Is Tailwind worth it?

Could automating Pinterest be the answer to perpetual traffic?

Caroline Cocker
6 min readJan 29, 2020


This article is not going to be a study in Tailwind bashing.

I think it can be absolutely incredible tool, capable of driving vast quantities of viewers to your website.

But I’m sick of it being portrayed as the easy, time-saving option. It’s a software to help you, like Canva or Wordpress. You still have to do the work.

If you think it’s quick fix, or get a subscription believing that you’re basically paying for traffic, you’ll probably be disappointed.

What does Tailwind do?

In a nutshell, it automates your Pinterest account.

(There’s other stuff too, but the main selling point is automation.)

Because you see, Pinterest wants people to use the platform every day. I think it sees itself as the magical lovechild of Google and Instagram.

You can hack this by pinning all your pins at once into Tailwind, and then Tailwind will drip feed them to Pinterest whenever you want. It even has a smart schedule, so it can work out when your audience are most active, so you have the best chance of getting traffic.

Does Tailwind work?

Does Tailwind do what it tells you it’s going to do?


But does that automatically mean a tonne of traffic?


The issues with Tailwind

A quick disclaimer: I don’t believe that Tailwind is duplicitous or a scam in any way. They’re a victim of that most dreaded of monsters: The Algorithm.

You still have to create pins that convert

Which becomes more and more difficult as more bloggers enter the arena. It’s so difficult to come up with original pins that drive clicks. Especially with the birth of Pinterest VAs.

Pinterest wants real users

Even though Tailwind is an official partner of Pinterest, Pinterest wants actual people on the platform.

I have no idea why it makes a difference to them, but it does.



Caroline Cocker

Writer, blogger. Rabbit parent to one. Plant parent to many. Occasional runner, jigsaw puzzle enthusiast.