How I Automated My Email Marketing with AI (Full Workflow Inside)

I Had 2,400 Subscribers and No System

Here's something embarrassing. For the first year of running my newsletter, I wrote every email the morning I sent it. No sequences. No segmentation. No automation. Just me, a cup of coffee, and the ActiveCampaign compose window at 7 AM on Tuesdays.

My open rate was around 24%, which I thought was decent until I learned that most of my subscribers had probably just forgotten to unsubscribe. The real tell was my click rate: 1.8%. Out of 2,400 people, about 43 were actually engaging with what I sent.

The problem wasn't my writing (okay, maybe partly my writing). The problem was that I was sending the same email to everyone regardless of what they cared about, when they'd signed up, or whether they'd opened anything in the last three months.

So I spent a weekend rebuilding the whole thing. Not a "strategic overhaul" or a "digital transformation." Just me, frustrated, deciding to actually use the tools I was already paying for.

The Before: What My Emails Looked Like

Here's the template I was using for every single email. I'm sharing it because I think a lot of people are stuck in the same pattern:

Subject: Weekly Update: [Topic]

Body: "Hey [first_name], hope you're having a great week! This week I want to talk about [topic]. [Three paragraphs of content]. Let me know what you think! Best, Avon"

Every. Single. Week. Same structure. Same energy. Same mediocre results.

The subject line format was killing me. "Weekly Update" is the email equivalent of a gray Honda Civic. It gets the job done but nobody gets excited about it.

The Rebuild: Step by Step

I'm going to walk through exactly what I set up, in order. This took me about 6 hours spread over a weekend.

Step 1: Clean the List (1 hour)

Before automating anything, I needed to deal with the dead weight. I created a segment in ActiveCampaign for everyone who hadn't opened a single email in 90 days. That was 680 people, nearly a third of my list.

I sent them one last email with the subject line "Should I stop emailing you?" and a single link to stay subscribed. 91 people clicked it. The other 589 got removed.

My list went from 2,400 to 1,811. My open rate immediately jumped to 31% because I was no longer dragging down the average with people who'd ghosted me months ago.

Painful? A little. But sending emails to people who will never open them actually hurts your deliverability. Gmail notices when 30% of your recipients ignore you, and it starts putting you in spam for everyone else.

Step 2: Set Up Tags and Segments (1 hour)

I created a simple tagging system based on two things: what people are interested in, and how engaged they are.

Interest tags (applied automatically based on which page they signed up from):

interest:ai-tools
interest:automation
interest:marketing
interest:development

Engagement tags (applied automatically by ActiveCampaign automations):

engaged:active (opened 2+ emails in the last 30 days)
engaged:warm (opened at least 1 email in the last 60 days)
engaged:cold (no opens in 60+ days)

This took about an hour to set up in ActiveCampaign's automation builder. The triggers are simple: "When contact opens an email, update their engagement tag." It runs in the background and I never think about it.

Step 3: Build the Welcome Sequence (2 hours)

This is where I spent most of my time, and it's been the highest-impact change. Instead of adding new subscribers to my main list and hoping they stick around, they now get a 5-email sequence over 12 days.

Here are my actual emails (abbreviated, but this is the real structure):

Email 1: Immediately after signup Subject: "Here's that [resource name]" Body: Deliver whatever they signed up for. One sentence about who I am. One sentence about what to expect. No fluff. No "I'm so excited you're here!" Just the goods.

Email 2: Day 3 Subject: "The [topic] post everyone keeps sharing" Body: I link to my single best-performing blog post. The one with the most organic traffic. I frame it as "if you only read one thing I've written, make it this." This email has a 44% open rate because the subject line creates curiosity without being clickbait.

Email 3: Day 5 Subject: "I screwed this up so you don't have to" Body: A short personal story about a mistake I made related to the topic they signed up for. For the AI tools audience, I tell the story about how I spent $400 on an AI writing tool before realizing the free tier of a competitor did the same thing. This email gets the most replies because people love failure stories.

Email 4: Day 8 Subject: "The tool I actually use every day" Body: One specific tool recommendation with my honest take. Not a listicle, not a comparison. Just "I use this tool, here's why, here's what's annoying about it, here's why I keep paying for it anyway." This is where I include an affiliate link, but the email is genuinely useful whether they click it or not.

Email 5: Day 12 Subject: "Quick question" Body: Two sentences. "I'm curious what you're working on right now. Hit reply and tell me." That's it. This email has the highest reply rate of any email I've ever sent (12% reply rate). The responses give me content ideas and tell me what my audience actually cares about.

Step 4: Connect the Automation Pipeline (1.5 hours)

Here's where Make comes in. I built a scenario that handles the entire flow from form submission to tagged, sequenced subscriber:

Tally webhook fires when someone submits a form
Make receives the data and checks if they're already in ActiveCampaign (to avoid duplicate welcome sequences)
If new: Create contact in ActiveCampaign, apply interest tag based on the form's hidden field (which tells me which page they came from), add them to the welcome sequence
If existing: Just update their tags, skip the welcome sequence
If they match my ICP (based on company size or role, if the form collected that): Send me a Slack notification so I can follow up personally

The ICP filter is important. Most of my subscribers are casual readers, which is fine. But about 5% are potential clients or collaborators, and I want to know about them immediately rather than discovering them in a CSV export three weeks later.

Step 5: Set Up AI-Assisted Writing (30 minutes)

I don't use AI to write my emails start to finish. I tried that, and the emails sounded like they were written by a helpful customer service rep from 2019. Pleasant, professional, and completely forgettable.

Instead, I use Claude for two specific things:

Subject line variations. I write my draft subject line, then ask Claude to give me 10 alternatives. I pick the best one or combine elements from a few. This takes 2 minutes and consistently produces better subject lines than I'd come up with alone.

First draft of the body when I'm stuck. Sometimes I know what I want to say but can't get the opening right. I'll give Claude my key points and ask for a rough draft, then rewrite it in my voice. It's like having someone hand you a lump of clay instead of staring at an empty wheel.

The important thing is that every email still sounds like me. My subscribers can tell when something is off. One time I sent an AI-generated email without editing it enough, and someone literally replied "did you write this? It doesn't sound like you." Lesson learned.

The Results (Real Numbers)

I've been running this system for about three months. Here's what changed:

Open rate: 24% to 36% (partly from cleaning the list, partly from better subject lines and segmentation)

Click rate: 1.8% to 5.2% (because I'm sending relevant content to people who actually care about the topic)

Reply rate: basically 0% to about 4% on regular emails, 12% on the "quick question" email in the welcome sequence

Unsubscribe rate: actually went up slightly at first (from 0.3% to 0.5%) because the welcome sequence forces people to decide quickly if they're in or out. I consider this a good thing. I'd rather have 1,500 engaged subscribers than 2,400 ghosts.

Time spent: I went from spending 2-3 hours every Tuesday morning writing and sending, to about 45 minutes writing one email per week. The sequences and automations handle everything else.

Revenue: harder to attribute directly, but my affiliate income from email went from about $200/month to $600/month. The targeted tool recommendations in email #4 of the welcome sequence account for most of that.

Mistakes I Made Along the Way

I over-automated at first. I set up a re-engagement sequence that automatically emailed cold subscribers every two weeks with "we miss you!" energy. It was annoying. Multiple people replied telling me to stop. I replaced it with a single "should I stop emailing you?" message after 90 days of inactivity, which is much more respectful.

I A/B tested too many things at once. For two weeks, I was testing subject lines, send times, and email length simultaneously. I couldn't tell what was actually making a difference. Now I test one variable at a time and run each test for at least two sends.

I forgot about mobile. My first few designed emails looked great on desktop and terrible on phones. Now I write plain-text-style emails with minimal formatting. They look the same everywhere, and honestly, they perform better than the designed ones did.

I ignored deliverability. I didn't set up DKIM and SPF records for my domain until month two. Before that, about 15% of my emails were landing in spam. Fifteen minutes of DNS configuration fixed a problem I didn't even know I had.

The Exact Tool Stack (And What It Costs)

ActiveCampaign (Plus plan): $49/month. Worth it for the automation builder and CRM. I tried ConvertKit first and it was too simple for what I needed.
Make: $9/month. Handles all the glue between tools. I use about 3,000 operations per month out of my 10,000 limit.
Tally: Free. Best form builder for the price (free is a pretty good price).
Claude Pro: $20/month. For subject line brainstorming and draft assistance. I'd pay for this regardless of email marketing.

Total: about $78/month. My email-attributed revenue is around $600/month. The math works.

What I'd Do Differently Starting Over

I'd clean my list on day one. I wasted months sending emails to people who were never going to open them, and it hurt my deliverability for everyone else.

I'd write the welcome sequence before anything else. It's the highest-leverage piece of email marketing because every single new subscriber goes through it. My welcome sequence has been seen by every person who joined in the last three months. My weekly emails get seen by maybe 36% of my list on a good day.

I'd skip the fancy email designs entirely. Plain text with good writing beats a beautiful template with mediocre writing every time. My best-performing emails have zero images and zero custom formatting.

And I'd start asking for replies sooner. The "quick question" email was an afterthought, and it turned out to be the most valuable part of the whole system. Replies build relationships, give you content ideas, and tell Gmail that your emails are wanted. Three birds, one two-sentence email.