Joy in the Inbox: How Insider and Twilio Power the World’s Busiest Shopping Week

To win the attention of busy shoppers this holiday season, brands need to reach them with fast, relevant, personalized experiences across every touchpoint. 

In our recent webinar, Joy in the Inbox: Holiday Playbook for SMS Marketers, Nazgul Kemelbek (Insider’s Director of Product Marketing) sat down with Ignacio Ayerbe (Twilio’s Senior Enterprise Account Executive) to shed light on what brands can expect this holiday season, how consumer behaviors are changing, and what strategies will make a difference in holiday campaigns this year.

Better Together: The Partnership Behind Billions of Holiday Messages

The partnership between Insider and Twilio represents a complete solution for holiday personalization at scale. Insider’s platform handles sophisticated orchestration across more than 12 channels, while Twilio ensures messages reach the right inboxes at the right time.

And the results speak for themselves: Twilio sent 5.2 billion messages during Cyber Week last year. Of these messages, 1.1 billion of them were sent on Cyber Monday alone.

The lessons learned from sending these 5.2 billion messages in 2024: 

• Cyber Week is turning into Cyber Month: Consumers don’t wait for Black Friday or Cyber Monday anymore, and they expect messages throughout the whole month of November. According to data shared in the webinar, 65% of consumers start holiday shopping earlier each year. 
• Cross-channel engagement is key to success: Single-channel strategies fall flat. Real engagement comes from combining channels in a deliberate and connected way: SMS for urgency, email for detailed information, and push notifications for in-app experiences, for instance. The 2024 data supports a multi-channel strategy as 82% made purchases on mobile during Cyber Monday and 93% of consumers shopped online.
• More messages don’t equal more engagement: Higher volume doesn’t drive better results. Holiday performance depends on sending messages that customers actually want, and these messages should be built on opt-ins, relevance, and real personalization. 

Best Practices: Holiday SMS Marketing

When it comes to SMS during the holidays, success is all about discipline. Customers are being bombarded with messages from every direction, so execution really matters: 

1. Meet compliance guidelines: Compliance isn’t optional; it’s your license to operate. Regulations like TCPA, GDPR, and new hyperlocal laws are constantly evolving. Stay up to date with these changes so you don’t have to scramble at the last minute due to flagged campaigns. 
2. Build a targeted subscriber list: Quality beats quantity every time. A small, highly-engaged list will always outperform a massive list of unengaged customers. A clean list is especially valuable as this is a time when people are ready to buy, not just to browse.  
3. Craft holiday-specific content: A generic message like “your cart is waiting” might work in June; but in December, frame it around urgency, convenience, and creativity. Kemelbek reminds us: “Tie copy to the season and the moment. Don’t forget to spread a little bit of holiday cheer. We all yearn for it, especially in times of uncertainty.”
4. Time text messages strategically: Even a perfectly crafted SMS misses the mark if the timing is off. Think about the rhythm of shopping: mornings before work, lunch breaks, evenings, and those frantic, last-minute gift purchases. 
5. Personalize content: Reference past purchases, highlight preferred categories, emphasize local availability, and promote free shipping. Anything to make customers’ lives easier during this high-stress time. 
6. Track performance: Holiday campaigns move fast, so be sure to constantly monitor open rates, click-throughs, and delivery rates.

Compliance for Holiday Success: What’s Changed in 2025

Two major compliance shifts have reshaped SMS marketing this holiday season, and the success of your campaigns will depend on how well you adapt to the new guidelines. 

Texas Senate Bill 140 expands the definition of telephone solicitation to include SMS, MMS, and even some graphics and image transmissions. If you’re engaging customers in Texas, you must register with the state, pay a bond, and follow strict quiet hours. Discuss this law with your legal counsel and ensure your SMS policies and holiday campaigns are compliant.

Platforms are also introducing stricter guidelines: In Apple’s recently unveiled iOS 26  update, promotional texts from unknown senders are filtered out automatically. 

These changes mean that your best performing channel might be getting more difficult to use. To respond, you can: 

• Utilize contact cards and encourage customers to save your brand as a known contact
• Encourage users to initiate contact through other channels: clicking an email link, tapping through an app, or scanning a QR code. This strategy establishes a two-way relationship and signals to your platform that consumers want to engage with your brand.
• Diversify your channel mix with old and new options. Pair SMS with email, push notifications, WhatsApp, RCS, and social channels. That way, if one channel is disrupted, your message still lands. 

Best Practices: Holiday Email Marketing

While it may be the oldest channel in the marketer’s arsenal, email remains the workhorse of holiday commerce. That’s because it excels at delivering personalized messages and rich content that showcase popular items while providing detailed information about products. But Ayerbe cautions that pitfalls like deliverability issues, spam filters, and compliance requirements can kill even the best holiday campaigns, so marketers should keep the following in mind: 

1. Understand what you can and can’t control: You can control list hygiene, cadence, and content. You can’t control new regulations, platform changes, or economic uncertainty. Know the difference and focus your energy accordingly.
2. Warm up your volume: If you suddenly triple your email sends in November, providers will flag it as suspicious traffic. Start ramping up gradually in September and October so your sender reputation is strong before the big days hit.
3. Create a holiday calendar with intentional pauses: Inbox fatigue is real, especially if your brand engages across multiple channels. Space out promotions, use teasers, and give subscribers breathing room so they don’t tune out your message. 
4. Maintain list hygiene: Remove inactive subscribers regularly and segment by engagement level. Don’t let old email addresses impact your sender score.
5. Identify “must-haves” and “nice-haves” for focus: Prioritize campaigns for Black Friday, Cyber Monday, and last shipping day. Nice-to-haves might include early bird promotions or New Year campaigns. This exercise will help your team focus on goals without bombarding customers. 
6. Implement a preference center: Give subscribers choices about frequency, topics, and product categories. This is the best way to reduce unsubscribes during high-volume seasons.
7. Execute ongoing prep throughout H2: Holiday success doesn’t start with last-minute campaigns. It comes from testing subject lines in September, warming up IPs in October, and locking down content well before the holidays begin.

Meet RCS: The Newest Channel on the Block

Rich Communication Services (RCS) is emerging as the next evolution of mobile messaging. Available in more than 20+ countries and supported by both Google and Apple, RCS offers branded messaging, rich media, interactive buttons, carousels, and even full shopping cart experiences within messages. 

Unlike SMS’s 160-character limit, RCS supports unlimited content with enriched media. Another key differentiator is stronger branding as the channel contains a verified sender profile that will reduce fraud and increase both trust and brand recognition. 

While RCS won’t dominate the 2025 holiday season, it’s positioned for explosive growth in 2026. 

Turn Insights into Action for the Upcoming Holidays

The path to a stronger 2025 holiday season starts with four fundamentals: prepare for omnichannel engagement and coordinated promotions, keep global compliance requirements top of mind, move from batch-and-blast to true 1:1 personalization, and track performance so you can keep improving in real time. Brands that follow these steps will be better equipped to adapt quickly, protect reach, and maintain trust across every channel.

It’s never been easier to deliver personalized customer engagement, and the brands that lean into these strategies early will see the biggest impact. The holiday season is critical for every brand, so use these insights to make your campaigns more meaningful, more compliant, and more profitable.

Watch the webinar.