Holiday advertising that delights customers and drives results: Expert Q&A

To help advertisers navigate the evolving holiday landscape, we spoke with Jennifer Kattula, Global GM of Marketing and CMO at Microsoft Advertising, about how to Celebrate Smarter this season with AI-powered strategies and customer-first campaigns.

1. What are the top market trends shaping holiday advertising?

From analyzing 2024 trends and original Microsoft Advertising research, we’re seeing several key patterns.

Shoppers are buying both earlier and later in the season, and they’re researching and buying across channels. The brands that launch full omnichannel journeys from October through January—not just during typical “Cyber Five” events like Black Friday—are set up to win in 2025.

At the same time, economic concerns have consumers watching their spending. Advertisers can reach these buyers by promoting deals, speaking about product value, and exploring purpose-driven creative.

Finally, consumer expectations around personalization and consistency are rising as they interact with AI tools. Instead of typing in keywords, shoppers ask questions and chat about what they’re seeking, sometimes with brand agents that already know their purchase history and preferences.

2. How do you see conversational AI influencing holiday campaigns?

Conversational AI can understand intent with precision, making it possible to show people personalized messaging that feels tailored for them. Whether you’re targeting sustainability-minded shoppers planning weeks ahead or impulse buyers looking for brands that reflect their identity, the best-performing campaigns are journey-aware and audience-specific.

For advertisers, this creates new opportunities in developing content, structuring offers, and aligning creative with the help of generative AI. It also means meeting customers across work, life, and play on desktop, mobile, and in-person for consistent storytelling. Winning campaigns should feel like an experience, not a search result.

3. Which holiday moment are you excited about this year?

My two favorite days during the holiday season are Small Business Saturday and Giving Tuesday. They have meaning beyond just buying holiday gifts. It's about giving back and supporting small, local businesses in your community.

There’s a huge untapped opportunity for brands here—participating in these days lets you support community-based retail and the causes that matter to you.

4. What's one piece of advice you can give brands this holiday season?

I would suggest getting your brand and digital footprint ready for conversational experiences like Copilot, so these tools can read everything that’s on your website. That means shoring up your SEO for the natural language web so it can be read and engaged with conversationally, and making sure your metadata supports it. AI is changing how people find information—and brands that are ready will have a big advantage this year.

We’ve just published an incredible guide for advertisers to receive the latest insights on holiday advertising and prepare for 2025. Make sure to check it out for more strategies to celebrate smarter this season!

Ready to elevate your seasonal strategy?

Shifting consumer expectations, economic uncertainty, the rapid evolution of conversational AI... These trends all present challenges for advertisers this holiday season.

But with the right strategy and AI-powered solutions from Microsoft Advertising, you can unwrap new opportunities to break through the noise and deliver unforgettable holiday experiences without overextending your team or budget.

• Celebrate Smarter with our 2025 holiday playbook. Download it today to get started.
• Get in touch with Microsoft Advertising and schedule a consultation with our team of experts today to discuss your holiday campaign needs.
• Replay our expert-led webinars and discover how to work smarter—not harder—this festive season. Join our upcoming webcasts to unlock AI-powered insights that maximise holiday ROI and drive campaign success.

Let’s make 2025 your most successful holiday season yet!