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AI can write the campaign, personalize the follow-up, and answer a prospect’s questions. But what happens when the positioning is fuzzy, the customer data is unreliable, and three teams disagree about who owns the next step? You get a faster version of the same problems.
Eight takeaways fresh from the CMO Super Huddle
AI can write the campaign, personalize the follow-up, and answer a prospect’s questions. But what happens when the positioning is fuzzy, the customer data is unreliable, and three teams disagree about who owns the next step? You get a faster version of the same problems.
That tension ran through Thursday’s workshops at the CMO Super Huddle. Our founding sponsors brought ideas designed to spark conversation, and Huddlers brought the questions, experiments, and occasional frustrations that made those ideas useful. Here’s an inside peek with eight takeaways worth bringing back to your team.
“Sell the problem, not the product,” urged Bob Wright of Firebrick. His example: a government technology company competing against newer, flashier alternatives. The positioning moved toward solving “civic gridlock” and delivering a “civic velocity advantage.” Anyone who has waited for a permit can appreciate the difference.
Your buyers shouldn’t need a product tour to understand why you matter. Before adding another “AI-powered” headline, give your team a simpler assignment: name the expensive, frustrating problem you solve in language a buyer would actually use.
“I want the CFO, the CMO, the CRO all to be looking at the same data,” one participant said during Neil Tewari’s Conversion workshop. Another surfaced the catch: “What we’re going through at the moment is actually a lot of work on definitions.” Even “who’s a customer?” turned out to be complicated.
Kishan Panpalia’s Pepper workshop raised a related question: are you measuring what your buyers actually care about? He described a company celebrating strong overall AI visibility while trailing a competitor on the specific searches most relevant to its business. His advice: use customer conversations and support questions to shape what you track. As one CMO put it, “Trust your primary research.”
Before asking AI for a definitive answer, agree on your definitions and check your assumptions against customer conversations. A shared dashboard needs a shared dictionary, plus a vocabulary your buyers recognize.
“We were struggling with the most basic things: industry and persona,” one participant admitted in Jim Bell’s LeanData workshop. “I was not confident enough to like really try to do the segmentation that we needed to do because I just didn’t trust the data.”
Then came the practical warning: “You do more harm by sending the wrong thing to someone than if you’re sending something more generic, right?” Pick one audience before scaling your personalization. Check the roles, customer status, and information driving the message. Getting someone’s first name right is a low bar. Getting their situation wrong can be costly.
The technical work wasn’t always the hardest part. “It was … the people … and feeling like there’s trust,” one CMO said in the LeanData discussion. Another described an AI council that improved visibility but created a bottleneck: “It hurt in that everything then had to go through that.”
A Conversion discussion offered a useful starting point. One CMO’s technology counterpart wanted to participate during ideation so they could “solve the problem together.” Bring your technology and operations partners into the business problem before arriving with a tool request. Agree on the outcome, the access required, and who will maintain what you build. Relationships still belong in your tech stack.
“How many handoffs does your buyer experience?” Amanda Kahlow of 1Mind asked. The answers added up quickly, especially when participants counted employee turnover and the transition from buying to onboarding. Each handoff creates another opportunity to lose the reason the buyer showed up.
One CMO was exploring combining growth marketing and business development responsibilities: “We already have the tools, the insights, the tech.” Another described being shut out of active opportunities: “Don’t touch them until after they’re closed, and you can nurture after that.” Follow one stalled deal through your process. Find the point where useful context disappears, or the buyer has to start explaining again. That’s a good place to begin.
“I want to measure revenue. I want to measure the cycle of a deal,” Kahlow said. “Did I shorten the deal cycle? Did I increase the ACV?” Her challenge to the room was to examine how much marketing attention goes into creating opportunities versus helping those opportunities become customers.
The incentive problem surfaced quickly. As one participant put it, “SDRs are so comped on getting stage one pipeline.” If you’re testing an AI buying experience, follow the results beyond meetings booked. Track which opportunities progress, what closes, and how long it takes. Keep the pipeline dashboard. Give it a revenue reality check.
“We are struggling finding authentic people who actually can put their faces on camera and tell a story,” one participant shared in Oana Manolache’s Sequel workshop. The expertise was there. Getting it comfortably onto a screen was another matter.
Manolache’s approach was straightforward: “We created the fireside chat,” and “we supply the questions in advance so they can prepare for those.” Give your expert a thoughtful interviewer and a few specific experiences to discuss. Capture the conversation, then use AI to turn the strongest moments into useful follow-up content. You don’t need every expert to become a polished presenter to help an audience learn.
“Even when it’s really good, it’s like seven pages of scroll,” one CMO said of increasingly elaborate vendor follow-ups. “And if I get that from four vendors a day, I mean I’m not going to read it.” Personalization has become easier. Earning someone’s attention remains stubbornly difficult.
Another CMO brought the discussion back to the work itself: “It’s the message. It’s the content. It’s your positioning.” Before sending the next AI-assisted masterpiece, read it as the recipient. Does it answer their question? Help them make a decision? Give them a useful next step? If the main accomplishment is demonstrating how much content you can produce, keep editing.
These conversations left me with plenty to try and a healthy respect for what still takes work. Our founding sponsors, including Conversion, Pepper, LeanData, 1Mind, Sequel, and Firebrick, helped surface a recurring challenge: the tools are moving quickly, and our marketing decisions need to keep up.
For a next step, explore our AI maturity calculator and the FOMO Task Force report, The AI-Ready Marketing Organization: A Strategy First Playbook for B2B CMOs. Bring them into your next team conversation alongside one question from these workshops: Where could we make marketing work better for the customer this week?