From Automation to Magic: AI-Powered Strategies That Delight Holiday Shoppers

by | Aug 4, 2025

AI has moved beyond hype. It’s now helping people shop smarter, faster, and in ways that actually feel personal. As we highlight in the Infillion Holiday 2025 Playbook, a remarkable 88% of consumers report a positive impact from AI in their shopping journeys, and 69% say they’re more likely to embrace it this year. In parallel, agentic AI is emerging as a powerful force in helping marketers meet high expectations for personalization, speed, and relevance.

That’s because shoppers want more than convenience – they expect brands to “get” them by surfacing relevant options, timing the message just right, and making interactions feel seamless. AI enables this by combining contextual awareness, behavioral prediction, and real-time adaptability.

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A third of current AI shopping use cases didn’t exist a year ago, with consumers increasingly using tools like chat agents, gift-finder quizzes, and curated lists to navigate options. Brands that tap into this mindset shift can meet shoppers with relevance and ease at every turn – even if they understandably aren’t yet ready to completely hand over their ad strategy over to a LLM.

Infillion helps brands deploy AI where it matters most – from personalized product recommendations to interactive experiences and cross-device retargeting. Whether you’re simplifying gift discovery, boosting engagement, or re-engaging high-intent shoppers, these solutions are built to meet the moment:

  • Dynamic creative tailored to real-time context like shipping deadlines, weather, or inventory changes. This ensures messages are never stale and they meet the standards of personalization that customers now expect.
  • AI-powered recommendations embedded in ad units, pulling from approved product feeds and aligned with campaign goals. Think personalized gift guides, not generic promotions.
  • Interaction-based retargeting triggered by real-time engagement signals like quiz answers, product views, or clicks. This enables AI to deliver follow-up creative that aligns with each shopper’s specific interests – making personalization feel intentional, not automated.

From Quiz to Conversation: Let Shoppers Guide the Journey

AI-driven formats go beyond superficial personalization and empower shoppers to steer the experience. Interactive tools like quizzes and chat-enabled ad units are quickly becoming preferred ways to discover new products in low-friction, engaging ways.

Infillion’s interactive Quiz ad format brings this to life. Shoppers answer a few quick questions – who they’re shopping for, their budget, and gifting vibe – and a GPT agent can assemble a tailored gift list from approved product feeds. It’s fast, intuitive, and eliminates irrelevant noise.

Brands can scale this further by pre-building quiz paths around occasions or personas, rotating them intelligently to stay fresh throughout the season. Prompt-engineered guardrails can keep every interaction purposeful, brand-safe, and relevant – ensuring creative control without sacrificing user agency.

Laying the Groundwork: How to Prepare for AI-Enhanced Campaigns

To get the most out of AI this holiday season, marketers need more than good intentions – they need a solid strategy. That means having the right assets, data, and guardrails in place to ensure AI delivers brand-safe, results-oriented experiences.

Start with structure: Even the smartest AI needs structure to perform well. Think of it less like a magic wand and more like a precision instrument – it thrives on clean, organized inputs. That means structured product feeds, clearly defined campaign goals, and modular creative assets. When everything’s mapped out up front, GPT agents can generate responses that are not just fast, but brand-aligned and contextually sharp.

Build brand-safe prompts: The magic of generative AI can only be unlocked when the instructions behind it are strategic. That’s where prompt engineering comes in. Before activating any quiz, gift guide, or chat-based ad unit, marketers should set clear parameters: What the AI should emphasize, where it should stay silent, and how it should sound. Infillion helps brands build these boundaries – so the output stays helpful, human, and unmistakably on-brand.

Make it modular: The best AI campaigns aren’t locked into a single narrative. Modular creative like swappable headlines, dynamic product carousels, or quiz formats tailored by persona gives AI the freedom to personalize without going rogue. It’s how you maintain brand control and meet the moment, no matter what’s changing in the feed, the forecast, or the customer’s mindset.

Best Practices for AI-Enhanced Holiday Campaigns

When AI’s done right, it doesn’t feel robotic – it feels like a little bit of magic. Behind that magic is thoughtful design in which AI amplifies the human element rather than replacing it. It removes friction, sharpens resonance, and delivers moments of relevance that feel almost serendipitous.

To unlock that kind of experience, a smart strategy is just as important as the right technology. Here’s how to get started:

  • Stay human: Let AI do the heavy lifting behind the scenes, but keep your voice warm, helpful, and conversational. The goal is assistive, not robotic.
  • Prioritize clarity: Recommendations land better when users understand them. A simple “because you liked…” or “based on your answers…” helps build trust.
  • Design for learning: AI thrives on iteration. Let each interaction improve the next, whether through feedback loops or dynamic performance insights.
  • Set clear boundaries: Always define what the agent can (and can’t) say. Smart prompt engineering ensures the AI stays on-topic, brand-safe, and focused.
  • Layer utility into delight: Convenience is king. Make it easy for shoppers to act, whether that’s clicking to cart, saving favorites, or following up later.

In an omnichannel, data-rich world, AI can be your strategic differentiator. In a holiday season defined by both urgency and emotion, brands that use AI to gain efficiencies while adding delight will rise above the noise. Whether it’s a helpful gift quiz, a well-timed reminder, or an ad that feels handpicked, these micro-moments are what turn browsers into buyers – and buyers into believers.

Ready to make AI more than a buzzword this holiday season?

Infillion helps brands go beyond automation to deliver truly intelligent, high-utility experiences – built for value-focused, time-starved shoppers. Let’s talk about bringing this magic to your holiday campaigns.

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