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Kristen Stiles' Sitter.me emerged from family inspiration

Tech startup Sitter helps parents find, book and pay babysitters in the new economy





Kristen Stiles worked in IT and business strategy at Hewlett-Packard and other companies. She co-founded the technology company Sitter with Matt Stueve, a software developer with whom she had worked for a decade. 


Sitter is an app that helps parents find, book and pay babysitters, and helps babysitters manage their jobs. Instead of calling or texting their favorite sitter, waiting for a response, then trying their second favorite, parents send a booking request to sitters on their contact list, and a sitter can respond by text. The app features profiles of the sitters, a timer to track hours worked and handles electronic payments.


Stiles was inspired by her own challenges when she and her husband, Dan Stiles, who handles operations for Sitter.me, would try to find child care. Her mother, who was divorced, also inspired her, having raised Stiles and her two siblings alone.

“I watched her work so hard to support our family. She just retired but she ended up being a CFO, so she was an inspiration on the business side,” – KRISTEN STILES


Sitter has four employees who work remotely and meet weekly. Stiles says flexibility helps make people more productive. The setup will change, temporarily, as the company was accepted into Techstars Boulder, a three-month accelerator program that includes investment, mentorship and office space.


The most important workplace trend, Stiles says, is conscious leadership and mindfulness. It includes, among other concepts, an emphasis on work/life balance. 

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Nora Caley

Nora Caley is a freelance writer specializing in business and food topics.

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