Holiday Shopping

How to Prep for Cyber 5: 6 Strategies to Win the Season

cyber 5

The Cyber 5 period, which includes the five days from Thanksgiving Day through Cyber Monday, is one of the highest-stakes shopping periods of the year. With consumers highly motivated, competition among retailers intensifies, and digital ad space becomes a battlefield where marketers fight for attention.

But, while Black Friday and Cyber Monday have become synonymous with deals, marketers need to do more than offer deep discounts if they want to win Cyber 5. To help you gain an edge this year, I’ve consulted with marketing experts and drawn on Taboola’s own Realize headline performance data to identify six crucial ad strategies.

6 Strategies to Prepare for Cyber 5

1. Create High-Impact Headlines

Marketers can no longer rely on generic headlines or discounted pricing when building Cyber 5 ad creatives. Taboola recently analyzed the performance of previous Black Friday and Cyber Monday headlines from Realize and found that the highest-performing headlines connected with consumers on a deeper level.

While Direct Discount headlines still resonate, marketers must include a mix of curiosity-driven, problem-solving, and urgency-based messaging in headlines to stand out. These “hybrid” headlines work well because they connect with shoppers on a human level by solving a real problem or sparking their curiosity.

For example, here’s how you could transform a generic headline (using Dyson as the brand) into a high-impact headline that incorporates curiosity-driven, product-solution, and urgency elements:

  • Generic: “Dyson Black Friday Deals — Shop Now!”
  • High-Impact: “Black Friday Sale Ends Tonight: Save 40% on Dyson — Breathe Cleaner Air Before Winter Hits”

As Esther Altomare, head of industry enterprise advertising at Taboola, puts it, “The key is balancing intrigue with clarity, making the benefit obvious while evoking just enough curiosity to prompt a click.”

2. Plan and Stress Test Creatives Early

If your ad campaigns haven’t been tested in advance, small cracks can become major problems. As such, by the time Cyber 5 arrives, your ad creative should already be a proven winner.

According to Aaron Whittaker, VP of demand generation at Thrive Internet Marketing Agency, “The brands that win aren’t the ones optimizing in November, but the ones that have started tracking lead indicators by late summer. I have personally witnessed campaigns where a mere 0.5% lift in click-through rates during September will lead to a double-digit revenue increase over Cyber 5.”

The key takeaway here is that you should test early and address any issues before November. That means preparing for Cyber 5 months in advance, rather than performing a last-minute sprint. As David Quintero, CEO of NewswireJet puts it, “By the time Black Friday hits, testing season is already over. Enter peak season with high-performing assets dialed in, not unproven ideas.”

3. Leverage Historical Data to Forecast Demand and Allocate Budgets

You can find valuable clues about where to focus your resources from previous years’ Cyber 5 sales events. While planning your creatives and allocating your budgets, take a close look at last year’s key performance indicators (KPIs), including traffic patterns, sales results, and channel performance. This should give you some ability to forecast which categories are likely to outperform last year.

Paul DeMott, chief technology officer at Helium SEO, follows this approach when planning for Cyber 5: “We start by examining past data from similar events to get an idea of the traffic and the key products that will sell. We use this knowledge to develop very specific campaigns that will touch the right users at the right time.”

For DeMott, certain KPIs provide additional insight. For example, he looks closely at conversion rates to measure the effectiveness of specific landing pages and offers. He also tracks order values to gauge the effectiveness of efforts to encourage customers to make larger purchases. But, he says, the most important one is return on ad spend (ROAS). According to DeMott, “It comes in handy when tracking the direct relationship between the amount of money used in the ad and the revenue.”

Of course, when using past years’ performance data to plan this year’s Cyber 5 campaigns, remember that you will still need to make real-time adjustments as you go.

4. Be Ready to Make Real-Time Adjustments

Smart marketers plan their Cyber 5 campaigns well in advance, by analyzing last year’s results and stress-testing their ads in the months leading up to Black Friday and Cyber Monday. That said, Cyber 5 is far too dynamic to rely on a set-it-and-forget-it approach.

As you’ve likely experienced, the landscape — including consumer behavior, competitive pricing, and even supply chains — can change within hours. A campaign that looks bulletproof on Friday morning could be underperforming by Saturday if your competitor offers a deeper discount or a popular item sells out.

As a marketer, you have to be prepared to make adjustments on the fly. That might include swapping out underperforming ad creative, shifting your budget to a higher-performing channel, or changing your messaging to keep up with shifts in consumer sentiment.

Himanshu Agarwal, CEO of recruiting firm Zenius, recommends that businesses develop a real-time agility plan: “Monitoring daily performance has helped me switch out underperforming creatives early. I replaced these with backup offers and/or creative assets prepared in advance.”

Fortunately, there are several AI-powered marketing tools at your disposal that can make real-time adjustments much easier. Platforms like Realize can monitor multiple KPIs, such as click-through rates (CTRs) and ROAS in real time, and quickly alert marketers to underperformance. They can then recommend next steps, like adjusting audience targeting or increasing bids on top-performing keywords.

5. Create Dedicated Cyber 5 Landing Pages and Exclusive Offers

By creating a dedicated Cyber 5 landing page, you can consolidate all of your offers. This not only makes it easier for shoppers to find your promotions and deals, it also makes for more accurate performance tracking.

Lou Haverty, owner of e-commerce brand Tank Retailer, takes this approach every year: “We negotiate exclusive manufacturer discounts one to two months in advance and direct all traffic to a Cyber Monday landing page, supported by targeted Google display ads and email campaigns.”

Ultimately, you can use a well-designed landing page, along with exclusive offers, as the centerpiece of your Cyber 5 campaign.

6. Use the BFCM Continuum to Maintain Momentum Across All Five Days

Many shoppers view Cyber 5 as one extended shopping event, rather than individual days. Marketers should do the same by building campaigns that cover the full period from Thanksgiving through Cyber Monday. Along the way, messaging can shift to match buyer sentiment at every stage.

For example, in the days leading up to Black Friday, you can leverage “early access” messaging to capture shoppers who like to plan ahead. Over the weekend, you can promote urgency and exclusive offers to drive sales. Finally, on Cyber Monday, you can frame your offers as a “second chance” for deals shoppers may have missed earlier.

Key Takeaways

While marketers must be prepared to make last-minute adjustments during Cyber 5, successful campaigns are often the result of advanced planning, including careful analysis of previous campaigns and rigorous testing of creatives in the months leading up to Cyber 5. Creative assets need to be validated before November, with ad variations and backups ready to go in case consumer demand shifts, supply chains break down, or competitors change their pricing strategies at the last minute.

Pay close attention to your headline strategy, too: Don’t settle for generic headlines or those that focus solely on price. Direct discount headlines are acceptable, but incorporating elements of curiosity, urgency, and problem-solving is critical if you want to persuade high-intent consumers.

Finally, remember to treat Cyber 5 as one continuous shopping event, rather than a series of disconnected sales days. You can choose a single narrative and allow it to evolve through the different stages of the period.

Frequently Asked Questions (FAQs)

For 2025, the biggest trends in Cyber 5 advertising include using hybrid headline strategies that combine persuasive elements, the ability to adjust ad creatives in real time, and producing and testing creatives early, long before November.

How can I craft abandoned cart email sequences for Cyber 5?

You can use a three-step sequence. Start with an immediate reminder letting the shopper know that they’ve left the item in the cart. Then, follow up within 24 hours, using urgency messaging: “Low stock” or “sale ending soon” keywords are good examples. Finally, make one last push before the sale ends. You may even want to include an extra incentive, such as free shipping.

What are the key KPIs to track during Cyber 5 to measure the success of my advertising campaigns?

Conversion rate, cart abandonment rate, average order value (AOV), return on ad spend (ROAS), and incremental revenue per visitor are all important KPIs to track during Cyber 5. Make sure you’re monitoring them in real time so that you can make adjustments as needed. This can include optimizing your creative or reallocating your budget to the highest-performing areas.

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