In this conversation, Annalect’s Kristin Reagan asks Microsoft’s Jennifer Kattula to unpack how CMOs can successfully navigate the shift from AI experimentation to integration. Drawing from her own experience leading marketing at Microsoft Advertising, Kattula shares practical habits, emerging tools, and insights into where things are headed — from building AI proficiency and fostering team adoption to measuring impact and preparing for a future driven by agentic experiences.
Kristin Reagan: You have noted that AI is shifting from experimentation to integration and CMOs are increasingly at the helm of that transformation. From your own experience as a CMO, what does it take to successfully lead an organization through this shift? What mindsets, capabilities, partnerships, or tools matter most now?
Jennifer Kattula: It’s energizing to sit within an organization like Microsoft through this time of massive transformation. We have access to all of these AI innovations and we’re focused on marketing them to the advertising ecosystem.
As CMO of Microsoft Advertising, I am responsible for driving adoption within my team so we can show up as credible business partners to our colleagues and our customers. This requires a ton of AI proficiency and experimentation.
Some of the ways that I’m helping my team increase adoption is through things like my “Prompt of the Week” and deeper exploration like generative AI hackathons, focused on building real AI-powered tools to improve our work.
In addition, here are some approaches that I’ve incorporated into my life that have helped me advance in my AI proficiency:
- Make AI a habit — I do this by blocking time … just a few minutes a day. Every single day there is dedicated AI time on my calendar to do something new, experiment, play around. I keep a running list of things to try.
- Unlearn old habits — I rearranged my home screen on my phone so that Copilot is front and center and is my entry point to the internet. I use it every single day and now prefer it to the search entry point.
- Let go of vanity — I’m a high performer who loves “nailing it” right off the bat. But just like my 6-year-old who misses 95% of baskets he shoots, so did I with 95% of my original prompts.
- Map out workflows — I spend the majority of my time in three ways: 1) understanding the landscape of our industry and insights from customers to form a point of view on our position, strategies and investments, 2) in meetings (pacing, leading, advocating, coaching), and 3) writing (thoughts, memos, strategies). I break down these workflows into detailed steps and then, for each task in the workflow, ask myself a few questions.
- Can/should this task be automated?
- Do I love/hate doing this task?
- How much time can I gain from automating?
- What are potential risks of automating this task?
- What mitigating steps might be needed?
- Use Voice — I’m a big fan of voice notes rather than writing long emails or Teams chats, especially when I’m on the go. I will sometimes record a note, transcribe it, and organize it with AI so that I can use a different modality, when needed.
I’ve been reinforcing to my team that building a practice takes patience; it’s part process and part psychological and we’re never going to be done.
KR: You recently shared that the future of advertising is conversational, personalized, and agentic. What will it take for marketers to strike the right balance between automation and authenticity in this next era of brand storytelling? How do you see AI tools like Omni, Omnicom’s open operating system, and Copilot continuing to play an important role in enabling marketers to build high-value connections?
JK: Generative AI is transforming marketing and how brands engage with their audiences. As much as I love AI, robots will not replace human taste, craft, curation, or nuance. It is, however, creating entirely new possibilities in advertising and unlocking better outcomes between people, brands, publishers, and ad platforms.
For example, AI is enabling entirely new surfaces to engage with consumers and build rich, valuable connections. We recently introduced Showroom ads and kicked off with our pilot partner, Mercedes. Showroom ads bring an immersive brand engagement right in the Copilot experience — much like a real-world showroom — where users can explore and discover in-depth information about a product shared in the brand’s voice to make more informed choices. Here a brand can join the conversation with users in an authentic way, complementing organic answers with rich, branded content. This connection embodies where we’re heading in this conversational, personalized and agentic future.
In addition, AI is transforming every step of the campaign process from creative generation to optimization and insights, ensuring precision and impact across full-funnel outcomes. This is evident with AI-powered solutions like Copilot in the Microsoft Advertising Platform and in Omni. Marketers can tap into insights, data and analytics faster and more efficiently — which then enables a more personalized, 1:1 engagement.
KR: What’s the ROI of AI — and how do we measure it? Which AI use cases on the Microsoft Advertising side deliver measurable value?
JK: This is such an important topic in the industry right now. We’re all grappling with how we prove the value of AI and measure the tangible business outcomes that it is driving. The time for hand waving and hyperbole about AI is over. Partners want to see that it drives real business results.
At Microsoft Advertising, we’re seeing results in multiple ways. First, we know that users of Copilot are more engaged with ads and it’s driving better relevance, reach, and results for advertisers. This is shown through 73% higher click through rates, 16% stronger conversion rates, and 33% shorter customer journeys. We know that chat drives action because we’re seeing 53% more purchases within 30 minutes of interaction and nearly 194% when the chat is about shopping. This is huge!
The efficiency gains for our clients are also clear. One of our tech clients used Copilot to cut campaign analysis and reporting time by 30–40%, enabling faster optimization. They also unlocked more than double return on advertising spend during Black Friday 2024 and their 2025 campaigns were their most efficient yet.
Measurement and results are still a work in progress as adoption builds but I’m excited to see how the industry works collaboratively towards defining measurement frameworks through deep partnership.
KR: As we look at what’s next in the era of AI, you’ve written about a concept you refer to as Zero UI — or the invisible interface revolution. What does that mean and how should brands prepare for a future where the internet is no longer confined to a screen?
JK: By 2028, 70% of customer journeys will happen entirely through AI-driven conversational experiences, and budgets are following this prediction; generative AI is already more than a 3-billion-dollar business and will only continue to grow. AI agents, ambient systems, and conversational interfaces that are no longer tied to a screen (think voice, hand gestures, etc.) are shaping what people discover, how they decide, and what they trust.
The race to Zero UI is a restructuring of our relationship with digital technology and the interfaces available to us. More often than not, we’re entering websites and exploring the internet through conversational interfaces like Copilot — where we expect assistance that feels human, instant, and helpful.
As these copilots become smarter and more agentic, they are effectively training the next generation of consumer behavior. This transformation has huge implications for how marketers evolve their role. Strategically, discovery, engagement, and loyalty are no longer only screen-based. They’re system-driven. To stay ahead, brands must become trustworthy, readable by, and useful to the agents acting on behalf of their customers.