Personalization Through Automation: The Vision For GuessBox

A lot of you may not know this but prior to receiving our seed funding from Leni Mayo in late 2015 GuessBox wasn't called 'GuessBox'. In fact, it didn't even have a team. But, it was still an operational business - a business that generated leads for clients using a spreadsheet I had created.

The spreadsheet in question was a project I started working on at my previous job at Influx - a company co-founded and invested in by Leni Mayo. The reason this spreadsheet came to life at all was because I was hired to effectively 'growth hack' a way of getting more sales for Influx.

GuessBox Spreadsheet Email Scraper & Verifier v1.01

When I first arrived at the company I realized that there was a discrepancy in the sales process. The sales numbers were good but to achieve those numbers there was a team of about 6 people individually searching the internet, finding ideal customers, looking for their contact details (or the contact details of someone who could get in touch with them) and finally sending through an email.

Coming from a background of automation I thought there must be a way to automate or at least simplify some parts of this process. So, in my personal time, I started working on this spreadsheet. At first, it would just verify the contacts' emails that we had collected were valid and since at this point all the outbound emailing was manual this process would save time in making sure the sales team would only be writing to people that would receive their email.

Fast forwarding a week or two the ability to list the emails of all employees at a company was added, then that was stripped down to include only the most relevant employees, then the verification element was added to the employee emails generated, then the option to filter and search for specific job titles was added... and onto industries, and countries so forth.

I apologize if that paragraph was a bit rushed but it is a tinge difficult listing the chronological development of an idea into a somewhat convoluted spreadsheet and finally app.

Returning back from that rather big tangent that we just embarked on. So before GuessBox was called 'GuessBox' there was a running joke between my friends and I that ended up in me just calling the business ELS, short for 'Eric's Lead Service' for as long as I could.

And hey, I think that was the official name for at least 3 months. After 3 months the business had enough traction and a solid enough idea to get funding and turn into GuessBox.

You might be wondering where that name came from? Well, that is a somewhat comical event too. There is a company called Kickbox (I won't link to them here but if you care enough I'm sure you can find them by doing a search) that offers email verification solutions and APIs. I wanted to build a spreadsheet that when given a company domain and an employee's first/last name could automatically create and verify multiple email patterns and then output the one that is valid. And in my effort to do so, I chose to use Kickbox's API for the verification process.

However, they wouldn't have that. It seems I broke their TOS and was deemed to be a spambot. Uh-oh. As you know that was never my intention, and here at GuessBox we don't condone spam in any way, and in fact constantly help our users to craft the least spammy and most personalized campaigns they can.

But, I digress. Having been banned from using Kickbox's service that I had purchased credits for I was a bit annoyed. Thus, I chose the name GuessBox since at that time, and to an extent now we would 'guess' a prospect's contact details, ala GuessBox!

This brings me to the crux of this article, and I thank you if you have read this far because I know I took you on a series of tangents. Luckily, we made it back before dinner!

Personalization Through Automation

What is personalization through automation? It's the vision we had from the day GuessBox became a reality. It's a concept that I have applied to the majority of my other software products in the past.

Take a look at the spectrum below and now imagine you are sending an email to a cold prospect. You can equip the email with full personalization (left of the spectrum) by spending time doing research about the business you're contacting, about the person you're contacting, you could mention and link to their latest press releases etc.

Automation Spectrum

After all is said and done you would be left with a highly personalized email that would receive an extortionately high open/response rate.

Great, but that's not feasible for every business.

On the other end of the spectrum sits full automation which would entail the likes of an ice cold email blast with no real targeting, no use of your prospect's name, no relevancy of product being pitched. Frankly, it's just downright awful and may end up in your junk. And we have all been a victim of that.

Now that you understand these two extremes, understand where I want to be with GuessBox. Judging by all the articles on this blog we aim to be as close to the middle of that spectrum as we can. Though, that's merely a temporary solution.

Instead at GuessBox we want to design an entirely new spectrum one without the limits of time-consuming research currently needed to achieve full (or close to full) personalization. By scanning through the world's data, defragmenting it and using machine-learning GuessBox will be able to better understand what you should add to your email based on the person you are speaking to. This would all be done automatically suggested and inserted into your emails with the use of GuessBox Snippets - a feature we will be in the process of developing soon.

The closest example of any company who achieved this so far is at DetectiveLabs. Detective is run by a company called Charlie which used to automatically give you research about the people in your meetings before the meeting so you could go in already having a brief understanding of the person and their company.

Benefits of Automating Personalization


  • Less spam.
  • Higher inbox rates.
  • More responses, more closed meetings, more deals.
  • Healthier email server reputation.

Here is an example of what we envision users being able to do with GuessBox in the future.

You have a list of 1,000 targeted leads that you want to contact. You work is subject to the amount of time and resources you have available. Therefore you are unable to do deep research for every lead on your list.

Instead you opt to automate the personalization in your email. You have an idea for a first-touch email and you write it down.

Hi {firstname},

I have been following the development of {company} ever since I read the press release titled, {title-of-release} where you revealed that {point-ofinterest} and {point-of-interest2}.

My name is Eric Azizian and I'm the CEO of I'd like to get on quick call with you to discuss how GuessBox may benefit {company} this quarter and help you reach {growth-target}. How does this Tuesday at 11am sound?

Looking forward to speaking with you!

The future of GuessBox and email automation dictates that the tags in your email are automatically replaced with relevant news excerpts and company information. All of a sudden those 1,000 people that you contacted open their inboxes to find a well researched, personalized email waiting for them. Thus greatly increasing the chance that they reply and get added to your sales cycle.

This is the vision we have for GuessBox and I'm sure there are companies working on this technology right now. We welcome it, because not only is it going to improve conversion rates for companies but it will improve the overall quality of emails being sent, and that's good for everyone.

I leave you with one question. What happens when email marketers are no longer able to compete on email quality because technology has advanced to the point where every email is perfectly personalized?