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Brill Street is proud to present its annual ranking of the 50 most Gen-Y friendly companies in the Chicagoland area.

#48 Cheeky Chicago

For Gen Y, having just any "job" isn't going to do. Gen Y wants to take pride in their work, feel good about what they do, and have a little fun doing it. CheekyChicago.com, which describes itself as "a woman's guide to the city," was founded by two of these types of gals, and the women who work for them are finding exactly what they want in their work life.

"We live a pretty fabulous life and that's because of the backbone of what we do, which is experiencing Chicago and writing about it."

"We look for people who represent the Cheeky brand," says Co-Founder Jessica Zweig. "You have to be down to earth and in tune with what's going on in Chicago. I look for people that are really cool, accessible, and approachable. We try to communicate a community where everyone feels important. And we don't discriminate against men, but we're all girls."

The reason for the female emphasis? "We really found that their was a void in the marketplace for a female centric website," Zweig says. "There was nothing out there for a young cosmopolitan girl in the city. We did it for ourselves and it's really resonated with a lot of women." Zweig adds that it's not just Chicago that needs her company's services. She has expansion plans for other cities, branching into New York and Los Angeles--which will provide more opportunities for Cheeky employees.

The pace is fast at Cheeky, and with an office of only eight, the work--while fun--is intense. New articles are published every day, and the calendar feature refreshes once a week. Because of this, utilizing social media is highly important to the company. "We rely on it," says Zweig.

And the city of Chicago is beginning to rely on Cheeky's service, too. If you work for Cheeky, you can dine for a discount. "The restaurant industry embraces us," says Zweig. "We claim to be what we are: real girls living in the city and interested in nightlife. We get a lot of concert and theatre tickets for free. We live a pretty fabulous life and that's because of the backbone of what we do, which is experiencing Chicago and writing about it. We get the hook up wherever we go."

The founders say they want Cheeky to be a national brand, for women to travel from city to city and view it as a strong resource. Gen Y is critical to that vision--in fact, 99% of the company is Gen Y already. "It's my dream come true," says Zweig. Cheeky, indeed.

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The Particulars

  • Industry: Entertainment
  • Location: Anywhere!
  • Office size: 1 - 49 Employees
  • Website: Cheeky Chicago

Fun Fact

"We have people that work for us that say it's the best thing in their life," Zweig says.

You Want to Work Here Because:

  • Remote working options.
  • Choose your own hours.
  • Contest incentives.
  • The "hook up" on discounts, concert and theater tickets, and more.