A Strongly-Worded Article About Dropbox's Upsell Emails
Photo by Sara Kurfeß on Unsplash
Quick note: This article is not meant to throw shade at the writer who wrote these emails. I have written a lot of bad copy in my day. So this article is a commentary on the copy not the person. Cool? Cool. Let’s proceed.
A few weeks ago, I begrudgingly signed up for Dropbox.
It wasn't my own choice. My hand was forced. A client I was working with would basically only use Dropbox…
So I signed up in order to help out with the project.
Now, I'm all for a little self-sacrifice for the greater good every now and then. But holy fucking shit…
Why would you ever use Dropbox?
Okay, maybe if you're a photographer or graphic designer and Dropbox is more friendly to those types of files. I get that. I absolve you of your sins.
But for literally any other reason — WHY?
Using Dropbox just seems silly to me in a world where Google Docs exists.
"Oh sure, Susan. Let's upload 67 versions of the same Word document. That sounds SOOO much more logical than doing a Google Doc where we can collaborate and make edits in REAL TIME!!!"
Okay, collaboration aside, there's another reason I have such strong disdain for Dropbox at this point in my life…
It's their upsell emails.
Check out this seemingly harmless email I got once my Dropbox was full.
That seems nice enough, right?
There's even a cute little illustration of a blob eating ice cream at the bottom! What's not to love?
My problem with this email is the fact that Dropbox is essentially telling me:
"Hey. We literally built this problem into our service. But if you give us money, it will go away!"
At this point, you might be thinking I'm some sort of Internet Scrooge who resents having to pay for any type of online service…
But you would be wrong.
I spend over $10k per year on courses, masterminds, and online services to keep my business running — but Dropbox will not get a cent of that money. Because THEY'RE NOT SELLING ANYTHING!
I'll explain:
Here are the features of Dropbox Plus and Dropbox Professional. Take a look:
Okay, so you're basically telling me that you will store my files, make them searchable, and allow comments?
Wow!
How innovative!
I wonder if there's a service that would let me do all of that for free?
There is. It's called Google Drive…
And it gives you 15GB of free storage compared to Dropbox's measly 2GB of free storage.
I repeat, Google Drive gives you 7.5x more FREE storage than Dropbox.
Alright, look — I recognize that Dropbox isn't all bad. I'm sure there are some benefits that I'm not accounting for.
Dropbox Paper actually seems pretty dope, and it's free. I also like Dropbox's branding. And I'm sure the people who work there are smart, talented, and lovely human beings.
It's very possible I'm missing something.
This post is, admittedly, more of a rant than a research article.
HOWEVER, if your sales emails inspire enough frustration for someone to write a 1,000+ word blog post about them…
They probably deserve a second look.
So I have a few suggestions:
1. Fix the Positioning.
The current upsell emails make you feel like a doctor has stabbed you in the gut with a rusty switchblade and then said:
"It's okay, I'm a doctor!"
I mean, great. I'm glad you're going to help… but maybe you could have just, oh I don't know, not fucking stabbed me in the first place!?
But seriously:
The current positioning makes it seem as if the reader is going to have to give you money now in exchange for the exact same service they've been receiving.
Ideally, this email automation would highlight how much better Dropbox Plus and Dropbox Professional are than the free service.
I know that stuff is mentioned on the landing page. But you gotta bring it into the email.
People need to be pre-framed on the value of the service before you try to get them to click a button or buy.
2. Give a reason why.
Okay, let's assume the worst.
Let's say that Dropbox Plus and Dropbox Premium are actually NOT all that different from a free Dropbox account.
Maybe you really are just paying more for the same service you were getting for free before.
Surprisingly, I don't think that's a dealbreaker if it's handled correctly.
And that could be easily done by adding a little empathy to these emails.
Call out the elephant in the room. Tell people exactly what's happening. Show them WHY it costs money to continue using the service.
Explain that, while to most people, the cloud is an invisible blob where all sorts of data is stored, it actually exists in real-life on hardware in data centers that cost money to use.
People don't hate paying for things. They hate paying for things they can't see the value in.
Help the reader understand the value.
3. Sell the damn thing! (Tastefully, of course.)
Much of the marketing world seems to fall into one of two camps:
They sell aggressively and relentlessly…
Or they hardly sell at all.
As with many things in life, I think the sweet spot is somewhere in the middle.
You don't need to tell people that you'll kill their grandma if they refuse to sign up for your service…
But you also need to do a lot more than say "Hey you should maybe possibly consider buying our thing because it's pretty cool okay please buy it thank you bye."
You have to give people reasons to buy…
You have to make the thing that you're selling sexy…
And you have to show them how what you're selling will improve their life and help them get what they want.
I think people often fall into the belief that, if their audience is more educated or tech-savvy, then they don't need to be sold.
They can read, right!?
Sure. But they're also busy AF. And you better believe they're not going to go out of their way to try to give you money.
Make it easy for them.
Write fun, entertaining emails that show the value of your product in a clear, non-aggressive way.
People will enjoy the emails. They'll buy more of your product.
And, at the very least, they won't write strongly-worded articles about your service or your email sequences. 🙃