No Longer the Only Women in the Room

Campaigns & Elections invited a group of women strategists — Republicans and Democrats, veterans of presidential administrations and campaign war rooms — to talk candidly about their careers in politics. What drew them in? What nearly drove them out? What does the industry still need to do to make more space at the table? 

The conversation touches on career choices, pay equity and mentorship; reflections on parenting and burnout, professional pivots, missed weddings and what it takes to succeed in a still-punishing business. These are women who’ve helped shape the last 20-plus years of campaigns, and they have a lot to say about the next generation and beyond. 

The discussion was led by Tracy Dietz, CEO of DonorBureau, and Kelly Gibson, senior VP at Bryson Gillette. Our participants: Rodericka Applewhaite, VP at Focal Point Strategy Group, Kristin Davison, VP and general consultant at Axiom Strategies, Ann Liston, partner at A|L Media, Nicole McCleskey, partner at Public Opinion Strategies, Ashley O’Connor, managing partner at Strategic Partners & Media, Jodi Quintero, managing director at GMMB and Emmy Ruiz, political strategist and former White House political director.

Tracy Dietz: I’d like to start by hearing a bit about everyone’s background in the industry.

Kristin Davison: I’m a Republican consultant and I’ve been doing this – I always say 10 years, but I actually think we’re getting closer to the 20-year mark at this point. I’ve done all sorts of campaigns from dog catcher to president.

Ashley O’Connor: I also work on the Republican side and I do advertising, messaging, content creation and digital. I’ve been working in this industry — I think it’s now almost 30 years.

Nicole McCleskey: I’m a partner at Public Opinion Strategies, a Republican political and public affairs polling firm. I’ve been doing polling at POS for 28 years.

Rodericka Applewhaite: I’m currently a VP at Focal Point Strategy Group. Before that I was in the Biden White House and have worked on a lot of campaigns, including Pete Buttigieg’s presidential run in 2020 and Gov. Gretchen Whitmer’s reelect in 2022.

Emmy Ruiz: I’m more of a general adviser in that I work with a lot of Democratic outfits and entities right now, primarily on the soft side — c3s, c4s, PACs. Previously, I was at the White House where I spent four years as political director. I’ve worked in every presidential race since the primary in 2008.

Ann Liston: I have a firm called A|L Media. I’ve been a partner of the firm for about 20 years. We do races all across the country, up and down the ballot. I’m a veteran of both the Obama and the Harris presidential campaigns. 

Jodi Quintero: I’m a managing director at GMMB, a Democratic firm. I make ads all over the country. I’ve worked in politics for more than 20 years. I just wrapped up the Wisconsin Supreme Court race, which felt really good on our end. I also do a ton of reproductive rights work.

Dietz: Let’s talk about how all of you got into politics, and then once you were in this business, what made you stay?

McCleskey: I was 24-years-old, in a political science PhD program, and I sat down to write a dissertation that I did not feel equipped to write because I had never actually worked on the ground in politics. So I decided to go to Washington to see what it was really like and maybe come back to the PhD. I went to Washington and never went back. Initially, I fully intended to go back to the PhD and teach, which I may still do. Now, after 30 years of experience in the industry, I feel equipped to teach it.

Applewhaite: I was raised by a single mom in a very small town in the South, where you didn’t really talk about politics, but you could see how policy would impact the community. I sort of always thought I would be going to law school, because that’s what you did if you were good at debate in high school. I ended up going to George Washington University for undergrad and realized that politics wasn’t just a thing that people refuse to talk about every two or four years and then silently go to the ballot box — there’s actually an entire industry around it. I got involved with College Democrats and that led me to my first job as a researcher. I went from firm life to actually being on campaigns and I loved that. I also do this because I’m not good at anything else.

O’Connor: I went to an incredibly liberal New England all women’s college, and when a conservative Republican called Mount Holyoke to say, “Hey, I have a Republican advertising firm and I’d like to hire a young woman who just graduated,” they said, “Sure, we have one Republican. Her name is Ashley.” I was pre-med at the time, but I just loved politics. No day was the same. I was on the ad side, specifically post-production, making ads up in New York City. When the 1996 cycle wrapped, I was told, “Okay, you’ll move back and be our office manager.” That sounded really boring. So I left for a while and worked at a production company that did big Madison Avenue things. Eventually I realized it didn’t matter if you sold more Eggos or what color the most popular toaster was — it was political advertising I really loved and made me feel like I was making a difference.

Kelly Gibson: What actually was the bestselling color toaster?

O’Connor: According to the work that we were doing in 1998, it was the silver toaster.

Gibson: Oh, disappointing! I was really hoping it was going to be red or something like that.

Ruiz: For me, the number one reason I got into politics was Hillary Clinton. I loved her. In 2007, I was actually working at the American Red Cross, and so I got to see firsthand that even the largest nonprofit in the world needed a very strong government to provide support to everyday Americans. That’s actually how I met Hillary Clinton, because at the time she was in the U.S. Senate and doing a lot around military families. She’s the number one reason I jumped in. I stayed because of a lot of the work that many of us have done. Whether it’s the people behind the doors we’ve knocked on, the volunteers that we’ve had or the teams that we’ve been a part of, I’m just a firm believer in the work we do. And like many of you, I have a story of where I came from and the people that really deserve to be better served by their government. I grew up in the Rio Grande Valley, a child of immigrants. I grew up believing in the American dream and I still believe in it, and so that’s why I’ve stuck around.

Quintero: I started stuffing envelopes for Carolyn McCarthy in New York when I was 15. She ran for Congress after her husband was murdered in a brutal train shooting on the Long Island Railroad. I just felt like I had to do something. Maybe it’s something we should talk to a therapist about, but I got the bug and haven’t been able to stop working in politics ever since. I think it’s the best way we can make a difference.

Davison: I didn’t think I would do this for a living. I thought I’d go to law school. I’m sure my parents still think I’ll go to law school. But I remember being in college and going to some protest and thinking “What are we actually doing here to make change?” We have to elect people who will go do it. That’s when I really shifted my focus to doing this for a living. There’s always a candidate, there’s always an election, there’s always a campaign that keeps your belief alive. And there’s nothing better than being on that campaign and electing someone you believe in.

Liston: I was the precinct captain in the 43rd Ward in Chicago for Mayor Daley just out of college. I wasn’t very motivated by any ideological issue, but I had three very important reasons to stick with it: beer, boys and pizza. There were some super cute boys at the ward office, lots of free pizza and all the beer you could drink. Right out of college, I thought, “this is a great job.” My interest has definitely evolved over the years. I became very committed to working for women candi-dates, and now I’m very committed to the operative world on the Democratic side becoming more female.

Gibson: Do you all do beer and pizza Fridays at A|L Media? Have you kept that going?

Liston: Yes, but a lot of Diet Coke now, too. I don’t know about the cute boys anymore, but we have beer, pizza, Diet Coke and candy.

Dietz: I actually got into politics working at an Applebee’s in New Jersey. A woman came in that had an opportunity to work at a lobbying firm and I was trying to find my first job right out of college. I went and interviewed and they hired me. At that point I sort of thought, “I guess this is what I’m going to do forever now.”

Gibson: My story is that I organized my college to come to DC for the original March for Women’s Lives and fell in love with reproductive justice. I thought I’d move to Washington and get the dream job at Planned Parenthood, but it turns out you can’t get exactly the job you want at exactly the time you want it. I got a job answering phones at a media firm and learned the production side of things first.

Dietz: What’s been the most challenging moment for all of you in politics, and did it change the trajectory of your career?

Davison: When I look back on my career, there’s a series of moments where you say, “This is the worst day ever.” It never really is, but I think every single one of us has that moment. I do think being women in this business, on both sides of the aisle, plays a role because there are so few of us and you do get treated differently. They finally let us in the room, but God forbid we talk, right? Your career is made in how you handle those challenges and how you learn from each one.

McCleskey: One moment that was pivotal for me in my career was working on Susana Martinez’s gubernatorial campaign in New Mexico in 2010. I’d been doing polling for a dozen years already, but this campaign was intensely personal. I worked on the campaign with my husband. I also live in New Mexico and was close with the candidate. We were successful and that was tremendous, but it was a pivotal point for me because it gave me a confidence that I didn’t necessarily have before. There’s a storytelling aspect to campaigns, which I always felt really good at, but then there’s an emotional part of campaigning that we sometimes forget. I think women are particularly good at it in a way that men often aren’t. So being able to do that on that campaign and be successful was a moment that showed me I had something unique to offer. It taught me that sometimes you have to keep pushing those things, even if the men you work with are a little bit resistant.

Quintero: The moment that always comes up for me is when I was in Afghanistan working for the U.S. military. I was there helping to stand up an embed program for reporters and I found out I was pregnant. I was 27 and I called my husband and I said, “I’m not coming home and I’m not telling anyone and I’ll see you in five weeks.” I was very lucky to have an extremely supportive husband. My mother was freaking out, but my husband said, “You stay there and do what you need to do.” To this day, it was one of the best career decisions I made because I realized what I was made of. I could work a 17-to-18-hour day, vomit in the morning and still support the public affairs officers and not tell a single soul that I was pregnant other than my female boss. My daughter is now 17 and she just founded the [National Organization for Women] chapter in her high school. And so I just believe that I made a really tough, kick-ass woman. 

Applewhaite: For me, the challenge was definitely on the Buttigieg campaign. That was a very formative campaign for me. I was 25 when I started, and at that point, frankly, had worked on a lot of dogshit races that were never going anywhere. This was the first time that I worked for a principal, and also quite directly with the principal. I think it’s the nature of the work we do that we wear our worldview on our sleeves. So what was particularly tough for me was to be the researcher that knew Pete’s record very closely, but then had to deal with this narrative about how he dealt with the Black community as mayor of South Bend. My DMs were crazy and racist at that time from other campaign operatives and folks in the Democratic Party, which was really disappointing. So you had to do all of that and put on a brave face every day as one of the spokespeople for the campaign. You had to be out there every single day to tell that story, but also lend credence to it with your face and what you look like. That made it a huge challenge. It is an experience that I’m really glad I had though because now nothing scares me. Though that’s also what happens when you work for Lis Smith.

Ruiz: I think very little compares to the last year in politics on our side. It hasn’t even been a year since the first presidential debate. So I was political director at the White House — we had the debate, we had the month that followed, we had the switch, we had the election, we had hurricanes and wildfires in between and now we’re into a second Trump administration. I couldn’t say with a straight face that anything has been harder than this last year. The night of the debate, I happened to be with my brother, and what he said to me as I was probably panicking, or because he could see it in my face, was: “What’s going to happen from here is already written. All you can do is think about your integrity and do the job you were hired to do.” That’s what we have to do.

One thing that I would say to all of us as women: Win, lose or draw, you still show up to work the next day. You lead your team through it and maintain your values. People look at me sometimes and ask, “Are you okay?” Or they say, “I can’t believe you’re still standing.” Well, I have two little kids. I have to get up every morning. I have to take them to school. We have to continue to live our lives. There are certainly more formative moments in our career, and those are when you really learn what you’re made of. 

O’Connor: I have two pivotal career moments. The first was going to work on the Bush-Cheney reelect and running ad production. I had a great boss: Mark McKinnon. He gave me a tremendous amount of responsibility and he gave me all the credit. It was delightful to be able to walk in a room and he would give me the floor and say, “Ashley knows what’s going on here.” I think I walked away from that realizing that hard work and being solution-oriented can really get you where you need to go. When there’s a problem, you figure out how to solve it.

That helped me gain a lot of confidence in my skills, but I really didn’t grow into my own skin as a strategist until the Romney campaign in 2012. When I ran advertising for that campaign, to Nicole’s point, I finally started to realize that I have a unique perspective and it’s highly valuable. I’m a woman at the table and we’re trying to influence independent, soft-swing, moderate women. So it was two pivotal moments. The first built my skill set and the second helped me understand who I was and how to make sure my voice could be heard in a crowded room full of men.

Liston: I was lucky enough over 20 years ago to partner with a very supportive, good guy. But I’ll talk about the finances for a second. I was doing half of the work and bringing in half of the business, and I was at 33 percent of the overall profit. It got to the point where it was one of the biggest challenges in moving forward. I didn’t know how to negotiate it or make it better. Eventually I had some kind of epiphany and I decided to go on strike. I went on a one-woman strike and just refused to do work or participate until we could negotiate at 50-50. That was early in our partnership, and so I became a 50 percent owner and partner and it seemed to work really well after that. My very supportive partner was even better as far as decision making and all of that as we went forward.

Dietz: I was recently at a conference training women who want to run for office and a woman asked me, “Can you have it all?” And listen, I’ve been on panels and gotten similar questions, and it’s sort of like, yeah, give me a break with that question. But I am genuinely curious about how those pressures of life and career have played out for everyone. 

Ruiz: You can chase a career all day long, but it might come at the expense of being home. It may mean feeling more unsettled in your personal life. I have been very lucky to have a supportive partner and supportive co-workers in my four years that I was at the White House. I started the job, got pregnant, was pregnant, had a baby. Never once did one of my colleagues, man or woman, say, “Can you turn your Zoom camera on? Can you be here in person for this meeting?” Truthfully, a lot of my team members made sacrifices so that I wouldn’t have to. And of course, it’s all reciprocal. There are times where somebody else takes that baton.

What I often tell other women in the profession is you have to really prioritize what’s important to you at this moment. If I had started a family much younger, I could not have bounced around from Texas to Nevada to Colorado. I could have, but I wouldn’t have chosen to. It all comes with thinking very clearly about what your priorities are. That’s how I negotiated my job at the White House. I was a caregiver for a parent at that time, as well. And so everyone went in eyes wide open and I felt very taken care of. But I also know that my story is oftentimes the exception, not the rule. 

McCleskey: Ashley brought up the Romney campaign as formative for her. Back then, I was doing focus groups in three different cities every week. It was a grind. The night before one of the trips my five-year-old son said, “Mom, can you just ask Mr. Romney if you don’t have to go?” And I said, “I’ll ask.” But I went. My son is now in college and he’s turned out awesome. So yes, you can have all of these things and you’re also showing your kids something in that process, too: women can do this. I left Washington when I got married and I’ve been in New Mexico for more than 20 years. Someone told me when I left, you’ll never be successful in this business if you’re not here. I think I’ve done okay.

Davison: I’m going to be the person who says, no, you can’t really. But I don’t think men can have it all either. All too often we get very caught up in what the ideal is supposed to be. I think we need to first give ourselves some grace and say we’re never going to hit every benchmark. I work with a lot of female candidates, and they’re always shocked when the voting bloc that doesn’t like them the most are women. We are just very hard on each other all of the time. So when younger women ask me for advice, that’s what I tell them. We need to be a bit more understanding of one another, especially in this business.

O’Connor: I’ve had lots of young women ask me this question, and I will tell you I think I’ve been able to have it all because of the partner I chose to spend my life with. Having an incredibly supportive partner who understands your goals, roots you on, helps when the school calls and the child’s sick but you’re on a pitch. I think having a really strong partner at your side is what makes the difference.

Gibson: I also think it’s a strong partner or a village. I ended up living in this neighborhood of Tacoma Park, Md. and the pandemic sort of solidified the “it takes a village” idea. I think my kids are being raised by six families and not just one. A really strong piece of this for me has been having very dependable, loyal and fun female friends who show up with the right energy. Not that I don’t have friends that are men, but people who can connect and identify in a moment and be empathetic about a particular thing that we’re all navigating — that’s been so important for me. One thing I’m interested in is how do we, as successful, experienced women, make space for women coming up in this business? There’s a lot of us in the media consulting space here. It’s still very male dominated.

Applewhaite: The thing I try to do as often as I can is demystify the process. I didn’t know there was a career to be had in politics until I came to GW. There are a lot of younger women, especially women of color, that also don’t know that. So anytime I speak at a conference or do a talk and someone asks, “Can we get coffee?” I say yes. I tell people this is the town where people say yes more often than you think, and so I think it’s important to make yourself available for that sort of thing. I take pride in the fact that people who raised their hand or were nervous to come up to me are now starting careers of their own in this business. I try to make sure I’m an open door.

Quintero: In my firm, I make an effort to do as much mentoring as I can. If there’s room on an account, I will try to bring a younger staffer in or have them listen into a call. Wherever there’s an opportunity to train, I really do try because I feel so grateful to the women who helped me. I feel fortunate to be able to pass that along.

Ruiz: It doesn’t always work because of time constraints and we’re all imperfect people, but I really do try to build and foster community among women consultants, women organizers, whether it be Latinas or with local communities in Texas, specific to where I’m from. You try to find those opportunities to come together in community. That can be as a reference or just an added resource for someone. I think just being self-reflective, no matter how much we all do, there’s so much more we can do.

Davison: It’s also just giving positive encouragement at the right moments. All too often, you go into a meeting and you get beaten down. Just being able to say, “Girl, go in there and don’t take any shit” – you get into these meetings and you’re fighting for what you believe in and sometimes you just need someone to tell you that you did the right thing. I try to have the backs of other women — and men, too. I don’t discriminate in who I mentor. But when you see someone having the same fight that maybe you were having 10 years ago, and she’s just trying to hold the ground — hold the ground with her.

McCleskey: I think this is a little harder on the Republican side just because of the political demographics in our country. So I want to punt it to Ashley first, because she’s really good at the mentoring stuff. Polling is unique, so I can follow up on that.

O’Connor: You take the coffees, you meet with the young women, you help mentor them — you do all of those things. One thing I’ve started doing is not being afraid of being constructively critical. I ask this of my business partners for myself as well. No one improves in a vacuum. One of the things I talk to women about is when you’re in meetings, this is not just about what you feel. You’re an expert, so make sure you ground what you’re saying with that experience. Back it up and be confident. Be an executive. I see the women that have worked with me that I’ve watched grow in their career and that really does help you get to that next level.

Dietz: Nicole, you mentioned that it’s harder for us on the Republican side, and you’re right. We were so frustrated a few years ago that some of us founded a Republican women’s group on Facebook. It was just a networking group to get together, meet up and talk about business or anything else. It was almost all women under the age of 35 and almost every woman who was working at a party committee in D.C. It was about having a group to get together and support each other, because there are some amazing women in this industry that often don’t get the recognition their male colleagues do.

McCleskey: In my company, we make a concerted effort to find women candidates for positions. There just aren’t a whole lot of women who are Republican and want to do polling, so it’s harder. It’s important to encourage them to do it though, because I sit on panels with male Republican pollsters and sometimes I think, “My God, you’re so boring.” There needs to be a woman’s voice in all of this and it makes campaigns more effective, whether that’s in polling or any other area.

Davison: Women do get pigeonholed. Often, it’s either that you’re the fundraiser or the comms person. It’s hard to find the general consultant or the campaign manager. There aren’t too many of us who do that and it’s mainly because not very many women want to live in a Baymont Inn in Reno, Nev. for a year and a half. I remember being 26 years old and wearing a fake wedding ring because I wasn’t always comfortable in these places. If you’re going to be on that path to be a manager you need to put in some grunt work on the ground. The harsh reality is that you’re going to miss your best friend’s wedding. I’ve missed all my friends’ weddings. Now, I can finally go to their second weddings. But I think we don’t talk about that part enough. There’s going to be a grunt phase.

Liston: On the Democratic side, I really thought in the last 20 years we would see a lot more women partners in media firms. At this point, I’m scratching my head on why we haven’t. What I’ve decided to do is help cultivate general consultants and partner with them on work where they get a piece of the profit. I am going outside of my firm and pitching with them. A lot of these women will either build up a book of business, and that means they’ll be able to start their own firm, or bring a book of business to another firm. Now, most of those firms will be male-owned and dominated, but the idea is they will now be able to negotiate a better deal because they’re coming in with skills they’ve learned partnering with us and some business they’ll be able to take with them.

At first, my other partners were skeptical. They’ve come around because these women love working with us and having the flexibility of a media firm and a production firm and a buying firm and a digital firm that can give them all these various services to help them build their business and build their life. So if anyone’s interested in that, we’re open for business.

This piece appears in the commemorative 45th Anniversary print edition of Campaigns & Elections magazine.