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Business Owners

Paying It Forward: Female CEOs on the Rise in the Middle Market


When Jill Vitiello first started working in the 1970s, the narrative of women in the workplace was completely different than the one today.

In 1970, women accounted for 38 percent of the workforce. In 2015, women comprised just under half of the workforce at 47 percent — a figure that represents over 73 million women. “The women I worked for [in the 70s] were true pioneers—doing jobs that only men had done before,” Vitiello says.

Working in that period, when things were so difficult for the new class of corporate women, has given Vitiello a strong sense of what it means to be a woman in the workplace.

Today, Vitiello is the President of the Vitiello Communications Group, a full-service communications agency she founded in 1990 and an Axial member. While one study showed that the “queen bee syndrome” Vitiello describes — where one woman climbs to the top of the ladder and makes it impossible for others is a myth — it’s a pervasive one that still dominates conversations in the workplace. Part of this is because old habits die hard, but another part stems from the facts: there are very few women at the top. While male and female college graduates have about equal opportunities, as they climb up the corporate ladder, female leaders become scarcer and scarcer.  But this story isn’t identical everywhere.

Women in the Middle Market

While women remain underrepresented in leadership positions in the S&P 500, there’s a different story playing out elsewhere in the markets. There has been growth in female representation in the last twenty or so years — in 1998, only one Fortune 500 company had a female CEO at its helm; by 2014, the figure had jumped to 24 (it has since dropped to 20).

But when it comes to female leadership, smaller companies are far outpacing their larger counterparts. In almost the same period, between 1997 and 2014, women-owned businesses increased by 68 percent.

According to a report by American Express and Dun & Bradstreet, the middle market represents a promising landscape for women entrepreneurs. The number of women-owned middle market firms increased by 24 percent from 2008-2014, compared to a 4 percent increase overall. Employment among women-owned firms also outpaced the average, at 38 percent growth vs. 4 percent overall. Still, only 13 percent of middle market companies are women-led — a figure that nevertheless dwarfs the meager 4 percent of women CEOs of Fortune 500 companies.

The Pipeline: Women Mentoring Women

We’ve written before on the value of women leadership and its domino effect: women leaders inspire women managers to keep going for the top spot, rather than leaving because of “concern for the lack of advancement opportunity” or “dissatisfaction with senior leadership,” the top reasons for women leaving their jobs, according to a LinkedIn survey. Women managers advancing to the executive level is key to changing the business landscape. As plenty of research shows, when it comes to women leadership, it’s all about the pipeline: 65 percent of women leaders of who are mentored become mentors to other women in their field.

Heather Leonard, CEO of app-building platform Throwing Fruit (an Axial member), is a prime example of how female relationships in the workplace can help one’s career trajectory. As a research assistant at PaineWebber, Leonard’s first job after college, she met Alice Schroeder, “the first analyst [at PaineWebber] to cover Berkshire Hathaway.” “[It] was a big deal,” says Leonard, who looked to Schroeder for advice on multiple occasions in her early career. “I remember her being this high-powered individual who people didn’t fear, but she had gravitas when she walked into a room. She always made time for me because I think she saw how hard I worked.”

Since working with Schroeder, Leonard has been lucky enough to work with a number of influential women. “I can’t say that I’ve had an official mentor,” says Leonard, “but there are women that I’ve looked up to and worked with along the way.” Afterward, she rattles off an impressive list of female coworkers spanning the duration of her career, a number of accidental mentors. Vitiello too emphasizes the many women who have have helped her advance her career and understanding of leadership. She says learning by example can be just as powerful — if not more — than having a clearly defined mentor-mentee relationship.

Vitiello is enthusiastic about the value of a strong network in the life of a professional woman. “There is a strong and supportive community of women business owners and leaders who want to support each other, want to help each other, and have also managed to get the backing and support of very important corporations. There are resources available, and not everyone knows that,” she says, listing names: the Women Presidents’ Organization, Enterprising Women, the Women’s Business Enterprise National Council, and Vistage.

Reaching Back and Paying It Forward

“I have noticed that women are increasingly paying it forward, lending a hand to other women who are newer in their careers,” Vitiello says. She cites Sheryl Sandberg’s Lean In, the book and movement of the same name that have become something of a rallying cry for young working women. This phenomenon isn’t and shouldn’t be limited by gender, Vitiello states. After all, “it’s equally rewarding to help men and women and afford them the same opportunities.”

The idea of reaching out and pulling others forward is one that features prominently in the growing body of research on what experts call “feminine leadership,” a leadership style that values traits that are traditionally associated with women, and that have also been historically devalued in the workplace. But there’s no conclusively biological basis for differences in the behavior of male and female leaders, something Leonard corroborates — there are only good leaders and bad.

“One of my mentors, a male Army Ranger, was very ‘feminine’ in his leadership in that he cared greatly about our goals, happiness and wellness. Not only at work, but in our personal lives,” says Leonard. “He knew that if we were happy outside of work, we’d likely be more happy at work.” But, as Leonard’s quick to note, that has less to do with gender than it has to with empathy toward employees. “Now as I manage my own teams,” Leonard says, “there’s that genuine care that I feel towards my employees. All good leaders should feel that [way].”

Vitiello agrees. “It’s true that men and women sometimes lead differently, but I don’t know that we want to make certain traits ‘masculine’ and ‘feminine’ — good leadership has components of both, and when you strive for one you miss the benefits of the other.” It’s about balance, she says. “I yearn for the day when we don’t preface the word ‘leader’ with the words ‘woman’ or ‘female’ or ‘feminine.’ Only then will we gain a true understanding of the full range of leadership.”

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