The AI Comeback Playbook
On May 19th, I watched something Knicks fans may be talking about for years. Down 22 points in the 4th quarter against the Cavaliers, with less than eight minutes left, the Knicks looked cooked. Then Jalen Brunson and company flipped the game, forced overtime, and won 115-104. By the final buzzer, my son and I were celebrating by text, and suddenly, a series that felt like it was slipping away had a whole new storyline. Knicks fans could dream again about their first NBA Finals appearance since 1999.
That comeback stuck with me during this month’s Leader Huddles on AI. Because many CMOs are in their own 4th quarter moment. The scoreboard is changing fast. The old plays are not enough. The crowd is restless. And yet, the CMOs who are staying calm, calling better plays, and trusting the right teammates are finding ways to shift momentum.
Here are four AI challenges CMOs are wrestling with right now, paired with four practical wins worth adding to your playbook.
1. Don’t Outrun the Scoreboard
AI is making it easier to launch more content, campaigns, and workflows than ever before, but several CMOs admitted that their measurement systems are not keeping pace. One Huddler put it plainly: “Too much is being launched in real time, and we can’t catch up with the measurement as fast.”
Another noted that their team can point to individual productivity wins, but not yet “the total impact to a function or a team.” In basketball terms, you can push the pace all you want, but if you are not watching the scoreboard, you may not know whether you are actually winning.
The win is to pick one metric that the CFO already cares about. Instead of trying to measure every AI experiment, one CMO chose a lower cost per acquisition because it factors in people, variable costs, and business impact. Another framed the goal even more boldly: Scale from $40 million to $100 million “without scaling my BDR team.”
That’s the kind of AI story board-of-directors understand. Not “we saved six hours,” but “we grew without adding expense.” The takeaway: Don’t let AI success live only in productivity anecdotes. Tie it to a business number that already matters.
2. Know When to Call a Set Play
A few months ago, everyone wanted to build agents. Now CMOs are discovering the fine print. Custom workflows can break, tools can change, token costs can pile up, and when the agent gets one tiny thing wrong, no one on the team may know how to fix it. As one Huddler warned, “If you build it, and it breaks even in its smallest way, no one knows how to fix it.”
This does not mean “don’t build.” It means build where differentiation matters and buy where reliability matters.
One CMO shared a powerful example from their AI SDR rollout. “We had already signed a contract with Qualified,” they said, before seeing 1Mind at a CMO Huddles Strategy Lab. And while 1Mind “blew me away and is probably even better,” their Qualified implementation was already producing results: 20 meetings booked and 12 opportunities worth $29 million. Even better, the AI SDR was uncovering opportunities “at all hours of the day and night,” booking meetings while human SDRs were sleeping.
That is not AI as a toy. That is AI as a set play that creates open shots.
3. Avoid the Unforced Turnover
One of the funniest and most useful moments came when a Huddler described an AI workflow that could build a sophisticated ABM strategy but still got a calendar date wrong. “All you have to do is let the agent run,” they said, “and then sometimes it can’t even get a date right.” That tiny mistake matters. As another CMO observed, one obvious flaw can cause the recipient to dismiss everything else that is good.
The more mature answer is not to trust agents everywhere. It’s to decide which agents can run on their own, which can recommend, and which need a human before anything customer-facing goes live. Some CMOs are already building narrow, useful “brains” for specific jobs: Event-vetting agents, citation-monitoring agents, persona-checking GPTs, and sales-enablement brains that draw on approved thought leadership.
One CMO described a dream scenario: Sales teams using marketing content inside AI prompts, then discovering that the output was stronger because the thought leadership added useful proof points and case studies. For years, marketers have wondered if sales was actually using their content. AI may finally make that content easier to find, trust, and apply.
4. Move from Pickup Ball to a System
Many CMOs have AI task forces. Fewer have a true AI operating model. One CMO described the tension perfectly: “It still feels like it’s off the side of a number of people’s desks.” Another said they had plenty of AI “superstars” but no clear way to turn their ideas into scalable workflows. That is the next maturity gap. A task force can spark motion, but transformation needs ownership, skills, and repeatable ways to turn ideas into working systems.
Not everyone on your team needs to become a technical wizard. But every team needs a way to pair business imagination with AI-building capability. In the Huddle, we talked about this as a buddy system: one AI power user working with a small group of marketers to test, build, and refine workflows. Human creativity plus technical fluency. Curiosity plus execution. That is how teams move from random shots to an offense. And that is how experimentation becomes an operating model.
Penguin-In-Chief Parting Thought
At the recent Imaginarium Summit, a unique conference hosted by Scott Stedman and Noah Brier, founder of Alephic, offered a useful warning: AI is “a mirror, not a crystal ball.” In other words, AI reflects the organization using it. If your processes are messy, AI will expose that. If your data is disconnected, AI will expose that. If your team is undertrained, AI will expose that too.
But here’s the good news: You do not need to be down 22 before changing the game. Start with one real business problem. Pick one metric that matters. Choose where to build and where to buy. Put guardrails around agents. Pair your curious marketers with your technical wizards. The CMOs who do this now will not just run more AI experiments, they’ll build the operating model for the next era of marketing.
And if you want to keep moving, join us at the CMO Super Huddle on October 22-23 in Palo Alto. This year’s gathering is dedicated to helping Huddlers join the top 5% of AI-empowered marketing leaders. We’ll have 10+ AI experts, including Noah Brier, fresh research on AI adoption and maturity, findings from our FOMO task force on the future of marketing org design, and so much more.
Did I mention it’s warmer in the Huddle? 🐧