Quick Verdict

Automating email workflows is one of those things that sounds like a massive project but actually saves you from going insane with repetitive "click send, wait, click send again" nonsense. It’s worth it — but only if you set it up right. For writing the actual emails, ChatGPT **** (4/5) is solid for rough drafts and sequences, while Claude ***** (4.5/5) writes warmer, more human copy that doesn’t sound like a robot on caffeine. Neither will fix bad strategy, though.

OK, so here’s the deal. You’re drowning in emails, right? Sending the same "thanks for signing up" note a hundred times a week. Following up manually. Forgetting to send that one important sequence because you got distracted by a cat video. I’ve been there. I once accidentally sent a welcome email with the subject line "Test" to my entire list of 2,000 subscribers. Nobody unsubscribed, but I felt like an idiot for a week.

The fix is automation. Not the scary "I need a PhD in Zapier" kind. Just a few simple steps that take the brainless repeat work off your plate. Here’s how I do it without losing my mind.

Step 1: Figure Out Why You’re Doing This

If you don’t know what problem you’re solving, you’ll automate the wrong thing. Seriously, sit down for five minutes and list the emails you send more than twice a week. Welcome emails? Abandoned cart? Follow-ups after a purchase? That’s your list.

What can go wrong: You automate everything and end up with a bloated system that sends your customers ten emails in a day. Nobody wants that. Start with one sequence. The one you hate sending most. For me, it was the "hey you left stuff in your cart" email — because I always forgot to send it manually.

Step 2: Pick Your Email Platform (The Right One)

You need a tool that can handle triggers and sequences. I’ve used Mailchimp (it’s fine but their UI changes every three months like a nervous chihuahua), ConvertKit (great for simplicity, pricey for big lists), and ActiveCampaign (powerful but feels like learning Excel 2.0). Honestly, if you’re starting out, just use whatever your landing page tool connects to easily.

Here’s the thing nobody tells you: don’t pick a platform based on features you might need someday. Pick the one that doesn’t make you want to throw your laptop out the window on day one. I spent $200 on SEMrush last March and never used it because the interface made me angry. Same energy.

Shortcut: Use a free trial of three platforms. Spend 15 minutes in each. The one that feels intuitive wins. For most people, ConvertKit or Beehiiv (for newsletters) is the sweet spot.

Step 3: Set Up Your Triggers

A trigger is just an event that kicks off an email. "Someone subscribes" — that’s a trigger. "Someone buys product X" — another trigger. You can also do time-delayed triggers: "three days after signup, send this."

Most platforms have a visual builder where you drag and drop. Don’t overcomplicate it. Start with one trigger and one email. Then add a second email for three days later. That’s a workflow.

What can go wrong: You’ll accidentally trigger a sequence for ALL contacts instead of new ones. Test with a dummy email. I learned this the hard way when I sent a "happy birthday" sequence to everyone who’d ever opened an email from me. In March. My birthday is in September.

Step 4: Write the Emails (Use AI but Don’t Be Lazy)

This is where ChatGPT and Claude come in. I use ChatGPT to brainstorm subject lines and write a first draft. Then I edit it heavily — cut the generic fluff, add my voice, throw in a stupid personal story. Claude is better for long-form emails where tone matters, like a nurture sequence that needs to feel warm.

The hack: Give the AI your previous emails as examples. Say: "Write an abandoned cart email in the same style as this one I