Women in wine: Chicago’s female wine professionals are driving change, but obstacles remain in an industry long dominated by men

The rising profile of women in the wine business has done much to reshape an industry long considered a boys club.

While statistics on women in the American wine industry are scarce, in recent generations women have flourished as winemakers and sommeliers, top executives and critics, educators and more. According to UC Davis, a top incubator for American wine professionals, since the 1990s, roughly half of the graduates of the school’s Viticulture and Oenology program have been women. In the past decade, the number of women undergraduates enrolled in the program has consistently, albeit slightly, surpassed that of men.

Despite the increasing influence and visibility of women, the wine industry continues to be led predominantly by men. Of the roughly 4,200 wineries in California, only 14% reported a woman as their lead winemaker in 2020, up from 10% in 2011. Of the 171 Americans who hold the title of Master Sommelier, only 25 are women.

For the most part, the obstacles women continue to encounter in wine aren’t physical — there’s no shortage of women who can hoist 40-pound cases of wine, drive tractors or power through double shifts on a restaurant floor. 

Rather, the challenges that persist are far more nuanced, says Jill Zimorski, a master sommelier and adjunct instructor at DePaul University’s School of Hospitality & Sports Business. Beyond gender biases, sexism and misogyny, women in wine still miss out on representation and access to leadership positions, she says. Women face pay gaps and distinct challenges in the pursuit of work-life balance, particularly when it comes to child-rearing.

The Tribune spoke with four prominent women in Chicago about some of the challenges they’ve faced and how they’ve navigated their careers in wine. Interviews and comments have been edited for clarity and brevity.

Rachel Driver Speckan, portfolio manager at Maverick Beverage Company

Whether juggling a dozen venues as the national beverage director for City Winery or managing a portfolio of wine, spirits and sake for Maverick Beverage Company in Chicago, Rachel Driver Speckan has navigated nearly every facet of the wine industry over the past two decades. More unusually for this industry, she’s tackled a steady climb up the management ladder while raising two children, now 8 and 10 years old.

On the distinct hurdles women with children face in the wine business

Driver Speckan: A lot of women I know step away from a career in wine after having children. Hospitality, particularly, is unforgiving for women with children. As a wine director or sommelier, for years, nights and weekends were prerequisites. The access and availability of child care is an enormous hurdle.

But opting out of the wine industry wasn’t an option for me. I knew I could make family life and a career in wine industry coexist. I wasn’t going to ask permission and if an employer wanted me, they’d have to deal with what they got.

At City Winery, I was the first woman in management to have a child. I had to advocate for myself and design a framework for benefits and time off from the ground up. At work, there wasn’t anywhere to pump or breastfeed or even to change diapers properly. Because I was traveling all the time, often I had to bring my kids to work with me. I still think I’ll write a book someday called “Oh, the Places I’ve Pumped.”

Maverick Beverage Company portfolio manager Rachel Driver Speckan at El Che Steakhouse and Bar in Chicago. (Armando L. Sanchez/Chicago Tribune)

Working in wine distribution is a little kinder to family life, but I specifically chose Maverick because it’s very much a family-first environment. It’s very rare, but everyone builds their schedule around what works for them and if you get the job done, no questions asked. Still, balancing home life with work is not easy. It’s been 10 years since I had kids and I still don’t sleep.

On pay gaps and learning to take, not ask for, promotions 

Driver Speckan: Over the course of seven years in one of my previous positions, I had to ask for a raise seven times. Ultimately, I got those raises, but when I left the job, I discovered I was still earning the bare minimum of what a man in the same position would have received. 

For years I thought that if I was qualified, if the merit was there, my employers would acknowledge that and promote me on my own worth. Meanwhile, I was watching men just demand the same jobs even if they weren’t qualified. So I came to adopt the same kind of body stature and assertiveness I saw in my male coworkers and learned to say, “I want this job, give it to me.” And it’s worked.

On how gender biases continue to hinder career advancement for women

Driver Speckan: The wine business is very much an apprenticeship-based industry. It takes years to incubate professionals who can function at the level they need to reach. It’s a business of relationships, and the connections you forge make a big difference in the jobs you get, or the kind of career development you get access to. It’s another reason why gender biases in hiring, or access to mentorship and training, are still big obstacles for women in wine.

Regine T. Rousseau, media personality, CEO and founder of Shall We Wine

Regine Rousseau, a veteran wine educator and sommelier, tries a sample of a 2024 Gassier Côtes de Provence Rosé before appearing on WGN-TV Daytime Chicago for a segment titled "The Rise of Women In Wine" on March 13, 2025. (Audrey Richardson/Chicago Tribune)
Regine Rousseau, a veteran wine educator and sommelier, tries a sample of a 2024 Gassier Côtes de Provence Rosé before appearing on WGN-TV Daytime Chicago for a segment titled “The Rise of Women In Wine” on March 13, 2025. (Audrey Richardson/Chicago Tribune)

In the typically staid landscape of wine TV, Rousseau’s disarming, dynamic approach to wine and spirits has made her a widely recognized media personality, especially in Chicago, where she’s been a mainstay on WGN-TV.

Rousseau’s journey in the wine industry began in 1998 with a sales position at a Chicago wine distributor. Her career path has taken a number of unexpected turns — positions in pharmaceutical sales, salon ownership and litigation consulting. But a corporate layoff in 2013 prompted her to pursue her passion for wine full-time.

Shall We Wine, the wine and spirits marketing company she founded, pioneered concepts such as digital content creation, brand activation and community-based marketing long before they were industry buzzwords.

On her experiences as a Black woman in wine

Rousseau: As a Haitian American born in Chicago but raised in Haiti, I’ve felt sexism and racism from the start. But culturally, I was raised in a way where you just shut up and push forward — not that this is the right way. So when I started my first job in the wine industry in 1998, despite being in a place where leadership was overwhelmingly white and male, I don’t know if I was even plugged into the idea of sexism or racism then.

It took me a long time to understand what people meant when they say “representation matters.” I get now that when you see an African American woman succeed in this industry, it can be enormously inspiring and motivating.

I’ve developed a really large platform and have supporters and fans from all walks of life. But the people who have been most excited about what I’m doing, the ones who’ve pulled me aside and said “Wow, this is really amazing,” are often people who look like me. So yes, I see now that representation absolutely matters.

On how the wine industry has broadened

Rousseau: One of the biggest changes I’ve seen is that there are so many more opportunities and paths for women today. Beyond a career in restaurants, retail or distribution, there’s this heightened interest in entrepreneurship, in forging your own way to engage people with wine. Whether that’s creating a wine app or hosting pop-ups, writing a book or offering independent wine dinners or classes, there are so many different avenues that we just didn’t see before.

On community building in the wine world

Rousseau: Much more than before, I see that women are supporting each other. They’re investing time and energy into building organizations for women in the wine industry, standing up for each other and making space for other women with talent.

There are so many dynamic women in wine who are innovative and collaborative, and this is what our industry needs right now.

Alpana Singh, former master sommelier, media personality and owner of Alpana Restaurant

In 2003, at age 26, Alpana Singh became the youngest American woman and first woman of color to be awarded the title of master sommelier by the Court of Master Sommelier. Unabashedly youthful, outspoken and media-savvy, Singh’s trailblazing achievements made her a figurehead for a generation of women who followed her path in the wine industry.

Alpana Singh, a former master sommelier, at her restaurant Alpana in Chicago on March 14, 2025. (Chris Sweda/Chicago Tribune)
Alpana Singh, a former master sommelier, at her restaurant Alpana in Chicago on March 14, 2025. (Chris Sweda/Chicago Tribune)

A veteran sommelier turned restaurateur, and for 12 seasons, host of PBS Chicago’s restaurant review show, “Check, Please!,” Singh owns and operates Alpana Restaurant, a wine-inspired bistro in Chicago’s Gold Coast neighborhood.

In 2020, following a highly publicized exposé by the New York Times on the culture of sexual harassment, manipulation and assault by male master sommeliers within the Court of Master Sommeliers, Singh was the first master sommelier to resign from the Court in solidarity with the alleged victims. In the aftermath of the scandal, the Court commissioned an external investigation that resulted in the expulsion of six master sommeliers. Another master sommelier who resigned before the investigation has been barred from applying for reinstatement to the Court. While the Court has undertaken numerous measures to change the structure and culture of the Court, many, like Singh, still find the Court’s response to be inadequate.

On resigning from the Court of Master Sommeliers  

Singh: 2020 was a crazy time. We were going through the pandemic and there were protests just blocks away from where I live in downtown Chicago. I was devastated about the situation surrounding the women who had come forward about allegations of abuse by men in the Court. As I surveyed the city, the destruction and damage and anger were so palpable, I just had to let go. 

When I dropped the title, I really lost my sense of identity. I viewed myself as a master sommelier for so long, if I wasn’t one anymore, then who was I? I think women struggle a lot with this loss of identity as we transition into new roles, as a mom, as a wife, or after a divorce. It took time to mourn and grieve, but ultimately, I think I resigned because I never truly felt at home within the organization.  

When I passed the exam, I was told, “You’re a master sommelier now so all eyes will be on you.” It was a statement I interpreted as a warning that I’m a bit much and that I needed to tone things down and watch my behavior. I really believed I had to live up to this higher standard to honor and respect the legacy of this organization. So when I found out about these abuse allegations, and what these male master sommeliers were getting away with, it really made me mad.

On how she perceived bias as a young, female sommelier of color 

Singh: As a young sommelier, I wish I could say I was more mindful and aware of these things. I always felt pressure to have a lot of bravado. People would say that I had a lot of chutzpah because I never questioned what the friction was about. If someone was being a jerk, if someone else had a problem with me, I simply refused to make it my problem.  

But I was raised by some very strong female personalities. My mother is a take-no-prisoners kind of woman; in fact, all the women in my family are bulldozers. These were my role models but I understand that this isn’t the reality for all women.

Jill Zimorski, master sommelier and adjunct instructor at DePaul University

Master sommelier and adjunct professor Jill Zimorski, left, shows Marvin Gibson, 21, right, and Carter Wideman, 22, center, how to open a bottle of brut rose while teaching a course on wine and beverage management at DePaul University in the Loop on March 11, 2025. (Armando L. Sanchez/Chicago Tribune)
Master sommelier and adjunct professor Jill Zimorski, left, shows Marvin Gibson, 21, right, and Carter Wideman, 22, center, how to open a bottle of brut rosé sparkling wine while teaching a course on wine and beverage management at DePaul University in the Loop on March 11, 2025. (Armando L. Sanchez/Chicago Tribune)

Jill Zimorski is one of just a handful of master sommeliers who has passed the notoriously difficult master sommelier exam not once, but twice.  

In 2018, the veteran sommelier and wine director became an unwitting casualty of an explosive cheating scandal within the Court of Master Sommeliers, the nonprofit organization that administers the elite exam. Zimorski was one of 23 candidates who passed the master sommelier exam that year but had their titles revoked after revelations arose that a proctor, a veteran master sommelier, leaked detailed exam information. Zimorski passed the exam again in 2019, reclaiming the master sommelier title, but has been an outspoken critic and proponent for systemic reform within the organization.  

Today, largely estranged from the Court of Master Sommeliers, Zimorski teaches courses on wine education and beverage management at DePaul and certificate courses for the Wine & Spirit Education Trust at the American Wine School in Chicago. 

On her difficult relationship with the Court of Master Sommeliers 

Zimorski: The Court’s handling of the scandal was an intense betrayal that I’ll never fully recover from. The stress, anxiety, grief and disbelief I felt were all magnified by a response by the Court that was thoroughly inadequate. Then, in 2020, when allegations about the Court’s failure to account for its lack of diversity and inclusion, and later, horrific accusations of sexual harassment and assault came to light, I became fundamentally disillusioned with the Court.  

I think there was a generational divide in how women master sommeliers thought the sexual abuse allegations should be dealt with. Many of the younger members, like myself, found the situation unacceptable, while some older master sommeliers were like, “I’ve dealt with worse so we shouldn’t make such a big deal of this.” There are still people in positions of influence within the Court who downplay the seriousness of it all and that’s not OK. I do believe a generational shift is happening and things have changed, but the situation is still not as it should be.  

On the impact of representation and mentorship 

Zimorski: The very first sommelier I ever met and worked with was a Black Jamaican woman, Nadine Brown, in Washington, D.C. She wasn’t representative of the industry at all, but through her mentorship, she became my reference point. Especially in hospitality and wine, where historically, there haven’t been a lot of women, it’s difficult to envision yourself in positions of leadership when there isn’t significant representation. 

Today, I’ll meet with anyone who takes the time to seek me out as a mentor or to ask questions. But I tell my students that if you want a mentor, you can’t assume that someone is going to tap you on the shoulder and offer to be your mentor. You have to advocate for yourself, to allow yourself to be vulnerable and to speak up.

Anna Lee Iijima is a freelance writer.

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