Women Who Lead: Kerry Barr O’Connor with Dress for Success Charlotte

As a young professional, Kerry Barr O’Connor learned to wish carefully. 

O’Connor had always dreamed of becoming a television broadcaster, but when that dream came true – when she spent her workdays covering school closings and tropical storms — she yearned for more.  

“I didn’t like the day-to-day reporting,” she says. “I wanted to get to know the individual. Not the famous people and not the celebrities, but the everyday person and what impact they have.”

O’Connor soon left the journalism gig, volunteering a year of her life to an AmeriCorps VISTA assignment with a food bank in New York. It was there that she realized her knack for storytelling could be applied to different industries, specifically the nonprofit sector.  

Today, O’Connor is the executive director of Dress for Success Charlotte, a local affiliate of a larger global organization that outfits women with the clothes and skills needed to grow their careers. We spoke with O’Connor to hear more about how communities can flourish by rallying around women.   

What type of services does Dress for Success Charlotte offer?

Dress for Success Charlotte is an organization that helps women secure employment or advance their employment as a means to achieving upward economic mobility and strengthening their families. As executive director, I oversee the organization which includes job preparedness, job acquisition, employment retention, and career advancement. As part of job acquisition, for instance, we may help a woman develop the tools for the job search including creating a LinkedIn profile and running a background check. 

We provide the full spectrum of workforce development services, but also the wraparound services that we as women often need because we have myriad challenges including childcare and eldercare. Helping them not only secure employment but successfully navigate into the workforce will lead to their success. Research also shows that when you lift a woman out of poverty, as many as six family members may follow.

Who is your typical client?

The average client with Dress for Success is a 46-year-old woman of color. She has two and a half children (although I’ve never met a half child), wears a size 16 suit and an 8.5 shoe, and has some college. 

That’s just our average client. We get referrals of more than 800 women every year from ages 17 to 81. Some women even have their Ph.D. What works well for us is treating each and every client with dignity and respect — honoring diversity. Each woman has her own story, so we try to tailor our programs based on what her needs are. 

What are the challenges faced by women? Are they universal challenges or are they specific to certain job types and industries?

Childcare is a very big challenge for women, and if the COVID-19 pandemic didn’t shine some light on that, I don’t know what will. For example, in the past year, we’ve had more than five million women leave the workforce. If you look at September 2020 alone, for each man who left the workforce, four women left. 

Eighty percent of the women we serve are mothers. Of those women, 86 percent are the single head of household. These women are not only parenting their children but also grandchildren. But childcare is only back to about 50 percent of what it was pre-pandemic. You can’t enter the workforce if you don’t have that support.

Also, if you look at what has happened over this past year, the industries primarily staffed by women were some of the hardest-hit — healthcare, education, hospitality and tourism. So what are some examples? Let’s look at the woman who has children in elementary school. She has taken a job in the school cafeteria because it works around the children’s schedules and helps prevent the need for childcare. That’s a job that was furloughed during the pandemic. It’s not work you can bring home. Then you have the school bus driver. That’s also work you can’t bring home. Then you have the hostess at a local restaurant that has shut down. You can’t bring that work home. 

Not to mention that, if you’re fortunate enough to have access to technology, your children are online schooling at home. So you can’t even look for a job if you have the skills to secure one. This has really created a horrific situation for women during the pandemic. 

Do you think the pandemic has affected all women, regardless of class?  

I do think the pandemic has affected all women. Now, if you have the resources to share childcare responsibilities with a colleague or a friend so that you can piece together a work schedule, then you’re very fortunate. But many women in poverty — both generational poverty and, in the case of the pandemic, situational poverty — lack social capital. They often don’t have a strong family foundation they can draw from to provide some of this care. 

What we need to look at is upskilling these women so they can apply for jobs that they can take home. I don’t know if we’ll ever see another pandemic like this in our lives — I certainly hope not — but we are seeing women who lost their jobs in the recession who are once again in that situation. It’s sad because some of these women were finally starting to build their financial capital. 

We want to get women back into the workforce. Women fuel the economy. Nearly 90 percent of all household buying decisions are made by women, so it’s a win-win to get them involved and engaged in the community.

Are there any self-imposed barriers that limit women’s potential?

If you look at any studies about men and women, one thing that you’ll find is that men tend to be more confident. When men look at a job posting and see they only have 60 percent of what the job is looking for, they still go for it. Whether it’s experience or learning a new skill, men are confident they can acquire what they need. Women tend to hold back. They say, “Gosh, you know what? I’ve got one through seven but I don’t have eight, nine, or ten.” They don’t apply for the job.  

Is this narrative of self-doubt changing?

Well, when you have a situation like a recession or a pandemic, it sets you back a notch or two. You start to question your strengths, your abilities, and how you fit into the workforce. 

These situations also shine some light on other societal issues. For example, a study conducted back in 2015 by Harvard University and the University of California Berkeley showed that in terms of comparable city size, Charlotte is ranked 50 out of 50 for economic mobility. That’s terrible. 

Poverty hides well in Charlotte. If you’re born into the lowest quintile, your chances of ascending out of that are pretty grim. Your chances of staying in that lowest quintile are 36 percent and, for women of color minority populations, even greater. This is truly an ongoing challenge. 

How can women with more resources help to remove or, at the very least, soften some of the barriers that exist for women living in poverty?

We passionately believe that one hour of your time can change the direction of a woman’s life. For example, we have an HR professional who comes in and volunteers to work with our clients on Wednesday afternoons in our Career Center. During one of those meetings, the HR professional has been helping a woman who served in one of the branches of service create a civilian resume. The woman doesn’t know how to identify transferable skills, so the HR professional is helping her build that resume so she can apply for jobs. 

Our model is based on volunteerism. We have more than 1,000 volunteers who help fuel the organization. We all possess gifts that can help others.

Did you always want to focus your career on empowering women?

My dream was to be a journalist. I like to write. I like to tell a story. I just had these grand plans of being a famous journalist. But what I found in my first job as a newscaster was that I really didn’t like it. I was very disillusioned, so I left that industry and committed one year as an AmeriCorps VISTA volunteer. I signed on to work with an anti-hunger organization — a food bank in New York. I was responsible for helping them with outreach and fundraising. 

That particular organization helped me understand that while many, many people go without food, 20 percent of the food we’re producing in this country is lost between the field and the table. That’s more than two and a half times the amount needed to feed every hungry American, and yet produce is being plowed under and manufacturing errors are leading to items being thrown out. The food bank worked with companies and producers to put that food into the hands of hungry people. 

That’s how I got involved in the nonprofit world. Then, when we moved to Charlotte 15 years ago, I read an article that the Dress for Success affiliate had shut down. I knew what a fabulous organization it was. When I lived in Ohio, I watched very closely and saw what the affiliate did to help women advance. So after reading that article, I reached out and began volunteering as a board member, helping write a plan to reopen the organization.