Good morning, Chase and Jimmy here!

You don't need to sell on Amazon to cash in on the biggest shopping moment of the year.

The momentum is already there, it's your job is to bend it toward your own site, where you keep the margins, own the data, and run the show.

Today we're breaking down how to win Prime Day without handing Amazon your customers (or your profits).

Also inside:
✔️ Claude + Omnisend, live - webinar June 9
✔️ The compound starts at order #2 (not order #10)
✔️ Warby Parker jumps into smart glasses
✔️ Brooklinen quietly relaunched 80% of its catalog

Now grab an iced coffee and let’s get into it. 🧋

What Happens When Claude Has Live Access to Your Omnisend Account

The email marketers winning in 2026 aren't writing more emails.

They're directing AI to run the program.

Motiejus (PM, Omnisend) is diving into how to actually do that. Not prompts and tips.

The real thing: Claude reading live Omnisend data, building segments you'd never have time to hand-craft, surfacing what's working before your Monday standup, and running reports on a schedule you set once and forget.

If you've felt AI in email marketing has been mostly subject line generators and copywriting this is the level up.

The operators who get this right are about to pull very far ahead.

→ Save your seat

👌 The Quick Take: Why Order #2 Is The Most Underpriced Moment In DTC

Most brands aim their retention budget at the 70% crowd... loyalty tiers, VIP perks, win back discounts for power users.

Wrong end of the curve.

The compounding starts at order #2. Fix that and the rest builds itself. 👇

How to win Prime Day without giving Amazon your customers

You don't need to sell on Amazon to capitalize on Prime Day.

In fact, if you're a DTC brand, you're probably better off keeping customers on your own site where you control the experience, own the data, and keep the margins.

The strategy isn't to compete with Amazon's logistics. It's to use the shopping momentum they've created and redirect it to your own channels. Here's how to do it in 2026.

Beat Amazon's pricing (or offer something they can't)

Shoppers are hunting for deals during Prime Day, but they're not exclusively loyal to Amazon. Give them a reason to buy directly from you instead.

Here's what works:

Match or beat Prime Day pricing on your site. If you're also selling on Amazon, make sure your direct site pricing is competitive. Better yet, beat it.

Offer exclusive bundles or limited editions. Amazon can't offer your custom product bundles or limited-run items. Use exclusivity as your edge.

Swap discounts for high-value perks. Instead of slashing prices, offer free shipping, free gifts with purchase, early access to new products, or subscription savings that deliver long-term value.

Brands like Cymbiotika do this well by pairing sitewide sales with free shipping thresholds, making the direct purchase feel like the smarter choice.

Track your on-site conversions during Prime Day. You'll see exactly how many shoppers you're pulling away from the marketplace and back to your owned channels.

Use AI-powered segmentation to out-personalize Amazon

Amazon's got logistics. You've got personalization.

They can't tailor messaging based on your customer's specific behavior, preferences, or purchase history the way you can. That's your advantage.

Instead of sending one generic Prime Day email to your entire list, use AI-driven segmentation to send hyper-relevant offers:

Segment by browsing and cart behavior. AI can identify which products someone's been eyeing and surface those in your Prime Day emails. "Still thinking about that jacket? Here's 20% off today only."

Segment by purchase history. If someone bought skincare last month, show them skincare deals. If they bought supplements, focus there. AI recommendation engines can automate this at scale.

Segment by engagement level. Your most engaged subscribers get early access or VIP-only deals. Lower engagement? Hit them with a stronger offer to re-activate.

Segment by predicted lifetime value. Use AI to identify high-LTV customers and give them premium offers that match their spending patterns.

The more relevant your message, the higher your conversion rate. And every interaction gives you more data to refine your strategy for next year.

Start your promo before Prime Day (and steal the momentum)

Why wait for Amazon to kick things off?

Launch your sale a day or two early. This lets you capture attention and orders before your customers get flooded with Amazon promotions.

Use email and SMS to announce early access. Frame it as a VIP perk: "Prime Day doesn't start until tomorrow, but your deal starts now."

Layer in urgency tactics:

• Limited quantities on popular items

• Countdown timers showing when early access ends

• Subscriber-only codes that expire before Prime Day officially begins

Brands like Meridian use this strategy to convert their best customers before the competition even starts. By the time Prime Day rolls around, those shoppers have already made their purchase with you.

Extend the window with a post-Prime Day recovery campaign

Not everyone shops on Prime Day itself. Some people miss it. Some people wait to see if better deals drop after.

Capture those late shoppers with a "Prime Replay" or "Last Chance" campaign via email and SMS.

Run a 24-48 hour flash sale right after Prime Day ends. Position it as:

• "Missed Prime Day? We've got you covered."

• "One more day of deals (because we like you)."

• "Prime Day's over. Ours isn't."

Your SMS list is especially valuable here. These subscribers are typically your most engaged and most responsive. A quick text like "Prime who? 20% off for the next 24 hours. Just for you." keeps the momentum going without feeling like you're trying too hard.

Use Prime Day keywords to hijack the inbox buzz

Even if you're not selling on Amazon, your customers are seeing "Prime Day" everywhere. Use that to your advantage.

Drop Prime-related language into your email subject lines to stand out in a crowded inbox:

• "You don't need Prime to save big"

• "Our version of Prime Day (better deals, no membership required)"

• "VIPs > Prime Members"

• "Your Prime deal is here (from us, not Amazon)"

A/B test different angles to see what resonates:

• Humor ("Prime who?")

• Urgency ("Prime Day ends tonight, ours doesn't")

• Exclusivity ("VIP-only Prime deals")

Just keep it playful and aligned with your brand voice. You're not trying to be Amazon. You're using the cultural moment to highlight your own offers.

Use AI to optimize send times and test creative variations

In 2026, brands that use AI strategically during high-traffic sales events have a real edge.

Here's where AI helps during Prime Day:

Send time optimization. AI can predict when individual subscribers are most likely to open and engage, then schedule your Prime Day emails accordingly. Instead of sending at 10am to everyone, you're hitting each person's optimal window.

Subject line testing at scale. Use AI to generate multiple subject line variations, then test them across segments to see what performs best. You can run more tests faster and find winners before the event is over.

Dynamic product recommendations. AI can auto-populate your emails with the products each customer is most likely to buy based on their behavior and preferences. No manual work required.

Real-time performance monitoring. Use AI-powered dashboards to track what's working mid-campaign and adjust on the fly. If a certain segment isn't converting, pivot the offer or messaging before the window closes.

The brands winning Prime Day in 2026 aren't just sending more emails. They're sending smarter emails that feel personalized at scale.

Be transparent about why shopping direct matters

This one's simple but effective: tell your customers why buying directly from you matters.

A lot of shoppers don't realize what it costs you to sell on Amazon, or what you lose in terms of data, margin, and control. So just tell them.

Let them know that when they shop directly from your site:

• They're supporting your team and mission

• You can invest more in product quality and customer experience

• You're able to offer better perks, faster support, and more personalized service

You don't need to bash Amazon. Just be honest about the difference it makes.

Here's an example:

"We're grateful you're here. When you shop directly with us, it helps us grow, improve, and keep doing what we love. Plus, you get access to deals and perks we can't offer anywhere else."

You'd be surprised how many customers are happy to buy from you directly once they understand the impact.

Track the metrics that show if it's actually working

Don't just measure revenue. Track the metrics that tell you whether your Prime Day strategy is pulling customers away from Amazon and into your ecosystem.

On-site conversion rate during Prime Day. Are more people buying directly from you compared to a normal sales day?

Email and SMS performance by segment. Which segments converted best? Use that insight to refine your approach next time.

Customer acquisition vs. retention. Are you attracting new customers or just re-engaging existing ones? Both matter, but the strategy differs.

Post-Prime Day engagement. Do customers who bought during your Prime Day promo stick around? Or are they one-and-done deal hunters?

Amazon vs. direct sales split (if applicable). If you sell on both channels, track where customers are choosing to buy. If direct sales are climbing, your strategy is working.

The goal isn't just to drive revenue during Prime Day. It's to train your customers to shop directly with you instead of defaulting to Amazon.

What to remember for Prime Day 2026

Prime Day isn't Amazon's event anymore. It's a cultural shopping moment, and you can absolutely use it to your advantage without giving up control, data, or margin.

Here's the playbook:

• Match or beat Amazon's pricing, or offer perks they can't

• Use AI-powered segmentation to send hyper-relevant offers

• Start your promo early to steal momentum before Prime Day begins

• Extend the window with a post-Prime Day recovery campaign

• Use Prime Day keywords in subject lines to ride the inbox buzz

• Optimize with AI (send times, creative testing, dynamic recommendations)

• Be transparent about why shopping direct matters

• Track metrics that show you're pulling customers away from Amazon

Play it smart, keep it personal, and make Prime Day work for you instead of your competitors.

🍦 DTC Scoops:

Warby Parker's next move: smart glasses with Google + Samsung
The OG DTC poster child is launching AI "Intelligent Eyewear" this fall. Good prompt for readers: when a brand expands into a whole new category, the email program is what carries existing customers across. New category = new flow.

Brooklinen quietly relaunched 80% of its catalog
Instead of chasing one viral product, Brooklinen overhauled most of its line to rebuild customer trust and set up future growth. Retention play disguised as a product play — worth a note to readers about what "brand resilience" actually looks like (hint: it's not a louder welcome email).

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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