Watercooler

It’s very common these days to hear talk of the consumerization of enterprise software. But in most cases, this phrase is simply an indication that software has been designed with an attractive and intuitive user interface, typical of that found in consumer software. Tomfoolery, a one year old, stealthy, mobile-focused startup, is taking this concept a level further by bringing fun and true social interaction into its enterprise productivity products. Today, the company whose credo is “Work Awesome,” is releasing its first product, Anchor.

Anchor is an intimate social communication and collaboration platform that is reminiscent of Path, but for the workplace. The app will challenge (but more likely augment) Yammer, Asana, and the like by taking communication away from to do lists and document sharing and instead focusing on fostering team cohesion, and intimate conversation. Anchor aims to be the digital water cooler or break room, a place that workers share their weekend adventures and pictures of their kids, make plans for lunch and after work drinks, and organize athletic activities. The app is highly visual and supports sharing links, pictures, articles, locations, videos and other content into company-wide or team specific feed. And if a document or two gets reviewed along the way, all the better.

“Our customer is the end user, not the enterprise,” says Tomfoolery co-founder and CEO Kakul Srivastava. “Which is why we held off on integrating with Sharepoint or focusing on calendars and task management. We hade some of these features built into early versions, but we found that they resonated far less than one-on-one and small group communication, which was truly habit-forming.”

The concept behind Anchor is simple. Co-workers do this type of sharing already but they have no natural destination for doing so. Email and existing enterprise communication tools are ill-suited for it, while Facebook, Path, Twitter and other general social platforms are too public. The Anchor app constructs macro-teams based on company email addresses, but users can create multiple purpose-driven teams with select invitees from within or outside their company. All content and conversations can be filtered according to team, and a user’s main feed is color coded according to these groups. The app also supports one-on-one or group chat, and offers a directory feature for one click chat, email, or phone calling.

“We believe that the core molecular structure of any organization, regardless of its size, is the team or working group,” Srivastava says. “If you look at the social enterprise space as a whole, the rhetoric is about productivity and tasks. But the relative portion of time spent managing time or co-authoring documents is minimal. Most of the time users are actually getting stuff done, communicating, and getting or giving feedback. Anchor is built to facilitate this working reality.”

At launch, Anchor is available on iOS and, although it considers itself a mobile-first company, concedes to the realities of office life with a full-featured Web app. The company promises Android and Google Glass versions in the very near future. Anchor is free to use today but will likely follow a Yammer-like freemium model in the future, offering premium features and support priced on a monthly subscription basis. The company set September 25, co-founder Sol Lipman’s birthday, as the cutoff point for free-for-life activations. Anchor will eventually serve as a central platform for a suite of mobile enterprise apps that Tomfoolery has planned and for those that third-parties build on its APIs and mobile SDK.

Tomfoolery was founded by veterans of the consumer Web and mobile space, including those leading Flickr and AOL Mobile, with a single lofty goal: Fix mobile enterprise software. The vision was compelling enough to raise $1.7 million in November, pre-product, from top Silicon Valley names like Andreessen Horowitz*, Morado Ventures, Sutter Hill Ventures, Jerry Yang’s AME Cloud Ventures, David Tisch, and YouSendIt CEO Brad Garlinghouse.

Enterprise workers are likely to gravitate toward Anchor and the product could easily go viral within an organization. The challenge for the company will be to make a business case to their employers to eventually pay for the product and incorporate it into their company workflow. The concept of fostering team happiness and cohesion is not a new one. Companies spend millions of dollars on team retreats, holiday parties, in-office massages and catered lunches, billiard tables, and the like. But despite all this, Anchor may be viewed as too frivolous, especially in an environment that may have already blocked users from checking Facebook on company time.

“Work doesn’t have to feel tough, or hard, or serious,” the company writes on its website. “In the best teams, work is awesome, it’s something fun, and creative — and you can’t wait to get started when you wake up in the morning.”

Tomfoolery sets itself apart in the enterprise market with a focus on fun, play and team culture. It’s an ethos that is sorely lacking in the market and will likely win it a number of avid supporters. Whether it can be translated into a scalable business will be the company’s primary challenge.

(*Andreessen Horowitz partners Marc Andreessen, Jeff Jordan, and Chris Dixon are individual investors in PandoDaily.)