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- Year Round Retention: How to Drive Engagement Beyond Peak Seasons
Year Round Retention: How to Drive Engagement Beyond Peak Seasons
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Good morning, Chase and Jimmy here.
Most brands go quiet after Q4.
Big mistake.
Your customers don’t disappear after December (they just stop hearing from you).
If you only show up for Black Friday and Cyber Monday, you’re basically training people to ignore you the rest of the year.
The brands that win are the ones that stay active when everyone else goes dark. They send smarter campaigns, tie their emails to real-life moments, and keep engagement rolling long after the discounts end.
Here’s how to drive retention year-round... without waiting for the next “big weekend” to make noise.
Also inside:
✔️ Your 2025 Black Friday Playbook (Built for Record Sales)
✔️ Knowledge Drop: Why Framing Pricing Around Adding Value Is a Mistake
✔️ Up Next on Send It: The Q5 Playbook - Your Easiest Money of the Year
✔️ DTC Wins: Grüns Hits $300M ARR in 24 Months
Let’s jump in👇.
Your 2025 Black Friday Playbook (Built for Record Sales)
Shoppers spent $10.8B last Black Friday. And if 2025 continues the trend, the competition for attention will be even tougher.
Omnisend’s new guide breaks down everything you need to win this year (from early prep to post-purchase retention).
Inside the guide:
Month-by-month timeline to prep your BFCM campaigns
Proven email + SMS strategies that drive the highest ROI
Black Friday promos that boost AOV (without crushing margins)
Retention tactics to keep customers buying into January
Don’t just run sales, run strategy.
Year Round Retention: How to Drive Engagement Beyond Peak Seasons
If your entire marketing hinges on Black Friday or Cyber Monday, you’re missing out.
Your customers don’t stop shopping after December. They don’t stop opening emails. They don’t stop needing great products.
So why would you stop showing up?
Off-season marketing keeps you in the game, even when things slow down.
Here’s how to pull it off.
1. Send Gift Guides All Year
Gifting isn’t just for the holidays.
People have birthdays, anniversaries, graduations, housewarmings, baby showers… life keeps happening. So keep those gift guides coming.
Try curating seasonal round-ups, like:
“Spring Birthday Picks”
“Housewarming Gifts They’ll Actually Use”
“Unique Gifts for the Graduate”
Break it down further by adding “For Her” or “Under $50” to target specific buyers and make it easier for people to shop.
SAYSO nails this with their Valentine’s Day gift guide:

2. Create Your Own Flash Sales
There’s a national day for almost everything now. Why not build a flash sale?
If you sell coffee, don’t skip National Coffee Day
If you sell pet accessories, you’ve got National Dog Day
These holidays might seem silly, but they give you a timely reason to email your list.
Here’s Jibby Coffee celebrating National Relaxation Day with a coupon code.

You can also create your own mini-events like a “Rainy Day Sale” or “Goodbye Winter Deals” to build excitement and urgency during the quieter months.
3. Align Your Campaigns With Customer Goals
New Year’s resolutions are great. But what about spring resets, summer bodies, and back-to-school routines?
People set goals all the time. Your marketing can ride those waves.
Here are some ideas to try:
If you sell fitness gear: “Spring Reset Challenge” or “Midyear Wellness Goals”
If you sell planners: “Back-to-Routine Boost” in September
If you sell meal kits: “30 Days of Clean Eating” in June

Turn it into an interactive or themed campaign with downloadable checklists, progress emails, check-ins, or rewards. Make it fun!
4. Double Down on Loyalty Rewards
Your biggest fans are already talking about you. Give them juicy incentives to keep going (and stick around), even when peak season is over.
Here are some ideas:
Double loyalty points during slow months
Launch refer-a-friend campaigns with instant perks
Offer exclusive early access to upcoming collections

Also: If you have a loyalty program, make it visible. Add a “You’ve earned 50 points!” reminder to your emails. Include perks in the footer. Keep it on their radar without yelling about it.
Here’s a simple points alert email from Dr. Squatch:
5. Highlight Customer Stories
Rave reviews, photos of people using your products, unboxing videos – social proof works all year round. Use it to build trust and break away from promotional emails every now and then.
Here are some ways to use it:
“How Our Customers Are Using [Product] This Spring”
A carousel of 5-star reviews in your newsletter
Short stories or before/after shots from happy customers

Pro Tip: Run a seasonal photo contest (e.g. “Show Us Your Summer Setup”) and offer a prize. It’s content, engagement, and social proof rolled into one.
6. Share Quarterly Recaps and Teasers
Staying top of mind starts with keeping your audience in the loop. Quarterly recaps and teasers are an easy way to do that, especially during slower months.
Here’s what to include:
A sneak peek of upcoming launches
Highlights from your most popular products
Quick hits of brand news or fun team updates
Links to helpful content or reviews

These emails give your audience a clear view of what’s happening (and what’s coming), so you stay relevant even when you're not running a big campaign.
7. Partner With Local Businesses and Charities
Off-season is the perfect time to give your brand more heart. For example, you could collaborate with local businesses that complement yours. Think:
Ski resort + coffee shop + cabin rental = a dreamy winter bundle.
Or, tie a promotion to a charitable cause (like donating a portion of March profits to a community initiative).

People love purpose-driven brands. It makes them feel good about buying from them. And the quieter months give you room to show that side.
Let’s Talk Execution (aka How to Pull This Off)
We get it. Cool ideas are great. But how do you actually make them happen?
Here’s your quick implementation checklist for email and SMS:
Segment smarter (and deeper): Send flash sales to deal hunters. Send loyalty perks and sneak peeks to your high-intent buyers. Use location data to adjust for weather or seasonality (sunny in CA? Still snowing in UT? Different promos!)
Automate what you can: Set up flows for gift guides, flash sales, restock alerts, and loyalty rewards. Automation keeps your brand present year-round without burning you out.
Track the right metrics: In off-season campaigns, pay close attention to unsubscribes and spam rates. These tell you if you’re over-sending or missing the mark. Revenue lift, repeat purchases, and average order value matter more than just opens.
Invest in good copy: Without the holiday hype, you need to earn attention with strong, purposeful copy. Use urgency for flash sales. Tap into curiosity for sneak peeks. And tell stories that connect, not just sell.
Use dynamic elements: Add countdown timers, low-stock alerts, and personalized recommendations. These real-time touches make emails feel more relevant and clickable.
Final Word: Don’t Vanish After the Holidays
You might be tempted to send filler content during the “off season”. But it’s actually a growth opportunity hiding in plain sight.
Here’s what to keep in mind as you plan your next campaigns:
✅ Gifting happens year-round, so don’t wait for December to drop your next gift guide.
✅ Urgency works any time of year, especially when tied to flash sales or niche holidays.
✅ Customer goals shift by season, so align your messaging with where they are.
✅ Loyalty, referrals, and UGC keeps your brand relevant even when you’re not selling.
✅ Connect with your audience by keeping them in the loop using recaps and teasers.
Point is: keep showing up, even when it’s quiet. That’s how you turn off-season into your unfair advantage!
💡 Knowledge Drop:
Most brands frame pricing around adding value... Jimmy says that’s the mistake. In this post, he breaks down how flipping your price tiers from “spend more” to “lose less” can instantly boost conversions and AOV.
Here's what most brands do:
Product: $47
"Premium" version: $97
"Deluxe" version: $197They think they're using price anchoring. They're actually killing conversions.
The problem: You're asking people to justify spending MORE.
That's the wrong mental frame.
Here's what
— Jimmy Kim (@yojimmykim)
6:08 PM • Oct 14, 2025
Up Next on Send It: The Q5 Playbook - Your Easiest Money of the Year
Most brands go dark after Christmas.
The smart ones don’t.
In next week’s Send It! episode, Jimmy and Chase break down Q5 - the “secret fifth quarter” from Dec 26–Jan 1 when inboxes are quiet, ad costs drop, and customers are flush with gift cards, return credit, and self-gifting energy.
Here’s what they cover:
Why Q5 can outperform BFCM in ROI
4 campaign angles that drive effortless revenue
How to automate your Q5 sends before taking time off
The perfect 7-day email + SMS cadence
🛎️ Subscribe to the channel and tap the bell to catch every new drop.
🔥 DTC Wins:
Grüns Hits $300M ARR in 24 Months
In just two years, Grüns has scaled from startup to $300M in annual recurring revenue (and they’ve done it profitably). With 1 billion gummies shipped, retail expansion to 6,300 stores, and limited-edition drops like Raspberry Lemonade and Grünny Smith Apple, the brand continues to blur the line between nutrition and lifestyle. It’s proof that a CPG brand built on science (and fun) can grow fast and sustainably.
Read more in a post from Founder and CEO Chad Janis here!
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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