Send it: Email marketing automation strategy to increase engagement

Christoph Trappe 5 minute read

Email marketing automation strategy remains a highly effective growth marketing channel for engaging customers and driving sales. That’s especially true since manual email marketing takes time. A good email marketing automation strategy allows marketers to scale their efforts and nurture relationships in an effective, relevant way.

In this article, we’ll explore email automation best practices, common pitfalls to avoid, and optimization strategies to help create more engagement in less time. Drawing on insights from marketing experts Chad White and Jeanne Jennings, we’ll cover:

Let’s dive in!

The Power of Email Marketing Automation Strategy

Indeed, a good email marketing automation strategy involves pre-programmed “if-then” logic to trigger emails based on user actions and preferences. This allows you to engage subscribers in a relevant, timely way without manual effort.

As Jeanne explains, Email automation lets you do more with less. It’s not necessarily set it and forget it, but leads to revenue because you set up an automation stream, triggered by a customer action or something else that happens, and then it goes out automatically.

Moreover, key benefits of email automation include:

  • Saves time by eliminating repetitive manual tasks
  • Allows you to scale your marketing efforts
  • Delivers timely, relevant messaging based on user behavior
  • Nurtures relationships and moves prospects down the funnel

While cold outreach email automation is possible, most experts recommend focusing your automation on subscribers who have opted in and existing customers. This helps build trust and loyalty. As Chad White explains, “Just because you have someone’s email address doesn’t mean that they’ve opted in…that permission part of things is really, really critical.”

Workshop alert: Understand your customer journey to draft better email campaigns

Must-Follow Email Marketing Rules

While automation can save time, effective email marketing still requires understanding best practices around deliverability, compliance, list growth, and more. As Chad emphasizes:

“I feel like email marketing rules are rooted in all of those shareholders – subscribers, inbox providers, governments, and businesses. You can feel free to try to break the rules, but most of the time, you’re just going against what consumers expect.”

Some of Chad’s top “must-follow” rules include:

  • Get clear opt-in consent: Never add someone to a marketing list without their permission. Use clear opt-in checkboxes, not pre-checked boxes.
  • Honor unsubscribe requests immediately: This is the law in most countries. Some ESPs will handle this automatically.
  • Include physical mailing address: Legally required in email footers in most countries.
  • Limit email frequency: – Avoid sending too often, which can lead to complaints, unsubscribes, and blocks. What’s the right amount to send depends on your audience.
  • Maintain list hygiene: Keep your list updated by pruning inactive subscribers and honoring opt-out requests.

Chad emphasizes that while some rules are flexible, others are firmly rooted in subscriber expectations and provider requirements. Follow email marketing rules to avoid deliverability issues, spam folders, blocks, and complaints.

Read next: Decode marketing performance: What is attribution in marketing?

Crafting Effective Automation Workflows

Once you have the basics down, it’s time to map out automation workflows to nurture subscribers. Jeanne suggests taking an in-depth look at your customer journey to identify key opportunities.

Some effective starting points include:

  • Welcome series: Onboard new subscribers by introducing your brand, content, and offers.
  • Browse abandonment: Win back customers who browsed your site.
  • Milestone or renewal reminders: Mark anniversaries, contract renewals, etc.
  • Re-engagement campaigns: Bring inactive subscribers back into the fold.
  • Nurturing sequences: Share educational and thought-leadership content and pieces of it from interesting company blog posts or a branded podcast to stay top of mind and useful with prospects.

Jeanne explains her optimization process: “With my clients, we set up a schedule, and we know the automations that we have running… We’ll check automations at least every six months, sometimes every three months or every month, to make sure the links are still working, the images are showing up.”

This allows you to monitor for any issues and identify opportunities to improve performance. Don’t “set and forget” your automations – revisit them regularly and optimize!

Read next: Driving pipeline: What goes into setting up a CRM correctly?

Optimizing Subject Lines and Content

Crafting compelling subject lines and content is key for email automation success. As Jeanne explains: “No one out there, no AI, no one can tell you what your audience actually wants, what’s actually going to resonate with your specific audience. And that’s why we do optimization.”

Follow these tips to optimize your automated emails:

Test different subject lines

Get ideas from tools like Use clear calls to action tailored to email. And then A/B test them.

Personalized content

Include merge fields to tailor content to subscribers’ names, interests, and history with your brand. Get more advanced with dynamic content blocks for greater personalization.

Match content to subscriber lifecycle stage

Send different information to new leads vs. long-time customers. Jeanne notes: “Content for people at the top of your business funnel will be very different from the content you send to people at the bottom of your business funnel.”

Experiment with different senders

See if automation sent “from” a person performs better than a generic brand name. Use A/B testing to determine the optimal approach.

Test days and times

While weekday business hours are fairly universal for email sends, you may find certain days/times improve open and click rates in your niche. Consider subscribers’ time zones as well.

With tools like HubSpot you can also send an email based on the recipients’ time zone, so instead of everyone getting the email at 2 p.m. YOUR time, they get it at 2 p.m. THEIR time no matter where they are.

Jeanne summarizes: “You never really know what’s going to work with your audience unless you test it. And if you choose the wrong thing, then you’re taking your program in the wrong direction.”

Testing and Iterating to Boost Performance

To explain, the key to long-term email automation success is continually testing and optimizing based on data.

As Jeanne explains: “ is the first of a two-step process…Those hypotheses are just the starting point. Because you never really know what’s going to work with your audience until you test it.”

Here are tips for optimizing through testing:

Start with a hypothesis

Make an educated guess about what subject line, content, or approach will perform best. Tools can help generate initial ideas.

Set up A/B split tests

Send one version to a portion of your list and another version to a different segment. Randomly divide your list.

Analyze performance

Then look at a conversion rate or revenue metric to identify the winning variation. This is important since a higher open rate or higher click-through rate isn’t a good indicator of more conversions or higher revenue.

Implement the winner

Roll out the best-performing version to your full list moving forward.

Many CRMs and email sending platforms allow you to send the tests to a small subset of your list, then will choose the winner dynamically and send to the remaining list.  This functionality makes A/B testing even easier!

Test frequently

Continually test new hypotheses over time. Don’t get complacent – there’s always room for improvement.

Leverage testing to determine the optimal approaches for your audience across every aspect of your automation campaigns.

Final thoughts

Email automation provides a scalable way to engage and convert subscribers based on behaviors. Focus on driving value for your audience while following established email marketing rules. Map automation workflows to key touchpoints throughout the customer journey. Continually optimize and test emails to improve revenue and conversion performance.

As Jeanne notes, “The more you can automate your standard business practices, the more time you’re going to free up for optimization and for higher level thinking.” Work smarter, not harder, with strategic email marketing automation.



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