Conspiring with the Babysitter
  • 12 min Read

As I sit to interview Katie and Tiffany, I think back to the first time I was introduced to the concept of Time Out Sitters. As a mom myself, I’d be lying if I said I wasn’t a little skeptical — “it’s like Uber for babysitting…are you sure?” I remember pushing back. It wasn’t until I met Katie and Tiffany in person that I understood. I immediately felt at ease. They are incredibly approachable, kind, and genuine. They own a sense of humor that is unashamedly real—if you are a mom, you can sit next to them and feel comfortable knowing that they’ve been there, they know, and they get it—for real. The interview is over the phone but conversations with them are always easy—with the two of them often finishing each other’s sentences and bantering between themselves.

Time Out Sitters is the story of two best friends who sought out to make a little extra cash to help make the ends meet and single-handedly turned the business into the San Antonio authority on child care.

Katie’s son was about to turn one and she didn’t want to go back to work but needed a way to bring in a consistent income.In 2012, Katie purchased the brand, Time Out Sitters, from the original owner. At that time, the company was a stable brand, they had a logo, a few sitters, a decent number of loyal clients.

Leah: What was your plan when you first bought Time Out Sitters?

Katie: I knew I only needed to make $500 a month to fill the gaps. That’s it. I figured at the very least, I could do that. I knew I wanted to grow the company. My five year plan was to franchise and help other moms stay home with their babies.

Leah: What were the first decisions you knew you needed to make?

Katie: In the beginning, I immediately knew I needed to revamp the logo and website. We had challenges with data and technology. Our website navigation was a nightmare. We had a spreadsheet for everything!

After operating for 2 years, Tiffany joined Katie in scaling the company in 2014. They had 50 sitters, averaging 350 jobs a month. Time Out Sitters was in a great position to grow.

Leah: When you joined Katie, what did you focus on first?

Tiffany: I actually started just doing social media and operations—scheduling sitters, confirming schedules, and reminders.  But before the end of 2014, I became a full partner.

By 2016, Time Out Sitters was seeing an average of 700 jobs a month — the company was growing faster than their current setup could support. It was time to scale.

Leah: Why did you reach out to Accomplice?

Katie: We hired the wrong web developers three times. We were at the end of our rope. We needed someone who understood business, could create software — I mean, three times, thousands of dollars spent on the wrong companies, countless hours — we needed help. It was so disheartening that we could not find a company who could do what we needed to do. We knew we were ready to grow, but I knew with our current setup we weren’t ready. We needed help. We were referred to Accomplice through a mutual friend.

Leah: At what point did you realize that Accomplice could do more than just build a technology solution?

Katie: During our conversations with Accomplice, we talked about their skill sets and we learned that they have a full development team that specializes in enterprise grade platforms and systems, as well as a full design team, marketing team, and research and business strategy team. They were a complete solution.

One of the first things we did with Time Out Sitters was consumer, client, and strategy research. The methodology included internal data audits, market analysis research, consumer behavior and perception research, user testing, focus groups, interviews, and complete acquisition and expansion analysis. The result was cross-functional – informing marketing strategy, target expansion areas prioritized by zip code, pricing perimeters, and product strategy and roadmap.

Leah: What can you guys do now that you couldn’t do a year ago?

Tiffany: Oh, man. Our hiring process has been made much more efficient, much more transparent, more automated. We can hire more quickly, turn around more jobs. Changes to our brand and logo has done a lot for our credibility, how we are perceived in the marketplace. We’ve done minor tweaks on how we book jobs — allowing families to have more transparency.

We are getting ready to move into beta testing on a new payment processing platform — everything will be automatic and mobile. That will be much more efficient, cleaner, and more user friendly. Allowing us to automate calculations and reconciliations. Next up, we are looking to automate matching families to sitters and automate job bookings but still be hands on when needed.

Katie: Accomplice has also helped with marketing and branding. They help us create themes, advertisements, brochures, and presentations that represent our brand and tone. They’ve had a lot of insight into business strategy and policy oversight — streamlining  policies, procedures, and processes to make sure our sitters and clients have a good experience.

Tiffany: Oh! And strategizing for the future. We definitely want to move into new markets. Anything we do now, Accomplice does with the bigger picture in mind down the road. Everything they build is built to allow for growth. They think about the whole picture, the end result—how will this impact Katie and me, how will these things change about how we operate.

Leah: What are you most excited about with pushing into new markets? And what are you most afraid of?

Tiffany: The potential growth, spreading the Time Out Sitters love. We know we have a really solid service and we take pride in who we hire and how we hire. Katie, what are you excited about?

Katie: We are successful in San Antonio, but moving into a new market and being successful will be incredible.

Tiffany: Katie and I have been best friends since 6th grade. We’ve always wanted to own our own business. Our first idea was to to open a baby boutique-like concept. It was a horrible idea. I am really glad it didn’t happen. But moving into new markets with Time Out Sitters will be like watching a piece of our dream come true.

Tiffany: What are we most nervous about? hmm… I think I’m nervous about it taking it longer than we expect.

Katie: I worry about losing the sense of community we have here in San Antonio. We don’t want to feel removed or corporate. What makes us unique is our approachable feel and sense of community.

Leah: Based on your experience with Accomplice so far, do you feel like you are well-prepared to move into new markets?

Tiffany: Yeah, for sure. Accomplice was great at honing in on what new markets we should be focused on and how best to expand.

Katie: Yes, the research gave us the foundation to understand what new markets want, while taking consideration what is important to Tiffany and me. I know we are building something sustainable.

Leah: What do you guys want out of 2017?

Tiffany: Continue to tweak the software, continue to build in automations. Growing the San Antonio market. We’d like to connect with more business, hotels, wedding planners —when people are coming into town and need sitters — that’s who we want to have conversations with.

Katie:  I’ll piggyback on Tiffany. Seeing San Antonio grow to the potential we know it has. Opening a new market and reaching more families, churches, companies, etc. FINALLY seeing the automation we have been dreaming of roll out will be the highlight!  This year will mark 5 years since I bought Time Out Sitters and if we can move into a new market, it will be surreal to see the little company that helped me stay home with my son become a household name in another city!

Leah: One more question…when talking to other business owners, what is the one thing you want them to know about Accomplice?

Katie: They get it. They come alongside you and add so much value to your business. They take the ideas that you could never find the time to accomplish and make them reality. They work with your strengths and fill in your weaknesses.  I can’t tell you who my favorite person on the team is – they are all amazing at what they do!

Tiffany: Yes! that’s it. They get it. They get our business. They take what we want, what we need, and find the best way to accomplish it. Walking through betas we were floored—they know our job minimums, they know our averages, our totals, and our workflows. We didn’t have to explain ourselves 100 times like some of the other companies we hired. They got it. Our dream, our business, our goals, our direction, and what we don’t want — they get it.

From all of us at Accomplice — working with Time Out Sitters has been ridiculously fun. We are looking forward to big things as they grow. If you are ever in the San Antonio area and in need of a sitter…timeoutsitters.com – you won’t be disappointed.  And keep an eye out for the Time Out Sitters in your area—we’ve got one direction around here and it’s forward.

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