Email Marketing and Automation

The Email That Started Everything

In the previous lesson, we explored campaign planning and execution. Now let’s build on that foundation. Before social media algorithms, before SEO, before influencer marketing—there was email. And here’s the thing: email still outperforms every other channel for conversion. The average ROI is $36 for every $1 spent.

Yet most marketing emails are terrible. “New feature announcement! Click here!” Or worse: “Hey {FIRST_NAME}, just checking in…”

Great email marketing doesn’t feel like marketing. It feels like a smart friend sharing exactly what you need, right when you need it. AI helps you create that experience at scale—personalized, well-timed, and genuinely useful.

The Three Essential Sequences

Every business needs these three email sequences:

1. Welcome Sequence — Turns subscribers into engaged fans 2. Nurture Sequence — Turns fans into customers 3. Win-Back Sequence — Re-engages people who’ve gone quiet

Let’s build each one with AI.

Building the Welcome Sequence

The welcome sequence is your first impression. New subscribers are most engaged in the first 48 hours—don’t waste that attention.

Create a 6-email welcome sequence for ContentEngine,
an AI writing platform.

Subscriber context: They signed up via our "Brand Voice
Guide" lead magnet. They're solo content marketers at
SaaS companies, overwhelmed by content demands.

Sequence goal: Get them to start a free trial by Email 6.

Emotional journey:
Email 1: "You're in the right place" (validation + deliver lead magnet)
Email 2: "Here's your real problem" (deepen the pain point)
Email 3: "Others have solved this" (social proof)
Email 4: "Here's how it works" (show, don't tell)
Email 5: "Common objections answered" (remove friction)
Email 6: "Your next step" (clear CTA with urgency)

Timing: Email 1 immediately, Email 2 day 2, then every
2-3 days.

Brand voice: Direct, conversational, example-first.
Use "you/your" language. No corporate speak.

For each email, provide:
- Subject line (3 options)
- Preview text
- Full email body (150-300 words)
- CTA button text
- P.S. line (optional, for personality)

Let me show you what Email 2 might look like:

Subject line options:

1. The real reason your content sounds generic
2. You’re not slow at writing. You’re solving the wrong problem.
3. Every content marketer hits this wall

Email body:

Hey {name},

Yesterday I sent you our Brand Voice Guide. If you’ve read it, you probably noticed something uncomfortable:

Most of the “before” examples… sound like your content.

That’s not a knock on your writing. It’s a knock on the tools. Here’s what’s actually happening:

You’re spending 4 hours on a blog post. An hour researching, an hour outlining, two hours writing and editing. By post three this week, you’re exhausted. The quality drops. The voice drifts. And your audience notices—even if they can’t articulate why.

Or you try AI tools. They’re fast. But the output sounds like… AI. Generic. Could-be-anyone prose that your readers scroll past.

The problem isn’t speed. It’s that speed and voice are treated as opposites.

Tomorrow, I’ll share how three content marketers solved this. One of them produces 12 blog posts a month. Solo. Without burning out.

Talk soon, [Name]

P.S. Hit reply and tell me: how many pieces of content are you producing per week right now? I read every response.

Notice what this email does: it validates the reader’s pain, connects it to the lead magnet they downloaded, and creates anticipation for the next email. It doesn’t sell anything. It builds trust.

The Nurture Sequence

For subscribers who didn’t convert during the welcome sequence:

Create a 4-email nurture sequence for ContentEngine.

Audience: Welcome sequence completers who didn't start
a free trial. They're interested but not convinced.

Sequence goal: Convert to free trial.

Strategy: Address the remaining objections.
Based on our research, the top objections are:
1. "AI content doesn't match my brand voice" (already addressed)
2. "I don't have time to learn another tool"
3. "My content needs are too specific for AI"
4. "What if my readers can tell it's AI?"

Each email should address one objection through a story
or example, not by arguing against it.

Timing: Once per week, on Tuesdays.
Brand voice: Same as welcome sequence.

The key insight: stories address objections better than arguments. Instead of saying “Our tool is easy to learn,” tell the story of a content marketer who was skeptical, tried it for 15 minutes, and had her first brand-voice post before lunch.

Quick Check: Email Diagnosis

Read this email and identify what’s wrong:

Subject: Exciting New Features at ContentEngine!

Dear Valued Customer,

We are thrilled to announce that ContentEngine has released exciting new features that will revolutionize your content workflow. Our team has been working tirelessly to bring you the best possible experience.

Features include:

• AI Voice Training 2.0
• Multi-format export
• Team collaboration

Click here to learn more!

What’s wrong: Corporate tone (“Dear Valued Customer,” “thrilled to announce”), no personal relevance to the reader, feature list without benefits, vague CTA (“learn more”), and it’s about the company, not the customer. Better approach: lead with the problem the features solve, use a customer story, and have a specific CTA.

The Win-Back Sequence

For subscribers who haven’t opened an email in 60+ days:

Create a 3-email win-back sequence.

Audience: ContentEngine subscribers who haven't opened
an email in 60+ days. Mix of trial users who churned
and subscribers who never started a trial.

Sequence goal: Re-engage or clean the list.

Emotional approach:
Email 1: "We miss you" — light, no pressure, share
  what's new
Email 2: "Things have changed" — highlight improvements
  since they left
Email 3: "Last call" — honest "should we remove you?"
  with easy re-subscribe

Keep each email under 150 words. Short = more likely
to be read by disengaged subscribers.

The win-back sequence serves two purposes: re-engaging interested people and cleaning your list of people who aren’t interested. A clean list improves deliverability for everyone else.

Subject Line Generation at Scale

Subject lines make or break your emails. AI is perfect for generating options:

Generate 15 subject line options for our Email 3
(social proof / "others have solved this" email).

The email contains a story about a content marketer
who went from 3 posts/month to 12 posts/month using
ContentEngine, without sacrificing quality.

Styles to include:
- 3 curiosity-driven (make them wonder)
- 3 benefit-driven (promise a specific outcome)
- 3 story-driven (hint at the narrative)
- 3 question-based (provoke thought)
- 3 unconventional (pattern interrupt)

Constraints:
- Under 50 characters preferred
- No ALL CAPS
- No clickbait (deliver on the promise)
- No spam trigger words (free, guarantee, act now)

From 15 options, pick the 2 best and A/B test them. Over time, you’ll learn what your audience responds to.

Automation Logic

Beyond the emails themselves, you need automation rules:

Design the automation logic for our email sequences.

Sequences:
1. Welcome (6 emails over 2 weeks)
2. Nurture (4 emails over 4 weeks)
3. Win-back (3 emails over 2 weeks)

Define:
- Entry triggers (what puts someone into each sequence)
- Exit triggers (what removes them)
- Transition rules (when do they move from one to another)
- Suppression rules (when should we NOT email)
- Branch logic (if they do X, send Y instead of Z)

AI designs logic like:

• Welcome → Nurture: If subscriber completes welcome sequence without converting, wait 5 days, then enter nurture sequence.
• Any → Exit: If subscriber starts a trial at any point, remove from marketing sequences, enter onboarding sequence.
• Suppression: Never send more than 3 emails in a 7-day period. Never send during a product outage.
• Branch: If subscriber opens Email 3 (social proof) but doesn’t click, send a follow-up with a different case study.

Personalization at Scale

AI enables personalization beyond {FIRST_NAME}:

We segment our email list by:
- Company size (1-10, 11-50, 51-100)
- Content type they produce (blog, social, email)
- Primary pain point (speed, quality, consistency)

Create 3 variants of our nurture Email 2 ("I don't have
time to learn another tool") customized for:
1. Blog-focused content marketers
2. Social media managers
3. Email marketing specialists

Same core message, different examples and use cases
relevant to each segment.

Three tailored emails take the same time as one generic email when AI does the writing. And personalized emails have 26% higher open rates.

Practical Exercise

Build your core email sequence:

1. Map your customer’s emotional journey from stranger to buyer
2. Identify 5-6 touchpoints along that journey
3. Use AI to write a complete welcome sequence
4. Generate 10 subject lines for each email
5. Design the automation logic with triggers and branches

Start with the welcome sequence—it’s the highest-impact place to begin.

Key Takeaways

• Email sequences build trust over time—each email has a specific purpose in the journey
• The emotional arc matters more than individual email quality
• Address objections through stories, not arguments
• Generate many subject lines and A/B test the best ones
• Automation logic ensures the right email reaches the right person at the right time
• Personalization by segment dramatically improves engagement

Next up: customer journey mapping. Email is one touchpoint—now let’s map the entire experience from first awareness to loyal advocacy.

Up next: In the next lesson, we’ll dive into Customer Journey Mapping and Optimization.