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AI in Marketing: Takeaways from Our Chicago CMO Roundtable
Wow. What a conversation.
Each time we bring together Chicago’s marketing leaders and CMOs, I expect thought-provoking conversations. But this one felt different. The energy, the urgency, and the candor around AI weren’t just theoretical – they were grounded in real experimentation, real pressure from boards, and real opportunity.
Our latest Chicago CMO Community luncheon centered on a timely theme: AI Beyond the Hype: How Marketing is Driving Revenue with AI, featuring Dave Anderson, Founder and CEO of evenflow.ai. What followed were practical, honest discussions on where AI is actually delivering value – and where it’s still falling short. Several big themes emerged around AI in marketing, and the throughline was consistent: AI is moving fast, but the fundamentals still matter.
Digital Twins
One of the most talked-about topics? Digital Twins. The idea of creating a digital version of yourself to host meetings, answer team questions, and even run interviews is quickly moving from novelty to utility. But the group made it clear: this isn’t plug-and-play.
Success comes down to two things:
- Curated, high-quality inputs. Your twin is only as good as the content you feed it – blogs, videos, transcripts, recordings. And recency matters. Your thinking evolves, and your inputs need to reflect that.
- Tone and voice tuning. This is harder than it sounds. Written content alone doesn’t fully capture how you think, react, and communicate. Without that nuance, the “twin” can quickly become generic – or even an off-brand version of yourself.
AI in Hiring
Another standout discussion: AI in hiring decisions. We’ve all been there – two strong candidates, each with clear pros and cons. How do you decide? Enter AI as a decision framework: feed in role descriptions, resumes, interview notes, and LinkedIn profiles – then ask AI to build evaluation categories and score candidates objectively.
It doesn’t replace judgment – but it sharpens it. A powerful use case that many in the room are already testing and applying.
Brand Is Where AI Hits Its Ceiling
As expected, branding surfaced as a critical theme – and perhaps one of the biggest opportunities ahead.
Why? Because we’re entering an era of AI-generated sameness. Campaigns are faster, cheaper, and more scalable – but also more uniform, more transactional, and often devoid of emotion. Brand is where AI hits its ceiling.
Great brands are built on emotion, context, memory, and human experience. That’s not something you can fully automate. In fact, as AI-generated content floods the market, distinctive, human-centered brand building becomes even more valuable.
Fundamentals Still Win
We also unpacked a compelling Forbes perspective: “Why Most CEOs See No Returns on AI Investments.” The takeaway wasn’t surprising – but it was important.
AI success still comes down to the fundamentals: people, process, technology, and data. As we’ve said before, AI isn’t the strategy. Right now, most organizations are over-indexed on the technology piece. But without the right data, aligned processes, and teams that know how to operationalize AI, results won’t follow. As one leader put it, we’ve officially entered the change management era of AI.
Perception vs. Reality
Another interesting thread: LinkedIn vs. reality. If you’re like me, you scroll LinkedIn and feel like you’re five years behind in AI adoption. But in the room, a very different story emerges. There’s a growing gap between perception and reality. And that’s exactly why these in-person conversations matter – they ground us in what’s actually working, what’s practical, and what’s still evolving.
BG vs. AG: A Useful Lens
We also debated a new lens: BG vs. AG – Before Generative AI vs. After Generative AI. It’s a simple but telling way to assess where organizations really are. Think of BG as structured around rigid rules, tasks, and prediction models – while AG is defined by natural interaction, dynamic processes, and the convergence of creative and knowledge within a single AI model. This lens helps assess where you are in the AI in marketing adoption curve: are you experimenting because the board told you to? Or is AI embedded into your workflows, driving productivity and revenue? If you’re not sure, this is a good place to start.
The Second-Order Questions of Agent Palooza
And of course, we couldn’t ignore what I’ll call “Agent Palooza.” Every day there’s a new post about AI agents replacing tasks, saving headcount, and driving efficiency.
But there’s a quieter, less discussed side:
- What happens when systems fail?
- What’s the operational risk when everything is automated?
- Who maintains and optimizes these agents over time?
- And candidly – what happens when someone automates themselves out of relevance?
These are the second-order questions leaders need to start addressing now.
The Real Takeaway: This Is a Leadership Moment
As we wrapped up, one thing was clear to me: this isn’t just an AI adoption phase – it’s a leadership moment. The CMOs who will win in this next era aren’t just the ones experimenting with tools. They’re the ones rethinking how their organizations operate – across people, process, data, and culture.
That’s why I continue to value this community so much. These aren’t surface-level conversations – they’re real, grounded, and forward-looking, exactly what’s needed as we navigate such a transformative shift.
I’m already looking forward to the next roundtable.
If you’re navigating AI in marketing and want a thought partner, let’s talk.
Are you a Chicago-based marketing executive interested in joining our next CMO roundtable? Request an invite here.
