Cyber Week 2025 preparation: Key insights and best practices for retail success

Cyber Week 2025 preparation: Key insights and best practices for retail success

The holiday season is upon us, and there’s no bigger event in the retail and overall consumer engagement world than Cyber Week, which includes Black Friday and Cyber Monday. With the pressure to maximize sales during this time, it's vital that businesses prepare to deliver high-quality, personalized customer experiences. 

Using Twilio data, our past Cyber Week experiences, and the expertise of our customers, Shopify and Klaviyo, we’ve compiled key insights, digital engagement tips, and strategic recommendations to help you prepare for the Super Bowl of the communications world. 

Key trends and insights from Cyber Week 2024

Cyber Week is known for its sheer volume of purchases and communications, demonstrating the scale businesses must be ready to handle:

• In 2024, digital sales throughout Cyber Week reached $76 billion in the US (up 7% YoY).

• Last year, Twilio handled 5.2 billion messages and over 65.5 billion emails! 

• Kalviyo sent 420 million messages in its peak hour on Black Friday, driving more than $3 billion in total Klaviyo-attributed value (KAV) between Thanksgiving and Cyber Monday.

• Shopify’s merchants generated $11.5 billion over the Black Friday-Cyber Monday weekend. 

As Cyber Week continues to grow, businesses need strategies in place to seamlessly scale communications, operations, and support well ahead of the holiday season.

What are Cyber Week best practices for success?

Preparation is the key to minimizing risk and ensuring success during the busiest week of the year. Learn how to prepare for Cyber Week with the following best practices. 

1. Start preparing early

A successful Cyber Week hinges on year-round preparation. As Kiersti Esparza, Email Deliverability, Strategy and Product Management Leader from Klaviyo shares in a Cyber Week Preparation webinar, "Preparation for the next Cyber Week will begin the day after this one ends." To make sure you’re ready, start planning your strategies, campaigns, and operational processes as early as possible.

2. Prioritize deliverability and list hygiene

Deliverability is crucial for Cyber Week. High message volumes make deliverability issues even riskier, with the potential to get on spam block lists or have messages throttled. Ensure you’re only sending to engaged customers who have given explicit consent to receive your communications. Maintaining list hygiene and validating lists using tools like SendGrid’s Email Validation API can save you from critical messages ending up in the spam folder. 

3. Segment audiences 

Segmentation allows your brand to personalize communications by audience type. Data from Klaviyo shows that brands see more new buyers during peak season than the three prior months combined. Using segments like, first-time customers, returning customers, location, order frequency, etc. can help boost repeat purchases and strengthen customer loyalty. By targeting the right audience with tailored messages across their preferred channels, you ensure your campaigns are relevant and engaging.

4. Maintain compliance and monitor metrics

Compliance requirements have evolved, and best practices are now necessary standards. Sending messages at high volume means mistakes are often amplified, increasing the risk of block lists and penalties. To stay compliant and avoid penalties, keep your complaint rates below 0.1%, and for messaging (such as SMS), always obtain documented consent. 

Remember to prioritize the value and effectiveness of the messages in driving action, not the volume of the messages sent. Shopify recommends using metrics like delivery rate, open rate, and conversion rates to gauge message performance.

Overcoming challenges: Stability, deliverability, and customer expectations

Common challenges during Cyber Week include platform instability, deliverability issues, and the heightened expectations from consumers. Both Klaviyo and Shopify stress the importance of "observability," or constant monitoring of systems and communication metrics to ensure everything runs smoothly.

Chris Borgia, Email Deliverability Lead at Shopify shares, “The deliverability concerns during Cyber Week are the same as any other day of the year, they’re just at a larger scale and with much higher expectations from our merchants and customers. Much higher volumes and a lot less room for error.” 

With more at stake, businesses need to consistently monitor performance metrics like inbox placement and complaint rates to mitigate issues before they escalate.

Why do multi-channel strategies matter?

Twilio’s Consumer Preferences Report found that 91% of consumers expect brands to communicate using their preferred channels. While email and SMS/MMS are the most popular communication channels globally, other options like RCS, WhatsApp, social media, and in-app push notifications can be great ways to reach customers.

By honoring customer channel preferences, you can boost satisfaction, increase brand loyalty, and ultimately drive more conversions. In fact, consumers are willing to spend 32% on brands that use their preferred channels, and 40% of consumers say they are more likely to make repeat purchases when brands use their preferred channels.

How will AI impact ecommerce this year?

Whether it’s automating customer support or personalizing product recommendations, ecommerce AI is already reshaping the online storefront. Here are a few ways we’ll see AI impact ecommerce during Cyber Week: 

• Consumer shopping habits: Nearly half of US consumers say they’ve used AI tools as part of their shopping journey, and we expect that number will grow as consumers gear up for holiday shopping. Implementing AI engine optimization (AEO) best practices into your site content will help your ecommerce business get noticed this holiday season.

• Operational improvements: 51% of businesses say AI is speeding up their response times. AI chatbots and agents can help support teams handle common requests, decreasing customer wait times and improving satisfaction scores by 45%. 

• Data-informed personalization: By leveraging data and AI, brands can align every interaction with individual preferences and past behaviors. This allows ecommerce brands to create unique, personalized experiences. With 75% of businesses sharing that personalization boosts customer spending resulting in a 32% average increase per purchase, personalization proves itself as a worthwhile investment. 

• Adapting content in real-time: Some brands will implement AI to analyze a customer's current, in-session behavior (clicks, scrolls, search queries) and instantly adjust the website, product recommendations, and pricing to match their intent. This moves beyond traditional personalization tactics to make the retail customer experience feel uniquely tailored to that second. Real-time personalization makes it much more likely that a purchase will occur and 88% of consumers agree with 35% saying they’d be significantly more likely to buy. 

Top recommendations for Cyber Week success

• Focus on quality over quantity: As tempting as it is to increase message volume during Cyber Week, the panelists reiterated that success lies in how effective your communication is—not just how much of it you send. Less can often be more if messages are personalized and relevant.

• Monitor engagement: Keep an eye on engagement metrics, like click-through rates, open rates, and conversion rates. These metrics indicate whether your messages are reaching and resonating with your audience.

• Compliance is non-negotiable: Following compliance regulations is critical regardless of the communication channel you are using. Make sure you have documented consent and are abiding by the relevant federal, regional, or provider’s compliance requirements.  

Prepare now for success during Cyber Week

Cyber Week is an unparalleled opportunity for retailers to maximize their revenue, but it requires detailed planning, preparation, and flawless execution. With rising consumer expectations and expanding communication channels, adopting best practices around deliverability, targeting, compliance, and customer engagement is more important than ever. 

For more insights into communication best practices during the holiday season, check out our guides, Holiday Sending 101 and Your 2025 Holiday Email Campaign Playbook. 

Frequently asked questions about Cyber Week 

Q: When is Cyber Week?

A: Cyber Week starts the Monday after Thanksgiving. This year, it takes place on Monday, December 1st. 

Q: What is the difference between Black Friday and Cyber Monday?

A: Aside from the day that they take place, Black Friday represents a mix of in-store and online sales ahead of the holiday season while Cyber Monday exclusively focuses on online sales. 

Q: How can automation support customer service during peak shopping periods?

A: Automation supports customer service operations in handling the surge in the number of requests. Chatbots and AI assistants provide instant responses to common questions, directing high-context questions to the correct human agent, and reducing wait times. 

Automated communication like follow-up emails, delivery notifications, and inventory alerts keep customers informed and create a better post-purchase experience. 

Q: What are popular product categories that customers look for on Cyber Monday?

A: Cyber Monday is for online and tech-focused deals, making electronics a top-performing category. Other popular purchases include: apparel and accessories, toys and games, home and kitchen items, and health and beauty. 

Q: What are the most effective communication channels for Cyber Week promotions?

A: A multichannel mix that includes messaging and email can be a great way to inform customers of your promotions. Email can be sent leading up to Cyber Week to inform customers of the upcoming sale. On the days of the promotion, consider sending SMS, Whatsapp, and RCS messages for time-sensitive communications that further engage customers.