Good morning, Chase and Jimmy here.

The holiday inbox isn’t slowing down anytime soon. And while most brands are turning up the volume, the smartest operators are focusing on precision.

Every email should serve, surprise, or sell with purpose. The ones winning this season are built on timing, segmentation, and emotion that feels human... not automated.

Here’s how to approach your holiday sends like a strategist, not a spammer.

Also inside:

✔️ These Email Marketing Tricks Drive 41% More Orders
✔️ Bad Tracking = Wasted Black Friday Spend
✔️ Knowledge Drop: One simple question to ask when emails stop performing
✔️ DTC Wins: Recess Raises $30M

Let’s jump in👇.

📈 These email marketing tricks drive 41% more orders

Marketers using automation generate 41% of all email orders (with just 2% of total sends).

The secret? Smarter workflows, sharper segmentation, and emails that sell while you sleep. Omnisend breaks it down in their latest video.

Here’s what makes the difference:

✅ Automated flows that do the heavy lifting
✅ Segmentation that turns “blasts” into 1:1 communication
✅ Real revenue tracking that shows what’s working

If your email strategy still feels manual, you’re leaving money on the table.

See the 10 features that make your emails work harder.

13 Holiday Email Strategies Worth Stealing in 2025 

1. The Segmented Gift Guide

Why it works: Shoppers are overwhelmed. A segmented guide simplifies decisions and increases purchase intent by showing products that actually fit their needs.

How to implement:

• Build guides around customer goals or interests instead of demographics.

• Use purchase data or quiz inputs to personalize each send.

• Make every product block feel curated, not copy-pasted.

Strategic tip: Lead with language like “Made for…” or “Perfect if you…” to anchor readers emotionally before they browse.

2. Early Access as Retention Strategy

Why it works: Giving subscribers or past customers early access builds exclusivity and improves inbox performance before the BFCM rush.

How to implement:

• Create a private launch window for subscribers 24–48 hours before your public sale.

• Keep the tone warm and inclusive instead of transactional.

• Track engagement to identify high-intent customers for future VIP segments.

  

Strategic tip: Use early access to gather behavioral data you can retarget with personalized follow-ups later in the season.

3. Gift Finder Flows

Why it works: Guided shopping removes friction and drives higher average order values. It gives shoppers the confidence they’ve found the right gift.

How to implement:

• Embed a short quiz or recommendation flow that leads to curated bundles.

• Follow up with an email that restates their results and includes a limited-time incentive.

• Use zero-party data collected from this quiz to refine future campaigns.

Strategic tip: End your quiz email with a secondary CTA like “See what others picked” to drive curiosity and extra clicks.

4. The “Year in Review” Thank You

Why it works: Not every email should sell. Gratitude and storytelling build long-term trust and re-engagement.

How to implement:

• Share simple metrics or milestones that show progress or customer impact.

• Keep visuals calm and copy personal, like a note from your founder or team.

• Close with a teaser for what’s coming next year to maintain momentum.

Strategic tip: Position this as your “inbox breather” between sales. It refreshes subscribers right before your next campaign wave.

5. Limited-Time Drops

Why it works: Short windows create urgency without exhausting subscribers. Limited offers feel exclusive instead of pushy.

How to implement:

• Announce product drops through a teaser email, then a “live now” email a few hours later.

• Include a visible timer or “while supplies last” tag.

• End with a recap to remind subscribers what they missed and build anticipation for the next one.

Strategic tip: Test short drop windows against long campaigns, you’ll often find shorter ones convert faster and fatigue less.

6. The 12-Day Journey

Why it works: Series-based campaigns build habit and familiarity. They create multiple touchpoints without overwhelming the inbox.

How to implement:

• Mix content and offers in your 12-day structure: education, entertainment, then conversion.

• Maintain consistent design templates to build recognition.

• Keep each email short with a single, focused theme.

Strategic tip: Make each subject line sequential to boost open curiosity, “Day 5 of 12: A Little Something for You.”

7. Post-Purchase Reinforcement

Why it works: The best time to influence a second purchase is immediately after the first. Reinforcement emails help customers feel confident in their order.

How to implement:

• Send an email confirming the customer made a smart decision.

• Add care instructions, pairing suggestions, or usage tips.

• Trigger an upsell or referral CTA once the order is delivered.

Strategic tip: Include a line like “What’s next?” to bridge the emotional high of the purchase into your next offer.

8. Community or Charity Tie-Ins

Why it works: A social mission adds emotional depth to an inbox full of sales. Customers want to feel their purchase matters.

How to implement:

• Announce your cause clearly and show progress with a live update bar.

• Involve customers through polls or matching donations.

• Follow up post-holiday with a recap and appreciation message.

  

Strategic tip: Keep the message about impact, not self-congratulation. Show how their purchase made a difference.

9. The Human Touch Email

Why it works: People buy from people. Showing the team behind your brand adds authenticity that AI-driven campaigns can’t replicate.

How to implement:

• Feature your team’s favorite products or holiday traditions.

• Use informal copy and candid photography to make it feel personal.

• Tie recommendations back to product benefits naturally.

Strategic tip: Include one small imperfection in design or tone, it signals humanity and builds trust.

10. Free Gift With Purchase

Why it works: A free gift feels generous and sparks reciprocity. It can also strategically move slow inventory without discounting your core products.

How to implement:

• Choose items that complement bestsellers or encourage repeat use.

• Set the threshold just above your AOV to nudge larger carts.

• Make the free gift visual and headline-worthy in the email hero.

  

Strategic tip: Position the offer as appreciation rather than promotion. “Our thank you gift” sounds better than “Spend X, get Y.” 

11. Custom Bundle Builders

Why it works: Personalization drives perceived value. Letting customers build their own set gives control while raising order totals.

How to implement:

• Create modular bundles where price adjusts dynamically.

• Add subtle upsells like “Complete the bundle” to increase cart size.

• Follow up abandoned bundles with a reminder showing total savings.

Strategic tip: End the email with “Your perfect combo is waiting” to reframe bundling as creative participation, not upselling.

12. Value-Driven Holiday Content

Why it works: Educational or lifestyle content resets the sales-heavy tone of the season. It re-engages readers who ignore discount emails.

How to implement:

• Share simple, useful tips related to your category or product use.

• Add visual storytelling. Step-by-step graphics, short videos, or guides.

• Use a light, conversational tone to invite readers to skim or save.

  

Strategic tip: Treat this content like your pre-sale warmup. It rebuilds engagement ahead of your next promo.

13. The Post-Holiday Reset

Why it works: December buyers are primed for January reactivation. A post-holiday campaign extends lifetime value instead of resetting it.

How to implement:

• Send reflective, encouraging messaging about “starting fresh” or “restocking favorites.”

• Offer loyalty points, early access to new launches, or referral rewards.

• Segment between gifters and self-buyers for personalized CTAs.

Strategic tip: Use this campaign to introduce your next quarter’s retention focus; membership perks, bundles, or seasonal restocks.

What’s Different in 2025

Behavioral segmentation outperforms batch sends. Group by intent (early planners, deal seekers, procrastinators) and tailor cadence and messaging for each.

Shorter campaigns convert better. Three to five-day sequences outperform long, open-ended promotions by keeping attention focused.

Cross-channel timing matters. Sync your SMS and push sends to complement, not copy, your emails. Consistency across channels drives nearly 20% higher conversion.

AI is the assistant, not the author. Use AI for testing, timing, and predictive logic, but keep storytelling and emotional tone human. 

The Takeaway

Holiday success in 2025 isn’t about sending more emails. It’s about sending the right message at the right moment, with clarity and care.

Make every send solve a problem, reduce friction, or make life easier for your customers.

If your emails feel like a service instead of a sale, you’ll stand out long after the holidays are over.

❌ Bad Tracking = Wasted Black Friday Spend

Black Friday and Cyber Monday bring more traffic than any other time of year.

But here’s the catch: if your tracking isn’t set up correctly, you’re already losing money.

When Meta, Google, TikTok, and Klaviyo can’t see your full funnel, they can’t optimize properly.

That means wasted ad spend, underperforming campaigns, and abandoned carts that never trigger an email.

TrackBee fixes that in minutes:

✅ Captures every conversion server-side
✅ Enriches data with persistent shopper profiles
✅ Sends complete data to your ad platforms and Klaviyo

The result?

Stronger ROAS. Smarter optimization. More revenue, even after the sale ends.

💡 Knowledge Drop:

When your emails stop performing, most brands send louder discounts. Jimmy says the fix is simpler: start listening. In this post, he shares how one brand turned a 49% open rate and 40% revenue lift just by asking a single question, “What do you actually want to hear about?”

🔥 DTC Wins:

Recess, a pioneer of the relaxation beverage category, just secured $30M in Series B funding led by CAVU Consumer Partners (the same firm behind Poppi’s billion-dollar success). Profitable and stocked in 15,000+ stores, Recess is gearing up to scale its Mood and Zero Proof lines as it leads the rise of functional relaxation drinks.

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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