18 Smart Questions to Ask Before Buying Newsletter Software

Read this if you need help choosing the newsletter business software that will help you build your business.

It’s Time To Buy Your Newsletter Business Software!

When starting a newsletter business, it is important that you choose a “newsletter business software platform” that will support the growth of your newsletter business over time as it scales up.

Before you read any further though…

Make sure that you have read and have taken action on every action step in the articles linked below!

Skipping ahead here won’t help you, so get this stuff done for your business before moving forward!

  1. Finish the first 5 steps in this article: Starting A Newsletter Business? Do These 5 Things First!

  2. Create a memorable name using this article as your guide: The 5 Things To Consider When Creating A Memorable Name For Your Newsletter Business

  3. Use this article to help you figure out the domain name for your newsletter business: Buying A Domain For Your Newsletter Business - 5 Things To Figure Out

It is Now time to jump into the specific things you must consider when choosing the newsletter business software solution that will work best for you as you scale up your business to success.

Table Of Contents

Searching For Newsletter Business Software Is Hard and Confusing (Especially If You Have Never Done It Before)

Eliminate The Confusion, Frustration and Overwhelm By Answering These 18 Questions Below About The Future of Your Newsletter Business, So That You Can Easily Pick The Best Newsletter Business Software On The Market For Your Business

Ready To Search For The Newsletter Business Software That Will Power Your Business?

It’s Time To Search For The Best Newsletter Business Software

Searching For Newsletter Business Software Is Hard and Confusing (Especially If You Have Never Done It Before)

We are not going to sugarcoat this one!

If you know absolutely nothing about starting a newsletter business, and/or have never purchased this kind of software before, jumping right into the market as a potential customer while using a search engine to find the “best newsletter business solution” will absolutely be overwhelming for you.

To help you understand what we mean, please keep reading.

Example Search Terms That Will Create A Lot of Confusion Quickly
  • “newsletter software”

  • “email newsletter software”

  • “email marketing”

  • “email marketing software”

  • “newsletter business software”

  • “software for newsletter businesses”

  • “software for newsletter business owners”

When you type any of these search terms into a search engine, you are instantly hit with multiple paid ads from many email marketing companies right at the top of the page.

As you scroll down the list of search results you have multiple links to click.

Some links in the search results are company websites selling newsletter business software.

Others links take you to specific articles that have been written about particular newsletter business software solutions.

As you begin clicking some of the links, and reading what has been written, you begin to realize that there are so many different solutions to choose from, which leaves you with the feeling of not really knowing what to choose at that moment.

That is why this article was written. We want to help you get the clarity you need to choose the best solution for you, and the future of your newsletter business.

The key thing to always remember while doing this kind of research is that there is no “one size fits all” solution, but you can still find the solution you need if you know what to look for!

Get Out Your Notebook Because It’s Time To Do Some Work!

Eliminate The Confusion, Frustration and Overwhelm By Answering These 18 Questions Below About The Future of Your Newsletter Business, So That You Can Easily Pick The Best Newsletter Business Software On The Market For Your Business

To eliminate the confusion and overwhelm that is connected to finding the best newsletter software solution, the first thing you need to do is step back and consider the answers you will come up with to these 18 questions first.

By having the answers to these 18 questions in front of you as you search the market for the best newsletter business software for you…

It will help you eliminate specific newsletter software platforms quickly from your potential list that don’t make sense for you or the future of your business.

Question #1

If you had to write out the vision for your newsletter business, in as much detail as possible (where you explain what will be done for visitors to your website, and newsletter subscribers, on a daily, weekly, monthly, quarterly and yearly basis) what would it say?

Writing out a vision for your newsletter business will give you the clarity you need when it comes to selecting the best software solution for the future of the business.

When creating your newsletter business vision, you want to focus exactly on what you plan on doing for your website visitors (and newsletter subscribers) on a daily, weekly, monthly, quarterly and yearly basis.

When you are 100% clear about how everything will run each month in your business, it will then allow you to figure out what specific features you want to have inside of the software platform you choose.

A part of your daily/weekly vision that you take the time to write out can look something like this:

Here is an example of a “Newsletter Business Vision”

“I will publish at least one piece of content to my newsletter business website every 7 days for new and future visitors to consume, and will be sending at least one email newsletter to my subscriber list once per week…”

“Every time I publish a piece of content on my newsletter business website, I will promote it via my social media channels doing A,B, and C.”

“I will also include a link to the specific piece of content I published in the newsletter for that week (with some teaser copy that makes sense) along with the other content I plan on including in the weekly newsletter I send that week…”

Question #2

What experience do you want to create on your newsletter business website for new visitors?

Keep in mind that most of the traffic that will hit your newsletter business website over the lifetime of your business will be brand new traffic.

Think about where you want the majority of your new visitors to “start” on your website, and how you want to craft that “custom” experience for them in a way that adds value, so that they want to sign up for what you are creating.

Make sure to think from these potential starting points on your newsletter business website.

Potential New Visitor Starting Points

(The Main URL To Your Website)

Newsletter Issue Page
(All Published Newsletters (Individual Issue))

Article Page
(Content Published To Attract Target Visitors(Individual Article))

Newsletter Sign Up Page
(Page That Builds Your Newsletter List)

Content Library Page
(Creates An Engaging Content Experience)

Archive Page
(Past Articles or Newsletters That Have Been Published)

Question #3

What experience do you want to create on your newsletter business website for returning visitors?

Knowing that a “segment” of your traffic will be visitors that return to your website (because they like the content and/or arrived there from a link in your newsletter), think about what specific things you want to have for them as well.

Building a long-term valuable relationship with your returning visitors will build more trust over time, and help you grow even faster over the long run.

Sit there right now, and put yourself in the shoes of a returning visitor.

Think about these specific questions from their point of view, and write down what comes up.

This exercise will really work your “empathy muscle” in a good way because it will force you to do the best you can to make sure your newsletter business site meets the “returning visitor” in the best way possible.

Questions From The Returning Visitors Perspective

Where will you want to go on the website as a returning visitor?

What will you want to read?

What will you want to check multiple times per week or per month?

What other things do you believe that you will want to do when you return to the website as a returning visitor?

Question #4

What experience do you want to create on your newsletter business website for those who visit it from paid traffic campaigns that you run online or offline?

If you are a serious newsletter business owner, you will most likely be spending money in the future driving traffic to your newsletter business website (via paid advertising) to build authority in your marketplace, and to build your subscriber list faster.

Think about what you want to create for this kind of traffic, and what you want to make sure that you have set up to handle this kind of traffic in the future.

Question #5

What experience do you want to create on your newsletter business website for people who choose to “Say Yes” to signing up for your online email newsletter?

When someone subscribes to your newsletter, what kind of experience do you want them to have during the signup process?

Do you want them to submit their email, and land on a page welcoming them to the newsletter, and then send them a welcome email where you insert a special call to action?

What is that call to action when they receive that email?

These are all important questions to ask, and you want to make sure your newsletter sign up process addresses each one!

Remember this…

You get to create the experience you want for all new subscribers.

Making sure your newsletter business software has the ability to customize the “sign up process” that you want to create is key.

Question #6

Do you want your brand new subscribers to go through a welcome series of emails within the first two weeks after becoming a brand new newsletter subscriber?

Sometimes, certain newsletter business owners want to create an “indoctrination sequence” for all new subscribers to the newsletter.

These “indoctrination sequences” allow new subscribers to “get up to speed” with the newsletter business in less than 7 days before the next newsletter is sent (assuming you send your newsletter on a frequency where you send one every 7 days).

The emails you send to brand new subscribers between the time they sign up, and the time that they receive the next newsletter, allows you to build even more trust and rapport with them (which is a good thing).

If adding an “indoctrination” experience for new subscribers is important to you, you want to make sure that this functionality is possible with the tool that you choose.

Question #7

When sending your email newsletter to your newsletter subscriber list, what features do you want to have available to you when designing the email newsletter content for your subscribers?

Designing the email newsletter that you send, and having the features you want in the email editor (to make your message look exactly the way you want it to look) is really important.

If you don’t have the features or functionality that you desire in the tool that you choose (for design purposes), working with your newsletter business software will be a total headache for you right from the start, and will always be something that you complain about!

Take a moment to write down the design elements you want in each email newsletter message, so when you are looking at certain newsletter software solutions, you will be able to easily select the one with the feature set that you want.

An example of something like this would be illustrated by a newsletter business owner saying…

“I want to have the ability to put a border around a block of copy I wrote in the email newsletter itself, and make it whatever color I want.”

Question #8

Do you want your email newsletter to be sent to your subscriber list AND published to your newsletter business website at the same time with one click?

Depending on what newsletter business software you choose, will determine if this feature is even possible for you or not.

Some of the software solutions provide this feature to you, while others don’t.

If this feature is important to you, write down “one click” on your paper right now and circle it, so you can make sure to use this “filtering mechanism” when going through the tools that you are considering.

By having this feature in your software solution will save you a lot of time and headache!

Question #9

Do you want your newsletter business website to have a navigation bar with separate pages that give you the freedom to customize those pages any way you want?

Sometimes on a newsletter business website, it makes sense to have a navigation bar at the top of the website with different pages of content to cater to new and returning users.

If you are on a computer right now…

You can explore the top menu bar of our website.

You will see that the menu items are clearly labeled, and each menu item you see has been placed there for a specific reason. Each one caters to either new visitors or returning visitors.

Feel free to scroll up to figure out what menu items cater to each type of visitor, and then dive deep into each one of the pages to see how we have set it up to scale up as more traffic comes into this website.

If you are on a mobile device right now…

You can click the menu bar icon in the top right hand corner of this page.

There you will see how we have set up the menu bar in the mobile environment for you to have access to whatever you need right now.

Given the specific experience you want new and returning visitors to have over the lifetime of your newsletter business, will determine if having this feature is important to you or not

Write down “nav bar” and circle it on your paper if you want to make sure that this feature is available to you with the solution you choose.

Question #10

Do you want your newsletter business website to have “deep link” pages that you will be able to “leave out of the navigation bar” of your newsletter business website?

Sometimes as a newsletter business owner, you will want to create what are called “deep-link” pages.

These “deep-link” pages are specific pages of your website that are still connected to your website, but are not required to be in the navigation or menu bar at the top of the website.

You can send free or paid traffic into these specific “deep link” pages in any way that you choose to (depending on what your goals are) for your newsletter business.

These “deep link” pages also give you a lot of freedom and flexibility with your websites functionality over the long run.

Here Is An Example To Help You Understand What We Mean

If you plan on creating digital products that you want to sale on your newsletter business website, each one of those pages will need a “deep link” page that is created.

Each one of these “deep link” pages will be selling a specific digital product, but will NOT be added into the website menu bar of your newsletter business site (unless you want it to be).

If you want to drive traffic to this specific “deep link” page in the future, you will just need to get access to it by going into the backend of your newsletter business software tool to copy the link that you will use.

There are many ways to take this “deep link” page conversation to the next level, but that is for another article to be published in the future on this website.

Depending on the type of newsletter business you want to build, and your personal motivations for doing so over the long run, will depend on if this feature is important to you or not.

Question #11

Do you want your email newsletter business to have a referral program that allows your current subscriber list to refer their friends and contacts with a unique link, and then get rewarded for doing so?

If you want your newsletter subscriber list to grow exponentially over a specific period of time, then you will want to make sure that your newsletter business software solution has this specific feature.

Imagine this for a second…

Imagine being able to give each one of your newsletter subscribers their own special link to drive traffic to your newsletter sign up page.

And then…

Your friend sends a 100 emails out to his friends list driving traffic to their special link.

And then…

A certain number of those people sign up for your newsletter.

And then…

You can decide to reward your friend for the # of referrals he sent you in whatever way you choose.

If it is not already clear by now, this is what we mean when we ask…

“Does your newsletter software solution have a “referral program” feature that can help you grow subscribers through unique links that track referrals?”

As you have probably figured out by now…

This feature allows you to leverage your current audience to grow your newsletter list even bigger without having to spend money on ads or other paid traffic methods.

If this feature is important to you, write down “referral program” on your piece of paper so you make sure the solution you choose has it!

If you really want to have this feature in your specific software solution, make sure that this is the very first feature that you look for when examining the list of features and benefits for each piece of software you are considering.

Here’s why using this “trick” when you look at certain solutions makes sense, if this feature is something you absolutely want…

Most of the email marketing programs (and other newsletter business software programs) do not have a feature like this.

This means that by solely using this one feature as your key “sorting mechanism” while your search in the market, it will allow you to narrow down the newsletter software solutions for you to consider in a more efficient way.

Question #12

Do you want your email newsletter software to have their own advertising network that you can “plug in” to that will help you to monetize your newsletter more effectively?

If monetizing your newsletter is really important to you, and you want a little help from the newsletter software company you ultimately go with, write down “ad network” on your piece of paper.

This is what you need to understand about a feature like this…

Given the way the newsletter business is evolving, software providers serving the “newsletter niche” must continue to add more valuable features into their specific software solution, so that they can stay competitive to current and future customers who want to enter into this type of business.

By plugging into, and using a feature like this, it will make monetizing your newsletter a little easier over the long run even if you sell your own ads in your newsletter’s publication in the future.

Question #13

Do you want your newsletter business software solution to give you an analytics dashboard that provides you key information about your websites traffic, and subscribers behavior so that you can be more effective in building your newsletter business?

Because you have read this far in this article, we are going to assume that you are serious about the future of your newsletter.

We will also assume that you most likely know and understand that having an analytics dashboard that is easy to look at and understand will be crucial to the growth of your newsletter business.

Take the time you need to look at the analytics feature set for each newsletter business software you are considering.

You want to make sure that it “checks all the boxes” for what you need before you decide to pull the trigger on the solution you choose.

A great place to start here with this question is this: What analytics data do I want to know for each newsletter that I send to my subscriber list?

The next question to ask yourself is: Is there anything else I want to make sure the analytics dashboard has before?

Question #14

Do you want the freedom to send specific emails to segments of your newsletter list (through special segmentation features) to help you grow your business more effectively?

If you want the freedom to send specific broadcast email to certain segments of your newsletter list (based on certain factors, criteria and other data points that make sense), make sure that you take note of this.

Follow These 4 Steps If You Want This Specific Feature

Step #1: Find the web page on the software product’s website you are considering that talk about the features/benefits.

Step #2: Look for the words “segmentation” or “advanced segmentation” in the list of features.

Step #3: If you see either one of those “segmentation” key words, you are golden!

Step #4: To confirm that the segmentation feature is set up the way you want it to be, send an email to the software company asking how their “segmentation feature” works, or find a video on the company’s YouTube channel that shows you exactly what can be done with it. This will either seal the deal for you, or force you to look elsewhere for another solution.

Question #15

Do you want the ability to create special audience polls, and insert them into your website and future newsletters?

If you see yourself adding polls into your newsletter business website and/or in certain email newsletters, make sure to look for this feature on the products website.

By creating specific audience polls on your website (and inside of specific newsletters), it will allow you to create another layer of data about your subscribers to help you make better decisions over the long run as you continue growing and scaling your newsletter up to serve more people.

Question #16

Do you want the flexibility to “add on” a paid newsletter subscription in the future, while still managing and creating content for your free newsletter too?

If you know that want to begin your newsletter business with a free newsletter, and then add on “paid” newsletter experience later (or have the option to), you need to make sure that the software solution you choose makes it easy for you get it done.

The last thing you want to do is make the process of adding a paid newsletter into your newsletter business difficult for you.

If you are reading this right now, and thinking that you are only going to ever create a free newsletter for your subscribers, accept the fact that in the future, you may change your mind about it.

Making it easy to add on a paid newsletter in the future (on top of your free newsletter that’s already up and running) should be quick, fast and easy without creating any challenges or hassles.

Question #17

Do you want to have the ability to have a pop-up message show up on your website for content you create that encourages visitors to sign up for your newsletter without disrupting the content reading experience?

Aside from having a newsletter business software platform that helps you publish and send newsletters to your newsletter subscriber list, do you want your newsletter software program to give you the special option that allows you to grow your subscriber list more effectively through the use of strategically placed pop-ups on current articles and future newsletters?

Here Is An Example Of What This Feature Does

Imagine that you write a piece of content on your newsletter business website that you know new visitors (who aren’t subscribers yet) will appreciate reading.

And then…

Imagine being able to invite them to subscribe to your newsletter through a strategically placed popup after they have read 50% of the article that they are fully engaged in?

Would that be valuable for you to use on certain pieces of content?

That is what is possible with a feature like this.

This also assumes that you will always have high-quality content on your website (not previous newsletter issues, but value-centric articles…like the one you are reading on this page…that address specific issues that you know your subscribers are having that they need help solving).

We know, we know…

We know that the idea of a pop-up is annoying to most people, but there is no denying the fact that if you have a pop-up reminder to subscribe to your newsletter on certain pieces of content, there will always be a percentage of people who sign up for your newsletter list because of that popup.

Again, most newsletter software solutions don’t have this feature available to you, which is why we are bringing the question up here in this list.

This one “popup on content” feature will allow you to quickly eliminate most of the tools you may be considering, so feel free to use it as another way to sort through the plethora of newsletter software tools that are currently on the market.

Question #18

Do you want to have the ability to “lock” specific content for new visitors to your website where they will have to sign up for your newsletter list to get access to it?

Depending on the type of newsletter you are writing, and depending on the kind of experience you want to create for new and current subscribers, there may be times where you want to “lock” the content you publish on your website so that only newsletter subscribers on your list will be able to read it.

This feature can be used in multiple ways, but the experience you create with this one feature is 100% up to you.

How This “Lock” Feature Would Work In The Real World

Let’s say that you see an article in your facebook stream with a title to a newsletter issue that sparks your interest.

When you click the link to the newsletter issue, a page comes up that says “This content is only available for newsletter subscribers, sign up here to view read this newsletter issue now.”

At that point, you have a choice to either subscribe to the newsletter so you can read the content, or you click off.

Ready To Search For The Newsletter Business Software That Will Power Your Business?

After taking the time to finish answering all of these questions, and writing down all the notes that matter to you, you are now armed with everything you need to invest the time in searching for a software solution that makes sense for your newsletter business.


All newsletter business software solutions are NOT created equal, and there is no “one-size-fits-all” cookie cutter solution that works for everyone.

The software solution you ultimately decide on will boil down to selecting the features that you need that are in alignment with the vision that you want realize with your newsletter business for your subscribers.

Make sure you take the time to really think about the experience you want to create for every person that engages with your newsletter business at all the different stages of their journey with you.

Whether they are coming to your sign up page for the very first time, or visiting your website 6 months later to read a new article that you just published, thinking about the experience for each one of those individual matters and influences the software solution you will ultimately choose.

By exercising your “empathy muscle” here before you choose the software to start your newsletter business with, you will be well on your way to creating the best possible experience for everyone who engages with your business now and in the future.

Are You Ready To Start Your Newsletter Business?

Now That You Know The 18 Questions To Ask (And Answer) Before Buying Newsletter Business Software, Now Is The Time To Take Action…

Here at The Pursuit Newsletter, we are focused on serving the “online newsletter business owner” who wants to reach their newsletter business goals as quickly as possible.

The content on our site and in our email newsletter, will absolutely give you the “entrepreneurial edge” you need as you start, build and grow your online newsletter business into what you know it can become.

We Want to Make One Thing Very Clear To You…

If you have never started an online newsletter business before, or if you are currently building or growing an online newsletter business, and you need help getting to the next level…

We recommend that you sign up for our newsletter right now.

The content you will find on our website, and in our email newsletter, will absolutely help you in a major way as you continue your pursuit of being an online newsletter business owner that reaches their goals.

Make it a great day!

-The Pursuit Newsletter Team