OK, we admit that we’re being a bit sarcastic here, but we actually have enough information to present a pretty good case around Dropbox trying to buy its way into the Enterprise File Sync and Share (EFSS) market.

We won’t bore you with all of the details, but consider that last week Dropbox acquired Droptalk and that late yesterday MobileSpan announced that it had been acquired by Dropbox as well. 

Each of these purchases seems to be destined for the Dropbox for Business side of Drew Houston’s $10 billion startup and both of the technologies -- and the teams that come with the deals -- have the potential to help the massively popular, 300 million user (mostly) consumer file sharing service become more enterprise-worthy.

This is not to say that Dropbox for Business hasn’t come a long way, but it’s still far behind industry leaders like Box, EMC Syncplicity, IBM, Microsoft and others in the enterprise space.

Want proof? Last month Box announced that it had struck a deal with 300,000 employee GE while Dropbox for Business announced that it had won a deal with Spotify, which a LinkedIn search suggests has less than a few hundred employees. CrunchBase pegs the number of employees as much lower.

What Exactly is MobileSpan?

We could give you the Dropbox-doctored spin from MobileSpan’s site, but we found a better description on (former) CEO of MobileSpan, Sanjeev Radhakrishnan’s, LinkedIn profile:

MobileSpan’s File Sharing for the Uncloud feels like Dropbox to the end user but works directly off a company’s existing file shares or SharePoint. No changes to the DMZ, no VPN needed. It supports offline, and resyncs documents, handling conflicts.

The Uncloud, of course, is a company’s existing intranet -- your documents, systems, and permissions. It’s everything you already built up and manage for your company.

It takes just 60 seconds to setup on a Windows machine and it’s free forever for small teams.”

If it works as promised and can be delivered with Dropbox’s new UI (where users can access their personal and business documents via the same Dropbox app), then it could give reason for IT bosses to breathe a sigh of relief because a big part of their “Dropbox problem” (i.e., employees using Dropbox on the job despite it being against company rules) would finally be gone.

Workers would be able to use Dropbox out in the open. And the rebel-geeks who found workarounds for using Dropbox even where it was blocked could become its evangelists.

That’s how it might unfold in Camelot, anyways.

We tried to ask Ilya Fushman, who leads Dropbox for Business, if this was his vision. While he did reply to our email, all he shared with us was that he was extremely excited about the MobileSpan acquisition. He also suggested that we get the details from MobileSpan’s website.

What Does MobileSpan Bring to Dropbox?

There was one particular sentence that we found interesting in the announcement (and trust us, every word in the post was carefully selected, reviewed and reviewed again, by marketers, lawyers and probably Houston himself):

Yet we still have some ways to go before business content is freed from its desktop-focused roots and is made readily usable yet secure on modern mobile devices.”

Decoded, we suspect that Dropbox might be saying something like, “Hey CIO, maybe you’re right and we’re not as enterprise-worthy as you’d like us to be at the moment, but, until we’re there, we have this MobileSpan technology that will meet all of your requirements and your employees are going to love it because it works just like Dropbox on the front-end and it even has our name on it.”

And if the Engineering teams from MobileSpan and Dropbox can work together well enough and fast enough, then the next group of Dropbox for Business users who use the mobile app won’t even have to think about where their documents reside, be they in SharePoint, a file share or in the cloud.

We should clarify that this is what we believe could happen, no one from Dropbox or MobileSpan has told us that this is their exact plan.

There’s a Prize Inside

Though we don’t have a list of MobileSpan’s enterprise customers, we suspect that they employ as many people, or more, as Spotify, Dropbox’s most recently announced business win.

And these customers will, no doubt, be the references and revenue generators that Dropbox for Business needs now.

What Does the Industry Think?

We reached out to a few EFFS experts to see what they thought of Dropbox’s latest acquisition and whether they thought the MobileSpan buy meant that Dropbox would soon provide on premises capabilities?

Yes, said EMC Syncplicity General Manager Jeetu Patel:

This is absolutely a validation of our 'no silos' strategy which recognizes that enterprises have millions invested in existing storage solutions and want a way to give users mobile access to that content without having to migrate it first. That said, this is actually not the same as providing on premises storage for EFSS, which is a critical requirement for enterprises that want to EFSS functionality at scale, and much harder to build architecturally. That is why we always make it clear that our enterprise customers can have on premises storage with full EFSS functionality and not have to compromise end user functionality as well as access existing on premises repositories."

Vineet Jain, CEO of Egnyte put it this way:

This acquisition is an acknowledgment from Dropbox that not everything is going to move to the cloud. Enterprises will continue to live in a duo-polar world where some content is readily available through the cloud, but a significant percentage will not leave the firewall perimeter of the enterprise. This is the hybrid world that Egnyte has been focused on -- building from the cloud down."

Aaron Levie from Box wouldn’t speculate. He led us to believe that he doesn’t think about what’s going on in Drew Houston or Ilya Fushman’s minds. Really? In any case, we do know of at least one cool thing Levie thinks about. We’ll share that in the next few days.

Alan Pelz-Sharpe of 451 Research said that adding on premises capabilities would be a huge change for Dropbox.

The challenge would not be so much technical (that would be quite easy) but it would also impact their entire sales and support structure,” he said. “Will they do it, in time maybe -- but I have long thought that Dropbox should be targeting SMB/SME’s where this is less of an issue -- rather than large ’true’ enterprises that have extreme complexity and support demands.”

We made a similar suggestion to Dropbox.

Circling Back

So do we think that Dropbox can buy its way into the enterprise? Three or four years ago, with acquisitions like MobileSpan and Droptalk, our answer would have been an easy yes.

But now, with file storage becoming commoditized, with Dropbox’s still incomplete set of enterprise features and with its strong branding as a consumer-facing solution, it's still a question, despite its cash and its 300 million users.

What Dropbox for Business needs now is not just an enterprise-grade offering (which it may very well be able to build), but also a marketing team that can figure out how to win the hearts and change the minds of CIOs who see Dropbox as a problem and have been fighting against it.

An Aaron Levie or Jeetu Patel-like evangelist would go a long way, but even the best headhunter might have difficulty luring them away from their current gigs. The chosen water-walker would have to be skillful enough to get CNBC and Bloomberg TV reporters to think Business and not Carousel or photo sharing when they hear the word Dropbox.

A sales team made up of account execs with deep, trusted relationships with the C-Suite would go a long way as well.

And, perhaps, most importantly, Fushman and his team need to wear blinders so that they aren’t distracted by Dropbox, which is undeniably a huge success.

If anyone knows the formula for growing fast in a shadow, you should pitch it to Dropbox. That’s what Houston needs to buy next.

Title image by Peshkova (Shutterstock)