Start up city

Written by Jenn Barnett

There’s a current debate raging over who’s in charge of families these days—the parents or the kids. In reality, it’s Big Babysitting—a loosely connected cartel of primarily teen girls and young women who have the final say in whether or not you’ll be cancelling your anniversary dinner plans or attending that after-hours work function.

Until now, parents have relied on increasingly frantic phone calls and texts to other parents and potential sitters to find reliable, safe childcare at a moment’s notice. Birmingham startup Wyndy aims to change all that and improve the process for both sitters and parents.

Both parents and sitters (called Wyndys) can register at While founders Tommy and Ginger Mayfield encourage parents and sitters to exercise due diligence, safety measures abound, including the ability to see past jobs for both parents and sitters and in-app connections who can vouch for either party. Sitters are heavily vetted. First, they must be 18 or over and enrolled at a top-tier local college. They submit a video and their personal stats, including GPA and major, for review. Finally, they receive a background check. If that’s not enough to put parents at ease, they can also see reviews from parent friends who’ve used that Wyndy.

The Wyndy app handles payment, too, and even clues parents in to the going rate for quality sitters. Sitters receive their payments in their bank or Venmo accounts. Local development shop Airship built the app for Wyndy.

  1. What’s your elevator pitch?

The lives of parents with young children are inherently hectic, and they’re made more hectic by the difficulties in finding, booking, and paying reliable babysitters. Despite living in a world where apps like Uber and Shipt make getting a ride or having your groceries delivered ridiculously easy, most parents are still using the same technology that parents were using 10 or 15 years ago to find, book and pay babysitters. Wyndy is disrupting the traditional babysitting space by leveraging modern technology to transform the way the that parents and college sitters meet and interact.

  1. What’s your value proposition?

Wyndy is ultimately about community. We bring together two segments of a local population (parents and college sitters) that would like to connect in a way that benefits both segments.

Wyndy gives parents more time. We’ve radically simplified the process of booking and paying sitters. With a large pool of reliable, background-checked college sitters at their fingertips, parents can consistently find a Wyndy to watch their kids so they can enjoy time together.

Wyndy gives sitters the ability to make babysitting a viable part-time job and defray the high cost of college while networking with local families.

  1. Tell me about your founders and their experience. How many employees do you have?

My wife Ginger and I are the founders of Wyndy and the parents of two young daughters. We met while attending Vanderbilt University and have been married for 10 years. After receiving my law degree from the University of Virginia, we moved home to Birmingham, where I practiced law for seven years at Maynard Cooper & Gale before founding Wyndy. Ginger earned her master’s degree from UAB and previously worked as a college guidance counselor at a local high school. We currently have one additional full time employee, Emma Crist, who serves as our director of marketing and communications.

  1. How did you get the idea to launch Wyndy?

Wyndy was born out of a desire to solve a very real problem that we faced. As working parents of two small children, we were constantly stressed about finding sitters for our girls. It was difficult to create a network of reliable sitters, and even when we had five or six sitters in our contact list, trying to book one for a particular date seemed to take forever. It was also frustrating to have to stop by the ATM or search for a checkbook at the end of a night out in order to pay our sitter.

College students were our favorite sitters because they were responsible, had flexible schedules, and our girls loved them. In talking with them, we realized that they suffered from some of the same frustrations. Many of them wanted to make babysitting a viable part-time job to help earn extra cash while in school, but it was hard for them to meet enough families, and even if they did, it was difficult to make their availability known. They were often left just waiting and hoping that a parent would text them a job offer when they were available.

The bottom line is that both we and our college sitters were tired of using outdated and inefficient methods to find, book, and pay for babysitting jobs, so we created Wyndy to help solve those problems.

  1. Why is now the right time for Wyndy? Why did you launch it in Birmingham?

Birmingham is a great initial market for Wyndy because it’s home to several outstanding colleges and universities and to lots of young families.

  1. What are your competitive advantages?

None of our competitors have combined trust and technology in the way that we have. I mentioned that we choose college students. In addition, all sitters must complete an online application process where they provide information about their major, GPA, babysitting experiences, and preferences and submit a short video of themselves. If we approve them, we then run a background check. Only after they have cleared the background check do they become Wyndys and gain access to the app.

In addition to our initial vetting process, we’ve also built filters that allow parents to quickly find sitters that match their preferences. Finally, we’ve added a social connections component that lets parents connect with their friends and see the Wyndys their friends have used, how many times they’ve used them, and the ratings they’ve given them.

Our product brings a level of convenience to parents and sitters that rivals any of our competitors. We have a roadmap of additional features will further differentiate us from our competitors and create additional value for our users.

Finally, we have a first-mover advantage in places like Birmingham and the next 25 or so markets where we’d like to expand.

  1. Where do you want the company to be in five years?

In the next five years, both parents and college sitters across the country are going to abandon the olds ways of finding and booking babysitting jobs and turn to modern technology to connect. We want Wyndy to be that technology.