Shop It to Me Gets New Look, Back Engine and Soon Expands to New Categories

I’ve long been a fan of Shop It to Me, a site that was early to the personalized shopping and promotion wave when it started back in 2004. It was a beautifully simple idea: Email newsletters that let you know when your favorite brands in your size were on sale. After some-six years of quietly building a business, Shop It To Me is finally invested in a new front end, back end and new retail categories. The users will start seeing changes today.

This is a site that execution-wise got everything right, which is why it has out-grown and out-lasted a few dozen companies that have had a near-identical approach. First off, it has great inventory—all the biggest designers and department stores. The site allows you to enter your size info on a brand-by-brand basis, recognizing that we all wear different sizes for different designers. The email newsletters contain all the information you want, you only click through if you have an intent to purchase. That means there’s no bait-and-switch or overly goosed click-through rates for retailers.

You can even set how many times and what day you want to get the newsletters,and set whether you only way to see items that are, say 50% off or more.

A lot of Web sites either don’t solve a big problem (ie, Plurk, Friendfeed in a post-Twitter world) or solve a problem in a far too complex, over-featured way. Shop It to Me fell into neither trap. It sought the simplest solution to solving the tricky problem of apparel discovery that the first generation comparison shopping sites like never came close to solving. It’s comparable to Kayak, only better because Kayak was replacing the pain of going to four or five sites to find the best deal—Shop It To Me replaces the need for going to hundreds of sites.

The site has 3 million subscribers, which puts it the range of peers like DailyCandy, Groupon and others. It has only raised one round of funding and won’t say how much, but this is a lean company with less than 20 employees. It doesn’t hold any inventory or a large salesforce, which is one reason it has been so quiet—the only barriers to entry are size, scale and execution. I read it religiously twice a week and must have bought hundreds of items at huge discounts of the past two years.

But while Groupon and Gilt have been getting loads of press for novel demand generation sites, Shop It To Me has been pretty quiet. Its product has been featured on the Today Show and InStyle but not so much on sites like TechCrunch, where let’s face it, the core audience isn’t exactly teaming with stylish women. That will start to change this week as the company rolls out the first of a series of changes that will take it from an in-the-know tool for stylistas to—it hopes—more of an ecommerce powerhouse ala Zappos. Today, it is launching a more modern and less-femme redesign, within six months a new back end will allow it to make better personal recommendations, and by the end of the year, it will be in at least one more new category—possibly housewares or even travel, says the founder Charlie Graham.

The curation aspect will be tricky. What’s made Shop It To Me so great is that you say exactly what you want and you get it. The problem is too much of a good thing. The site offers up some two billion recommendations over email per month. During the recession the site got more stores on board and more sale inventory and users who loved the service, just didn’t have the time to go through the pretty lengthy emails. People need a five-minute solution, Graham says.

There is a risk here the site veers off track by trying to be something more than it is now. Can the purchases of other women who also like Diane Von Furstenberg dresses and Tori Burch shoes really help inform what other brands I may like best? I’m dubious. But Graham says the site isn’t straying from the approach of individually personalizing each newsletter, and after all, it only makes money when we click or buy, depending on the contract. If the changes don’t result in more purchases, they won’t last. Whether you’ve heard of it before or not, this is a site big enough it has something to lose at this point.

My biggest problem with the site is still unsolved. While Shop It To Me compresses demand generation into an easy, consolidated experience, buying items still require you to go to each individual site, each requiring its own separate checkout process, user names and passwords. That is a huge friction point. It’s a hard problem to solve since most retailers want to own the customer relationship, but Graham assures me they are working on a solution. The ideal would be some sort of one-click “ShopItToMe NOW!” purchase button, ala the Digg or ReTweet buttons. But nothing like that is in the offing anytime soon.