Your team probably has five different ways of using AI right now.

And that's becoming a bigger problem than whether you're using AI at all.

Someone's writing emails, another’s building reports, meanwhile someone else is sitting on the best prompt in the company... and nobody else knows it exists.

This morning, we're breaking down why every retention team needs an AI operating manual, and how a simple playbook can turn AI from a collection of individual habits into a system your whole team can build on.

Also inside:
→ When did calling your customers become a finance question instead of a marketing one?
→ Knowledge drop: You're putting too much effort into your campaigns
→ The best brands already cracked retention. Now you get a look inside.
→ Glossier just locked in $45M in non-dilutive financing

When did calling your customers become a finance question instead of a marketing one?

Somewhere around 2005, ecommerce quietly fired its phone. Outbound calling required a call center (that costs $100K+ a year) and only enterprise brands had a CFO willing to sign off. 

Everyone else clicked "send" on another email and convinced themselves it was the same thing.

It wasn't.

Twenty years later, the phone is back, and it doesn't come with a department attached. That's Outcraft. 

The voice channel that used to require a building full of headsets now runs for less than the cost of one SDR, in 40+ languages, sitting alongside the email and SMS you already send.

Voice used to scale with headcount, but now it scales with the system.

See what recovered revenue sounds like → outcraft.ai

*Sponsored

Knowledge drop: You're putting too much effort into your campaigns

Those campaigns you sweat over every week? Turns out that's not where most of your revenue comes from. Your flows are the secret workhorse, pulling in 40% of revenue from just 5% of your sends.

In this post, Chase breaks down the three flows behind 87% of automated orders, the timing for each, and the 2026 benchmarks to beat.

Why every retention team needs an AI operating manual

The first month of using AI is kind of a mess.

Everyone figures out their own way of doing things. One person has a prompt they swear by. Someone else has a completely different workflow. Before long, the output is all over the place.

Your brand voice starts drifting, quality depends on who's behind the keyboard, and AI feels a lot less helpful than it did on day one.

Let's dig into how an AI operating manual fixes that.

1. Decide where AI belongs and where it doesn't

One of the fastest ways to create inconsistency is letting every team member decide for themselves what AI should be doing.

Some marketers ask it to write entire campaigns, others only use it for brainstorming, and the rest won't touch it at all.

That usually leads to inconsistent outputs and unpredictable quality.

Instead, define which parts of your workflow AI should own and which parts should always stay human.

Think of AI as another member of your team, since every good team performs better when everyone knows their role.

2. Build prompt libraries instead of starting from scratch

One of the biggest mistakes we see is marketers treating every conversation with AI like it's the first one.

That means rewriting prompts, reinventing workflows, and solving the same problems over and over again.

Instead, build a prompt library that everyone on your team can reuse. Some of the highest-value prompts to standardize include:

• Campaign brief generation

• Subject line creation

• Email and SMS copy reviews

• Landing page critiques

• Flow audits

• Weekly reporting summaries

• Customer journey analysis

• Brainstorming seasonal campaigns

Instead of hunting through Slack or Notion every time someone remembers a great prompt, create one source of truth.

Over time, your prompts become assets instead of one-off conversations.

3. Teach AI how your brand actually sounds

Teams often spend hours teaching new employees how to write for the brand. Then they open ChatGPT and expect it to magically understand the same thing.

It doesn't work that way.

If you want consistently useful outputs, your brand voice needs to be documented just as clearly for AI as it would be for a new hire.

Your operating manual should answer questions like:

• Which words do we use repeatedly?

• Which words do we avoid?

• What does a good subject line sound like?

• How long are our typical paragraphs?

• What's our reading level?

• How do we structure CTAs?

• Which previous campaigns best represent our voice?

The better your instructions, the closer every output starts to feeling finished.

4. Build review systems before you build more prompts

The more your team relies on AI, the more important quality control becomes. Before anything gets scheduled, every campaign should pass through the same review process.

The goal is to make sure faster production doesn't turn into more expensive mistakes.

5. Capture what works so the whole team gets smarter

Great ideas and breakthroughs happen all the time. But without a system to capture and share those wins, they rarely spread beyond the person who found them. The knowledge stays siloed and a month later, someone else ends up solving the exact same problem from scratch.

Every time your team finds something that works, it should be captured and made accessible so the entire team can benefit.

Your operating manual should continue growing with things like:

• Winning prompts

• New workflows

• Automation ideas

• Prompt improvements

• Lessons from successful campaigns

• AI use cases that didn't work and why

Build your own AI operating manual

If you're starting from scratch, don't overcomplicate it.

A simple document that answers the questions below is enough to create far more consistency than most teams have today.

You don't need a hundred-page handbook, you just need everyone working from the same playbook.

Make good execution repeatable

AI is becoming something every team has access to. That access alone won't set you apart, since your competitors are typing into the same tools you are.

What actually creates an advantage is how intentionally your team uses it day to day: clear workflows, documented wins, and systems that make strong execution repeatable instead of accidental.

That's what an operating manual gives you. It keeps the prompt someone stumbled onto last Tuesday, or the workflow that halved campaign setup, from vanishing in to a Slack thread. It turns one person's good day into something the whole team can run on.

Build that, and AI stops being a tool a few people use well and becomes the way your team works.

The best brands already cracked retention. Now you get a look inside. 👀

Be honest. You've signed up for a brand's list with a burner email just to see what their welcome flow does.

We all have. It's how retention marketers actually learn: screenshotting campaigns, forwarding emails to ourselves, saving that one popup that made us go "oh, that's clever."

The eCom Retention Vault is that instinct, organized. It's a real look inside the emails, campaigns, and full customer journeys from 20+ high-performing eCom brands, with the prompts and frameworks to turn what you find into something of your own.

- 75+ real brand emails to pull apart and swipe
- 50 campaigns, each with an AI prompt to spin up your own version
- 130+ pages of opt-ins plus welcome emails & SMS
- 10 copywriting frameworks
- A private community of 350+ retention marketers

→ Access the vault

DTC wins:

Glossier isn't chasing another big equity round.

Instead, the brand just secured a $45M revolving credit facility from Tiger Finance, its first major funding since 2021. Combined with its push into retail and Sephora, it signals a different chapter: building a healthier business instead of chasing the next sky-high valuation.

Annnnd that’s a wrap for this edition! 

Thanks for hanging with Chase and me, always a pleasure to have you here.

If you found this newsletter helpful (or even just a little fun), don’t keep it to yourself! Share ecomemailmarketer.com with your favorite DTC marketer. Let’s get them on board so they don’t miss next week’s drops.

Remember: Do shit you love.

🤘 Jimmy Kim & Chase Dimond

PS - Your next best customer might be reading this right now. Want in? Email Jimmy to sponsor this newsletter and more.

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