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Easy File Sharing Apps Make Life for Sales Reps Hard

Cloud computing and file sharing

First, I need to make a few disclaimers before you read this post regarding easy file sharing apps:

  1. We use file sharing apps like Dropbox and Box all the time… to transfer files.
  2. Most of our clients use file sharing apps… to transfer files.
  3. I have nothing against an easy file sharing app as a BUSINESS APP or TOOL.

So let’s get to it…

The majority of the articles we write are extremely positive and aimed at teaching companies how to get business mobility right; however today I need to take a stand and relay the other side of the equation for our readers.

Most sales managers that deploy iPads or other tablets will try to use file sharing apps, like Dropbox, or extensions of content management systems, like SharePoint or, as a sales tool on the device.

The advantages of using a free file sharing app or a ‘dressed up’ file sharing app are:

  • They are either free or cost nominal amounts to deploy
  • They utilize web-based systems to keep update versions of the files
  • The people on your team are likely already familiar with desktop versions of these systems

More than four million businesses use Dropbox, including 97 percent of Fortune 500 companies, see major advantages to using the file sharing service.

I can guarantee you hardly any of those Fortune 500 companies are using it as a sales engagement tool.


I get it.


Companies that write code for file sharing services need to market their apps and “sales enablement tools” are easy to market.

But I actually see these file sharing apps as disabling your mobile sales process.

Here’s why…

Lost in Moment of the Big Meeting

Have you ever been on sales calls and were unable to find the PDF or video or pricing you needing?

Gut wrenching.


Making excuses.

Crap! We’ve all been there and felt that.

It is much worse when you are fumbling around with a tablet.

Like you’re trying to show a new friend a picture of your dog on your phone and they couldn’t care less. You just feel a little silly.

This happens with file sharing apps far too often.

Research from Aberdeen Group discovered 92 percent of organizations say producing high-quality sales collateral is valuable, but just over half (54 percent) execute it effectively.


Because with most of them, files have to be manually downloaded or synced to the device. And most reps just won’t do it consistently enough. They’re too busy!

If this happens once, I can promise you they will never use the tablet again unless they are techies and super comfortable with experimenting.

Does that sound like your sales team?

Not My Fault

Another instance where file sharing apps fall short as a sales engagement tool are in regards to analytics.

So if you want to see if your reps are using that new product video marketing created and added to your Dropbox, you’ll just have to take the word of your reps and not have the hard data to prove it.

Enterprise mobile sales apps come with built-in analytics for tracking, integration to existing systems like, and branding to personalize the app on the tablet.

Many free file sharing apps do not have these capabilities, or if they do it is very limited.

I’m not knocking file sharing apps as great business tools. We use them all the time. But only to share files.

Out in the field, there’s just too many risks with file sharing apps.

Are you going to put your reps at risk?

About J. Rusty Bishop, PhD

I've spent the last 5 years helping great brands create amazing experiences for their sales teams during one on one sales interactions. Helping sales people do their job is my passion. When I'm not working, I am on the ocean fishing in San Diego, Ca.