Women Who Lead: Meggie Williams with Skiptown

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.