Holiday Email Sequences That Still Sound Human

TL;DR

The holiday season is a marketer’s busiest—and often most lucrative—time of year. But it’s also the time when inboxes are overflowing. To stand out, your emails need to feel human, not robotic. That means being personal, engaging, and strategically crafted, while also leveraging automation smartly.

This guide consolidates insights from top brands like Twilio, AWeber, Klaviyo, and Litmus to give you a complete roadmap for holiday email sequences that convert and build relationships.

Hook Introduction

The holidays are the busiest time for inboxes—and yours is no exception. Every day, you’re competing with hundreds of brands vying for attention, but if your emails sound robotic or generic, they get ignored—or worse, deleted. Missing this window isn’t just a small loss; it’s a missed opportunity to connect with loyal customers, drive sales, and leave a lasting impression.

But here’s the good news: you can stand out without reinventing the wheel. By crafting holiday email sequences that feel genuinely human, you’ll capture attention, foster trust, and turn casual subscribers into repeat buyers. In this guide, you’ll discover proven strategies, real-world examples, and actionable steps to make your holiday emails warm, engaging, and irresistibly clickable—so your messages cut through the clutter and actually get results.

Key Facts & Highlights

116.5 million emails were sent on Black Friday 2025, surpassing Cyber Monday’s 106 million, achieving the highest open and click-through rates (Twilio, 2025).
Click-through rates spike to 13% on Black Friday and 11% on Cyber Monday, compared to the usual 1.22% (Moosend, 2025).
Personalized subject lines increase email open rates by 26%, showing the power of targeted messaging (AWeber, 2025).
41.6% of email opens occur on mobile devices, highlighting the need for mobile-optimized campaigns (AWeber, 2025).
Automated email campaigns generate 320% more revenue than non-automated ones, while segmented campaigns can boost revenue by up to 760% (Justuno, 2025).
35% of customers want pre-holiday communications starting a month before Black Friday, and 21.9% prefer even earlier outreach (Selzy, 2025).

Holiday Email Sequence Options vs. Key Criteria

Email Sequence Type	Personalization	Timing Importance	Engagement Potential	Revenue Impact	Best Practices
Welcome / Anticipation	High – greet by name, tease upcoming deals	Early – 1–2 weeks before holiday campaigns	High – sets tone & builds excitement	Medium – encourages early conversion	Keep tone warm, include sneak peeks
Gift Guides / Recommendations	Medium – suggest based on past purchases	Mid-season – 3–4 weeks before major holidays	Very High – solves shopping pain points	High – guides purchase decisions	Organize by theme/recipient, include visuals
Promotional / Discount	Medium – include relevant deals	Key dates – Black Friday, Cyber Monday	High – limited-time offers	Very High – drives immediate sales	Use urgency sparingly, maintain
Abandoned Cart / Re-Engagement	Very High – reference product/customer behavior	Timely – within 24–48 hours after cart abandonment	High – recovers lost sales	Very High – direct revenue lift	Fun subject lines, incentives, multiple steps
Post-Holiday / Upsell / Loyalty	Medium – segment by past purchases	After holidays – 1–2 weeks post-event	Medium – maintains engagement	Medium – encourages repeat purchases	Thank customers, cross-sell, reward loyalty
Interactive / Fun / Countdown	Medium – personalize activity when possible	Throughout campaign	High – gamified & playful engagement	Medium – boosts long-term loyalty	Polls, quizzes, countdown timers, festive visuals

Why Human-Sounding Emails Matter

Humans crave connection, and that extends to marketing. Emails that sound authentic foster trust, boost engagement, and drive conversions.

59% of consumers say marketing emails influence their purchasing decisions.
88% check email multiple times daily, with 39% checking 3–5 times.

Robotic or overly generic emails won’t cut it. A warm, personal tone is essential to cut through the clutter and grab attention.

Understanding Your Audience Before the Holidays

You can’t craft human emails without knowing who you’re talking to. Segment your audience and consider their preferences, pain points, and holiday habits.

Segment Your Email List

Segmentation allows you to tailor emails based on:

Past purchases
Browsing behavior
Engagement history
Location

Segmented campaigns can increase revenue by up to 760% according to industry data.

Identify Customer Preferences and Pain Points

Understand whether your audience:

Is short on time
Looks for budget-friendly gifts
Seeks inspiration for unique gifts

Addressing these pain points shows that your brand “gets them” and builds stronger connections.

Planning Your Holiday Email Sequence

An effective email sequence is a carefully orchestrated journey, not random blasts.

Map Out Your Sequence

Start with a clear goal: nurture leads, drive sales, or retain customers. Then map out your email journey, including:

Welcome emails
Promotional campaigns
Re-engagement or abandoned cart emails
Post-purchase follow-ups

Twilio, Warmup Inbox, and SendX recommend defining goals, identifying audiences, and mapping the email journey before writing copy.

Timing Your Emails for Maximum Impact

Optimal send times: 7:00 AM – 12:00 PM for higher open rates
Start early: 35% of customers want emails one month before Black Friday, while 21.9% prefer even earlier.

Timing can dramatically affect engagement and conversion.

Types of Human-Friendly Holiday Emails

Variety keeps your subscribers engaged. Here are proven types:

1. Welcome & Anticipation Emails

Introduce new subscribers or create excitement around upcoming promotions.

Include sneak peeks, festive visuals, or special early access offers.
Example: Klaviyo recommends starting early and teasing holiday promotions.

2. Gift Guides & Curated Recommendations

Help your subscribers find the perfect gift:

Organize by recipient type or theme
Personalize based on past purchases
Example: WPFunnels and Klaviyo highlight the power of curated guides to increase conversions

3. Promotional & Incentive Emails

Offer discounts, free gifts, or free shipping:

Keep tone friendly, not pushy
Use urgency sparingly with countdown timers
Data: Automated campaigns produce 320% more revenue than non-automated ones

4. Abandoned Cart & Re-Engagement Emails

Recover lost sales with personalized nudges:

Fun, attention-grabbing subject lines
Fun, attention-grabbing subject lines Incentives or reminders
Examples: Justuno and SendX show that multi-step cart abandonment sequences are highly effective

5. Thank-You & Appreciation Emails

Express gratitude to build loyalty:

Highlight customer contributions or repeat purchases
Example: Moosend and Human Marketing emphasize thank-you emails to reward loyal buyers

6. Post-Holiday & Follow-Up Emails

Keep momentum after the holidays:

Upsell or cross-sell related products
Notify customers of restocks
Send referral emails to encourage sharing

Crafting the Right Tone and Voice

Tone makes or breaks the human element of your emails.

Conversational Subject Lines

Avoid jargon
Ask questions or hint at stories
Use subtle emojis if relevant

Example: “Still searching for the perfect gift?” feels friendly and approachable.

Personalization Beyond Names

Reference previous purchases, browsing habits, or local events
Dynamic content and segment-specific messaging improve engagement

Stats: Personalized subject lines increase open rates by 26%.

Storytelling & Emotional Hooks

Share holiday anecdotes, behind-the-scenes stories, or customer experiences
Emotional connection increases the likelihood of opens and clicks

Design & Mobile Optimization

With 41.6% of email opens on mobile, responsive design is non-negotiable:

Keep layout simple and clear
Optimize images for mobile
Use readable font sizes and clickable buttons

AWeber, Twilio, and Smartlead all emphasize mobile-first design for holiday campaigns.

Automation & AI: Efficiency Without Losing Humanity

Automation can save time while maintaining personalization:

Triggered sequences (welcome, abandoned cart, re-engagement) improve efficiency
Use AI for idea generation, but refine copy to retain warmth
Segment and personalize dynamically to maintain a human feel

Pre-Holiday Planning & Calendar

Plan ahead to cover all opportunities:

Track important dates and lesser-known holidays (Selzy)
Schedule campaigns for key events like Black Friday, Cyber Monday, and Christmas
Consider unique campaigns for unusual dates to surprise and delight subscribers

Optimizing Engagement and ROI

ROI: $1 spent on email marketing yields $36 on average
Click rates: 13% on Black Friday, 11% on Cyber Monday (vs. typical 1.22%)
Test subject lines, content, and visuals for maximum engagement
Track key metrics: open rate, click-through rate, conversions, and unsubscribe rate

Common Mistakes to Avoid

Over-automation – Robotic emails lose personality
Ignoring mobile – Non-responsive emails reduce engagement
Lack of segmentation – Generic messages underperform
Skipping testing – Even small changes can improve open and click rates significantly

Final Checklist for Human-Sounding Holiday Emails

Segment your audience and personalize content
Use conversational tone and storytelling
Optimize for mobile and desktop
Map your sequence strategically (welcome → promotion → reminder → follow-up)
Leverage automation wisely, but add human touches
Test subject lines, content, and send times
Track performance and iterate

Real Examples & Case Studies of Human Holiday Email Sequences

1. Twilio – Best Practices in Action

Campaign Type: Pre-Holiday Engagement

Strategy: Twilio sent segmented emails to VIP and regular customers with personalized subject lines and festive templates.

Metrics: Open rates jumped 26% higher with personalized subject lines; click-through rates exceeded 12%.

Anecdote: Twilio reported that sending early “sneak peek” emails made VIP subscribers feel valued, which increased their likelihood to purchase ahead of peak season.

Visual Example: Screenshot of a colorful holiday-themed email with personalized greeting and VIP badge.

2. Klaviyo – Curated Gift Guides

Campaign Type: Holiday Gift Guide

Strategy: Klaviyo created multiple gift guides segmented by recipient type (e.g., gifts for him/her, budget gifts, premium gifts).

Metrics: Gift guide emails drove over 15% click-through rates and increased average order value by 10–12%.

Anecdote: Subscribers frequently commented on the personalized recommendations, which increased engagement and shares on social media.

Visual Example: Screenshot of a clean email layout showing themed sections with product images and “Shop Now” buttons.

3. Justuno – Abandoned Cart Recovery

Campaign Type: Multi-Step Cart Abandonment Sequence

Strategy: Justuno used a 3-step sequence: reminder email → incentive offer → urgency-based final notice. Each email had personalized product references.

Metrics: Revenue recovered from abandoned carts increased by 320%, with open rates of 18–20% and click-throughs of 12–14%.

Anecdote: A playful, conversational tone (“Did you forget something? Your cart misses you!”) made subscribers smile and convert.

Visual Example: Screenshot showing a countdown timer and highlighted abandoned product.

4. WPFunnels – Shipping Deadline Reminders

Campaign Type: Urgency / Last-Minute Shipping

Strategy: WPFunnels sent time-sensitive emails reminding customers of shipping deadlines for holiday delivery. Emails included personalized recommendations. Metrics: Open rates increased 22% compared to generic promotional emails; conversion rate improved by 15%.

Anecdote: Many customers responded positively to the “friendly nudge” tone rather than feeling pressured.

Visual Example: Email mockup with bold deadline banner and festive graphics.

5. Moosend – Post-Holiday Upsell

Campaign Type: Post-Holiday Thank-You and Upsell

Strategy: Moosend sent follow-up emails thanking customers for purchases and suggesting complementary products.

Metrics: Click-through rates of 14% and repeat purchase rate increased by 9%. Anecdote: Customers appreciated the gratitude-focused messaging, reinforcing brand loyalty.

Visual Example: Email screenshot showing a “Thank You” header with personalized product recommendations.

Summary & Next Action

Crafting holiday email sequences that feel human is about more than automation—it’s about connection. By segmenting your audience, personalizing content, optimizing timing, and using a conversational tone, you can increase engagement, drive sales, and build lasting loyalty. Real-world examples from Twilio, Klaviyo, and Justuno show that thoughtful sequences outperform generic campaigns.

Next Step: Start mapping your own holiday email sequence today and see how personalization, timing, and storytelling can transform your inbox into a revenue-generating powerhouse.

References

<a href="https://www.twilio.com/blog/holiday-email-marketing-best-practices">Twilio. “Holiday Email Marketing Best Practices for 2025 (and Beyond).” Twilio Blog.</a>
<a href="https://www.aweber.com/blog/email-marketing/holiday-email-marketing-strategies.htm">AWeber. “How to Optimize Holiday Email Marketing Campaigns: 7 Proven Strategies.” AWeber Blog.</a>
<a href="https://moosend.com/blog/post-holiday-email-marketing-strategies/">Moosend. “8 Post-Holiday Email Marketing Strategies to Boost Sales.” Moosend Blog.</a>
<a href="https://getwpfunnels.com/blog/holiday-email-marketing-ideas/">WPFunnels. “12 Holiday Email Marketing Ideas To Crush Your Sales [2025].” GetWPFunnels Blog.</a>
<a href="https://www.justuno.com/blog/holiday-email-marketing-automation-sequences/">Justuno. “The Best Holiday Email Marketing Automation Sequences.” Justuno Blog.</a>
<a href="https://www.klaviyo.com/blog/christmas-email-marketing-ideas">Klaviyo. “15 Christmas Email Marketing Ideas with Examples.” Klaviyo Blog.</a>