Most people treat email like a broadcast channel. You send the same message to everyone, hope it converts, and wonder why it feels like so much work for so little return. Today Holly is joined by Cheryl Rerick, an email strategist and automation expert, to break down what it looks like to build an email system that converts without you constantly writing more.

About Cheryl Rerick

Cheryl Rerick is an email marketing strategist, automation engineer, and deliverability expert. She created the Automate and Chill method, a framework for building a full year of automated emails so every new subscriber gets the right message at the right time, no matter when they join the list. She hosts The Email Diaries, a twice yearly event where she surveys email experts on what is actually working right now, and she is an EmailSmart certified deliverability expert who tracks how Google, Yahoo, and Microsoft are updating their spam filters. Today she teaches course creators and coaches how to automate their email, protect their deliverability, and use AI as a thought partner without losing their voice.

Why an automated email journey outperforms a newsletter

Most people treat email like a broadcast channel, sending the same message to everyone and hoping it converts. Cheryl Rerick, an email strategist, automation engineer, and creator of the Automate and Chill method, joins Holly to explain why that approach leaves money on the table and what to do instead: build an automated customer journey that gets every subscriber the right email at the right time, whether they joined yesterday or two years ago. Instead of guessing what to write each week, Cheryl reverse engineers each sequence from the offer itself, working backward from what someone needs to believe before they buy.

The conversation turns to AI's growing role in email, and there are three sides worth understanding: AI is reading emails for your subscribers through tools like Gmail's preview and inbox digest tools, AI is writing a growing share of emails, including spam, and AI is filtering emails on the back end at Google, Yahoo, and Microsoft. Over 50% of spam email today is AI generated, so writing that sounds too polished can quietly work against your deliverability. Cheryl explains why cleaning your list is still the fastest way to protect your sender reputation and raise your open rates.

Cheryl also shares how she uses AI as a thought partner instead of a ghostwriter, why reading an email out loud catches the parts that sound like a robot wrote them, and how liquid code lets a single email show different content to different subscribers based on their tags. If you write emails and wonder whether they are actually working, or whether AI is helping or hurting your results, this episode has a plan for both.

Key takeaways from this episode

• Over 50% of spam email today is AI generated, which means AI-sounding language can quietly hurt your deliverability even when you are not a spammer.
• Cleaning your email list can raise open rates by about 10% for most people who have never done it, and it is worth putting on the calendar every month.
• Getting to the point in the first three to five lines of an email helps AI tools like Gmail and inbox digest assistants summarize it accurately.
• When an AI assistant reads and summarizes an email through the API instead of opening it, the email still shows as unread, so the sender gets no credit for that engagement.
• Editing a heavily AI-written email can often cut about 40% of the words without losing anything the reader needs.
• Liquid code lets one email show different content to different subscribers based on their tags, without building separate emails for each segment.

The best tool can't fix a broken plan.

Cheryl Rerick

This episode is for you if

• You are sending emails every week but are not sure why they are not converting into sales.
• You want to build an automated email sequence but do not know where to start.
• You are using AI to write your emails and wondering if it is helping or hurting your results.

Tune in to hear:

• Why treating email like a broadcast channel is costing you sales
• How to reverse engineer an email sequence from your offer instead of guessing what to write
• The difference between batch writing emails and writing them on the fly
• What AI tools are actually doing when they summarize your emails for your readers
• Why an AI-read email does not count as an open, and what that means for your engagement
• Why over 50% of spam email today is AI generated, and how that affects your deliverability
• How to use AI as a thought partner for your emails without losing your own voice
• Why reading your email out loud is the fastest way to catch AI-sounding copy
• How liquid code lets you personalize email content based on subscriber tags
• Why cleaning your list is the fastest way to raise your open rates

It's 2026, they can just sign up again tomorrow if they want to. They can come back. Just let them go.

Cheryl Rerick

Episode chapters

• 00:00:00 Why treating email like a broadcast channel is costing you sales
• 00:01:30 What building a life-first business means to Cheryl
• 00:06:00 How to reverse engineer an email sequence from your offer
• 00:10:30 The three ways AI shows up in email right now
• 00:13:30 Why an AI-read email does not count as an open
• 00:15:00 Why over half of spam email today is AI generated
• 00:16:30 Using AI as a thought partner instead of a ghostwriter
• 00:22:30 Using liquid code to personalize emails based on tags
• 00:25:30 The biggest email trends right now: segmentation and gamification
• 00:28:30 The number one quick win: cleaning your list

More to explore: Want more on building an automated customer journey? Check out how a welcome sequence formula turns subscribers into lifelong customers.

CONNECT WITH CHERYL:

Website: cherylrerick.com
Instagram: @cherylrerickmarketing

Free Resource: AI Inboxes - How Google, Apple, & AI are judging (and summarizing) your emails - https://cherylrerick.com/ai-inboxes/

Listen to this episode

Find Crush the Rush wherever you listen, and subscribe so the next episode finds you.

Apple Podcasts · Spotify · every episode of Crush the Rush

Frequently asked questions

Who is Cheryl Rerick?

Cheryl Rerick is an email marketing strategist, automation engineer, and deliverability expert who created the Automate and Chill method for building a year of email in advance. In this episode she covers how to build an automated customer journey instead of a weekly broadcast, and how AI is changing both email writing and email deliverability. She also hosts the twice yearly Email Diaries event, where she surveys email experts on what is actually working right now.

What is the Automate and Chill method?

Automate and Chill is Cheryl's framework for building a full year of email in advance so new subscribers get the right message at the right point in their journey, no matter when they join the list. Instead of writing a broadcast each week, you map your sales milestones for the year, then reverse engineer the emails from there. It is designed for people who want their best email working in the background instead of starting from a blank page every week.

How is AI changing email right now?

Cheryl breaks it into three parts: AI is reading emails for subscribers through tools like Gmail previews and inbox digests, AI is writing a growing share of emails including spam, and AI is filtering emails on the back end at Google, Yahoo, and Microsoft. Over 50 percent of spam email today is AI generated, so email that sounds too polished can work against your deliverability. Getting to the point in the first three to five lines also helps AI tools summarize your email accurately.

Should you let AI write your emails?

Cheryl uses AI as a thought partner, not a ghostwriter. She leans on it to brainstorm ideas, poke holes in an argument, or smooth a rough sentence, but writes higher stakes storytelling emails herself. When she edits students emails that were written mostly by AI, she can often cut around 40 percent of the words without losing anything, and her top tip is to read every email out loud before sending it.

How often should you clean your email list?

Cheryl recommends putting list cleaning on the calendar every month. Removing subscribers who never open or click can raise open rates by about 10 percent for most people who have never done it, and it protects your sender reputation with Google, Yahoo, and Microsoft. She points out that anyone you remove can always resubscribe later if they want to hear from you again.

Is an automated email sequence better than a newsletter?

For driving consistent sales, yes, according to Cheryl. A newsletter is a one off broadcast about whatever is on your mind that week, while an automated sequence leads a subscriber through a customer journey built around what they need to hear before they buy. She is not against sending newsletter style updates too, but says the sequence is what actually moves people toward a sale.

Curious what is actually standing between you and consistent income in your business? Take the free 2-minute quiz and find out where the gap is. hollymariehaynes.com/quiz 💛