Why July Is The New November: Building Your Holiday Retail Strategy

Writer: Kerri O’ Connor
Date: June 16, 2026

The holiday shopping season looks different than it did five years ago. Shoppers start researching months before Black Friday, move fluidly between mobile, streaming, social, and search, and still close a significant share of purchases in-store. By the time Cyber Week arrives, the window to capture high-intent buyers is narrow and the brands that haven’t already built awareness, audience signals, and channel presence before it opens are playing catch-up.

U.S. holiday spending surpasses $1 trillion for the first time in 2025, and it’s projected to keep growing.^[1]

That kind of scale means opportunity, but only for retailers with strategies in place before the rush. The brands that treat holiday advertising as a Q4 sprint rather than a full-funnel, full-year effort consistently leave revenue on the table.

July isn’t too early. For competitive retailers, it’s right on time.

 
As retailers look ahead to the most competitive shopping season of the year, having the right strategy in place early makes all the difference. Simpli.fi’s Holiday Retail Strategy Snapshot outlines the key capabilities and targeting approaches retailers can use to reach the right shoppers, activate across every channel, and connect digital campaigns to real-world outcomes.

THE HOLIDAY JOURNEY STARTS LONG BEFORE ANYONE SHOPS

Holiday shoppers don’t convert in a single click. The path from awareness to purchase spans months, devices, and channels. Shoppers layer in research, compare options, bookmark products, and revisit brands multiple times before committing, often not completing the transaction until the promotional window finally opens.

$257.8 billion was spent in online holiday sales from November 1 through December 31, 2025, up 6.8% year over year, with no signs of slowing.^[2]

For retailers, this extended consideration window is an opportunity to build familiarity before competitors ramp spend. Campaigns launched early can:

• Stay visible during the long research phase before promotional events
• Build brand recognition with consumers across devices and environments
• Re-engage high-intent audiences as the season heats up
• Drive stronger conversion rates when peak moments like Black Friday and Cyber Week arrive

MOBILE IS WHERE THE HOLIDAY JOURNEY LIVES

The device at the center of holiday shopping isn’t a desktop or TV, it’s the phone in a shopper’s pocket. Consumers use mobile to research products, compare prices, look up store locations, and increasingly, to complete purchases outright.

56.4% of online holiday purchases were completed on mobile in 2025, making it the device that bridges digital research and real-world action.^[2]

A mobile-first approach to holiday advertising isn’t just good practice, its table stakes. Retailers need strategies that intercept shoppers across the channels and environments where mobile activity is highest, connecting that digital engagement to both online conversions and in-store visits.

CYBER WEEK IS A WINDOW, NOT A CAMPAIGN

Cyber Week continues to concentrate an enormous share of holiday spend into a few days. Retailers who show up only during that window are competing for the same shoppers with the same message as everyone else. Those who built presence and audience signals earlier in the season walk in with a distinct advantage.

$44.2 billion was spent online during Cyber Week 2025 alone — a window no retailer can afford to miss, or arrive at unprepared.^[3]

The retailers who perform best during peak periods share a common approach: they don’t treat Cyber Week as the start of the campaign. They treat it as the payoff.

CONNECTING DIGITAL REACH TO THE REAL-WORLD RESULTS

Even as online holiday sales grow, physical remains central to how consumers shop. The challenge, and the opportunity, is connecting what happens on a screen to what happens in a store. Simpli.fi is purpose-built for exactly that.

Drive consumers to physical locations with address- and location-based targeting that influences store visits from early-season promotions through last-minute purchases.

Reach high-intent audiences through contextual, search, and LLM-driven keyword targeting, layered with location, behavior, and household signals that surface the right shoppers at the right moment.

Activate across every channel to coordinate messaging across display, mobile, CTV, video, social, DOOH, and search, on the open web and across walled gardens, keeping your brand present throughout the full holiday journey.

Measure real-world impact by connecting campaign performance to physical outcomes through store visitation measurement, foot traffic insights, and offline attribution.

HOLIDAY ADVERTISING SHOULD DELIVER MORE THAN IMPRESSIONS

Scale and reach matter during the holiday season, but they’re not the finish line. The question isn’t how many people saw an ad, it’s how many walked through the door, made a purchase, or converted after engaging with a campaign. Modern holiday strategies need measurement frameworks that connect digital activity to real business outcomes, not just media metrics.

Simpli.fi is the only partner in the media ecosystem that can consistently and effectively connect digital engagement with real-world outcomes, helping retailers reach the right consumers and measure the impact that actually matters.

For retailers building their holiday strategy now, Simpli.fi’s Holiday Retail Strategy Snapshot outlines the capabilities, targeting approaches, and measurement tools designed to help brands reach shoppers earlier, activate across every channel, and tie advertising performance to results that show up in store.

Ready to build your holiday retail campaign before the competition does?
Contact us at hi@simpli.fi to get started today.

References

1. “CNBC/NRF Retail Monitor’s December Data Shows Strong Holiday Season Spending”. NRF.
2. “Adobe: Holiday Shopping Season Drove a Record $257.8 Billion Online with Consumers Embracing Generative AI Tools”. Adobe.
3. “Record shoppers, online sales surge signal strong US holiday season momentum”. Reuters.

Kerri O’Connor Senior Manager, Content Marketing | Simpli.fi Kerri O’Connor is a strategic product marketer with deep expertise in digital advertising, audience engagement, and campaign performance. As a Senior Manager of Content Marketing at Simpli.fi, she leads go-to-market strategy, messaging development, and product adoption for innovative ad tech solutions. Kerri brings a strong background in programmatic media, digital strategy, and client enablement, translating complex industry trends into clear, actionable marketing. She excels at blending data with storytelling to drive results and help brands connect with the right audiences. A passionate storyteller and data-driven marketer, Kerri is committed to helping brands navigate the evolving digital landscape and maximize their marketing impact.