A big chunk of our paid customers start out on the free plan and then upgrade to paying plans. It’s a bit of an art to figure out when, where, and how to suggest an upgrade. Too often and it’s irritating. Not enough and your customers may never see it. Too big and it’s annoying. Too small and people may miss it.


Here’s how Backpack used to let people know they could upgrade to get more pages, etc:

This message was always displayed right under the “Make a new page” button. It worked pretty well, but it was always there. It was too in your face.

The first time you go to click the “Make a new page” button you’re hit with a sales message right below the button. That’s not an impression we wanted to make.


A big part of the new Backpack upgrade was a focus on the experience. We wanted to make things smoother, more elegant, and more streamlined. This included the upgrade pitch. We think it’s more polite now.

Here’s the new free account sidebar with a few pages:

You’ll see there isn’t an upgrade pitch under the “Make a new page” button. The free account includes 5 pages. This example account has 3 pages. We don’t need to tell people about upgrading to get more pages until they need more pages.

Now here’s the new free account sidebar after they’ve hit their 5 page limit:

Since they’ve hit their limit we replace the “Make a new page” button with a yellow “sticky” notice. We delicately explain they’ll need to upgrade (or delete pages) if they want to add more pages. We give them a link to upgrade or find out more.


Before it felt like you were walking into a store and a salesperson immediately came up to you and told you about today’s sale. That’s an unpleasant experience.

Now it feels like a helpful suggestion when the time is right. We think that demonstrates better manners. It’s how we’d want to be treated while evaluating something new. A quick sales pitch feels rotten. A natural pitch when it makes sense feels right.