Hey it's Chase and Jimmy here.

Most loyalty programs feel like afterthoughts – customers sign up, earn some points, then completely forget they exist. But CALPAK's VIT series? It's different.

They've managed to turn their "Very Important Traveler" program into something that actually feels exclusive and worth engaging with – from birthday perks to VIT-only product drops that have people checking their email. We tore apart their entire retention sequence to find out what's actually driving repeat purchases and long-term value.

Also inside:

✔️ Stop wrestling with email copy. Let AI do the heavy lifting.
✔️ The DTC leaders behind $200M+ in sales are sharing their playbooks in San Diego
✔️ AI Power-Up: Creative Fatigue Detection

Let’s get into it 👇

🤝 Stop wrestling with email copy. Let AI do the heavy lifting.

Join the live Omnisend AI masterclass on July 29 and discover how to build emails that convert, without the endless rewrites.

You know that feeling when you're staring at a blank email template at 2 PM? Or when you've spent an hour crafting the "perfect" subject line only to second-guess it? This webinar kills that struggle.

Watch the Omnisend team demonstrate how their AI handles the stuff that usually eats your time: writing subject lines that actually get opened, creating email sequences that feel personal, and building audience segments without wrestling with complex filters.

This hits different if you're:

• Flying solo and need to 10x your output

• Running a lean team that's already maxed out

• Sitting on AI tools you're not actually using

The best part? You'll see real examples, not just theory.

Live demos of AI writing entire email flows, natural language segmentation that actually works, and product recommendations that drive sales.

July 29 | 7:00 AM → Grab your spot before it fills up!

CALPAK’s VIT Series: A Masterclass in Loyalty Marketing for Their “Very Important Travelers”

If there’s one thing CALPAK knows how to do, it’s make loyal customers feel like first-class passengers. Their VIT program, short for Very Important Traveler, is CALPAK’s elevated take on the traditional VIP experience, tailored for shoppers who love stylish, functional travel gear.

From birthday perks and redeemable points to exclusive product drops and in-person events, CALPAK turns repeat buyers into lifelong brand fans. And their email retention series? It’s a sleek, rewards-packed journey designed to keep VITs engaged, appreciated, and always ready to come back.

But is it just a pretty sequence, or is it actually deepening customer relationships and boosting long-term value? Let’s break down the VIT series to see what’s working, what could use a refresh, and what your brand can take away.

The Breakdown: CALPAK’s VIT Loyalty & Rewards Email Series

1. You’ve Earned a $20 Reward!

Focus: Points reward + redemption instructions

Why This Works:
 ✅ Frames the points as a luxury. “Basically first class” sets a strong tone.
✅ Walks customers through the redemption process in three easy steps.
✅ Showcases a wide range of product categories to encourage browsing.

What Could Be Improved:
 ❌ Could use more personalization (e.g., “Based on your last purchase, here’s what $20 gets you”).
❌ The muted design feels less VIT-exclusive and more general promo.

2. Here’s 100 points for your thoughts...

Focus: Post-purchase review request with reward

Why This Works:
 ✅ $5 in points for a review is a smart, low-lift incentive.
✅ Formatted for easy submission, rating, comments, and feature checklist.
✅ Builds social proof while reinforcing loyalty.

What Could Be Improved:
 ❌ Could benefit from examples of strong reviews or UGC.
❌ No clarity on when the 100 points will be added.

3. NEW FOR YOU, VIT 🌟

Focus: VIT-exclusive product drop for points redemption

Why This Works:
 ✅ Exclusive product for points redemption feels like a real perk.
✅ Clear CTA and cost (350 points) makes it easy to act.
✅ Hints at upcoming launches to build anticipation.

What Could Be Improved:
 ❌ No inventory messaging, “while supplies last” would increase urgency.
❌ Missed opportunity to bundle with other VIT-exclusive items.

4. Account Update: $27.70 Points Available to Use

Focus: Points reminder + community highlights

Why This Works:
 ✅ Personalized dollar amount makes the value crystal clear.
✅ Spotlights real-world events like the matcha meetup humanizes the brand.
✅ Includes referral program and product launch teaser to drive engagement.

What Could Be Improved:
 ❌ Doesn’t show specific items customers can redeem for $27.70.
❌ Lacks visual urgency around using points before they expire.

5. Our VIT Program is getting an upgrade!

Focus: Loyalty program changes and new perks

Why This Works:
 ✅ Clearly communicates a move from points to direct rewards for birthdays and anniversaries.
✅ Transparency around point expiration builds trust.
✅ CTA to add birthday info helps CALPAK gather zero-party data.

What Could Be Improved:
 ❌ Would benefit from visualizing “before and after” benefits.
❌ No direct reminder of how many points you currently have to use.

6. Psst, you have $27.70 and up to 60% OFF!

Focus: Dual incentive email/sale + points reminder

Why This Works:
 ✅ Strong dual hook: limited-time sale and personalized reward reminder.
✅ Big hero image creates an emotional, aspirational pull.
✅ “Stack the savings” CTA is punchy and memorable.

What Could Be Improved:
 ❌ Could showcase products eligible within your points range.
❌ Lacks urgency-building tactics like countdowns or “ending soon” messaging.

7. Not a Drill: Make Those VIT Points Count

Focus: Final reminder to use points during a promo window

Why This Works:
 ✅ Brings the series full circle with a deadline-driven nudge.
✅ Adds value to points by pairing them with a sitewide discount.
✅ Uses trending products to tempt clicks and drive urgency.

What Could Be Improved:
 ❌ Could reinforce point expiration dates more clearly.
❌ CTA could shift from “Shop Now” to something more VIT-specific like “Spend Your Points.”

What CALPAK Is Doing Right

Brand Consistency: From warm tones to polished layouts, every email feels uniquely CALPAK.

Value Transparency: They don’t hide the value of the points, dollar equivalents are shown upfront.

Member-Only Exclusivity: The term “VIT” isn’t just a name.. it shapes how each message is framed.

Engagement Across the Funnel: From review requests to events and product launches, the series hits multiple loyalty drivers.

What CALPAK Could Improve

More Personalization: While point values are personalized, product recommendations and curated picks would elevate the experience.

Template Variety: Several emails use similar layouts. A mix of formats or interactivity could keep things feeling fresh.

Point Redemption Guidance: Not every email explains how to use points, and few connect your balance to specific products.

Post-Purchase Connection: They nail the transactional reward, but follow-up content like “How to Pack with Your CALPAK” could build stickier relationships.

Final Takeaway: A Stylish, Strategic Loyalty Journey

CALPAK’s VIT series blends exclusivity, rewards, and soft-sell storytelling in a way that feels natural and elevated. It’s not just a loyalty program—it’s a lifestyle loop. With a few improvements in personalization, content diversity, and clearer redemption paths, this retention engine could be even stronger.

Key Lessons for Other Brands

✅ Make the reward value obvious and tangible
✅ Give loyalty tiers a lifestyle identity, not just a label
✅ Use every touchpoint to reinforce value and urgency
✅ Let reviews and community moments drive re-engagement
✅ Diversify content and design to maintain curiosity

🙃 Meme Drop

Marketers are now on Do Not Disturb til the new year...

💥 The DTC leaders behind $200M+ in sales are sharing their playbooks in San Diego.

Commerce Roundtable brings together the kind of speakers who don't just talk theory, they've built the brands, scaled the campaigns, and driven the results that every DTC operator dreams of. This isn't a lineup of talking heads; it's a masterclass from founders and marketers who are still in the trenches, running million-dollar brands and willing to share the strategies that got them there.

Who's joining the San Diego line-up:

• Ezra Firestone – CEO of Zipify Apps & BOOM! Beauty, driven over $200M in sales across multiple 7- and 8-figure brands

• Taylor Holiday – CEO of Common Thread Collective, helping consumer brands scale from zero to $20M

• Robyn Nissim – Founder of Social Proof Agency, scaled Ulta's influencer program to $1M and grew Anastasia Beverly Hills to 24M+ followers

• Savannah Sanchez – Founder of The Social Savannah, social media strategist for top DTC brands

• Mariana Patiño – Executive Assistant at Portland Leather Goods, operations expert behind high-growth DTC success

... just to name a few!

Get direct access to these operators and 25+ more at commerceroundtable.com before tickets sell out.

🤖 AI Power-Up: Creative Fatigue Detection

You’ve probably heard of subject line fatigue, but what about full-blown creative asset fatigue?

AI can now spot when specific visuals, messaging formats, or even button placements are starting to lose their punch. By analyzing your last 3–6 months of campaign performance, you can identify which elements are wearing thin before results tank.

Prompt Example:

"Analyze the last 6 months of email campaigns and surface creative elements (subject line structures, visual layouts, offer language) that have shown declining performance.”

Here’s how this AI power-up works in practice:

• Flags subject line formats that are driving lower open rates over time

• Identifies visual layouts or banner styles that are no longer converting

• Spots CTA or offer language that’s getting ignored

• Helps you test and refresh more proactively (before performance drops)

Why it works:

Creative fatigue doesn’t hit all at once, it creeps in quietly. This AI use case helps you catch subtle dips in engagement and refresh content with intention, not guesswork.

👉 Bonus tip: Pair this with campaign segmentation analysis to see if certain fatigue patterns are audience-specific (e.g. high LTV buyers vs one-time purchasers).

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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