A Small Business Guide to Explosive Email Marketing Follow-Up

David Baer
Small Business Marketing Strategy
6 min readNov 11, 2023

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You know that classic bomb defusing scene where the film’s hero has to choose just the right wire to save everyone?

In some respects… that’s email marketing — except the bomb is your business, and the right wire is the send button.

You’re knee-deep in the digital trenches, trying to get your message across in a sea of inbox overload.

The thing is, while the world’s been chasing after the newest shiny object in tech (like not-ready-for-primetime AI chatbots or LinkedIn Cold DM automation)…

…the old guard — email — has been quietly, effectively, winning battles in the background.

Now, imagine if every email you sent was like a chess move, strategic and precise, leading you to a checkmate — that is, more sales.

The pawn in this game?

Follow-up (the most underrated player on the board, often forgotten until it’s too late).

Here’s the funny thing: some folks treat email follow-ups like they’re the plague-bearing rat of the digital world — steering clear so they don’t risk contamination.

But what if I told you that the secret to more revenue was actually… more emails?

Stick with me here.

The art of email automation is like gardening; you plant seeds (emails), then nurture them (follow-ups), and watch them grow (sales).

Your garden needs consistent care, and so do your leads.

Let’s break it down:

Imagine your email campaign as a series of dominos meticulously lined up.

Each email is a domino, and the actions of your prospects are the flick that sets everything in motion.

Your job is to align these dominos so perfectly that once the chain reaction starts, it leads inexorably to a sale.

Behavioral Stages: The Fine Art of Reading Digital Tea Leaves

This is where you play detective.

Did they peek at your offer? Ignore your cart?

Track their moves, tag accordingly, and let your email sequence do the tango around their actions (or inactions).

  • The Window Shoppers: Let’s say a prospect peeks at your offer but doesn’t bite. Tag ’em: “Curious — Needs a Push.” Follow up with an email that nudges them closer to the edge of decision-making. Something akin to a little whisper in their ear at just the right moment.
  • Example: “Noticed you checking out the Ultimate Business Booster. It’s the protein shake for your profit muscles — why watch from the sidelines when you could be in the game?”
  • The Hesitators: They fill their carts but abandon ship like a nervous bride or groom at the altar. Tag ’em: “Cart — Deserted.” Your next move? A reminder that’s like the scent of fresh apple pie wafting from the window, impossible to ignore.
  • Example: “Looks like you left something behind. It’s not Cinderella’s slipper, but it’s just as valuable. Plus, here’s a slice of pie (aka a discount) to sweeten the return.”

Contingencies: Your Email Campaign’s Secret Weapon

Here’s where it gets fun.

They didn’t click? Didn’t buy? Missed your killer pitch?

It’s not the end — it’s just a twist in the plot.

Enter contingency-based follow-up sequences, the plot twist in your marketing story that brings them back to the main storyline — your sales funnel.

  • The ‘Too Busy for Clicks’ Crowd: Some prospects treat your CTA as if it’s coated in Teflon — nothing sticks. Tag ’em: “CTA — Skipped.” Hit them with something that’s part ‘Hail Mary,’ part ‘Eureka!’ moment.
  • Example: “Seems our ‘Learn More’ button’s gone incognito. We’ve sent out a search party, and look what we found: a treasure trove of insights, just one click away.”
  • The Tire Kickers: The ones who perennially kick the tires but never drive off the lot. Tag ’em: “Offer — Passed.” They need a sequence that’s half educational seminar, half fireside chat — something that says, “I understand you.”
  • Example: “You’re circling, I get it. It’s a big decision. Here’s how others made the leap and didn’t just survive — they thrived.”

Tagging: The Compass in the Forest of Commerce

Imagine each tag as a breadcrumb on the trail to customer enlightenment.

No click? Leave a breadcrumb. Webinar no-show? Another breadcrumb.

These tags guide your follow-up sequence like a wise old owl leading the way through a dark forest.

  • Ghosts at the Feast: They RSVP but don’t show to your webinar. Tag ’em: “Webinar — Ghosted.” Send them a recording with a note that’s the digital equivalent of “Wish you were here.”
  • Example: “We missed your voice in the conversation today. But fear not, the party’s still going with this replay. Pull up a chair and join in, on your terms.”
  • Watchers in the Wings: For those who consume your content like a critic at a movie premiere, silently and judiciously. Tag ’em: “Content — Consumed.” They’re biding their time, and your job is to draw back the curtain for their grand entrance.
  • Example: “I see you there, enjoying the show. Ready for a backstage pass? Let’s peel back the curtain together and reveal how the magic happens.”

In essence, your email campaign is not a barrage but a symphony, each note played at just the right tempo to bring the house down — ‘the house’ being any barriers to sale, of course.

This isn’t just ‘spray and pray’ marketing.

This is strategic, calculated, and personalized.

It’s a system that turns prospects into buyers and browsers into believers.

It’s not just about sending emails; it’s about sending the right emails at the right time to the right people.

And that’s where the real gold is.

Time For Some AI Alchemy…

Give this prompt a try using ChatGPT, Claude, or your favorite advanced AI tool:

Act as a seasoned Fortune 500 Email Marketing Strategist and Educator. Your mission is to craft a masterclass-level guide on developing a sophisticated follow-up email sequence tailored to lead behaviors within a digital marketing campaign.

Begin by meticulously defining the behavioral stages relevant to a specific product or service engagement in an email campaign — such as clicking a link, viewing a product, or ignoring the email altogether. Illustrate each stage with real-world examples from high-performing campaigns, explaining the significance of these behaviors in understanding customer intent.

Construct comprehensive contingency plans for each behavioral stage, detailing strategies to re-engage leads at critical points in their journey. Discuss the psychological principles behind each tactic and provide case studies on successful re-engagement campaigns, emphasizing what to do if leads deviate from the anticipated conversion path.

Develop a systematic approach for creating and applying tagging categories within an email campaign to accurately monitor and react to user actions. Provide a step-by-step guide on setting up these tags in common email marketing platforms, and explain how this data-driven strategy can yield insights for optimizing the email sequence.

Design an intricate series of follow-up emails, with each one uniquely tailored to respond to the leads’ tagged actions. Offer templates that incorporate best practices in email copywriting, design, and call-to-action placement, each designed to incrementally move the lead closer to the final desired action — whether that be a sale, a consultation, or another measurable conversion goal.

To effectively operationalize this plan, input detailed specifications of the product or service you are marketing, along with the existing structure of your email campaign — identifying current strengths, weaknesses, and opportunities for enhancement based on the enhanced strategies provided.

Your end goal is to equip email marketing strategists with a deeply analytical, behavior-driven approach to lead nurturing that significantly boosts engagement and conversion rates for Fortune 500-level companies.

Each email is a critical decision point, a chance to defuse customer doubts and objections with surgical precision.

And when you do it right, when you follow the blueprint I’ve laid out, you’re not just avoiding a marketing mishap — you’re orchestrating a symphony of success, where every note is a cha-ching of your cash register.

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David Baer
Small Business Marketing Strategy

Longtime marketer writing and thinking about strategic and systematic small business marketing + artificial intelligence