An Automated Email Marketing Strategy Designed To Get Absurdly Amazing Results

Nicolas Algoedt

Dec 7, 2021

An Automated Email Marketing Strategy Designed To Get Absurdly Amazing Results Featured Image
Nicolas Algoedt

Dec 7, 2021

Email is one of the most lucrative marketing channels that almost any business can take advantage of. When done right, it’s a direct line of communication that you can automate to increase brand loyalty and sell your products and services. 

Of course, this is when it’s done right. If it’s not implemented correctly, emails from your company may end up unopened (maybe even in spam boxes), wasting money, and possibly pushing customers away from your brand. 

Thankfully, you’re reading this guide, which will walk you through an automated email marketing strategy that will capture leads and convert customers while you sleep. 

Table of Contents
  1. What Is Email Marketing?

  2. Why Is Email Marketing Important?

  3. Email Marketing Rules: GDPR, CASL, and CAN-SPAM

  4. Step 1: Choose An Email Marketing Service

  5. Step 2: Building Your Email List

  6. Step 3: Segmenting Your Subscribers

  7. Step 4: Email Automation

  8. Step 5: A/B Testing

  9. Step 6: General Tips For Email Success

  10. Get To It!

What Is Email Marketing?

Email marketing is a digital marketing channel that organizations use to send emails that promote their products, services, and brand. Because it can be tested, tailored, and automated based on the email recipient, email is the perfect channel to nurture leads, maximize conversions, and increase brand loyalty.

Why Is Email Marketing Important?

Email marketing is important for multiple reasons:

  • Ridiculous ROI – With the ability to create and automate funnels that convert, email marketing has a huge return on investment (ROI). A study by the Data & Marketing Association (DMA) found that for every dollar businesses spent on email, they averaged $42 in return.
  • Control – Email marketing does not put you at the will of another company’s algorithm as much as channels like social media & SEO do, giving you more control over when and how your marketing messages are received. 
  • Personalization – With email, you can tailor the individual experience for each of your subscribers to fit their needs, allowing you to send the right message, to the right customer, at the right time.

Email Marketing Rules: GDPR, CASL, and CAN-SPAM

Before you begin, you should know about the various laws and regulations that determine what you can do or say through this channel. Governments around the world have established regulations that affect email marketing, including CAN-SPAM in the United States, CASL in Canada, and the General Data Protection Regulation (GDPR) in Europe, all of which carry heavy fines for those that don’t abide.

As this page is in no way legal advice, you can and should read more about these regulations. However, here are some of the main things that email marketers should know to protect themselves and their businesses.


Just because you have their email address does not mean you can send promotional emails. People must “opt-in,” or consent to receive email marketing communications from you. In the case of GDPR, it can’t be implied or assumed.

An easy way to get consent is by having an unchecked box that asks the user to opt-in to email communications. Be sure to note about all the cool things they would be missing if they don’t. Take a look at Insider’s opt-in form for an example:

Graphical user interface, text, application

Description automatically generated

Another way to do this is with a double opt-in. This is when someone enters their email address, and the company sends a follow-up confirmation email that asks if the user wants to receive emails. This gets consent and ensures the email address is valid. 

Here’s an example of a double opt-in from the often-sarcastic device customization company, brand:

Graphical user interface, text, website

Description automatically generated

Keep Track Of Consent (GDPR)

You also need to keep a record of when and where all your email subscribers opted-in to your emails. 

Don’t Mislead or Be Deceptive

Don’t use deceptive or misleading email addresses, subject lines, or names. It should be clear that the email is coming from your organization or someone inside your organization. 

This is generally good advice for all your marketing efforts.


It should be easy to opt-out/unsubscribe from your email list and requests to opt-out should be honored promptly.

Step 1: Choose An Email Marketing Service

Okay, now that you know what email marketing is, why it’s important, and the rules you need to follow to do it right, we can get to the first step of your email marketing journey: selecting an email marketing service. 

Today, there are countless platforms that can help you send emails. However, for those that are serious about email marketing and getting the most out of their marketing efforts, Insider is the solution.


Description automatically generated

Insider does more than just help you collect and send emails. It’s a full-service growth management platform that can help you create the individualized cross-channel experiences that your customers desire. 

Using Insider’s powerful AI technology, email marketers can collect and analyze customer data to send hyper-personalized messaging faster than ever. More than that, this personalization can seamlessly expand across channels to maximize conversion rates. 

Step 2: Building Your Email List

After choosing an email marketing service, the next step is to start to build or grow your email list. To do that, you need to think about how you will incentivize your target clientele to subscribe. 

In other words, you need a lead magnet.

  1. Lead Magnets 101

A lead magnet is an incentive that you promote to incentivize potential or current customers to sign up for your email list. 

Lead magnets are often associated with free content that a company gives away, like an eBook. But this isn’t always the case. Your lead magnet could be anything that provides value to your customer. Here are some examples:

  • White Paper
  • eBooks
  • Templates
  • Discounts
  • Coupons
  • Special Promotions
  • Case Studies
  • Research Study
  • An Email Course
  • A Webinar
  • A Free Sample of Your Product/Service
  • Free Consultations 
  1. Understanding What Your Target Customer’s Needs

Of course, a lead magnet that works for one industry may not work for the other, so you need to understand your customer’s needs to find the right lead magnet for you.

For example, let’s say you sell supply chain software. If this is the case, you’re likely trying to sell to business professionals that need supply chain solutions. Those professionals are probably hungry for information that can solve their supply chain issues, so a white paper on effective supply chain strategy may be a fantastic lead magnet. 

On the other hand, if you are a B2C apparel company, your target customer wouldn’t want a complicated white paper that outlines the methods you use to manufacture your products. A much more enticing lead magnet for them would be a 20% off coupon.

Only you can understand the right lead magnet for your customer. Thankfully, you don’t only have one shot at this. You can try and test out multiple lead magnets to find the most effective one for your business.

  1. Promoting Your Lead Magnets

After you find the right lead magnet, you need to consider how you are going to get it in front of your target market. To do that, you will need to create an opt-in form where people can subscribe to your email list.

Here are a few ways to do that:

  • Homepage Opt-In Form – An easy way to get visitors to your site is to promote your lead magnet or email list on your website’s homepage.
  • Pop-Up – To ensure a user sees your lead magnet, use a pop-up.
  • Exit-Intent Pop-Up – Sometimes regular pop-ups can negatively impact user experience, so a better option may be an exit-intent pop-up. This only appears when the user’s mouse leaves the webpage. 
  • Landing Page – Create a specific page on your website that’s solely dedicated to your lead magnet. Landing pages allow you to test multiple versions of the page to see which converts the most visitors into subscribers. If you already have an email funnel that converts well, you can even use pay-per-click (PPC) ads to increase the number of subscriptions.
  • Social Media – You can also promote your landing page through your social media platforms to get some of your most loyal followers to sign up for your newsletter.
  • Resource Page – Have a page on your site solely dedicated to lead magnets. Take a look at Insider’s resource page for an example.
  • On Your Blog Post – If your lead magnet is related to a blog post, you can promote it through the post. This is especially advantageous for those with blog posts that get consistent organic traffic.
  • GamificationGamification is a unique way to stand out from your competition and capture leads for your email list. For example, Insider’s platform has the Wheel of Fortune, which allows users to spin for a discount or free trial. 

Graphical user interface, application

Description automatically generated

Step 3: Segmenting Your Subscribers

To take advantage of everything email marketing has to offer, segmentation is a must. 

Segmentation is when you categorize your potential and current customers based on certain attributes. It allows you to tailor and personalize your messaging based on the subscriber’s segment. 

Ways To Segment Your Email

You can segment your email list in many ways:

  • Purchase History
  • Demographics
  • New Subscribers
  • Location
  • Weather 
  • Interests
  • Which Lead Magnet They Subscribed Through
  • Engagement
  • Lead Score

When it comes to segmentation, you don’t only need to pick one. You can segment customers in multiple ways, and customers can belong to more than one segment. How you segment subscribers depends on the nature and needs of your business.

For example, a sporting goods store would likely segment by purchase history. This would allow the company to upsell customers with products related to the ones they purchased. So, if a customer purchases a golf club, the company could send them emails promoting its other golf-related products.

On the other hand, a consulting business that only sells one service would not benefit from segmenting by purchase history. With its email list, it would be better to segment by lead score, which assigns points to each subscriber based on their likelihood to purchase. Using these lead scores, the business could send conversion-focused emails to those with high scores and send more value-based emails to nurture those with lower scores.

The Importance Of Personalization

Segmentation allows you to personalize messages, which is extremely important in any email marketing strategy. Studies have shown that emails with personalized subject lines have 50% higher open rates and that personalized emails can generate 6 times higher transaction rates.

Remember, email can act as a direct line of communication between your business and your subscriber. Your emails should reflect that, and not be some generic mass message that may or may not be relevant to them.

Segmenting With Insider

Figuring out how you want to segment your customers may be easy enough, but ensuring that segmentation is effective, automated, and scalable is a different story. That’s why Insider’s predictive segmentation is so crucial.

A picture containing timeline

Description automatically generated

With Insider’s AI-powered predictive segmentation, you can automatically segment based on likelihood to purchase, likelihood to churn, discount affinity, lifetime value, and much more. In fact, there are over 120 attributes to segment every single one of your potential and current customers. 

Step 4: Email Automation

Email automation is when you automatically send personalized emails based on a subscriber’s actions or segmentation. These automated emails are called autoresponders, and once they’re set up and optimized to convert, your company will truly begin to see email marketing’s massive ROI potential.

The types of autoresponders you can create are almost limitless, but here are some of the most popular:

  • Lead Nurturing Autoresponder – Series of emails designed to nurture leads and connect them with your brand.
  • Sales Promotion Autoresponder – Sent to raise awareness of sales on your products or services and entice people to buy. 
  • Trigger-Based Autoresponder – Sent when a user takes a specific action that you set. With Insider, you can set triggers for entire cross-channel customer journeys
  • Lead Magnet Autoresponder – Lead magnets are often sent through autoresponders.
  • Abandoned Cart Autoresponder – Remind customers to complete their purchase. Quick tip: A series of three abandoned cart emails result in 69% more orders compared to sending just one.  

However, an autoresponder that’s a must for every email list is a “welcome” autoresponder.

Autoresponder Example: Welcome Autoresponder

There’s nothing worse than signing up to an email list and getting no indication that your sign-up was successful. That’s why it’s important to have an autoresponder set up to send a “welcome” email sequence.

At the very least, this should be an email you send after someone signs up to your email list that confirms that their sign-up was successful and thanks to them. However, this does not take full advantage of what a welcome sequence can do.

These emails may be your subscriber’s first impressions of your company, so it’s good to show the value it can provide. Here’s an example:

  1. Email #1: Sent After Sign Up – Say thank you for signing up and discuss some of the things they should expect as an email subscriber. Provide the lead magnet they signed up through (if applicable) and link some content/products they may be interested in. You can even use what they click on to learn about these subscribers and further segment them.
  2. Email #2: Sent 24 Hours After Sign Up – Send an email that focuses on a topic related to your product or service. It could focus on a specific problem that your target market often faces.  
  3. Email #3: Sent 2 Days After Sign Up – Offer something of value outside of your lead magnet. This could be another piece of content that expands on the email from the day before, a free consultation, or maybe an exclusive new subscriber sale. 
  4. Email #4: Sent 3 Days After Sign Up – Send a success story about how someone overcame their problem with your business’s/product’s help. You can also promote the offer from email #3 again.  
  5. Email #5: Sent 4 Days After Sign Up – In this last email, you can directly promote how your business or product can solve your customer’s problem and go in for the sale. 

This is just one example, and the welcome sequence that works for your business may be different.

However, the general advice is if you’re trying to nurture leads, you don’t want to try and sell them right away. You want to focus on providing value and free solutions to their problems, which often comes in the form of free content.

On the other hand, if your subscribers have already shown intent to purchase from you, it may be best to go straight for the sale. Still, providing value in the form of limited-time discounts or sales will get your customers excited about your email list and get them hooked on your brand.

Step 5: A/B Testing

Okay, at this point in the guide, you have the overall idea of how to build and automate your email list. Now we are going to go a little more into detail about how you test and perfect your emails for maximum impact.

To do that, you will need to perform A/B tests, or split tests. This is when you test two versions of the same email to see which one is more effective. Here are the basics for email split testing:

  1. Formulate A Hypothesis – Come up with a specific hypothesis to test. For example, you could hypothesize that a shorter subject line will increase an email’s open rate. 
  2. Create A Second Version To Test – Create another version of the email that will test your hypothesis. Only the variable you are testing should be different. All other variables should stay the same. For example, if you’re testing two different subject lines, the subject lines should be the only thing that’s different between the two emails. If it’s not, you may not know the true cause of your results.
  3. Run Your Test & Analyze The Results – Take a segment of subscribers and split them into two test groups. Send one group the original email and send the second version to the other group. You can then implement the version that gets better results.

While almost everyone will run A/B tests on subject lines, they are not the only thing that you can experiment with. You can use split tests to find which call to action (CTA) has the highest clickthrough rate, which autoresponder has a higher conversion rate, and more. 

Know Your Email KPIs

To monitor your email lists performance and run split tests, you need to know some of the key performance indicators (KPIs) for email:

  • Open Rate – The percentage of subscribers that open a particular email
  • Clickthrough Rate (CTR) – The percentage of subscribers that click on an email link to your site or another site. 
  • Conversion Rate – The percentage of subscribers that purchase something through an email.
  • Bounce Rate – The percentage of emails that do not reach your subscriber’s inbox. 
  • Unsubscribe Rate – The percentage of subscribers that unsubscribe from your list after opening a particular email.
  • Forwarding Rate – The percentage of subscribers that forward an email.
  • ROI – The return on investment for your email marketing efforts.

Step 6: General Tips For Email Success

Throughout the rest of this post, we are going to discuss some general tips for your email content, subject lines, timing, and frequency. 

It’s important to note that this is general advice and won’t work for everyone. If you have a gut feeling that something said here may not apply to your business, test it! That’s what A/B tests are for.

Email Content: What Should You Send Your Subscribers

This is an area where there are not too many general rules outside of “provide value.” But it can be hard to say what that is. In some industries, customers may love long-form informational emails with unique insights. In others, they just want to see emails with high-quality images that showcase the business’s product offerings.

You should ask yourself what your target customer/client wants from your email list. For ideas and a place to start, you can sign up for some of your competitors’ email lists to see what their email content consists of.

Optimize For Mobile

However, if there’s one rule that everyone should follow when it comes to your email content, it’s to optimize for mobile. According to Adobe, 85% of users use smartphones to access their email. If your subscriber can’t easily read your emails on their phone, they are much more likely to ignore your emails or unsub from your email list.

Subject Lines: Increase Open Rates

The right subject lines could be the difference between 2% open rates and 30% open rates. Taking your time to craft and test out subject lines that work for your business can make or break a campaign.

The basic advice is to keep your subject lines between 40 and 60 characters to ensure they won’t be truncated. But with so many using phones to check email, many are trying to shoot for 40 characters or less.

Here are some other good rules to follow:

  • Create Urgency – Emphasizing that an offering is only available for a limited time can increase open rates.  
  • Personalization – Already touched upon this, but email rates with personalized subject lines have been shown to have 50% higher open rates.  
  • Be Concise – A short and concise subject line is often more powerful than a longer one.
  • Allude To What’s In The Email – Pique your subscriber’s interest by alluding to what’s in the email with a question or a provocative statement. Be careful with this one though. If you go too far and misrepresent what’s in your email, it could end up labeled as spam.

Email Timing: When Should You Send Your Emails

When working on your autoresponders, you’ll want to spend a good amount of time testing which days and times of day have the highest open and conversion rates.

Studies show that the best time to send your marketing materials is midday Tuesday, Wednesday, and Thursday. But again, every industry is different.

For example, every Saturday between 3-5 PM, Domino’s pizza sends out an email. This breaks the rule outlined in the paragraph above, but this likely doesn’t matter for a pizza company. People still need to eat on the weekend, and 3-5 PM is when people start thinking about what they want for dinner.  

A picture containing application

Description automatically generated

Email Frequency: How Often You Should Send Emails

Finding the right number of emails to send is about striking a balance. You need to send enough so your emails don’t get lost and your customer doesn’t forget about you, but you also need to not send so many that your customer gets annoyed and unsubscribes.

At the very least, you should send out one to two high-value emails a month. However, you shouldn’t be afraid to do more. A study of 2,057 US adults found that over 60% of people want businesses to send them emails at least once a week. More than that, 15% say they want daily emails.  

Again, as with email content, look around to see what competitors in your industry are doing to see where to start. If you’re experimenting with a higher email volume, you should add an option next to the unsubscribe button that lets your customer choose to lower the number of emails they receive from you. 

Get To It!

That’s it! You have everything that you need to implement an automated email marketing system that will bring in leads, convert customers, and increase brand loyalty all on its own. Be sure to check out Insider and its email marketing capabilities to see all the ways our growth management platform can help your business.

Or you can talk to our experts and request a demo to see Insider in action.

Nicolas is VP of Marketing EMEA at Insider. Passionate about new technologies and e-commerce, Nicolas has held various position at leading e-commerce and tech companies including Groupon, Microsoft and Bwin.