Can the E-mailman Deliver?

Ron Wiener wants to open your mail. He doesn’t want to read it, but he’ll scan it, track it, forward it—even shred it if you ask him to.

As CEO of Seattle-based Earth Class Mail, Wiener has a vision to drag the world’s postal services into the 21st century by digitizing them. Trying to transform such an established, complex system—the oft-ridiculed “snail mail” of the U.S. Postal Service (USPS)—may seem like a Herculean task, but Wiener has a way of winning people over.

Just ask Rajeev Dujari.

In October 2006, Dujari, a 15-year Microsoft veteran, attended a Keiretsu Forum angel investment presentation from Wiener about an early version of Earth Class Mail, then called Document Command.

“Before I heard him speak, I thought it would be the most uninteresting presentation in the bunch, honestly,” Dujari now admits. “I thought the postal industry was a dull subject.”

But as Wiener spoke, Dujari became intrigued with the business model: For a fee, postal mail is sent to a facility, where it is scanned, digitized and sent electronically.

A little more than a year later, Dujari joined the company, serving as senior vice president, products. “It took Ron a little while to persuade me to sign up,” he adds. “But I liked the sheer audacity and boldness of his vision. At Microsoft, I got hooked on doing things with big impact, and it seemed like there were so many ways to take [Wiener’s] technology.”

In January 2008, Earth Class Mail completed a Series A financing round worth $13.3 million, most of which came from members of the Keiretsu angel network. Wiener’s board now includes chairman Chris Kwak of 2K Advisors LLC, Jonathan Roberts and Robert Headley of Ignition Partners, and document-scanning whiz Kenn Dahl of Prime Recognition Corp.; his board advisor is Ken Lynn, former assistant postmaster general of the USPS.

How did a serial entrepreneur, who’s had only mixed success with five other venture-backed startups, convince this high-powered lineup to take on the mighty postal service?

“This is one of the most potentially life-changing companies I’ve seen,” says M. Todd Dean, president of Keiretsu Forum’s Northwest chapter. “Ron is an excellent communicator. He is able to present very effectively to his investors.”

If anyone can take on one of the world’s biggest bureaucracies, the supremely confident Wiener thinks he’s the guy to do it. He seems to enjoy the spotlight.