Mobile enterprise software is like strapping spreadsheets to carrier pigeons

By Michael Carney , written on January 30, 2013

From The News Desk

“In your personal life, social, mobile applications are beautiful, their functionality is meaningful, and they let you to make real, human connections,” Tomfoolery CEO Kakul Srivastava says. “At work, today’s mobile enterprise software makes us feel about as close to our coworkers as strapping spreadsheets to carrier pigeons."

Tomfoolery is a stealthy startup announcing its existence today, not to mention $1.7 million in Seed stage backing from some 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. The company was formed by veterans of the consumer Web and mobile space with a single lofty goal: Fix mobile enterprise software.

There’s little to judge Tomfoolery on at this stage other than the pedigree of its founding team and the endorsement of its investors. In addition to Srivastava, who is the former GM of Flickr and was VP at Yahoo, the company was co-founded by CPO and former VP of mobile at AOL and Rally Up,, and Sticky founder Sol Lipman.

It’s fairly trivial for these entrepreneurs to argue that mobile enterprise software could stand to be improved. It’s another matter entirely to do so effectively, and then successfully put that software in the hands of millions of the knowledge workers who so desperately need it. But that’s the mountain Tomfoolery looks to climb. The company’s credo has become, "Work awesome."

“People at work aren’t robots - they’re consumers who expect great software,” the CEO says. “We’re creating an entirely new kind of collaboration toolset, built from the ground up, for the modern worker.”

The founders quickly assembled a six person team and raised an oversubscribed seed round within weeks of initially meeting one another in October, and outlining their uncannily similar visions for the next generation of enterprise software. Additional members of the founding team include former Flickr head of back-end engineering and Yahoo senior search engineer Simon Batistoni, and former AOL senior technical director mobile first and CTO of Rallly Up Ethan Nagel.

While details are scarce at this early stage – because the team is deliberately making them so, not because they don’t know what they’re planning, I’m told – the message is “mobile first.” In a world where employees are increasingly bringing their own mobile devices into the workplace, and are rarely without them throughout the day, the founders are adamant that future communication and collaboration software must be built around mobile.

Srivastava and Lipman are correct in pointing out that none of today’s leading enterprise products were designed for a mobile environment first. Rather, whatever mobile products are available from the likes of Salesforce, Yammer, Asana, and company werecreated as an afterthought to a PC version, shoehorning existing features and paradigms into a smaller, often less functional mobile approximation.

What may seem trivial, actually has profound design and functionality impact on the final product. For example, it is easy to design desktop software that does not take advantage of sensors like GPS or a camera. Designing a product with a mobile-first mindset puts these resources at front of mind.

How often to team members across an office send email and chat messages, or make a phone call simply to ask a colleague a question like, “Where are you right now?” It’s equally common for someone to contact an administrator to ask about boardroom availability. A team communication and collaboration platform built for mobile first could easily incorporate passive location awareness, so that colleagues know when one another are in or out of the office, when a boardroom is free, and the answers to other trivial, but time-wasting questions. These are just a few examples of the kinds of ideas that Tomfoolery is exploring.

In the meantime, there remain more questions than answers.

Can a team of consumer product experts really develop first rate enterprise products? Ask Srivastava that question and she’ll say it’s precisely because her team hasn’t been brainwashed by years of making design and experience compromises to develop in the enterprise world that they can succeed.

Suttter Hill Managing Director and former Twitter software engineer Sam Pullara says he invested specifically due to the team’s unique perspective. “This is really greenfield territory,” he says. “Making mobile first enterprise software that allows employees to interact and communicate naturally, while defining their own culture is pretty fundamental.”

Even if they build it, distribution and monetization provide a whole new layer of unknowns. Can the company charge enterprise-grade price points for a mobile-first product? We don’t know, because it’s never been done before. While the Microsoft Office suite costs hundreds of dollars for a PC version, it has been widely speculated that once released, the mobile applications will be priced at $10 to $20. That’s a steep drop off. Srivastava is less worried about this question, arguing, correctly, that revenue comes in exchange for value created. Create enough value and the monetization will come.

It all sounds well and good, but talking points are easy to come by. We’ll all get a clearer idea of what the team has been working since October when the company launches its first app in late Q1.

Tomfoolery promises a world where workplace software is fun, creative, and productive. It sounds a lot like a utopia. But until they build it, it remains a lot of promises and conjecture. Now have to actually deliver.

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