In 1994, brothers Bert and John Jacobs started the Life Is Good company, an American apparel retailer founded on a relentless belief in the power of positivity. Ten years later, freelance graphic designer Jenny Moates did something similar. 

Hoping to provide more value to clients, Moates and her husband, Brian, established Moving Ideas in 2004. Just one year later and with opportunities in front of them, Jenny invited Yvette Salerno, her lifelong friend and a marketing executive with Bank of America, to join forces as her business partner. At face value, Moving Ideas is a strategic marketing and graphic design agency focused on providing astute brand communications. But like the Life Is Good company, Moving Ideas also spreads the word of optimism. 

“Positivity is a core philosophy personally, but it also drives business results,” says Moates. “When you have a positive attitude, you’re going to have better ideas.”

We chatted with Moates, whose official title is Chief Possibilities Officer, to learn more about the role of positivity in graphic design. 

What motivated you to open Moving Ideas?

I wanted to grow beyond a freelance business and, in 2004, it felt like the right time to do that. I was already working with other partners — folks who are contractors who we still work with today. The whole thing was starting to feel much bigger than me. It evolved to require a team effort. 

Opening an agency also gives your clients access to a larger talent pool. As a freelancer, you’re just one person. But as a business, you can do so much more with a group of people. As with any business, the success of what you offer is 100 percent about the people involved. That’s why I don’t like titles because, at the end of the day, it’s about who produced the best ideas and the best results, no matter their title.

Speaking of titles, you’re the Chief Possibilities Officer at Moving Ideas. What does that mean?

Technically on legal documents, I am the president but that doesn’t say a whole lot. We prefer to have more creative titles around here, so I’m the Chief Possibilities Officer which fits my role as essentially the creative director. 

My business partner, Yvette Salerno, is the Chief Reality Officer. We have a lot of fun with that because it fits our dynamic. She and I have an amazing balance. The things that she’s good at aren’t necessarily the things I’m good at and vice versa. Our clients benefit from a very well-rounded approach. 

What lessons have you learned as a business owner?

One piece of advice that was given to me — and it’s been rock solid since the very beginning — is that you should always be a cash business. Don’t go into debt. Borrowing money was something I could’ve easily done over the years, but being strategic about the money we spent allowed us to hold on during the very lean times. It’s good to embrace challenges like the recession and the pandemic, pull the team together, and say, “Okay, how are we going to keep moving forward?” 

I also believe in this principle: give more in value than you take in payment. If you always do that, the work will come. Our group has always been that way. We have retainer clients that go above in terms of monthly hours but we’re okay with that because we want to give more in value than we take in payment. Many creative agencies aren’t necessarily invested in the business results of their clients. But to me, good design is just a baseline — it’s expected. Driving business results is what separates us from other agencies. More importantly, it’s what gives value to our clients.

Your website describes you as someone who leads with an “optimistic approach.” Can you unpack that? 

I just have an overarching philosophy in life that optimism leads to more success. I believe that having a positive, can-do attitude will get you through difficult times. If you look at kids who are in the hospital suffering, for instance, it’s positivity that pushes them past those hard things.

Optimism is also a key cornerstone of any good business. One of the books that I’m reading right now is called “Life Is Good.” It’s by the two brothers who started the Life Is Good brand. Their whole brand is built on optimism, and they’ve been so successful because the world craves positivity. We need positivity.  

What’s your secret to staying positive even when times are tough?

I’ve had people ask me, “How are you happy all the time?” And I say, “Well, it’s better than the alternative, right?” But here’s the thing you must understand: Optimism is not necessarily happiness. Optimism is just a positive outlook. As I said, a child in a cancer ward isn’t necessarily happy but they can still be optimistic and hope for a positive outcome. It’s not false happiness — it’s just a way of looking at the world. 

One of the things I love in “Life Is Good” is that the authors suggest saying “I get to go to work” instead of “I have to go to work.” It just completely changes your mindset. I get to go to work. I get to go to this amazing place and work with my best friend. I get to have fun. I get to be creative. I get to do this and get paid for it. That’s so crazy, right? 

I will say that my hope is fueled by my faith. I’m a very faithful Christian, and I believe that God is with me and in me. He’s the one in control. I’ve seen him move mountains in my life personally and professionally. That gives me tons of optimism.

Continuing to learn and grow as a leader is essential to providing those outcomes. With that being said, what’s a new skill you’re developing right now? 

I’m always learning how to better use technology. I’m a big believer that technology can make you more efficient, it can make your life easier, and it can create better results for your clients. So that’s an ongoing learning process for me. When I was a kid, my grandmother would say, “If you stop learning, you’re dead.” I think she’s right. You should always be reading and talking to others. 

Listening to other people’s perspectives is a great way to learn too. In 2017, I published a book called “50 Coffees.” It was a social experiment to meet 50 people a year over coffee as a way of building community. In doing so, I learned a lot about the importance of relationships. I wrote a book so I could help other people who are like me — people who are good at what they do but not so good at building community. 

Over the years, how have you balanced being a business owner and a mother?

I don’t feel like my family has to take a backseat. I’ve never felt that way. I think you can be a good example for your children while doing good things in the business world. I have three kids — one is a junior in high school, one is in seventh grade, and one is in sixth grade — and I don’t feel like I’ve had to sacrifice anything. That’s mainly because I have flexibility here. We’re a culture that embraces family values. 

You’re never going to look back on your life and wish you worked more. So while I want to do good work and serve our clients, family comes first. We even have an employee’s kid who is homeschooled and goes to school in our office. She’s grown up with this business since the very beginning. She knows what clients are and will even look at logos and say, “I like this one, but what if you changed this?” Family is just a huge priority here.    

Very few people hope there comes a day when their job is obsolete. Then there’s Neville Poole. 

As the North America Enterprise Agility Partner for IBM, Poole collaborates with C-suite executives of Fortune 500 companies to develop new technology strategies that modernize their ability to deliver value. Simply put, her job toggles between business and technology consulting. But when she envisions the future, she sees something entirely different.

“The future of business is not business and IT,” says Poole. “The future of business is an organization that is laser-focused on delivering business outcomes. Consulting then becomes about solving organizational problems, not selling widgets.”

We spoke with Poole to hear more about how a marketing major from a small historically black college climbed the ranks to work for one of the largest technology and consulting companies in the world.  

This is a two-part question: Would you say the business and technology industries are male-dominated? If so, why?

Yes, these industries are very much dominated by men. 

There are a couple of different reasons why. A lot of women never found a connection with technology as young girls. If you look at the STEM programs, there’s not a lot of girls because we do a poor job explaining the available opportunities. Technology is just presented as someone writing a bunch of code, but that might not be the right entrance for everybody — girls and boys — into the field. 

Today, there’s a lot of effort to expose young girls and boys to STEM. I have a daughter in middle school and I get emails all the time for classes like Girls Who Code. Now, there are all these initiatives to expose women to the field. But before, the industry just wasn’t geared toward girls. 

Also, technology roles can be super demanding and a lot of women exit the field because they can’t balance their family and a job in IT. Technology jobs are demanding and, until recently, it was frowned upon to balance your job and home life. It was like, “Oh, you can’t work 60-hour weeks? What’s wrong with you?” Over the last couple of years and especially this last year with COVID, organizations have become more aware of the imbalance. 

What are some barriers that existed at the start of your career that have since evolved?

When I first started in IT, the biggest barrier was mentorship. I didn’t come from a traditional technology background. Since I was a marketing and economics major, I had created a network that was very different from the field I was going into. I didn’t have men or women who could be my voice to help me get opportunities.

That was a big barrier because my counterparts had mentors in the technology industry that they’d known for a long time. But now, because of the emphasis on diversity and inclusion in the workplace, many organizations are being very intentional about ensuring everyone has a sponsor to help them maneuver through the organization or their career at large. Organizations are being super intentional about setting people up for success and giving them the tools that they need.

Throughout your career, you have continuously climbed the ranks and accepted bigger and better opportunities. What’s the secret to your success?

It’s important for me to feel like I’m adding value and being challenged. If at any point in my journey both of those pieces aren’t true, then it’s time to be vulnerable and do something that stretches me. 

When I’m asked to do something uncomfortable, I have to ask myself, “Have I created a succession plan? If I were to leave this role, who would be my successor?” I have this natural knack for coaching. I always want to be providing knowledge to enable someone else to step in and be ready for their next challenge. 

It’s interesting that you always consider who will be your successor. Why is that?

I actually think about it when I start a new role — I don’t wait until the end. For example, within my first month at IBM, I identified some people on my team who, if I were to move on, would be the next leaders of this group. So I started coaching them without them even knowing it. 

I’m always thinking about how I can add more value. That way, when I get tapped on the shoulder or identify an area I want to explore, I can leave the area better than when I found it. I can feel great about leaving it in the hands of people who care and want to see the company grow. 

Did you have mentors who, as you do with select employees now, started coaching you without you realizing it?

Yes. I can look back and identify two people who did that. I didn’t realize it at the time but they took a liking to me and gave me some of their pet projects. Later on, I realized they were testing me, trying to see if I could handle it.

More people need to acknowledge they have a responsibility to help. There’s somebody in your network, in your neighborhood, or in your company who has the potential to do something they didn’t even think was possible. They just need a leader to give them a little nudge and give them a place to learn. If I were to retire tomorrow and I hadn’t shared any of my knowledge or experiences except to make money for my company, that’s just not cool. 

It doesn’t matter what level of leadership you’re in, there’s always somebody who needs support. It’s not always convenient to set aside time to do it, but it’s a failure if you, as a leader, walk away and haven’t equipped anyone else.

Of course, self-growth never stops. What new skills are you developing today?

A big focus for me right now is leadership development. Working with the C-suite of Fortune 500 companies, especially right now in a pandemic, I have to stay several steps ahead in my research and my strategies to help them. That’s something I’m working on — anticipating what’s next for my clients.

I’m also advancing on how to communicate with CEOs who risk their entire livelihoods if their companies don’t turn around post-pandemic. I have a lot of empathy and I need to tether that. I want my clients to feel comfortable and know that I feel for them but I also have to quickly turn that empathy into something productive. I don’t always have a day or two to think about it. Many times, I have to come up with a plan while I’m on the phone with the client. That skill is ever-evolving.

Another thing is feeling comfortable with my skills and taking them to an industry I’m passionate about. When you’re coming up in your career, you don’t get to pick and choose. You take what you can get, make the best of it, learn, and move on. But I’m at the point now where I can pick what industry I want to work in, what type of work I want to do, and where — whether it’s for IBM or if I decide to do something on my own. I can now step out and make that call.

Why’s it important that you impart lasting value?

It’s a personal thing. I grew up in a very poor area and went to an HBCU. I always felt like I needed to take five steps to match another person’s single step. So I’m always trying to demonstrate that I can bring something valuable to the table.

Growing up the way I grew up, I always wanted to prove that I could accomplish something. That has carried forth with me my entire career. I’m always going into situations thinking, “How are they going to perceive me when I walk away?” I want to walk away feeling like I did good and provided the value they expected so they won’t hesitate to do business with another black woman in the future. There aren’t many black people in IT, so I want to bring my A-game all the time so that someone else has the opportunity to show up. 

What advice would you give to your younger self?

Just believe in what you know and be transparent about what you don’t. There are lots of leaders who tell people, “Fake it ‘til you make it.” I just can’t do that. When you’re transparent about what you don’t know, it opens up so many opportunities for you to learn, grow, and create trusted relationships. 

I would also tell my younger self to be vocal. Don’t suppress it because you think you’re being bodacious. Speaking up is huge because I never did. I would wait until somebody called my name and, if they didn’t, I didn’t offer input. I tell my daughters all the time, “Don’t hesitate to say it.”

Charlotte is an entrepreneurial haven — a thriving metropolis where growth-oriented companies can put down roots and flourish. But the Queen City wasn’t always so hospitable towards business owners. 

In 2003, when Terry Cox moved from San Francisco to Charlotte, she noticed a dearth of entrepreneurial culture. “There was no ecosystem or connectivity,” says Cox. “Entrepreneurs were out there swimming upstream alone.”

Two years later, Cox founded Business Innovation & Growth (BIG), a membership organization that fosters a peer-to-peer network of like-minded companies. Through offering mentoring for early-stage entrepreneurs, access to resources and capital, and best practices for high-growth enterprises, BIG has emerged as a daily staple in Charlotte’s business scene. Cox also serves as the Executive Director at TechWorks Gaston, a learning center design to create economic opportunity for businesses and residents in Gaston County.

We spoke with Cox — the unofficial matriarch of the city’s entrepreneurial movement — to learn more about what it takes to be a woman in business. 

You’ve accomplished a lot in your career: You worked as a CPA. You ran a wholesale and retail ice cream business in Georgia. You took over the helm at the Metrolina Entrepreneurial Council. With all of that experience under your belt, what motivated you to found BIG?

When I moved to Charlotte from San Francisco, I was searching for high growth entrepreneurs and when I talked to each person, I realized no one knew one another. I was like, “This is crazy.” I came from San Francisco where there’s such an ecosystem of entrepreneurship in the Silicon Valley. In Charlotte, there was a huge void that needed to be filled.   

What were the challenges of founding a peer-to-peer network in the Queen City?

Most venture capital firms have never seen enough deal flow come out of Charlotte to warrant having an office here, much less even spending a day in Charlotte. They just fly right through Charlotte and on to Raleigh. They don’t even stop to see what companies are here. 

That’s slowly changing. We are now on the radar of investors because we got very intentional about building out the entrepreneurial ecosystem. In 2006, I realized we needed to build a critical mass of entrepreneurs and then seek capital. But you’ve got to find entrepreneurs who are willing to take that bet with you. You have to have a compelling value proposition for them to do something they haven’t seen before.

Were there any other personal or professional challenges rooted in moving to the East Coast?

The biggest challenge for me was the culture. Charlotte has a very conservative culture whereas San Francisco does not. San Francisco is very much about taking risks. It’s a different mindset but you’ve got to listen, observe, alter your behavior and strategy accordingly. 

For example, when I moved from San Francisco to Charlotte, I appeared pretty aggressive for the first year. I was aggressive in terms of my thinking. I was just like, “Let’s go. Let’s just get on with it.” I had to learn how to slow down and meet others where they are. 

Funny enough, in the early nineties, I moved from Savannah, Georgia, to San Francisco and that was a huge culture shock for me. Holy cow. I spent so much time trying to get rid of my southern accent. I would replay a voicemail message over and over and over before I hit “send.” They thought southern bells were dumb gals. 

You make an interesting point about cultural differences. In your experience, how do San Francisco and Charlotte compare in terms of attitudes towards women in business? 

When I went out to California in 1993, the firms I worked with were much more open-minded about promoting and encouraging women. They were also definitely more accepting of LGBTQ+ individuals and other minorities. It was just a melting pot out there.  

We’re probably ten years behind that in Charlotte. It’s just shocking to me that women still have a tougher road here. It’s unconscious bias. A lot of men don’t even realize how they think of women, perceive women, and treat women. It’s just ingrained in them. It’ll take a long time to reverse this but I think we’ve made some headway. 

For instance, I’m thrilled by how many more female startups I’m seeing. Female and minority-owned startups are finally getting capital, even though historically that’s been hard for them. We’re finally getting somewhere. There’s truly a strong women’s movement happening and I hope it continues. 

What is your professional personality style?

I am who I am. I’ve never tried to be anything different. For instance, I can’t be political. I just can’t play politics, especially corporate politics. I’m just not a politically-minded person. 

I always take the high road. I believe very much in integrity and honesty and transparency. I’m always considering my reputation and brand because, at the end of the day, that’s all I have. When I put my head on my pillow at night, I have to own what I did that day. I’ve got to feel good about it. If I was being told to do something that wasn’t ethical, I would walk out the door before I’d stay for the paycheck. 

All that being said, I don’t work for the money. I work to drive impact and change.

You work to drive impact and change. Can you provide an example of when you did just that?

I worked with county commissioners in Gaston County to push this model we have — this model that promotes entrepreneurship, technology, co-working, tech education, and more. At the time, Gaston County didn’t have an entrepreneurial center. It didn’t have an ecosystem for scalable entrepreneurs because the people who live there hadn’t been exposed to that culture. 

Though they had never seen this concept before, it hit home when I told one of the county commissioners, “Your grandkids are not coming back to this county. We need to start to create an ecosystem that creates and supports jobs for the future of Gaston County.” 

Earlier you noted that you never work for the money. Has that always been your philosophy?

Years ago, I ran my own business in Savannah, Georgia, and was one of maybe three female business owners in the whole city. I struggled. It was hard. So when I left that behind, it was nice to just be making good money. That’s when, like many other people, I became a victim of money. I started staying at jobs, not because I was happy, but because of the money.

I got stuck on that career track. I was working all the time, making decent money, and enjoying that money. But when my mother came to visit me one time, she said, “You’ve become a person I no longer know.” I was like, “Wow.” It hit me right between the eyes. 

I had become very aggressive. I was in a highly competitive culture — a firm of Type A people — and to survive I had to be like that. But when my mother made her comment, I left the whole game and chose to travel the world for a few years. Now, I’ve come back to the business world with a different approach. I’m driven by purpose, not money. 

I won’t lie — sometimes I still get frustrated because I don’t make the money I used to make. But I’ve developed a huge, meaningful network and great relationships. And that’s what makes me happy day in and day out — relationships.

Meggie Williams may be the world’s most successful dog walker.

In 2016, after boarding a few pups in her Manhattan apartment, Williams founded a Charlotte-based dog walking enterprise called The Waggle Company. The business has since rebranded as Skipper, a pet care service and smartphone app with a presence across the southeast. Last year, Williams also unveiled Skiptown — a brick-and-mortar doggy oasis that caters to pups and humans alike. 

Though the company has grown tremendously in just five years, trust has and always will be a core value. “It’s integral to everything that we do,” says Williams. “Our clients not only trust us in their homes, they trust us to care for their pets.” 

We caught up with Williams to learn more about how she made a small dog walking endeavor into a howling success. 

Which came first — your passion for business or your passion for animals?

I’ve always been an animal lover since I was a little girl. We used to rescue injured animals, nurse them back to health, and let them go — mostly squirrels and birds, but we also had our fair share of dogs. When I moved to New York, I worked at IBM as a Global Business Services Consultant and couldn’t have a dog. I was in Manhattan and was traveling, but I really wanted a dog in my life. 

So I started a side business that involved me boarding a couple of dogs on the weekend. That’s how I got to understand the pet parent pain points, lifestyle, and needs in a way that was intriguing to me. I saw it as an opportunity and I always had it in the back of my mind. 

What motivated you to take a leap of faith and branch out on your own?

When I moved to Charlotte, I joined a company called Move Loot. I started their Charlotte office and then eventually ran the southeast division. I learned a lot about business — how to start one, how to run one, and, ultimately, how to not run one. We ended up scaling too quickly on a model that wasn’t proven and that was part of the reason why Move Loot failed. 

When that company failed and my job was eliminated, it was a great moment of introspection. I was sitting with my husband and I said, “I think I want to do this idea that I’ve talked about since I lived in New York.” I knew that there were more pet parents than ever before and that operators in the market weren’t meeting their needs. There was nothing that accommodated the modern lifestyle. So that’s what we did — we started as a dog walking business called The Waggle Company in 2016. 

Technology played an instrumental role in the development of The Waggle Company. Can you discuss this in more detail?

From the very beginning, I knew my business was about one thing: trust. It became so obvious to me. I was getting keys and access to be in someone’s home and then taking care of their dog, which is the most important thing in their life. That was the impetus. We started asking ourselves, “How can we be the most trusted provider for pet parents?” 

But quality control can be hard. At first, it’s easy for pet sitters to manage a block or two but once you scale the quality control, you need to have the infrastructure in place. We knew that to have the impact we wanted to have, we would need to create our own technology. Tech in the pet care space is, as you may imagine, very limited. 

That’s when we raised our first round of funding to support tech development. My husband and I took out an SBA loan. We put all of our personal savings into building out the technology. And then we grew. The tech was a big part of how we built our team and our clientele. 

In 2018, the dog walking enterprise expanded to out-of-state markets and began offering other services, right?

Right. In 2018, we got accepted to an accelerator called Techstars, which is based in Austin. We moved to Texas to understand how to frame the business and that’s when we launched the Austin and Dallas markets. At that point, we had three dog walking markets. But we were also learning that there was an increasing need for pet care outside of dog walking. We had been building this whole foundation and driving it toward a very narrow service focus, but people wanted more than that. We realized we could amplify our impact. 

We came to that realization after we started partnering with apartment communities. We were the first company to build on-site daycare and boarding facilities inside of apartments. The largest is still running at The Village at Commonwealth in Charlotte. It’s a testament to how much demand there is, especially in the apartment-dwelling community where more than 50 percent of apartments have dogs but there’s no great infrastructure to support those dogs. They have no play areas or pet relief stations. Sometimes they have dog stations, but they’re not particularly well-managed or supplied. When we started building out these facilities, we realized we could do more to care for pets and their people in a way that’s still foundationally about trust, and then fun and adventure. 

That’s when we took the dive. In June 2019, we started looking for our own facility — a space for Skiptown. When we found the location where we’re at now in South End, we were like, “Oh my gosh. If we could create a dream space in the perfect location in the perfect city, it’s right here.” So we signed the lease and started working on this dream that we could take what we built as a dog walking company and morph it into an oasis for dogs. That was the new vision.

How did the pandemic affect that vision?

When we signed the lease, I was on my way to the company holiday party. I was in a nice dress and heels, it was like eight o’clock at night, and I was at the lawyer’s office because we needed to handle it before the holidays. After it was signed, I started raising funds to support the build. Then COVID hit. It was February and I was in California for a work conference when three investors called to say that they were pulling out. Within two hours, more than half the round was gone.

I got on a red-eye and flew back to Charlotte. I pulled the whole leadership team together at like 6:30 in the morning and said, “We need to have a game plan. We need to figure out what is critical path work and we need to do that and only that. Everything else needs to go away.” Our singular focus became building Skiptown. We decided to do everything we needed to do to support Skiptown.  

We majorly cut back on our dog walking. We narrowed the focus to a very small radius and laid off more than 80 employees. Most of them were dog walkers but we also had to lay off several positions in our back office that supported the dog walking. We had to cut expenses down as much as we could. Then we went back out to fundraise with a much different pitch, which was that the pet industry has outlasted a recession in the recent past. In fact, the pet care industry was one of the only industries that grew in 2008. People are here to invest in their pet’s health and happiness despite financial setbacks. 

Once people calmed down a bit, we got the funding in place and moved forward. We launched in August 2020 and pre-sold almost 1,000 memberships before we launched. It was huge because this was in the middle of the pandemic. But we had space on our side. Since we have a large footprint, we were able to provide an environment that people felt good in. 

Ever since we’ve launched, it’s just been more validation that people want and need this, as do their pets. There’s no good space to go to when you want to hang out with your dog. There are “dog-friendly” spaces but are they? Your dog isn’t having a great time and usually you’re not either because you’re worried about your dog. So we created a place where you can relax and have a good time but you don’t have to drop your standards.

Your company has continuously evolved since 2016. How did you learn to lean into those changes?

It requires a reframing of what failure is. You usually learn the most when things don’t happen the way you expect them to. I’ve made it a focus for myself, my team, and my organization to  constantly try to predict what’s going to happen in the market. In that mindset, change is the only option. If you’re not changing, you’re dying. We have adopted that as an ethos. 

Do you have any suggestions for other business owners who are faced with hard and sometimes painful decisions? During the pandemic, for instance, you had to lay off more than 80 employees. How do you make those calls? 

It’s about not hovering too long in a place of indecisiveness. I think sometimes the wrong decision is better than no decision at all. You need to make the call. That’s just my nature — I’m decisive. But we also hire decisive people. We look for that during the hiring process. We look for changemakers who understand that you need to move forward. 

It’s also the nature of a startup. We’ve always looked at resources like they were finite and operated in a world where we had to pivot. We’ve had to take customer feedback and ask, “Is the product that we’re putting out there the right product? Is the client that we’re targeting the right client?” We’ve always been forced to go back to the drawing board and look at things under a microscope again and again and again. Doing that just puts you into a rhythm.

So when COVID hit, we just went back to the drawing board. We’ve always had an extra big crisis looming over our heads, whether it was running out of money or opening a new market. There has always been an impending sense of doom that we just worked through. 

But few people are brave enough to work through that “impending sense of doom.” Who or what made you the person you are today?

First and foremost, I was lucky enough to be well-parented. I was lucky enough to come from a very supportive household where my parents helped me build confidence and autonomy. At a very young age, I felt like I could take risks and make decisions and learn from them. That parenting has done a lot to make me realize that the worst-case scenario isn’t that bad. 

For instance, if my husband and I lost our house, what would we do? Well, we have two sets of parents who would easily take us in. We’ve got a great group of friends who would love to give us their guest bedroom while we figured things out. That network is so valuable. 

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. 

Not all people see the power of women in business. That’s just one reason 70 percent of senior management roles are held by men. But Sara Giles knew her boss was different. 

In 2013, when Giles started working at Anita Goodesign, an embroidery design company based in Charlotte, she got a “different vibe” from the company’s owner, Steve Wilson. 

“Steve respects women,” says Giles. “He says that we are better leaders than men — that we can multitask and handle more projects. Because of that, we’re essentially a woman-based company.”

Wilson’s progressive attitude created the perfect environment for Giles to climb the ranks. After five months as an event planning assistant, she was promoted to marketing coordinator and then organizational development director. Today, she serves as CEO, managing almost 50 employees and a worldwide enterprise. 

We chatted with Giles to learn more about how hard work, long hours, and a fresh perspective catalyzed her career. 

How did you land a job as CEO of the top embroidery design company in the world?

When I started at Anita Goodesign in 2013, I left a job that I had been at for five years. I just wanted a change. I wasn’t quite sure ​​what I wanted to do with my career, so I just started exploring and applying to jobs. I didn’t know anything about this company or embroidery, but I applied for the event planning assistant position. I was the very first person to apply out of like 100 people and they hired me. 

They were looking for someone to organize the whole system itself. Because of my background experience in Excel and just being a super organized person, I was able to listen to what they were looking for and implement it. Whenever Steve Wilson, the owner, asked for something, I was very quick to get it done. 

I just wanted to do a good job, and Steve consistently rewarded me for doing so. That was something I had never experienced. At most jobs, you work really hard and you get a very small pay increase, if any, in return. You have to leave if you want a bigger pay increase or a promotion. But at Anita Goodesign, I learned that if I worked really hard, never said no, and just kept learning, I would be presented with opportunities. Because of that, I was able to become CEO of the company.   

Many young professionals hop from company to company in search of higher pay and bigger promotions. From your perspective, what are the benefits of climbing the ranks at one business? 

I’ve been able to do so many different jobs at Anita Goodesign — from sending emails to planning events. Now as the CEO, when my team is presenting problems to me, I’m able to quickly help them come to a conclusion because I have the experience. I’ve been there before.  

Because of my experience, I’m more confident in the decisions I make. I know the customer. I know what to expect. I can guide an employee who is newer to the organization and give them information regarding what did or didn’t work well over the years. When you come from a lower position and move up, you carry all of that great company history. You can guide your team. 

After you took the job as CEO, was there anything about the role that surprised you?

I wasn’t expecting to be so involved in the “people” part of business. Since we’re a small business — we have 47 employees — a lot of the HR responsibilities fall under my to-do list. 

People aren’t afraid to come to me, whether they just need a new chair or they’re experiencing something bigger like an issue with a coworker. I hear everything and get a lot of direct interfacing with the employees. But the conversations aren’t just about their jobs. You learn a lot about their families and you also learn to be compassionate. 

On a related note, how would you describe your leadership style? 

Hands-on. I would never ask somebody to do something that I haven’t done or wouldn’t do myself. I think that people respect me a lot more because of it. I’m the type of person who, if I see something that needs to be done and there’s no one around to do it, I’ll do it. That’s helped me build a better working relationship with the people I manage because when I delegate a task, they don’t push back. They know I’ll get in there and do it too. 

Being hands-on is 100 percent the best way to be a leader. If you know how to pack a box, you appreciate the employee doing it each day even more. Being hands-on helps you realize that every role is important at the company. 

What are some specific challenges you have faced as a woman in business?

At my first job at a fashion company in Charlotte, there was one person who was pretty high up and he would make these very inappropriate comments about what I was wearing during meetings. I was in planning for children’s clothes and he would hold up a little girls’ dress and be like, “Oh, would Sara fit in this?” It was so ridiculous. 

Because I was so young and I was early in my career, I didn’t feel empowered enough to say something even though I totally should have. Older women who worked for that company would even come up to me and say, “He shouldn’t be talking to you like that.” But again, I was young and didn’t want to cause waves. 

From that experience, I learned that men are looked at differently in the business world. It has changed some over the years but women are still underrepresented in company leadership. 

Is there any advice you’d give to your younger self, besides maybe to learn to love accounting?

I wish that I had connected with a career coach, even before starting college. I wish I had a better grasp on the jobs that were available because I felt very lost going into school. I had just turned 18. I was still young and yet I was supposed to know what I wanted to do for the rest of my life. I felt very lost with that.

I did enjoy fashion, so I went to school for fashion merchandising and marketing. I intended to be a buyer and I didn’t end up there. I think some additional career planning or coaching would have helped me understand what I’m good at and what I ultimately wanted to do.

So how did you eventually discover your unique strengths and talents?

Honestly, by working at this company and doing everything through trial and error. At Anita Goodesign, I was given the opportunity to learn everything from how to order boxes to inventory. I got to figure out that I’m good at the planning and organization piece — knowing a little about each department, reeling it in, and getting it done. 

Sometimes when you have so many departments working on a project, you need one person who can be the glue to stick it all together and finish it. That’s what I’m good at. I can anticipate what’s coming and get it done.