byline: M.J. McAteer

By age 10, Kim Roy knew she wanted to build skyscrapers.

Now she leads Hitt Contracting, a $3.3 billion commercial construction business that builds structures across America.

Roy is passionate about recruiting women into her firm to help diversify the next generation of leaders in her industry. Women comprise about 10% of the construction workforce today, according to the U.S. Bureau of Labor Statistics.

“Unfortunately, many young people — especially women — lack exposure to construction and are unaware of the incredible career opportunities this business offers,” she says. “It’s more important than ever that we encourage women to explore careers in construction.”

Roy advises anyone who wants to scale a career in her industry to first master the basic principles of construction.

“Most importantly, have the courage to get out of your comfort zone,” she says. “Some of my biggest leadership jumps were when I was very uncomfortable.”

Roy joined Hitt in 1999 as an assistant project manager and became CEO in 2017, after working her way up the corporate ladder. She credits her mentors with playing a role in her success, and she aims to pay that forward.

“Our challenge is not only to entice women to consider construction, but also to ensure they have the resources to develop their skills and advance their careers,” Roy says. “I enjoy coaching emerging talent, empowering them into leadership and creating a culture where all team members feel valued and heard.”

Lauren Sweeney founded Richmond-based creative agency Dotted Line in 2014 when she was 26 years old — building on insights from her family.

“I come from a family of small business owners,” she explains, “so a lot of the language that I heard growing up around the dinner table was … the typical topics you have in a small business.”

One takeaway she learned was the responsibility of making sure that one’s company is “being used in a way that has a positive impact on employees as well as doing good in the local community.”

Sweeney has involved Dotted Line in community engagement through nonprofit organizations and performing pro bono work for aspiring entrepreneurs. For several years, she and Dotted Line supported UnBoundRVA — a now-defunct local nonprofit that helped low-income entrepreneurs start their own businesses —helping its clients develop branding for their emerging companies.

This year, Sweeney joined the Virginia Chamber of Commerce’s board of directors. As a new board member, she’s still finding her footing, she says, but is excited to support businesses around the commonwealth.

Additionally, in January, Sweeney launched a yearlong leadership development pilot program in her own agency that features peer-led and expert-led workshops.

“Everyone on our team,” she says, “leads in some type of capacity.”

Jayme Swain is the first woman to serve as president and CEO of VPM and the Virginia Foundation for Public Media.

She leads a 100-person team that creates content and programs for a network of public media television and radio stations and digital properties serving Central Virginia and the Shenandoah Valley, a notable achievement in a time when many news outlets are shrinking.

Swain, who has more than 20 years of experience in broadcast, print and digital media, says she hasn’t thought much about her status as a “first,” but she recognizes that she’s paving the way for the next generation of women leaders.

“I’m proud to be the first female president and CEO,” she says, “I’ve spent much of my career in male-dominant industries, such as news and sports, and I’ve worked hard in these environments to help women be seen as equals at the table.”

Before joining VPM in 2019, Swain spent nearly a decade as senior vice president of strategy and operations at the Arlington-based Public Broadcasting Service. She enjoyed her time working in national public media but felt called to make a difference at the local level. Her passion is delivering news to keep people informed and engaged with the community.

“When people ask me what keeps me up at night, it’s really the collapse of local journalism across this country,” she says. “I think local journalism is the bedrock of an informed society.”

Karen Wigginton is a passionate mentor who encourages women to dream big. Her secret to success, she says, is boldly taking on leadership roles that push her outside of her comfort zone.

Since 2013, Wigginton has overseen marketing and sales strategies for Sunnyside Communities, which has three senior living properties in Virginia. It was a shift from her earlier career as an administrator at James Madison University and Bridgewater College.

While she was working in higher education, Sunnyside recruited her as its vice president of marketing and public affairs. After a couple of years, she left to become the first vice president for college relations at Bridgewater, but she returned to Sunnyside in 2013.

Wigginton’s career has been full of impressive leadership titles, and she has served on numerous boards in her community. But the leadership role that made her most reflective was being elected as the first woman president of the Rotary Club of Harrisonburg in 2000.

Being the first woman to lead the organization, she felt pressure to do an excellent job.

“I was one of just a handful of women in the club, so it was unimaginable to me that I would be asked to serve in that role,” she says. “It was a wonderful experience and we’ve had a number of women presidents since then.”

When Loretta Cataldi started out in the real estate business 25 years ago, only a handful of agents were women. “Not very many doors were open,” she says, “so I had to climb in through the windows.”

That determination has taken her from being an executive assistant to principal and managing broker at Divaris Real Estate’s Richmond office, where she leads office operations and leasing activities, representing both tenants and landlords.

“Being assertive is what it takes in a male-dominated business,” Cataldi says, but that doesn’t mean going it alone. “Help others succeed, and you’ll succeed with them.” To that end, she started a mentorship program at Divaris. Through Realty Resources, a national alliance of independent brokerage firms, she also initiated monthly Zoom sessions to help newbies learn things that they might not learn day to day.

“They can ask what they are nervous about asking,” she explains. Cataldi also recently was accepted into Virginia Commonwealth University’s Real Estate Circle of Excellence, a position in which she will share career insights with students.

Not surprisingly, Cataldi’s choice of leisure activity — running trails and 50-mile ultramarathons — requires buckets of determination, and, next up, she’d like to start a running organization for girls. She envisions a program that will build girls’ self-esteem, so that one day they might have the confidence to run not just races but companies.

Cathie J. Vick was the first woman to join the Port of Virginia’s executive leadership team eight years ago.

Vick had no direct experience in the male-dominated maritime industry, so she almost didn’t apply for the job, but a male colleague encouraged her to try.

“Just having my job is shattering the glass ceiling,” Vick says. “I’m so proud that I’ve built a team that’s brought in over $1 billion in state and federal funds to help build this port.”

Today, she helps recruit other women into leadership roles and nudges women to take a shot when they doubt themselves. She often advises women to lead even if they aren’t managers.

“You don’t have to wait to have a certain title to lead,” Vick says.

Previously, Vick served as director of government relations for Virginia Natural Gas and deputy director of energy policy for the Virginia Department of Mines, Minerals and Energy (now the Virginia Department of Energy), and she has served on several organizations’ boards, including LEAD Hampton Roads, the Sorensen Institute and Optima Health.

After Vick became a mom, she struggled with juggling her business and home roles. She was inspired by her former boss, the late Jodi Gidley of Virginia Natural Gas, who blocked time off on her calendar every day to speak with her kids.

“I saw a strong female leader who kept the right balance,” Vick says. “She helped me see the bigger picture, and I try to emulate that.”

Early in her career, a client at the ad agency where Connie Connelly O’Brien worked threatened to take their business to another firm. Determined to fix the situation, she spoke with the client and learned that they did not feel heard, and quickly offered a solution.

“By really listening to the problem they were trying to solve, I was able to stop the agency review,” she says. “And from that moment on, I knew that my listening skills were going to serve me well.”

After that experience, O’Brien knew she was destined to solve business problems.

In 2019, PRA Group, a $1.1 billion company that acquires nonperforming loans, hired her to develop digital solutions for debt collection with an empathetic approach. O’Brien revamped PRA’s website to allow customers to communicate with the company online and created educational tools to help people get out of debt.

O’Brien, who has also worked in marketing for AXA Equitable, Vonage and Tungsten Network, oversees 52 team members and manages customer marketing and digital operations across 12 countries.

She leads an employee resource group for women in business and is passionate about mentorship and educating her coworkers on ways men can be allies in ensuring that women are considered for job openings. She also mentors young adults who are exploring career options.

“I get a lot of energy from helping women in college and starting their career,” she says. “It jazzes me.”

DeEtte Gray began her career as a middle school math and science teacher in the late 1990s. Her passion for STEM education eventually led to her role at CACI, where she’s involved in modernizing government agencies’ operations.

“One of my great experiences was integrating computers into the science curriculum, making the classroom more interactive and getting children excited about science,” she recalls.

Gray went on to work for defense contractors Lockheed Martin Corp. and BAE Systems Inc. before joining CACI. Over her 20-year career, she has advocated for students to pursue STEM jobs.

“There are simply not enough young men and women entering the technical career fields that we’re going to need for the future,” Gray says. “Particularly in my industry, there’s a talent shortage already for developers, engineers and cyber professionals.”

Toward that goal, Gray served as chairperson for the Armed Forces Communications and Electronics Association International — and won its 2022 Women’s Appreciation Award. She’s particularly proud of the association’s STEM-focused scholarships and teacher grants.

Says Gray: “We have to expose more kids at an early age to these types of skills so that we can build the workforce of tomorrow.”

Jennifer Taylor’s birthplace of Middletown, Ohio, is the backdrop of GOP U.S. Senate candidate J.D. Vance’s 2016 book “Hillbilly Elegy,” a memoir about growing class divisions in the Rust Belt.

While Taylor now lives in Northern Virginia and leads one of the largest regional technology trade associations in the nation, she honors her roots by advocating for training opportunities for people traditionally underrepresented in the tech sector.

“My passion is focused on making sure we don’t leave people behind,” Taylor says. “Let’s give Americans a chance to have meaningful wage-sustaining jobs in tech fields.”

One way to do that is through apprenticeships, which allow people without college degrees to complete training to fill in-demand technology roles.

In partnership with IBM, Taylor launched an apprenticeship coalition when she worked for the Consumer Technology Association as vice president of industry affairs in 2017. Hundreds of tech apprenticeships have been created since the coalition started, she says.

“I am very proud of my work to encourage tech companies to offer apprenticeships,” she says. “Apprenticeships give access to talent that may never have considered careers in technology, which ultimately helps diversify the workforce.”

Taylor became president of the Northern Virginia Technology Council in 2020, following the retirement of longtime NVTC leader Bobbie Kilberg. Her experience also includes sales, strategy and marketing positions at AARP and the American Red Cross, and Taylor has prioritized modernizing the organization and implementing a strategic plan focused on accelerating tech innovation and creating more tech jobs in the region.