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Room at the Top—or Not?

How Southwest Florida’s women feel about their challenges in the workplace.



Gail Markham had noticed their absence in the place where she least expected it: her own accounting firm she had founded years ago in defiance of the good ol’ boys network that ruled the financial sector. Where were the women?

She employed plenty of them, but they were idling at the associate’s level, not pushing toward partnership. Odd, Markham thought, for a company run by women executives.

Markham started peeking behind curtains in other industries to see who waited in the wings for the roles she and her aging contemporaries would vacate. She saw an awful lot of suits—and not of the Hillary-style variety.

“We are aging out,” Markham, 67, told a group of local professional women at a dinner last spring put on by members of the International Women’s Forum. “What is our succession plan? We have got to figure that out.”

Lately, Markham has been challenging her staff, civic groups, women’s organizations and public audiences—and us here at Gulfshore Business—to take stock of women’s status in leadership circles. So we did. Over the course of several weeks, we examined who’s sitting in executive suites and boardrooms and similar places of influence. And then we met with 23 highly regarded Southwest Florida women of different ages and career stages to find out whether Markham has reason to worry.

Yes, we concluded. She does. But with these women’s insights, we pinpointed what’s holding women back, what could move them forward—and why Markham’s fears could soon be put to rest.

Most of us may not be giving much thought to women’s leadership these days— not with national figures like Facebook’s Sheryl Sandberg and General Motors’
 Mary T. Barra, or Southwest Florida’s Shelley Broader at Chico’s FAS and Kathryn Marinello at Hertz. We assume women have “arrived” because of ceiling-shattering local figures like Markham and Adria Starkey, the FineMark National Bank & Trust Collier County president. And Robbie Roepstorff, president of Edison National Bank/Bank of the Islands; and Kitty Green, the former CEO of Bonita Bay Co.; and Sarah Owen, philanthropic powerbroker at the Southwest Florida Community Foundation; and attorney Kimberly Leach Johnson, who heads one of the nation’s leading law firms from her office in Naples.

But the data void our rosy perceptions. Nationally, women start out as 47 percent of the workforce at the entry level and most remain employed, even after having children. But they’re not advancing alongside their male counterparts. At the vice president level, women hold just 29 percent of jobs. In the C suite (chief executive officer, chief financial officer, chief operating/administrative officer), women are outnumbered by a margin of 8 to 2, according to a 2017 study by McKinsey & Co.

Southwest Florida doesn’t look all that different. Sure, we have Broader and Marinello and Beasley Broadcasting’s Caroline Beasley heading three of our nine publicly traded companies. Our cultural and civic nonprofits are dominated by women. But dig deeper, and you’ll be hard-pressed to find women at the top of our major employers. We examined some 30 large public- and private-sector organizations headquartered in Lee and Collier counties and found just five woman CEOs or equivalents.

“Glacially slow,” is how Lynn Yeakel, one of the nation’s leading voices on women’s equity, calls women’s pace of progress. (Yeakel, the founder of the women’s advocacy group Vision 2020, owns a home on Sanibel and has tapped some Southwest Florida women for her national work toward parity.) “In the Fortune 500s, there are 476 men and only 24 women [CEOs]. When you think of it that way, it’s pretty shocking.”

If you think this doesn’t matter to you (as in you have a Y chromosome), think again:

Companies with 50 percent women in senior operating roles show a 19 percent higher return on equity, according to the Credit Suisse Research Institute. A shift from no women leaders to 30 percent female leaders drives up net revenue an average of 15 percent, finds the Peterson Institute for International Economics.

“We bring something different to the table,” says Natalie Ashby, 34, a corporal with the Collier County Sheriff ’s Office who is pushing through the ranks there. “I think the men I work with see it. There are certain times when they call and say, ‘Hey, can you come over here and help me with this?’ We play off of each other’s strengths.”

Yet today’s mid-career and young professionals are still running into many of the roadblocks their mothers and grandmothers encountered.

“What I heard about people going through 20 years ago, I’m going through that today,” says Michele Hylton-Terry, 52, the executive director for the City of Fort Myers Redevelopment Agency. She’s talking about women having to work extra hard to prove themselves and stand out in organizations where male managers far outnumber female ones. She’s not imagining it, Yeakel says. “It’s clear from the research that women have to be more qualified than men to get the job.”

Why are we still having this conversation?

Gender bias persists

At a recent Gulfshore Business banquet last spring honoring her achievements, Markham (pictured right) recalled a job at a car dealership where her boss insisted she, then a teenager, sit on his lap every morning.

That kind of blatant harassment is being purged from workplaces (thank you, #MeToo). But sexism is nowhere near eradicated, as women of all ages reminded us.

“I got passed over [for partner] the first time around,” says Jamie Schwinghamer, 37, an attorney who is a partner in her current firm, Roetzel & Andress LPA, but who did not make the first cut at a previous one. “If I had come to the table with what I had the year I was up for partner, and I was a guy, I would have made it.”

Tracy Duhaney senses the enhanced expectations, too, working in the hospitality industry, which has a predominantly female workforce and a predominantly male leadership pool.

“I have to work three times as hard just to prove that I belong at the table—just to push open the door and be in the room,” says Duhaney, the assistant director of catering at the Hilton Naples. Adding to her advancement challenge: age (28), color (black) and birthplace (Jamaica).

The problem originates early, and not in the workplace. Consider what financial adviser Kylen Moran, 28, of Naples experienced a few years ago during a college business class:

“The guys went to their corner to work on Excel sheet calculations,” she remembers of a group project. “They told the girls, ‘You can do the PowerPoint.’ They basically commandeered the analytical side of the project.”

The boys, incidentally, messed up the calculations. Moran found the mistake. But she—not they—learned the bigger lesson. The climb is steeper for women.

Public perception and the ‘good ol’ boys’

Women can have an empowering boss, supportive co-workers and enabling partners and still absorb endless snubs.

“I don’t feel discrimination from my agency. Not at all,” says Ashby (pictured left), the corporal. Backed by co-workers and superiors, she’s advancing at work while pursuing a doctorate and raising a 5-year-old on her own. “But I feel it when I go out in public. I think society is not used to seeing women (in authority).”

Among the many things she’s been told: “You’re too pretty to be a cop!”

“What does that even mean?” she wonders.

Or how about what Margo Brewster experienced working for a bank in east Lee County: “It was still that good ol’ boys kind of a thing. You could feel the men treating me differently—almost like, ‘Oh, look at how impressive it is that you know all those big words.’ Or, ‘Listen to you talk about them mortgages,’” she says, laughing in mock imitation. “It definitely felt like that old-school deal-on-a-handshake kind of mentality. It’s still very much there.”

After eight years in banking, Brewster, 29, made a career change and now works as a special projects associate for the PACE Center for Girls in Fort Myers. She also heads the women in business committee of the Greater Fort Myers Chamber of Commerce.

Even the strong-minded Diana Willis, who owns the Jason’s Deli franchises in Lee and Collier counties with her husband, Scott, sometimes caves to the machismo.

“In lease negotiations, which I handle for our company, when it gets down to the nitty gritty, I sometimes give it to Scott to do,” she confesses. “I do all the work, and I hate to say it, it’s just part of getting business done. It’s ridiculous, I know. But that just goes to show you it’s still happening.”

Ageism is as big a hurdle as sexism

“I am a very young-looking person,” notes Stacey Cook-Hawk, 46, who runs SalusCare, the predominant substance abuse and mental health treatment provider in Lee County. Even in previous positions where she had a good deal of autonomy, her superiors found ways to remind her she was young and female, and she had to be “more careful with her work.” “It wasn’t once or twice,” Cook- Hawk says. “It was often. I was dreaming about the day I would have gray hair, and wouldn’t that be nice!”

Those stories are almost endless: Schwinghamer mistaken for the court reporter; Moran assumed to be secretary; Duhaney encountering clients satisfied with her services by phone but wanting to do business with another administrator once they see her—young, black, female—in person.

“It doesn’t happen often, but I do feel I have to prove them wrong,” Duhaney says.

These women are pretty sure young men don’t have to put up with the same. “I don’t think it even crosses their minds,” Schwinghamer says.

It’s a chicken-and-egg problem

Successful women breed other successful women.

“There was maybe one woman in upper management when I started at Barron Collier [Companies], and now we’re talking four or five or six women, and that continues to grow,” says Priscylla Oliva, 27, the executive assistant to Barron Collier Companies’ CEO. She watches these women—how they dress, how they carry themselves, how they interact with others—and emulates their attributes. “I pick from all these strong women around me, and every day I feel more myself, more comfortable in what I do.”

At the Greater Naples Chamber of Commerce, Amanda Beights is surrounded by a cadre of female senior executives. “I can’t think of any time in my life when I felt I couldn’t accomplish something because I am female. I have never felt any situation where there has been a roadblock,” says Beights, 36, a vice president who oversees the chamber’s leadership development programs.

But if high-ranking women influence the advancement of other women, their absence has an equally detrimental effect.

In law firms, for example, Schwinghamer (pictured right) says women are making partner at reasonable rates, but they aren’t advancing to the next tier. Without a senior title, they’re not eligible to lead their firms, sit on the board—or have a say in who makes partner.

“I feel like in a majority of these places, it’s men who are making the decisions because women aren’t in upper management positions,” says Schwinghamer.

Bias may not be deliberate.

“I don’t think it’s malice,” says Sarah Owen, president and CEO of the Southwest Florida Community Foundation, who came from corporate America before shifting to the nonprofit sector. “We gravitate toward the people whom we trust, whom we know and who have worked alongside of us.”

But that’s why parity matters. “We need to get more women into policy positions, whether in business or in government, because that’s where the decisions are made,” says Yeakel, referring to family-friendly policies, budget allocations, promotions and a host of other matters.

Family matters

When Owen, 54, worked as a communications strategist in the automotive and engineering industries, she did not talk about her kids. “I didn’t go to award ceremonies,” she says. “It wasn’t a choice. I had to be there first and I had to stay late.”

Fortunately for moms—and dads—workplace norms have loosened up. But the internal conflicts are still intense.

“I definitely feel leadership is a possibility for me, but right now, I’m in an interesting place in that I have a full-time job and I have two small kids, so that part of my life is very crazy right now,” says Allyson Ross, 32, who works with Brewster at the PACE Center as the development manager. If she were to define her career path, Ross might simply stamp a question mark on it—for the time being anyway.

Women who had intended to stay in corporate jobs still find it hard to do so in some industries. In law, for example, some young moms end up abandoning their firms, unable to keep up with office, courtroom and revenue-driving expectations. Some find new ways to use their legal degrees and some just drop out, frustrated about falling behind their male or childless contemporaries.

But there’s an important shift happening. Employers, especially executives like Owen who wrestled with parenting and career-building, are offering greater workplace flexibility. Men are absorbing housework and parenting responsibilities, and technology is facilitating home-and-work connections.

Women are finding leadership opportunities in ways that circumvent the traditional corporate track. Take Melisa Tropeano of Naples, who had started her career at Johnson & Johnson and went on to establish her own public relations firm, MTL Communications. “I started it because I wanted to be there for my kids. As they get older they need you more,” says Tropeano, a single mom to 13-year-old twins. With a small firm, she won’t count in national studies of female corporate CEOs, but nonetheless, she’s been nationally recognized for her entrepreneurship, including with a feature in Working Mother magazine.

And young professionals are strategizing how to parent and excel at work—sometimes before babies ever arrive.

Oliva and her fiancé have discussed the roles each wishes to play in eventual childrearing. Schwinghamer, who has a young son, is setting herself apart not by putting in 70-hour workweeks, but by growing a niche practice. Ashby works nights. And Duhaney is pushing hard now to advance as much as she can before she settles down. “[My mother] told me, ‘Get to the level where you can afford to take time off, where you can leave the office so your child does not miss a beat. ... Be that mother.’”

Want to elevate women? Change the workplace culture, our interviewees agreed. And then they offered a host of other solutions—some of which are easier to implement than you might think.

Acknowledge the problem

When Sheryl Sanberg’s Lean In: Women, Work and the Will to Lead hit bookshelves in 2013, Diana Willis bought a copy. And then she bought lots of additional copies for lots of other women.

“I don’t think we realized that glass ceiling was still so there,” says Willis, 54. Eyes newly opened, she recognized that none of her six restaurants had a female general manager. Since then, three women have been promoted.

Willis started reflecting on her own leadership, too. “I think I took a more active role in the decision-making.” Today she thinks she defers less and speaks out more when the issue is something important to her.

“I think it’s all about creating opportunity,” says Kimberly Leach Johnson, 62, the Naples-based attorney who chairs Quarles & Brady LLC and one of 14 women to chair an Am Law 200 law firm. “Whenever a big administrative position comes open or certain trainings come open, we have to consider minorities and women for that position. Does it mean they’re going to be picked? Not necessarily. We’re going to ultimately pick the best person, but it’s an opportunity to consider them.”

Tap ’em!

Traditionally, women have not been good at raising hands and thrusting themselves into new opportunities. There are many “whys,” including self-esteem, fears of failure and women’s propensity to underestimate themselves.

A tap on the shoulder can change the outcome of a woman’s career.

Dawn-Marie Driscoll, 71, the emeritus executive fellow at the Hoffman Center for Business Ethics at Bentley University, recalls how decades ago her boss (one of the “good-guy” CEOs dedicated to advancing women) assigned her to take a seat on the board of another organization. “I had no idea what the organization was. I had no idea what it did. I had no idea I was the only woman,” Driscoll remembers. She thinks the experience—and the exposure to a broader professional community—was essential to her advancement (her résumé includes serving as vice president and general counsel for the former Filenes department store chain).

Women across the age spectrum recount similar stories.

“I never anticipated myself in this role,” says Hylton-Terry at the Community Redevelopment Agency. “I always saw myself as part of the support team that made things happen, but not as the leader. Why is that? I’m not sure.” Part of it, she concedes, comes from her upbringing with immigrant parents who stressed family over work. City leaders invited her to step up, and Hylton-Terry is embracing the opportunity and the chance to empower others.

Christin Collins, at Lee Health, laughs when she considers her rise through that company. “I didn’t move down here to become system director of health and wellness for a $1.8 billion company. I came down here to play some golf,” admits Collins, 50. But senior leaders saw her talents and urged her up one rung, and then another, and another. “It’s been tap-tap-tap. Can you do this? Can you do that?”

Markham finally realized what
 was going on at her firm: She was 
waiting for her talented young associates to stick up their hands; they
 were waiting for her to lead them by
 the hand. Markham and her partners decided to illuminate the pathway to partnership. They offered training, established mentorship programs and met one-on-one with associates. This wasn’t the way she and her hard-charging contemporaries had operated. But it worked.

“Now they are so engaged. They are at the table. They have solutions. They have ideas. It’s a whole different position than we were in five years ago,” she says.

What do you really want to accomplish?


Stefanie Ink-Edwards (pictured, right, with Priscylla Oliva, left), 34, had a successful career in personal finance. A few years ago, however, in the midst of having her “best year ever,” she had a change of heart.

“I would spend literally all of my spare time, when I wasn’t actively working or with my family, sitting on a nonprofit board or chairing a nonprofit event or scheming ways to make money for nonprofits,” she says. She made a change, taking her financial acumen to the nonprofit sector. “I have to 100 percent believe in what I am doing. Whether I am selling a widget or selling company XYZ,” says Ink-Edwards, the development director for Community Cooperative, a social service organization in Fort Myers. “I want the women behind us or my kids to see you can pivot, you can change, you can be successful across multiple careers.”

The professionals we interviewed universally agreed—women gravitate toward jobs they find meaningful regardless of whether they come with big titles.

“I believe leadership is still associated with men and power,” says Kitty Green, 56, the former commercial developer who left the private sector during the real estate crash and now runs Habitat for Humanity of Lee and Hendry Counties. “Typically it’s men who have that focus. Women, and I’m making generalizations, want to do things that make them feel good and make them feel they are making a difference.”

Adria Starkey, 62, the Collier FineMark president, agrees. “For women, money is the second factor; it’s really about, ‘How can I make a contribution? How can I really give back?’”

“So maybe,” posits Leach Johnson, “we need to do a better job of defining the jobs, and saying what a positive difference you can make in leadership.”

She may be on to something.

Artis—Naples CEO and President Kathleen van Bergen, 41, was training as a concert violinist until someone suggested to her, “The world doesn’t need another violinist, but the world does need people who understand violinists.” She reimagined her future, as an arts leader. “That was probably the permission I was looking for. ... I think you want people to express that they believe in you and your potential, and it makes you think differently about the what-ifs.”

Ditto for Cook-Hawk at SalusCare. “The reason I accepted this position is I didn’t knock on the door and say, ‘Hey, I’d like to interview for this,’” she says. “It was more, ‘Hey, we need you. Would you do it?’”

Now, as CEO, she uses similar language in promoting her peers.

It’s not just gender; it’s generational

“We wanted it,” Markham says of her generation’s push into the business world. “We wanted to succeed and be leaders in our professions and in our community. ...We had to prove something—that we could do it.”

But now some in her age group wonder if there’s an “ambition gap” among younger women, accounting for the stubborn under- representation.

No, younger women say. But aspirations, work habits, attitudes and the definition of “success” started to shift among Generation X and is embedded in DNA of the millennials.

“We communicate different,” says Oliva, whose company recently hosted a retreat to discuss multigenerational communications. “We think different. We work different. Everything is different. While they worked 12 hours a day, we work eight and maybe do it more efficiently.”

When our group of young women in Naples discussed their career aspirations, they did not speak of professional advancement alone. They wanted time away from work for philanthropic endeavors.

“I think what businesses are finding with the millennials they are hiring is that two things are pretty important to them: flexibility and giving back,” Beights says.


There’s a risk to this, of course, says Tropeano, the PR executive. “We understand flexibility, but the work needs to happen. I feel the expectations need to be addressed from the get-go,” she says.

“I wouldn’t call it an ambition gap,” says Maria Jimenez-Lara, 49, CEO of the Naples Children & Education Foundation, one of the most influential organizations in Collier County. “With devices and electronics and email, I think we’re available for much longer during the day. ... So if someone needs to leave to go do something at their child’s school, by all means leave, but that doesn’t mean they are less ambitious. I do think they will make up for it at some point. ... As long as the work gets done, I don’t care.”

To Owen at the Community Foundation, these changing attitudes signal a need for bosses to ask staff members about their aspirations. “We could be missing the boat. And maybe that’s why we’re not moving the needle enough.”

Is the tide turning?

Roepstorff, the Edison National Bank president, felt buoyed on the day she and other Southwest Florida senior executives got together to talk about women’s leadership.

“I really think we’re on the cusp,” says Roepstorff, 66. The previous day, a woman had been named to head the New York Stock Exchange, the first one in its 226-year history, now putting two major indices in the hands of women CEOs (NASDAQ is the other). “I pray they will be successful, and their performances will shine!”

That’s the kind of optimism voiced by some of our young professionals.

“I can’t tell you the number of meetings I go to where it’s mostly women around the table,” says Beights (pictured right) of the Greater Naples Chamber. The selection committee for Leadership Collier had recently chosen its next class of area professionals to undergo leadership training. More women had applied than men—a stark contrast to previous years, when the organization struggled to find female candidates.

And many of our interviewees pledged to do what they can to keep trends like that on the rise.

Duhaney thinks back to a college exercise in which she was first assigned to be a secretary and then reassigned to play CEO because she’d protested the stereotyping.

But role-playing the boss, she remembers, felt uncomfortable, even frightening. Now, as a rising young executive, she’s determined to overcome such fears—and encourage other female colleagues to do the same.

“The gap is that intimidation we put in ourselves. ... We stop ourselves before we even get there,” Duhaney says.

That is why the conversation needs to keep going. “Open dialogue and open conversation,” Oliva says. “That’s helping us. ... Let me grab your hand, and let’s conquer this together.” 

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