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Cheeky is perks, access and VIP treatment for 50,000 women who belong to our exclusive club. Cheeky makes social networking social.

  • Stage $500K in TTM Revenue
  • Industry Lifestyle
  • Location Chicago, IL, USA
  • Currency USD
  • Founded October 2008
  • Employees 3
  • Website

Company Summary

Speaking to a niche demographic of cosmopolitan & affluent women, we provide a 360º social experience unlike any other that enhances her lifestyle. Our online magazine serves as the ultimate resource for all the hottest goings-on in the city, our exclusive social events bring together this elite online community into the real world & the “Cheeky Card,” our loyalty program, provides access to perks & VIP treatment at the city’s swankiest spots.


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    Jessica E Zweig
    Director of Sales & Marketing

    Jessica is in charge of facilitating new sales leads, managing existing advertising campaigns, customizing sponsorship packages, writing proposals, closing sales & building long term client relationships with national brands. She leads the planning, marketing, branding & promotions behind all of CheekyChicago’s monthly events. She writes content for all sections & oversees the creative direction and strategy for Cheeky’s social media efforts.

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    Erica Bethe Levin

    Erica is responsible for managing & editing all content for Cheeky. She hires all freelancers, oversees an editorial staff of 30+ & edits 35+ articles a week, plus marketing materials, press releases, newsletters & ad campaigns. Under her watch, the site evolved from a city guide to a fully-realized lifestyle magazine. She spearheads all PR efforts, HR & bookkeeping, maintains client relationships, writes content & manages Cheeky's interns.

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    Joran Thompson
    Creative Director

    Joran is the Cheeky Card evangelist. She oversees CheekyChicago's unique loyalty program by prospecting potential clients, curating enticing partners and perks, and managing all Cheeky Card member, merchant, and partnership relations as well as relevant marketing and promotional efforts. She writes the member exclusive newsletter and editorial content, and is supervising and streamlining the research and planning for the Cheeky Card mobile app.


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    Jim Jerue, Horwood, Marcus & Berk
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    Jim Clarke, Jim Clarke CPA

Previous Investors

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    Friends & Family. Cap Table available upon request.