Karen Appleton, Queen of the Cloud - OZY | A Modern Media Company

Karen Appleton, Queen of the Cloud

Karen Appleton, Queen of the Cloud

By Sanjena Sathian


Because solving something as simple as office workflow can actually make a huge difference.

By Sanjena Sathian

It’s a Friday-morning brunch at San Francisco’s chic — and exclusive — social club the Battery. The crowd: power women (majority white) from entertainment, media and tech-tech-tech industries. Comedian Chelsea Handler is there. Re/code founder Kara Swisher. The Wrap founder Sharon Waxman. The British consul general.

Among all these strong personalities, one of the main instigators of the event, Karen Appleton, is relatively quiet. She perks up to introduce the brunch (“Oh my God, I can’t even tell you how excited I am!”) and when bidding begins on artwork, dinners and a Ferragamo handbag to support charity. During the panel with Handler, Swisher and others, though, Appleton is often talked over. Her mic doesn’t seem to work. She doesn’t exactly own her seat at the table.  

Appleton, though, might be one of the biggest people there. Or, she will be. She’s the senior vice president of global alliances at Box, one of the more prominent cloud and workplace “disruption” companies in the Valley — it IPO’d in January with a valuation of $1.7 billion — and the founder of its philanthropic arm, Box.org. That arm is trying to make some serious noise in the land of giving, a notoriously plodding and low-tech land, by offering all the work-flow technology that private sectors take for granted but most philanthropies can’t afford. I mean, have you ever met a nonprofit that wasn’t steep in technology circa 1988?

She’s a veritable “lean in” role model.

Lousy technology and work flow, while not all that sexy, can lead to a terrible waste of charitable funds. It’s an oft-overlooked weak point that Appleton has managed to vault into. Box hands out the technologies for free or at a steep discount, a move that not only feels good but is also good for her firm’s business, as it battles in a competitive sector. Indeed, many cloud companies, like Salesforce and Microsoft are doing as Box does, says Rick Cohen of the National Council of Nonprofits. For some, it’s even a competitive strategy to gain broader footing in the market.

But back to Appleton. A minute one-on-one with her leaves an entirely different impression than her brunch demeanor did. Dressed in a flared black dress and chic black shoes, with a gray shawl draped around her shoulders, Appleton is deeply elegant. Dirty-blond, well-coiffed, fast-talking, efficient. You can smell the competence. And the ambition. Appleton, 48, has had a varied career: A Baltimore native and graduate of Towson University with a master’s from Johns Hopkins, she worked for LexisNexis in Hawaii, logged time as a sales/marketer and headed up business development for Prosper, a peer-to-peer lending company. 

Karen Appleton

Karen Appleton is the senior vice president of global alliances at Box, a prominent cloud and workplace “disruption” company in Silicon Valley.

Source Rachel Tine for OZY

She’d never been an entrepreneur, and was an unlikely eighth employee for a team that, in 2007, consisted entirely of young, male engineers, who often went shoeless in the office. Appleton, on the other hand, was a divorced mother of two boys. “I came in in a dress and heels and they didn’t much know what to do with me,” she says. She was the first non-technical hire, which, combined with her maturity, meant instilling some order in the place. In case you missed the similarity: That’s almost exactly what Sheryl Sandberg’s start at Facebook looked like. Today, Appleton is a veritable “lean in” role model, making it to every one of her sons’ games and tearing up a bit as she tells me her 18-year-old is headed to Nepal on a gap year.

World Bank Chief Information Officer Stephanie von Friedeburg, who uses Box at a discount rate, says that three years ago the organization didn’t have a “defined policy” for file sharing or security; employees occasionally put confidential docs in Dropbox, which, von Friedeberg says, wasn’t secure enough. Now, though: She recalls her team having to lift out from Kabul on short notice, when, once upon a time, they’d have tried to grab a pile of servers out of the closet and go-go-go. Of course, the tech doesn’t always do its job. Like the World Bank, the International Rescue Commission works in remote areas; David Goodman, the organization’s CIO, says bandwidth has sometimes prevented his team from using Box to its full potential — a reminder that all the well-intentioned tech in the world can only do so much when it comes to inaccessible corners of the earth.

Sure, this all seems basic. But it’s how workplaces work, right? And, says Amy Sample Ward of the Nonprofit Technology Enterprise Network, it’s what nonprofits need to start doing: investing internally. There’s sometimes an ethos in nonprofits of promising that 100 percent of donations will go to XYZ cause — but that, Ward points out, means you’re donating to an organization that probably doesn’t take care of its systems or staff, which means it’s “not an effective organization that you should really feel comfortable donating to.”

Which is exactly the sort of down-to-earth statement you might expect from Appleton herself, and who tells me she was “never the homecoming queen, but always on the homecoming court.” So will the always-a-bridesmaid Appleton be a CEO one day? I ask Wendy Lea, the CEO of Cintrifuse, a startup-networking group that also invests in venture capital, and Appleton’s friend and mentor. She considers. Maybe of a small organization, high growth, full of thrills, Lea guesses. The thing about those, though, is that if they succeed, they end up on top of an empire. 


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