Good morning, Chase and Jimmy here.

Cyber Monday isn’t just another sale day... it’s a $13.3 billion opportunity.

But with inboxes flooded, ads overpriced, and shoppers bouncing between tabs, most brands get lost in the noise. The winners? They’re sharper, more strategic, and more intentional with how they show up.

In today’s guide, we’re breaking down 9 Cyber Monday strategies that actually work. From reshaping your offer and learning from Black Friday behavior to nailing urgency and building real trust, these are the moves that turn Cyber Monday chaos into conversions.

Also inside:

✔️ Holiday 2025 is already here (and it looks different)
✔️ Knowledge Drop: Sometimes, the best hook is the negative one
✔️ Sneak peek: iOS 26 Is Here… And It Changes Everything
✔️ DTC Wins: Alice Mushrooms raises $8M for retail expansion

Let’s get into it. 👇

Holiday 2025 is already here (and it looks different)

Shoppers aren’t waiting until December this year. Omnisend's survey of 4,000 consumers across the US, UK, Canada, and Australia shows the season is starting earlier, with more cautious spending.

• Timing: 1 in 3 shoppers start late October–mid November, and 1 in 5 begin before October.

• Budgets: $250–$499 is the most common spend range.

• Tools: 40–45% plan to use BNPL, while nearly 30% are using AI for deal-hunting and gift inspiration.

📌 What this means for brands: If your campaigns are tied to BFCM weekend, you’ll miss the wave. Start earlier, lead with value, and make buying as seamless as possible.

9 Cyber Monday Strategies to Win More Sales

Cyber Monday is one of the biggest eCommerce moments of the year. Last year, shoppers spent $13.3 billion online. That’s a whole lot of potential sales!

But here’s the catch: inboxes are flooded, ads are expensive, and shoppers are bouncing between tabs all day.

Here are 9 strategies that separate the winners from the rest.

1. Don’t Just Hike Your Discounts

It’s tempting to outdo Black Friday with even steeper discounts on Monday.

But this doesn’t just hurt your margins, it can damage trust. Customers who bought on Friday feel burned, and those who didn’t will learn to wait you out every time.

What to do:

• Switch the value: Offer free gifts, bundles, or shipping upgrades instead of discounts.

• Highlight exclusivity: Position Cyber Monday as a different event, not just “Black Friday part two.”

• Communicate clearly: Tell shoppers upfront that your Black Friday and Cyber Monday offers are distinct so they don’t feel tricked.

2. Put All Your Channels on One Calendar

Shoppers rarely stick to one platform.

They’re scrolling Instagram while checking email, clicking ads while texting friends. If each touchpoint feels disjointed, you miss the chance to reinforce your brand story.

What to do:

• Map it out: Create one calendar showing what messages go live on which channels and when.

• Keep the theme consistent: Whether it’s urgency, gifting, or bundles, make sure every channel reinforces the same big idea.

• Avoid overlap fatigue: Don’t blast identical copy everywhere. Adjust the tone and format to fit the channel while keeping the core consistent.

3. Tailor Content for Each Channel

Nothing kills the Cyber Monday vibe faster than a cropped-off ad or an email that looks broken on mobile. In fact, it can cost you money by losing shoppers’ interest.

Every channel has its quirks, so play by their rules.

What to do:

• Check specs early: Resize assets for stories, feeds, carousels, and ads before the weekend rush.

• Run device tests: Preview emails on desktop and mobile, and test SMS on both iOS and Android.

• Use channel-native features: Polls on Instagram, countdown timers in emails, short sharp text for SMS. These little touches feel native and boost engagement.

4. Focus on Quality, Not Volume

With inboxes overflowing, the instinct is to “send more.” But that doesn’t always guarantee more sales. It can just as easily lead to unsubscribes or annoyed customers.

It’s smarter to respect attention spans and focus your efforts where they’ll have the most impact.

What to do:

• Segment by preference: Identify who responds best to email, SMS, or push and prioritize those channels.

• Stagger your sends: Don’t drop everything at 9 a.m. Monday. Experiment with late-night or lunchtime sends to catch different behaviors.

• Cut redundancy: If someone opened and clicked your email, don’t hit them with the exact same SMS.

5. Learn From Black Friday Behavior

Cyber Monday is the sequel to Black Friday, not a brand-new show.

Use Friday’s clicks, carts, and buys to shape Monday’s messages. When your follow-ups feel personal, shoppers know you’re paying attention. And they’re more likely to hit checkout.

What to do:

• Target browsers: If someone viewed products but didn’t buy, send them a personalized Cyber Monday reminder with urgency.

• Reward engagers: Shoppers who clicked but didn’t convert might need a sweetener, like free shipping or a bonus gift.

• Upsell past buyers: To those who purchased Friday, suggest complementary items or accessories Monday.

6. Build Anticipation With VIP Early Access

Cyber Monday is a madhouse, and your best customers shouldn’t have to elbow through the crowd. You have to make them feel like insiders.

It’s not just about racking up early revenue, it’s about loyalty. Shoppers who feel special during the busiest shopping weekend will keep coming back long after.

What to do instead:

• Define your VIPs: Use criteria like multiple purchases, high order values, or loyal engagement.

• Offer exclusivity: Give them early access codes or a one-hour head start before your sale goes live.

• Expand beyond BFCM: Reuse this VIP list for product launches or seasonal drops throughout the year.

7. Personalize With Zero-Party Data

On Cyber Monday, cookie-cutter blasts fade into the chaos. What makes someone stop scrolling is when your offer feels handpicked for them.

That’s where zero-party data comes in – info shoppers willingly share with your brand.

What to do instead:

• Collect data early: Run quizzes, polls, or surveys about preferences, budget, or gifting needs in November.

• Curate bundles: Use that data to send targeted “gift under $50” or “tech lover’s picks” offers.

• Segment year-round: Keep using this data long after Cyber Monday for tailored promotions.

8. Use Abandoned Cart + Deadline Reminders

Cyber Monday shoppers are juggling tabs, deals, and distractions… so yes, they’ll procrastinate. That’s where abandoned cart flows earn their keep.

Add urgency and FOMO, and you’ll recover a big slice of almost-lost revenue. The trick is balance: remind without being spammy.

What to do:

• Add countdowns: Insert timers in abandoned cart emails and banners to make deadlines visual.

• Stack urgency messages: Follow up with a “final hours” campaign to catch procrastinators.

• Highlight popularity: Phrases like “X people are viewing this” or “selling fast” can nudge hesitant buyers to act.

9. Be Honest About Deadlines and Stock

Urgency works wonders on Cyber Monday, but only if it’s real. Shoppers can spot fake scarcity a mile away, and nothing kills trust faster.

Being honest pays off, because customers know you mean what you say. And trust built in Q4 carries into the rest of the year.

What to do:

• Stick to promises: If the sale ends at midnight, don’t quietly extend it unless you say so upfront.

• Show real numbers: Display exact stock levels (“Only 12 left”) instead of vague terms like “low stock.”

• Avoid manipulation: Customers know when they’re being played. Be transparent as it converts better and builds loyalty.

Your Cyber Monday Checklist

Cyber Monday is noisy, but you don’t have to be louder. You just have to be sharper.

Keep this in mind as you roll into the big day:

✅ Value beats bigger discounts every time.
✅ One clear message across channels > scattered campaigns.
✅ Personal touches make people stop scrolling.
✅ Say what you mean and mean what you say.

Nail these, and Cyber Monday can be the start of long-term customer love.

Knowledge Drop:

Most brands chase hype and positivity. But sometimes, the best hook is the negative one. Jimmy shares why leaning into doubt can earn more trust (and more opens).

Sneak peek: iOS 26 Is Here… And It Changes Everything

iOS 26 just made retention marketing harder. Tracking is blurrier, opens are noisier, and SMS promos risk disappearing into “Unknown Senders.” The old playbook won’t cut it.

In next week’s Send It! episode, Jimmy and Chase break down:

• What iOS 26 actually changes for email and SMS

• How attribution and metrics get distorted

• Tactics to stay visible in SMS (and avoid the promo filter)

• New KPIs to track now that opens are useless

• Lifecycle examples to keep revenue flowing when messages vanish

🛎️ Subscribe to the channel and tap the bell to catch every new drop.

🔥 DTC Wins:

Alice Mushrooms raises $8M for retail expansion 🍫🍄

Functional mushroom chocolate brand Alice secured $8M in Series A funding led by NewBound Venture Capital, with support from Unilever Ventures and Tiësto. Founded in 2022, Alice plans to expand into 1,300 new retail doors.

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

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