Startup Spotlight: Kristen Stiles of Sitter

Kristen Stiles is a self-proclaimed hacker turned entrepreneur. Over the past few years, Kristen and her team at Sitter have launched an initial product, raised their first round of outside financing, and are now in the midst of charting the course for the next phase of the company. Kristen is a great example of a startup founder who is constantly testing their business thesis and listening to customer feedback to drive product strategy and execution.

What impresses me most about Kristen is her thoughtfulness and preparation in executing her vision for the company. While many startups burn through cash to test a product hypothesis with the market, Kristen builds conviction around her strategic options before ramping up spending. She is also quick to cut expenses when the feedback she receives from the market dictates a course correction. This combination of thoughtful financial stewardship and aggressive strategy execution is a hallmark of a top-tier startup operator.

BZ: What is Sitter?
KS: Sitter is revolutionizing the care industry by giving care companies, big and small, the technology needed to compete in today’s world.

BZ: What sparked the concept?
KS: Sitter started as a consumer app that allows parents to book and pay their own babysitters instantly. After being approached by a nanny agency that wanted to use it for their business, we discovered that these business owners were drowning in operational inefficiencies. There was no technology on the market built to support the specific needs of care businesses. Agency owners were burning out and struggling to grow and compete by trying to run their temporary care businesses manually 24/7. Sitter’s new Sitter Pro technology gives them a booking and management platform to automate and transform their operations so they can focus on what they do best — caring for their customers.

BZ: What does your business do that is better than anyone else?
KS: Our highly unique combination of extensive technology, operations, and care industry expertise gives us the ability to build a caliber of solution the industry has never seen. Plus, by using our original Sitter consumer app as a lead into our Sitter Pro app, we are best positioned to build a national network of care agencies accessible by families everywhere.

BZ: Why is now the right time for your business?
KS: Millenials are starting to become parents. Gen Xers are starting to care for their elderly parents. Both generations expect to be able to use technology for all of their needs, including booking care providers. These care agencies recognize this shift and realize that they need technology to best serve their customers.

BZ: What nuance about your business is most difficult to convey?
KS: We’re not only trying to give technology to the businesses to help run their operations but also elevate the awareness of these care agencies as a whole to the families who need their services. 98% of new parents don’t even know nanny agencies exist. These businesses are the experts in finding the best caregivers in the industry and have dedicated their lives to helping families. More families need to know about the services they provide and be able to book them easier.

BZ: What part of running a startup has been harder than you imagined?
KS: Staying focused. There are so many opportunities for improvement in the space that it’s extremely hard to not get distracted by shiny objects.

BZ: What part of running a startup has been easier than you imagined?
KS: Haha! Good one. :) Nothing.

BZ: What is your superpower?
KS: Besides my uncanny ability to know when either of my sons is sneaking up on me with a Nerf gun, I have a unique ability to see how any process can be more efficient. If you’re a parent and have seen any of the Lego movies, I’m like a master builder. I can’t turn it off. It’s a blessing for my business but a curse for my family. My sons roll their eyes every time we go into a store with a long line — not because of the wait but because they know I’m going to start rattling off all the ways it could be shorter.

BZ: How do you define success for the next 12–18 months for your business?
KS: Successfully onboarding hundreds of care agencies onto the Sitter Pro platform.

BZ: What lesson(s) do you take from this experience that you would convey to other founders/CEOs?
KS: As a founder/CEO, you’ll get advice from so many different sources as to how to run your business — from family, friends, colleagues, books, etc. The reason there are so many opinions is that there is no one way to be successful. Listen to it to get perspective and ideas but don’t take any of it verbatim. Only you know the business you want to build and the leader you want to be.

BZ: What piece of advice has been the most valuable to you for this experience?
KS: My entire life, I’ve been somewhat of a perfectionist. If I made a mistake, I would dwell on it and rerun it over and over in my mind. My business coach, TC North, has helped me overcome this. He was a sports psychologist for a long time so he has lots of analogies from the world of sports but there’s one that I use all the time. When Peyton Manning goes out there on the football field, he might throw an incomplete pass or interception. But, he can’t sit there and analyze everything he did wrong otherwise he’d surely miss the next pass and the one after that. He’s got to get his head back in the game quickly so the next pass can be a touchdown.

BZ: What do you currently need help with?
KS: We need help getting the word out to nanny agencies, pet sitters, tutoring businesses, and companion/senior care agencies that we’re here and ready to help them help others. If you know anyone who owns one of these types of businesses or you use one of these types of businesses, please send them our way so we can see if we can help them.

BZ: How will you pay it forward once you’ve accomplished your goals as a Founder?
KS: I think the best way to pay it forward is to be honest with other founders about your true experience. If you ask the majority of founders in this world how things are going, they’ll tell you everything is fabulous even if their world is crashing down around them. The reality is that this is a very hard job that affects you mentally and physically. Things can be going wonderfully one minute and crash the next. It’s a roller-coaster ride that we happily got on. We get great thrills from it but we get great anxiety as well. The anxiety is compounded if you think everyone else is having a grand ol’ time except you. I’m committed now, and in the future, to being 100% honest about my experience so others know they’re not alone.

Many thanks to Kristen for taking time to respond to my questions. You can connect with Kristen via LinkedIn. And as Kristen requested, please help spread the word about Sitter Pro!