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How to schedule your Pinterest content in Tailwind and outsource the task to your VA

How to schedule your pins with Tailwind and save time

Here comes the 3rd and final episode of my Getting Started with Pinterest Series in which I showed you fundamental techniques on how to gain more traffic on Pinterest. In the previous episodes you’ve learned: 

Today, I’m going to show you how I schedule my Pinterest content in Tailwind so that I always have original content pinned to my boards that lead to my blog, shop or freebies. 


Scheduling your content is a great way to work ahead and avoid burnout. Especially on Pinterest that requires a higher volume of content than other platforms. 

While it’s ok to post only 1 content a day on Instagram or Facebook, this article from CoSchedule recommends adding 11 original content on Pinterest. Some even suggests more, between 15-30 pins per day. 

11 pins every day can be quite a burden, especially if you want to achieve this amount from original content, not repins. Scheduling helps you tackle this workload in a more effective way. 

(This image is from CoSchedule) 


Why am I suggesting “original content”? Well, of course you can reach that 11 pins/day by just repining your or other’s existing content. But would it really help your Pinterest engagement? 

No, because Pinterest prefers original content over repins. 

This amazingly helpful article from Social Marketing Writing says it best: 

Over 80% of the pinsyou see on Pinterest are repins. Only 20% of pins are either directly uploaded onto Pinterest or they have been pinned from a website. The rest are repins of these pins. Therefore, if you want more people to repin your pins you need to upload or pin original images. Create the 20% pins that get repined again and again and again! 


Before Tailwind I used an app called BoardBooster. It worked quite well but Pinterest decided that BB wasn’t in line with their policies and they had to shut down. I also used CoSchedule for a while but it lack some features that my old BB subscription had. At that time, I heard great things about Tailwind so I gave it a shot. 

And, oh boy, I wasn’t disappointed. 

At first, I found Tailwind a bit too complex compared to the above apps. But I soon realized that this tool is quite simple. It’s just packed with so many clever features that it can feel overwhelming first - hence this tutorial.  

If you are a Tailwind Beginner, I hope I can make you feel a bit more at ease by the end of my post. 



Duh! I know, it’s quite obvious. First you must create the content you want to schedule. This involves: 

  • Creating the pin images (use templates to make this step quicker and easier) 
  • Writing the copy for your pins: pin title, description with a big emphasize on proper SEO (keywords, hashtags, meta data, etc.) 
  • Collecting the URLs you want your pins to lead to 
  • Deciding on which Pinterest Boards you want to add your content. If you are contributing to Group Boards, make sure you understand the rules the board owner set. Some group boards allow content looping (more on this later), others don’t 

You can be more effective in Tailwind if you gathered all of these in advance. In addition, you can summarize all the data in a spreadsheet and outsource the scheduling part to your VA (this is what I do). 

To further help you in this, I’m giving you access to my Pinterest Scheduling Spreadsheet. This is the Google Sheets file I create for each of my blog posts or promotional campaign in order to collect all the above data in one place. Then I send it to my VA who can continue with the scheduling part of the task. 

How to schedule your pins with Tailwind and save time


You have everything you need, you’re ready to log into Tailwind, yay! 

Go to Publisher / Drafts (in the left side menu). You’ll have to places where you can start adding your content: 

  • If you don’t have any drafts, you’ll have a drag & drop upload section in the feed of content suggestions Tailwind offers you 
  • Or you can also click on the “Create New Pin” button in the upper right corner and choose “Upload Photos / Videos) 

Choose all the images you want to schedule. 

My VA gets this information from the first column of the Pinterest Scheduling SpreadsheetI list here all the video or image files that she has to schedule. 


Next up, your uploaded images appear in the drafts. Start inserting all the data you collected in Step #1. 


You can either choose boards at the top, and then all your drafts are going to be pinned to those boards or choose individually under each image. 

One image can be scheduled to multiple boards and the first board in the list should be the most relevant to your content. 

provide the board names in the second column of the Pinterest Scheduling Spreadsheet.  


You continue by adding the description and the URLs to each pin. This requires some copy and pasting if you schedule many images at the same time. It still goes quite fast. 

Note that the first part of your description will act like your Pin Title, so include your most important keywords here. 

In the Pinterest Scheduling Spreadsheet, I have 2 columns for the description: 1 for the main caption, 1 for additional keywords that my VA inserts below the main caption. There’s of course a separate column for the URL. And if the URL is the same for all the images that needs to be scheduled, I just simply merge the cells into one. 


Tailwind Tribes is a fantastic way to get your content in front of other influencers, bloggers, entrepreneurs. These Tribes are groups where you can add your own pins and other members can also add them to their Tailwind schedule.  

You can join up to 5 Tribes and add up to 30 pins per month with the basic Tailwind membership – or purchase PowerUps that give you access to more Tribes and more monthly Tribe contributions. 

Most Tribes have rules that requires you to add other’s content to your schedule if favour of them doing the same. Affiliate links can also be prohibited. So make sure to check the Tribe rules before you join them.  

Last but not least, you can’t add another image or video from the same URL to the same Tribe. If you do this, you get an error message from Tailwind (see image below). So make sure that you contribute with your best pins. Choose those that have the most eye-catching graphics with the best headline. 

In the Pinterest Scheduling Spreadsheetthere’s a column showing my VA which Tribe the pin has to be added to. 


Looping is a Tailwind feature that automatically reshares the pins that you add to a SmartLoop. You create SmartLoops under Publisher / SmartLoop. You can set how often you want to reshare a pin and to which board you want to reshare. 

SmartLoop keeps your evergreen content fresh and on top of your Pinterest feed. 

By default, Tailwind gives their subscribers 250 SmartLoop slots. 1 slot means 1 image that is looped to 1 board. If you have 1 image that’s looped to 2 boards, that will require 2 slots. Of course, you can use PowerUps here too to get extra slots. 

It’s best to only add your most amazing pins to SmartLoops. This is why on the Pinterest Scheduling Spreadsheet I don’t request all pins to be added to the loops, just a few selected ones.  

A few month later when I’m checking my pin performances in Tailwind, I remove the least repinned content from the SmartLoops and add the mosrepinned ones. 


This is the final setting I do before clicking on “Schedule”.  

You can leave the timing of your pins to Tailwind if you wish and they are going to automatically set up your schedule. However, I like to make sure that there’s content for every day of the week. 

I schedule 7-10 images for each of my blog posts. When I get to timing, I set the first image to the day after the blog post goes live. The next image to the following day and so on.  

also set a 7-day delay before the same image lands on another board it is scheduled to. Which means that if I pin 7 blog images to 4 different boards, they are going to be shared every day for 4 weeks. 

If you find this too much, you can leave out this step and trust Tailwind to fill up your queue. You can also click on the “Shuffle Queue” button which mixes up the content in your queue a bit. 


I hope you found this article helpful.  

Even if you don’t plan to use Tailwind, I suggest you to look into it or check other schedulers (there are a lot). Tailwind works for me, but everyone is different, so CoScheduleBufferLater, etc. might work for you more. 

No matter which tool to choose the Pinterest Scheduling Spreadsheet will come in handy. It will help you summarize your data, your assets in one place. It will even help you in outsourcing Pinterest scheduling when you decide to do so.  

Click on the image to get access to this file or visit the free Brand Builder Library where you can also find other helpful freebies. 

How to schedule your pins with Tailwind and save time

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