Google will begin advertising its Google Apps and Gmail for businesses on billboards in major cities. Google Enterprise, the wing of Google that sells Gmail and Google Apps to businesses, has faced some fundamental challenges in competing with Microsoft. One is that Microsoft Office is perhaps the most recognized piece of enterprise software in the world. And secondly, while so many people use Google search and Gmail, probably only a fraction know those tools are available for business use.Today, Google took a step towards rectifying that problem, releasing billboard advertisements in New York, San Francisco, Chicago and Boston. The messages on the billboards will change, citing common frustrations people have with on-premise, installed software the requires frequent IT maintenance, time and help. The company hopes that it will encourage more companies into “going Google,” its marketing term for organizations that switch from traditional IT systems (think: Exchange, Office and Lotus Notes) to Google products (see: Gmail).Next time I drive up 101 here in San Francisco, I’ll be interested to see what messages they flash up there. Marketing enterprise software and services in mainstream areas is difficult. IBM’s TV ads that focus on innovation and collaboration give you absolutely no clue as to what the company does. Oracle and SAP ads must go unnoticed to 99 percent of the people who pass them at airports. Others just don’t even get noticed at all, even by people who write about the stuff for a living. SUBSCRIBE TO OUR NEWSLETTER From our editors straight to your inbox Get started by entering your email address below. Please enter a valid email address Subscribe Often, Google’s consumer roots has been its barrier to selling software: Stodgy CIOs wrongly deem it not fit for enterprise use. But by reaching the same consumers who use Google products like Gmail, perhaps they will begin asking their CIOs and IT administrators questions when they get to work that will force the issue. What kinds of questions? We know them well. Why can’t I find an e-mail when I search for it? Why do I have to run all these clunky desktop apps when I can just do this on the Web? Why do I have these eight installed applications, when I only use two of them?One foreseeable problem: It seems easy to see a billboard like this, drive to work, and forget about it.As a result, it might be more effective for Google to capture people’s attention while they’re at work, when the annoyances caused by their IT troubles are front and center. While you must respect the fact Google keeps the Gmail homepage for consumers clean and pretty much free from ads, it should consider pushing its business products a little harder there. Right now, you see pitches for Google products under the inbox (at the bottom, above the message that tells you how much storage space you have left), but they’re hard to notice. The “invite to Gmail” box seems like wasted real-estate as well, especially since consumer Gmail hasn’t run on an invite-only model in years. In its place, Google could run some not-so-subtle slogans.Maybe something like:“Attention 95 percent of businesses. Tired of filing helpdesk requests and three year old software? It doesn’t have to be this way.” Related content opinion Yahoo CEO Uses GIF, Tumblr to Announce Acquisition Marissa Mayer bets a billion dollars on the blogging site, vowing Yahoo won't 'screw it up.' By Kristin Burnham May 20, 2013 2 mins Consumer Electronics opinion Funny Facebook Video Spoof Personifies User Frustration What if Facebook was a person who rearranged the contents of your home while you were away? That's the premise of a new video spoofing the social network and the changes it makes, often to your dismay. By Kristin Burnham May 13, 2013 1 min Facebook Social Networking Apps opinion 6 Spectacular Google Glass Video Spoofs Want to know what John Stewart, Steven Colbert and Conan O'Brien think of Google's augmented-reality glasses? Take a look at these six hilarious Google Glass spoofs and parodies. By Kristin Burnham May 10, 2013 1 min Internet opinion YouTube Maps Most-Watched Videos Across the U.S. Which videos are on the verge of viral? YouTube's newest tool displays the top trending videos in the U.S. by age, gender, views and shares. By Kristin Burnham May 07, 2013 2 mins Consumer Electronics Podcasts Videos Resources Events SUBSCRIBE TO OUR NEWSLETTER From our editors straight to your inbox Get started by entering your email address below. Please enter a valid email address Subscribe