest venture, Vintage Wine Estates?

JK: Vintage Wine Estates acquired Cameron Hughes Wine in 2017 and is the parent company to more than 12 winery estates, 10 lifestyle wine brands and three digital native e-commerce companies. My role is to oversee the digital convergence of e-commerce on behalf of all our business channels (DTC and B2C) and ensure that we are offering the best possible customer experience wherever a consumer chooses to engage, connect, and purchase our wine brands.

IC: What are some ways you’ve led digital transformation over the course of your career?

JK: For many, digital transformation has centered around improving business processes. For me, digital transformation is about access, connection and community. My leadership began with communicating borderless access to global fashion sportswear brands. After this, I focused on implementing borderless equities trading and connecting with experts and later real-time views and commentary of luxury fashion shows. I aimed to create a new, consumer-driven editorial point of view from the customer. For wine, it has been all about access: changing the narrative on opaque distribution and gate-keepers within the three-tier system, and providing access to consumers on their terms.

IC: The wine industry is heavily male dominated and has pretty traditional, old-school roots. What challenges have you faced being both a woman and an innovator in the wine industry?

JK: The best way to describe this challenge is to imagine yourself playing basketball. The opposing male team has five starters and five superstar subs. The female team has three superstar players, and no subs. The odds of winning are low, and of being patronized high. The best way to deal with it is to believe in yourself, in your work, and find amazing mentors who will help you navigate the full-court press and picks which happen often. Though you are the minority, there is no reason why you do not deserve to be exactly where you are, most especially when you are focused on disrupting an inherently unfair game. Resistance to innovation is not a gender or minority issue, it is about the displacement of old ideas and ways of being and ultimately comes down to money and the protectionism of the status quo that is generally not in the best interest of the consumer.

IC: How can the industry as a whole be more encouraging of women joining its leadership ranks?

JK: In general– and this is not specific to just wine, but any consumer product vertical and likely all categories of business – if we want women to take on leadership roles, they need to be compensated equal to men, they need to be surrounded by mentors who take an active interest in their development, and they need family support. They do all of this plus fees for golf clubs, etc. for men. The same should be done for women who show real potential. Until this happens, we will continue to see women exit the workforce despite having matriculated to higher degrees of education than most of their male peers and mentors.

IC: What are some skills you use in leading a team?

JK: Using the sports metaphor, I see myself as a coach to my team. My job is to help my team see the problem and brainstorm the solution. It is their job to execute. Sometimes execution is great, and sometimes it is not. I never view failure as a problem – only moments in which we can learn, grow, and improve. In general, I treat everyone first amongst equals and try to flatten the team structure so there is constant collaborative learning across generational cohorts. I am adamant in facilitating work ownership regardless of level. Accountability is the difference between good and great teams.

IC: What advice do you have for the next generation of female leaders in business?

JK: Know you belong at the table. Though you might be the lone voice, being different is OK and in fact, makes you more valuable. Find mentors that support you and are willing to help you with your communication. Many times, when working in a male-dominated environment, it comes down to how you present information and the not quality of your thinking. Take classes on communication – it is as valuable as your college degree.

IC: What’s a setback you faced in your career?

JK: When I realized my business partner and husband did not view me as his equal.

IC: What are two wines (a red and a white) that you recommend?

JK: Two wines I absolutely love are:

Read part 1 and part 2 of Women in Retail’s Women’s History Month interview series.