GuessBox began from an idea to create a simple, yet effective B2B lead generation app. GuessBox v 1.0 came to life within a Google Spreadsheet. It wasn't fast, it wasn't flashy but it got the job done!

Read more about this story here.

Almost a year later the GuessBox of today looks like a far removed cousin of the spreadsheet app from back then.

But, I digress..

In this guide you will learn how to create your first automated B2B email campaign using GuessBox.

Step 1: Setup SendGrid

Right now GuessBox integrates with for sending. It makes the entire process super easy, and provides you the user with a set of nice analytics.

Visit and create an account. You can start with the free one, though if you want higher inbox rates it is encouraged to get a paid account.

Once you have created an account, click on settings > API keys within SendGrid. From this page you will now need to create an API key and then copy it into the respective field on the GuessBox settings page.

Please refer to this guide for the rest of the information involving this step.

Step 2: Configuring Your IMAP Settings

As per the guide in the link above, please proceed to setup your IMAP settings. These are important as they ensure that GuessBox will correctly reply to emails that have yet to receive a reply.

Note: A few things have changed (mainly design elements) from the guide above, but they should be pretty self explanatory.

The picture below is of your settings page, note where it allows you to toggle on/off the auto follow up settings, and specify how many follow ups the application should send (and when).


Step 3: Domain Authentication (optional)

This step is technically optional though I wouldn't suggest skipping it unless you want your emails to go straight into the junk folder of your prospective client.

For more information on how to authenticate your domains so that mail servers will be able to distinguish your email from spam, read this guide.

Step 4: Uploading Contacts

Let's assume in this case you already have your contacts, and won't be emailing them directly from the GuessBox search results.

Click on the 'Contacts List (Beta)' link that is located on the left hand side of your screen, in the navigation menu.

And then all you need to do is press 'Upload CSV' in the top right corner, and select your .csv file with the leads / people you would like to add into an email campaign.

Note: As you can see in the demonstration below, there are a few guidelines that your file must abide by in order to be accepted by the website.


Step 5: Configuring Automatic Follow Ups

In the case that a person you email does not reply to your email, you can set GuessBox to automatically send him/her a reminder email of your choice after a certain period of time.

Go back to your settings page, and scroll down to IMAP settings. Select how many follow ups you would like to send, and the after how long they should be sent out. Once you have done that, press 'Add More' to create different follow up messages.

Toggle the IMAP / Auto Follow Up switch to On and then press 'Save' down the bottom.

Example below:


Step 6: Using Personalization & Spintax when Sending Emails

When writing your first touch emails, and follow ups remember to make use of the personalization tags available, and spintax.

Here are some examples of the tags you can use:





More will be available very soon

By putting words, phrases or links in curly brackets and dividing them with a line as per the image below, GuessBox will automatically rotate through those options with every email it sends. This can be used in both the subject, and body of your email.

GuessBox Spintax & Personalization

To send an email to your uploaded contacts, press 'Send Email' next to the group you uploaded on the Contacts List page.

Write your email, then press 'Preview' to view your email, and send a test email to an address of your choosing.

If you have already set up auto follow ups from your settings page then you don't need to press the 'Auto Follow Up' button.

Once you are ready, press 'Send' and your campaign will be sent out. Check Google Analytics & for analytics regarding your campaign.

Step 7: Miscellaneous

Want higher response rates? Remember to use a professional email signature and add it automatically to every email sent by visiting 'Mail Settings' on and clicking on 'Footer'


Note: Don't forget to add an option for users to unsubscribe at the bottom of your emails. If you fail to do this, you will be technically breaking the law, and we will have to launch an investigation into the type of email you are sending.

To automatically append an unsubscribe link / message at the bottom of each email, visit 'Tracking' on SendGrid and click on 'Subscription' to activate it.


Note: When writing your emails try to keep them to five sentences or less in length. Don't ramble too long about your product, and establish objective early on.

  • Always remember to follow up (because people are typically busy) and keep an eye on your sender reputation.
  • Configuring your DNS settings for domain authentication is easier done using
  • GuessBox can be used for sending out newsletters and general communication emails as well. You don't only need to use it for B2B cold email outreach.
  • If you can't find a specific data set on the website, don't hesitate to contact us using the live chat form on our homepage or email us here.

And that's it! This was an introductory guide on getting started with GuessBox and its email functionality for your B2B marketing campaigns. Stay tuned for our upcoming eBook and remember if you found this post valuable - share it with your friends!