Tailwind vs BoardBooster: A Comprehensive Review of Pinterest Tools

Which One Works Best for You and Your Workflow?

Updated: June 6, 2017

You understand that social media can play a huge part in your blog’s success, but the problem is staying on top of your social media efforts can take a lot of time.

Let me say this a different way. Maintaining your social media profiles can be a huge pain in the ass.

Thankfully, you have a ton of wonderful social media tools at your disposal. Unfortunately, you have so many options that it can be hard to choose which one is best for your situation. If you are interested in using Pinterest as one of your social media platforms, then this post will teach you two of the tools that I use to greatly help out my Pinterest marketing efforts.

Choosing Pinterest

When I decided to create Obstacle.co I thought about which social network I wanted to put most of my efforts into and I ended upat Pinterest. This is pretty surprising considering I created a Pinterest account a couple years ago and only had 15 pins on it.

I wasn’t the ideal Pinterest user, to say the least.

So what led me to choose Pinterest as the social media platform to focus on? It’s the fastest place to get up and running in my opinion with regards to your promotional efforts. Every other network you have to build a following, but on Pinterest, you can build up a library of pins that people will randomly come across. It’s a place where people go to actively search for content. None of the other social networks offer that.

Think about it. People don’t go to Pinterest to casually read content. They go and hunt for specific content.

This makes Pinterest extremely powerful since you can find people who have the intention of solving a problem. Why is this important? It’s important because the people that have the intention of solving a problem are the ones you can convert to subscribers and later customers.

Over a span of a couple of weeks, I dove head first into Pinterest to better understand how the successful pinners got to where they were. I’ve found that one of the keys to Pinterest growth is the number of pins you pin each day.

Now people will dispute the number of pins you should go with each day, but everyone agrees on the fact that if you’re an infrequent pinner you will not get the results that you want. If you want your Pinterest count to grow at the beginning you need to constantly be pinning awesome things.

However, it’s a huge pain in the ass to head to Pinterest every single day and pin stuff. While I have become one of Pinterest’s top fans, even I know that most of my time is better spent working on other aspects of my blog. What this means is that you need to utilize tools that will help take care of your pinning activity while you do other things.

The two big dogs to handle such a feat are BoardBooster and Tailwind (both are affiliate links because I recommend them both as you will see).

When trying to figure out which tool I should use it was hard to tell the differences between them just by looking at their websites so I decided to use both for a month. That’s right, I spent my hard earned money to make your life easier.

In this post, I am going to explain the pros and cons of each tool and show you how I use each of them to help grow my Pinterest profile.


Tailwind is a wonderfully designed app. As a designer, the design of an app plays a huge role in my decision-making so it was nice to see an app that is easy to use right off the bat. If you’re familiar with Buffer, then you will be right at home in Tailwind. The premise is the exact same.

You create time slots for each day of the week and then you put pins within those slots and they will be automatically posted for you. If you’re uncertain about what time slots you create, Tailwind will offer you suggestions. You can simply click on these suggested time slots and they will be automatically added to your schedule.


If you run out of recommendations then when you come back for other sessions, more recommended time slots will appear. Currently, I have random times spread out through the day with a heavy concentration on the morning and evening. Tailwind automatically pins 30 pins Monday through Friday and 40 pins on the weekends.

This might seem like a lot to you, but if you spend one day a week getting all of your pins set up, it really becomes a set it and forget it solution.

The Dashboard

Every great web application should have an awesome dashboard. The dashboard should provide you with a nice snapshot of the activity that is happening with your account. This is what Tailwind’s dashboard does.

Tailwind dashboard

On the dashboard, you can quickly see how many repins, domain pins, and followers you’ve gained over the past 7 days. This is helpful to spot trends and ensure that you are seeing consistent growth over time with your account.


One of the things you will love most about Tailwind is the analytics that it provides. They act as a nice complement to the ones you get with Pinterest (assuming you’ve setup your account as a business account).

Monitor Your Domain

One of the main reasons to use Pinterest is to promote your own site and that means having an easy way to track how well pins from your domain are doing. Tailwind makes this easy and shows you a nice trending chart.

Here you can see that because I haven’t pinned anything from my site for a couple of days, the graph is going down. Not a big deal in the short term, but in the long run I want to make sure that line is going up.

Tailwind Domain

Profile Performance

Of course, you will always want to check on how well your profile is doing. This means seeing your follower count, pins, repins and likes.

We all like these vanity metrics going up and Tailwind makes it really easy for you to keep track of them.

Tailwind Profile performance

Pin Inspector

The Pin Inspector is great because it allows you to get an idea of what type of pins people like to repin, like, and comment on. As a new Pinterest user I wasn’t quite sure what type of pins do the best on Pinterest. Sure you can read awesome tips from other people, but nothing beats understanding these things for yourself.

Of course, you can’t just look at a certain pin and think that it succeeded solely due to its design. A number of factors play a role in a pin’s success like board posted to and time of day. However, it’s still nice to be able to see how pins perform.

Looking at the Pin Inspector table for the Obstacle.co account, you can see that the Blogging Tips & Tools board seems to be performing the best. This means I want to make sure I take extra special care with regards to pins that I post in there.

Board Insights

One of the most important things to keep track of with your Pinterest account is the performance of different boards. On Pinterest you can have 3 different types of boards:

  1. Regular boards
  2. Secret boards
  3. Group boards

You do not care about the performance of secret boards because they are meant for your eyes only. Tailwind offers you the ability to check on the performance of each of your boards which is great, but what makes it even better is that you can sort the boards. If you do not want to see any information on your secret boards then you can hide them. If you only want to see the performance of your group boards then you unselect the two other types and you are good to go.

So what kind of metrics does Tailwind provide for these board insights? Tailwind tells you 5 different metrics for your boards:

  1. Pins
  3. Repins
  4. Virality Score (Repins / Pin)
  5. Engagement Score (Repins / Pin / Follower)
  6. The Virality Score and Engagement Score are the interesting metrics to keep an eye one and it’s fascinating to see how the different boards perform. Again, just looking at these metrics in a vacuum can lead you to some incorrect conclusions, but looking at them along with the other analytics provided by Tailwind can really help you in figuring out the best methods to grow your profile.

    How I Use Tailwind

    Now that you’ve seen some of the major features of Tailwind, I want to explain to you how I use it.

    Essentially I treat Tailwind the same way that I treat Buffer. I use it to schedule pins across Obstacle.co’s public boards. I don’t use it to pin to group boards or secret boards. You’ll understand why when you read the BoardBooster section.

    I spend one or two days a week filling up my queue in Tailwind so that I’m good for a week. When I first started off I only had 10 time slots scheduled every day and was able to fill up two weeks worth of pins in a single day or weekend. Now that I’ve increased the amount of pins I do daily, it takes me a bit longer to fill up the time slots.

    However, Tailwind makes it extremely easy to ensure that I have 230 pins ready to go every single week. One of the great things about it is that if you decide a pin belongs on multiple boards, you can spread the times it is pinned to those different boards over a set interval. I currently have the interval set for 1 day, so when I find something new to pin, it is only pinned to my boards once a day.

    You can do them all on the same day, but I like the idea of having pins spread out throughout the week so there is no chance that I’m overloading my followers with the same pin on a single day.

    Tailwind Multiple boards

    If you’re looking for an easy to use and intuitive Pinterest scheduler, then I have no problem recommending Tailwind.


    BoardBooster is the other heavyweight contender for Pinterest scheduling that I saw recommended by a number of different bloggers.

    BoardBooster is interesting because it’s a tool that isn’t officially sanctioned by Pinterest.

    What does this mean? It means that if Pinterest wanted to they could shut them down. It doesn’t look like that will happen as BoardBooster has been around longer than a year and it is still up and running. However, this is something to keep in mind when choosing which tool fits your workflow better. By putting this information first you’ve might have already been put off by BoardBooster, but please continue reading because I do believe it does a great job of filling in the gaps that Tailwind misses.

    Right off the bat you will find that BoardBooster doesn’t have as nice of a design as Tailwind. It doesn’t have a terrible design, but it doesn’t offer the same polished or professional feel that Tailwind provides.

    BoardBooster offers 6 main features:

    1. Campaigns
    2. Scheduler
    3. Looping
    4. Pin Mover
    5. Pin Doctor
    6. Group Manager

    Let’s go over each one.


    Campaigns allow you to periodically repin your pins to different boards. Campaigns are broken up into two different methods: scheduled and random.

    Scheduled Campaigns

    This is my favorite feature of BoardBooster and if this was the only feature it included, I would still use it.

    Campaigns allow you to fill up a secret board (or any board) with pins and then automatically repin those pins to other boards on specific days. My strategy for Obstacle is that I create 6 different Pinterest specific images for each post. 3 of these designs I have been using on Pinterest to test the effectiveness of them.

    I’m part of a number of group boards so the idea is to have these pins pinned to each group board over a set of days. To do this on Tailwind you would have to keep track of which pin is going on which board on which day. You can easily get confused, but with BoardBooster campaigns life becomes real easy.

    BoardBooster Scheduled Campaigns

    Take a look at my Morning campaign. Every morning, BoardBooster goes into my secret morning board, pulls the latest pin and enters it into a campaign. This pin gets pinned to 12 different group boards over a course of 12 days.

    I do the same thing for afternoon and evening pins. One of the keys to success with doing well on Pinterest is to continuously pin your pins on group boards. BoardBooster allows me to do so easily and without making it seem like I’m spamming my pins across the same boards.

    Random Campaigns

    Being part of a group board means that you are doing your duty in contributing awesome pins from other sites. Group boards aren’t meant for you to just spam your own pins so it’s important to be a good member.

    If not you can get kicked out and that is a very sad thing to have happen to you.

    I use Random Campaigns to make my life easier and ensure that I am filling up my group boards with awesome content daily.

    BoardBooster Random Campaigns

    This type of campaign is even more set it and forget it than the scheduled campaigns. What a random campaign does is take a number of pins from my own boards and repins them to my group boards throughout the day.

    Looking at the screenshot you can see that I have four source boards from where BoardBooster take pins and I am able to post to all of my group boards.

    Every group board has different rules that you need to follow. Some only want two pins a day while others might have unlimited. Random Campaigns allow you to create different rules for each board to ensure that you don’t break any, while also remaining a good citizen.

    Pin Scheduler

    Pin Scheduler is BoardBooster’s response to Tailwind. The Pin Scheduler requests that you select the boards that you want to pin to and then it creates a secret board.

    Instead of pinning to your public boards, you pin to this secret board and throughout the day, BoardBooster will take pins from this secret board and pin them to your public boards.

    I don’t use this feature because I have Tailwind for this, but if you don’t want to use both tools, then you can go with BoardBooster and get the same thing done.

    One of the cool things you might like about the Pin Scheduler is that it can source pins for you. What this means is that you don’t ever have to visit Pinterest if you don’t want to. The Pin Scheduler will find pins using your sourcing agents.

    I gave this a shot for a couple of days but turned it off because the pins it was finding weren’t the quality I wanted for my boards. Also, depending on what type of boards you have, you might spend more time curating the pins the sourcing agents are finding than doing any actual pinning.

    If you do decide to give this a shot, you will have better luck using the board agent where you can select specific boards to source from than you will the search agent.


    Looping works well if you have an old board with a lot of pins. I don’t use this feature so I’ll just let BoardBooster explain how it works:

    Looping helps you revive the older pins that you created or curated before you gained most of your followers. Chances are, some of the boards that you started long time ago have hundreds of pins by now, and most of your current followers have never seen those pins. The easiest way to bring those pins back to life is repinning them to the same board. Looping can automate this process for you. It can also prevent content duplication on your board by automatically deleting one of the duplicate pins. For example, you can configure Looping to wait a week after repinning, then compare the number of Repins on the new pin vs. the original pin, and delete the pin with the lowest number of repins.

    The reason why I do not use this feature is because my account is still young. I can see the benefits of using this feature maybe after 6 months when my boards are really filled up, but for the time being it doesn’t make sense for me to use.

    It seems like a great feature nonetheless.

    Pin Mover

    Pin Mover helps you split or clean up large boards. It finds all pins that match your criteria and moves them to a board that you specify.

    This feature can be extremely useful if you are creating new boards and need to fill them up with your awesome pins quickly.

    Pin Doctor

    This tool will test pins on your boards, identify 9 common problems like broken links and content duplication, and help you fix them.

    I have yet to try this feature, but it looks like it can provide some awesome information about your pins. Please note that this is a feature that you have to pay money for on top of your current subscription. Pin Doctor will give you a price quote before you click anything so there aren’t any surprise charges.

    Group Manager

    Group Manager is a tool for owners of Collaborative Boards. It monitors all pins added by your contributors, and identifies your best contributors as well as any contributors that don’t follow the rules of your group board.

    I currently do not run any group boards so I can’t offer any feedback on this feature.


    Similar to Tailwind, BoardBooster offers a variety of helpful reports.

    The most useful one shows you the best times to post to your Pinterest account.

    BoardBooster Best time to pin

    Secret Board Chaos

    One of the major downfalls to using BoardBooster is that a lot of its functionality is dependent on the creation of secret boards. When I was using the majority of BoardBooster’s features, I was overloaded with secret boards.

    This can be pretty annoying when you are trying to do some simple pinning because you have to go through your list of regular boards and secret boards. It just clutters things up and I didn’t like it. This is one of the main reasons I kept Tailwind around because it isn’t reliant on secret boards.


    Tailwind is priced at $120 a year or $15 a month. I went with the yearly plan since I knew Pinterest was going to be the main social media platform I would invest in and it means I could schedule unlimited plans. The monthly plan only allows you to schedule 400 pins.

    BoardBooster’s pricing is a bit different. You get the first 100 pins for free and each pin after is $0.01. So 1,000 pins will cost you $10 a month. Cheaper than Tailwind, but that doesn’t necessarily make it better.


    Hopefully this overview of Tailwind and BoardBooster has provided you with enough insight to make an informed decision on which to use.

    I definitely prefer to use both since they do a great job of complementing each other. Tailwind handles my regular boards while BoardBooster takes care of the group boards.

    However, you might not want to fork over the money for two services which is completely understandable. If that’s the case then I would recommend BoardBooster for those people that have no problem with a ton of secret boards filling up your Pinterest profile and a less intuitive design.

    For those that want a cleaner interface with a bit more analytics and easy to use tools then I would go with Tailwind.

    However, they are both relatively cheap so why don’t you give both a shot? BoardBooster gives you the first 100 pins free so you can dive right into it and see how it works for yourself. Both are great tools and it’s really hard to go wrong with either one.

    Whichever you decide you will find that both save you a lot of time and allow you to focus on growing your blog instead of worrying about your Pinterest profile.

    If you are a Pinterest junkie, then you should follow the Obstacle.co Pinterest account. It’s filled with awesome blog tips and other goodies daily.

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