Groupon digs in Chicago heels

The daily deal giant partners with ChicagoShopping.com, reaffirming its Chicago roots

Groupon has long defied tech startup logic, not only in its most recent snub of Google’s rumored $6 billion buyout offer, but also in the company’s resistance to relocating to the Silicon Valley.  Now Groupon is bolstering its Chicago roots by partnering with ChicagoShopping.com to spread the reach of its daily deals for local Chicago businesses.

ChicagoShopping.com is the recently launched local-shopping arm of the Chicago Tribune Media Group, which publishes the Pulitzer Prize-winning Chicago Tribune.  Under the terms of the deal, ChicagoShopping.com will feature a new local deal on its website every weekday, and what makes the deals unique is that while they come from Groupon, they will be exclusive to ChicagoShopping.com.  And the partnership has been sealed just in time for holiday shopping.

So how does this pay off for Groupon?  Users who frequent ChicagoShopping.com and register with the site will now be able to sign up to receive both the Groupon-powered daily deal offered through ChicagoShopping.com, as well as the standard daily deal offered on Groupon’s website.  So, essentially, the partnership translates to Groupon offering two deals a day instead of one.

“If you like Groupon deals, you’ll now like them twice as much,” said Belinda Englman, GM of ChicagoShopping.com, in a prepared statement.

The Chicago Tribune Media-owned company allows users to personalize their shopping experience by identifying their favorite brands and stores so that their daily deals are customized.  The site also offers editorial content related to shopping, including tips and advice.

“We’re excited to offer something special to users of ChicagoShopping.com just in time for the holidays,” said Sean Smyth, Groupon’s VP of business development, in a prepared statement.  Groupon could not be reached for comment.

Groupon founder and CEO Andrew Mason has attributed much of Groupon’s success to its Chicago roots.  “I kind of think about starting a business in Chicago as similar to recording music on a 4-track before I could do it on a computer,” said Mason at the DEMO conference in September.  In other words: “I think it’s good to operate within constraints.” 

Mason developed Groupon on top of his earlier Chicago-based startup, The Point, a collective-giving platform that failed to spread its wings and fly. 

While Groupon maintains its headquarters in Chicago (and evidently hires some 70% of its customer service representatives from the local Chicago theater scene, many of whom use their professional headshots as their Groupon team-member photos), the company recently set up an office in Silicon Valley when it acquired Mob.ly in May 2010.