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CitySquares is a Boston based startup whose web application is devoted to hyper local search and discovery. Now before you write off the company with your “these guys can never win, they’re in the same space as Google” thinking, hear me out. Hyper local matters, and we’ve yet to see a real winner in the space – something CitySquares is trying to do.

The coolest feature that I’ve seen from CitySquares is the ability to simply start my search process by entering in the neighborhood I was searching in, instead of the restaurant name and type. I knew I was going to be in Union Square, Somerville MA, and was wondering what sort of restaurants I had to choose from.

CitySquares has broken out cities by the local neighborhood names that people constantly refer to (i.e. ‘Nob Hill‘ in San Francisco or ‘West Village‘ in NYC) – which is a very cool feature in itself.  You can enter in your neighborhood and then begin refining your search form there (by type of business, then category).  The neighborhood breakdown feature is so intuitive, and also really fun and interesting to play around with and jump form one neighborhood to another.

The notion of hyper local goes way beyond just search too. This hit home for me within the CitySquares app when I brought up the page for Union Square, Somerville, MA (a square rather close to my house).  Not only was there a map present with featured businesses (apparently based on votes that users can place for certain spots), but there was host of other Union Square content that was helpful and relevant.  This content included coupons to neighborhood businesses (one of which I printed out right away), video demos from local businesses (a chiropractic firm) and hyper local ads – something that could provide CitySquares with their most lucrative feature of all.

Hyper local ads provide businesses with the opportunity to target consumers within their local markets – there are also immense opportunities around the idea of providing coupons and locally targeted video advertising.

CitySquares needs to get a little better in terms of their interface however.  I would love to see the site focus more on the neighborhood centric approach and less about simply searching for businesses (something Google does very well).  Perhaps enabling the user to jump more easily from neighborhood to neighborhood would be a help (keep the city map up at all times).  Another potential issue that CitySquares faces is the way that businesses are entered into the system (via the actual business owners).  It would be nice if City Squares could somehow aggregate this information into their system…something they’ve thought of already I’m sure.

I do believe that CitySquares has happened upon a great spot in the market though.  An advantage they have is that as their service grows and their users increase, so will the number of businesses and reviews – and slowly the overall value of the site (like Yelp).  The company is based in Boston and has raised two rounds of funding from Mark Cuban and Jonathan Kraft and the eCoast Angel Network.  Here’s some screen shots and whatnot:  Check them out!