Today’s email is about creating irresistible offers. But it is not about bigger discounts. Instead …

🤩 Matt Bertulli step-by-step on how to get people to buy more

🤖 Cody Plofker reveals his AI-pilled email + retention system

🤑 MacCoy Merkley with how he funds his revenue stack for free

Four 9-figure executives + one new operator are building an ecommerce brand in public.

Cody Plofker

Advisor, Jones Road

How I Built Winks’ AI Email System

We’re a five-person team, but Matt and I are the only ones on marketing. Even though we’re a single-SKU brand, it’s a big lift.

Creative
Ads
Landers
Emails

We chose tools that have MCPs or APIs. That way, we can operate them directly from Codex or Claude.

I’m most proud of our email system.

Omnisend won us over because they have a robust MCP. We tell the AI what we want, and it sets up our email flows, drafts campaigns, builds customer segments, and creates pop-ups.

The only time we go inside the platform is to review things before hitting send. Even then, it’s only with new content.

This has allowed us to run our retention program lean. It’s pretty incredible. There are lots of other great features. Deliverability has been exceptional. They have all the bells and whistles, but its MCP is what set it apart.

Not an Omnisend user?

More than 150k brands trust them, generating on average $79 for every $1 spent. Migration is free, takes up to 5 business days.

They’re offering our audience 30% off the first three months.

Highly recommend you check it out.

Click Here to Try Omnisend

Matt Bertulli

CEO, Pela + Lomi

11-Point Offer + Funnel Checklist

Winks’ offer looks simple: 35% discount, $42 per month, cancel anytime, 60-day guarantee, gifts with purchase.

However, a great offer is more than price.

It makes someone believe:

This is for me
It’ll actually work
It’s worth trying

We’re still figuring out how to nail all three. So we brought in two people to tear our offer and funnel apart.

Jordan Menard, a growth marketer behind Instant Hydration, challenged our pricing and subscription economics.

Lina Fahizul, aka the “Chief Ovary Officer,” helps brands sell to women. She went through our ads and landing pages.

We walked away with an 11-point checklist.

☐ Explain The Problem
☐ Deliver On The Ad
☐ Explain Why It Works
☐ Sell The End Result
☐ Speak to Sub-Cohorts
☐ Show Relatable People
☐ Address Spending Guilt
☐ Simplify Buying Options
☐ Offer Gifts They Want
☐ Give a Reason to Buy
☐ Set Their Expectations

☐ Explain the Problem

My wife understands how hormones affect her sleep. She is health-conscious, takes supplements, and talks to doctors.

That doesn’t mean our customer does.

Plus, there is an even bigger TAM in going after the women who don’t understand any of that.

Before someone will believe your product works, first they have to wrap their heads around the problem.

Which means we have to explain the cause of sleeplessness … before we bring up our solution.

Lina mocked up an example landing page that connects the dots: why sleep can change during perimenopause, what that feels like, and where Winks fits in.

We added this section immediately below the fold on our website, right on the homepage.

Why Your Sleep is Broken - Winks Website

☐ Answer the Ad’s Question

Before Lina opened our landing page, she tried to guess what it would say based on the ad she clicked.

Our ad said sleep changes after 40. She expected the page to explain why. Instead, we just sent her to a lander with sleep tips.

It’s a useful exercise. Read your ad, think about what you expect to see on the lander, then open the page.

Does it deliver? Every angle you use in your ads needs follow-through. We are driving to this page now.

☐ Explain Why It Works

Our previous website jumped into ingredients without explaining why they belonged in the supplement.

After Lina called that out, we went back and connected each ingredient the problem we’d just explained.

What does it do?
How does it help?
Where is the proof?

We added all our ingredients with explanations for why they are included + links to the research.

☐ Sell the End Result

Lina noticed a lot of our ads show the problem. A woman lying awake at night or exhausted dropping off her kids at school.

Good illustrations of the problem (if not a little over-reliant on AI creative). What we were missing was the end result.

More patience with kiddos
Energy to go for a hike
Feeling sharp at work

This is what gets people to buy. Not only feeling understood, but seeing how their lives could get better.

☐ Speak to Sub-Cohorts

“Women who struggle with sleep” covers a lot of different people.

Moms with young kids
Women in perimenopause
Ladies who have anxiety

They might all need Winks. But for different reasons. To bring that to life, she created a bunch of mock creative around the sub-cohorts in our category.

Each sub-cohort needs an ad that speaks to what’s keeping them awake.

☐ Show People Like Them

Lina worked with a brand selling to busy moms who barely had time for themselves.

Their creators were … super-fit yoga moms.

That’s almost as bad as when I tried to create founder content at Pela while our target customer was young women.

If the customer can’t see themself in the people representing your product, then they won’t think it’s for them.

☐ Address Spending Guilt

We’re not just competing with other sleep supplements. We’re competing with all the other things a budget-conscious mom could spend that money on.

A discount only gets a bottom-of-funnel customer to buy sooner.

We need to connect the purchase to something our buyer already values:

More energy
Better mood
Longevity

That way, she understands the value and has a reason to make room for it in her budget.

☐ Simplify Buying Options

Our original PDP asked how many sleepers were in the household. It would toggle more bags for more people.

What if someone wants to buy in bulk? Stock up for a few months? Split a bag with their partner?

It was confusing.

We’d organized the options around how we imagined customers using Winks. We’ve since simplified that to number of bags.

Clarity remains undefeated.

☐ Give Gifts They Want

We currently have these GWPs …

Caden Lane $25 credit
RISE Sleep app, 1mo
Better Sleep ebook

Jordan pushed us to test physical gifts. So we’re working on it.

Frother
Sleep mask
Mouth tape

The goal is high perceived value at a cost the business can afford. We’ve learned the hard way that adding non-physical gifts, like an ebook, doesn’t make the offer better.

☐ Give a Reason to Buy Right Now

Humans procrastinate. Someone can want your product and still put off buying it.

At Pela, we give people a reason to buy right now with weekly design drops. We need to find a similar rhythm for Winks. Jordan stressed this.

Plan buying moments, then line up the offer, ads, emails, and website around them.

Limited gifts
New flavors
Collaborations

Put those moments on a calendar. A countdown timer doesn’t create urgency if the same offer is still there tomorrow.

☐ Tell Them What to Expect

Lina liked the timeline on our product page. It shows customers what to expect as they keep using Winks.

If someone expects a result on day one and doesn’t get it, they might think the product failed.

That’s why this is so important.

Explain how to use it, what results they’ll notice, and when. Keep those expectations grounded in what you can actually support.

It’s easy to look at a struggling offer and think you need a bigger discount. Great offer get someone to buy … even at full price.

Every item on this checklist helps us earn one of those three beliefs.

This is for me.
It’ll actually work.
It’s worth trying.

Before you make the offer cheaper, make it easier to say yes.

MacCoy Merkley

CMO, Portland Leather

Our Black Friday Revenue Stack Pays for Itself

Every Q4, CAC spikes and discounts eat your margin.

At Portland Leather Goods, our playbook shifted from focusing exclusively on “how do we buy more traffic?” to “how do we squeeze more profit out of every order?”

We focus heavily on the post-checkout experience.

Upsell Without Friction

We use Aftersell for one-click post-purchase offers. If you’re behind on prep, they just dropped high-converting templates so you don’t have to build funnels from scratch.

Monetize Your Thank-You Page

Rokt Thanks shows customers offers from other brands after they buy — brands they already know and trust. Those offers generate revenue from an order we’ve already won.