Alright – so today we’ve got the honor of introducing you to Amy Gray. We think you’ll enjoy our conversation, we’ve shared it below.

Amy, appreciate you joining us today. Can you talk to us about your team building process? How did you recruit and train your team and knowing what you know now would you have done anything differently?

When my mother-in-law Marion Gray started Marion’s Childcare (now Sitterwise), she was the only babysitter. She babysat in San Diego hotels almost every single day, in addition to hosting International students in her home and working a regular daytime job as a church secretary. By the time I took over the business in 2005, she had been “just” doing the office work (taking jobs and filling them and hiring caregivers) for over a decade. I stepped into that place and was immediately overwhelmed by the volume of phone calls. I had an eight-month-old baby, and it seemed that the phone was ringing off the hook and I could never catch up or relax. I decided to hire someone to take Fridays (the busiest day) so that I could have a day off. In the first few years, I hired my sister and several friends to take that spot, and it wasn’t long before I met our current Executive Director, Sarah, at church. She was wonderful at handling Fridays until, one day, she let me know that she was going to pursue photography full-time. That was the end of Sarah’s help with Sitterwise for a while, but it was the beginning of my introduction to family photography! Now, 15 years later, she is running Sitterwise, and I am doing family photography full-time. It’s funny how things work out.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your background and context?

I was an eighth grade English teacher, but I wanted to stay home with my kids, so when our first daughter was born I took over my mother-in-law’s already-thriving hotel childcare business. Marion had done an amazing job for 25 years, but she was 75 and ready to retire. I was happy to step into the role of business owner, but I didn’t know much about running a company. I read a lot of business books, brought my experience with technology to the situation, and did everything I could to grow Sitterwise while also making the systems and processes more efficient.

Sitterwise provides childcare to San Diego vacationers and residents. We go to hotel rooms, vacation rentals, private residences, and churches, and we take care of children on-location. Caregivers are fully background-checked and reference-screened, and they bring toys and activities to keep children occupied during the time they’re together. At hotels and resorts, our caregivers can also take children to the pool or the beach. Our caregivers come to us referred by people we know and trust, and we have a 40+ year record, working with hotel concierges across the county to provide a safe option for parents who need to be away from their children for a bit during their stay in San Diego.

Can you tell us about a time you’ve had to pivot?

The first real problem I came across when running Sitterwise was the economic downturn of 2008-2009. We had a major reduction in jobs as tourism was hit hard with the recession, and even our private residence clients were more conservative about making reservations for childcare. In the midst of the downturn, I took a leap of faith and increased our hourly minimum to four (instead of three) while simultaneously raising the hourly rate. It was scary, but we found that those who were still traveling and booking childcare were happy to pay the new rate and were also unfazed by the four-hour minimum, since it had become the industry standard and was somewhat expected. All in all, we actually had a more profitable year thanks to the changes.

We’d love to hear the story of how you turned a side-hustle into a something much bigger.

During the second year of owning Sitterwise, I found that the event portion of the business, which we call Playtime Pros, could be quite profitable, so I poured my energy into systemizing it and making it more efficient. I also decided it needed to be marketed separately from Sitterwise. I wanted to make a brochure and website, but I found that we had no photos of the childcare events that Playtime Pros provided. I considered hiring a photographer, but (having just started learning photography myself) it seemed like a better idea to put that money into purchasing better equipment so that I could take the photos myself. In the end, the eBay purchase of a very used professional digital camera led to my start as a professional family photographer, as well as excellent photos for Playtime Pros.

Contact Info:

• Website: sitterwise.com
• Instagram: http://instagram.com/sitterwise
• Facebook: facebook.com/sitterwise
• Linkedin: https://www.linkedin.com/in/amycothrangray/
• Yelp: https://www.yelp.com/biz/sitterwise-san-diego
• Other:  Photography business link: amygrayphotography.com