From the May 2012 issue of Entrepreneur
Based in San Francisco
Five employees
2,500 babysitters registered
2,000 bookings per month

What It Is
UrbanSitter uses Facebook Connect to access, with permission, the networks of parents and sitters and bring the two together. It trawls contacts, groups and "likes" for sitters known through friends. When a parent needs help on date night, the service spits out a list of possibilities. Parents can review rates, schedule interviews, conduct background checks and book the sitter--all online. Like the restaurant reservation service Open-Table, the parent is notified immediately after the sitter accepts the gig.

How It Started
In November 2010, Lynn Perkins, who has twin boys, had had enough. Why was it, she wondered, that she could book an online restaurant reservation in minutes, yet had to spend hours calling and e-mailing around to find a babysitter? Armed with an idea and her background running online clothing retailer Xuny.com, Perkins turned to Facebook to solve the problem. She wrangled three friends to help her figure it out: Daisy Downs, an interactive media producer at ad agency Goodby, Silverstein and Partners; Andrea Barrett, a product manager at travel site TripIt; and Hadar Wissotzky, CEO of interactive digital agency Streamline Social.

Why It Took Off
UrbanSitter's success is built on trust. Parents looking for help can see which sitters their friends have booked and reviewed. "That goes a long way toward easing a parent's mind when hiring someone new to take care of their children," Perkins says.

Within six months of its September 2011 launch, UrbanSitter expanded beyond its Bay Area roots to New York City, Chicago, Denver, Seattle, St. Louis and the Lake Tahoe/Reno, Nev., area.

The Business Case
UrbanSitter began as a free service, but plans are in the works to start charging parents a small processing fee to pay sitters online. That feature was one of the most frequent requests from sitters who wanted to eliminate the mutually awkward "How much do I owe you?" moment at the end of a job.

What's Next
UrbanSitter has $1.75 million in venture capital and angel investments. Beyond using the cash for expansion to new cities, the team is considering repeating its model for other in-home service providers, such as tutors and pet-sitters.