What 100 CMOs said they are worried about (Dave’s Newsletter)

What 100 CMOs Say Their Biggest Challenges Are Right Now

We’re on the road this week. In Arizona with ~100 VPs and CMOs, all in-house B2B marketing execs, for the first annual Exit Five Marketing Leadership Retreat. Yes yes I know; the power of marketing automation has allowed us to schedule this email in advance (don’t tell anyone this dirty secret), but it really is me. Writing this now, and then making sure we had a place holder for a good photo here for proof:

Since we’re here, I wanted to share something with you all back home as it relates to how leaders are thinking about marketing right now.

Before the retreat, we polled all of the marketing leaders at companies ranging from $50M to $500M+ in ARR. We asked them a simple question: what are your top marketing priorities and challenges heading into 2026? The results were telling about the state of B2B marketing today, so I wanted to share in today’s newsletter.

Ground breaking? No. But that’s not the point. This will make you feel like you aren’t alone and there’s probably someone out there going through the same stage of growth and challenge you are.

1. AI Is the #1 Priority. But Nobody’s Figured It Out Yet.

No surprise here. 85% of respondents named AI adoption as their top priority for 2026. But the interesting part is what they’re actually saying about it. This goes way beyond the cute use cases you see on LinkedIn and from AI creators showing you all the new things to do with new tools.

The pressure looks different depending on where you sit:

“I need practical use cases and quick wins to show.” — VP of Marketing, $25M ARR

“We are expected to be using AI to scale marketing efficiently.” — VP of Marketing, $30M ARR

“We are under pressure to demonstrate hard savings and additional value created via AI adoption.” — CMO, $450M ARR

“Wondering am I moving fast enough on AI transformation — not just adopting tools, but truly rethinking how marketing works from the ground up.” — CMO, $600M ARR

Read those in order. The anxiety scales with the company. At $25M you’re trying to find quick wins. At $600M you’re wondering if you need to rethink how the entire function operates. Or on a simpler level, just trying to figure out which AI tools you can safely get through compliance and legal. Different problems, same theme: everyone knows AI matters, nobody feels like they’re far enough along.

Also important to note something I keep hearing: huge gap between perception and reality. What people are saying about AI on LinkedIn is dramatically different from what is actually happening inside a marketing org at one of these companies.

Btw, if you need a good resource on AI here’s a live session we did on How Marketers Are Creating High Quality Content with AI (That’s Not Slop!)

2. Grow More, Spend Less, and Prove Marketing Did It. No Problem, Right?

Every single respondent talked about revenue growth in some form. But the framing has evolved. Nobody is talking about driving more MQLs anymore. The language has shifted to marketing-sourced and marketing-influenced pipeline, pipeline quality over volume, and tying marketing to ACV expansion and retention, not just new logos.

“We need to tie marketing more directly to revenue outcomes — not just MQLs, but marketing-sourced and marketing-influenced pipeline, ACV growth, and expansion revenue.” — VP of Marketing, $85M ARR

That quote could have come from any of the 100 responses. The mandate is the same everywhere: grow more, spend less, and prove that marketing did it. Prove is the key word. The bar for accountability has gone up. One leader shared that marketing directly contributed $3M in bookings and influenced 80% of total bookings last year. That’s not a vanity metric for the sake of this newsletter. That’s the new standard people are being held to. It’s not enough to grow. You have to prove marketing did it, for better or worse. I didn’t make up the game, I’m just telling you the rules everyone is trying to follow.

The sad part is it almost doesn’t matter if marketing drove the growth if you can’t prove it.

3. Everything Else Keeping Marketing Leaders Up at Night

Beyond AI and revenue accountability, a handful of challenges showed up again and again across the group:

Team too small for scope. Multiple leaders described teams of 2 to 7 people responsible for demand gen, brand, events, PMM, content, and operations. With aggressive growth targets on top. Realistic?

Caught between strategy and execution. Marketing leaders noted feeling pulled between the strategic work they were hired to do (positioning, GTM, C-suite influence) and heavy day-to-day execution that eats up all their time. One VP put it this way: “I’m the face of the company, but for that you need time, and I don’t have time because I’m so busy with the operational work.”

AI search disruption. This one is newer. Companies that built their growth engine on SEO-driven inbound are watching AI search behavior change fast. For inbound-dependent orgs, this is a real funnel risk, not a hypothetical one.

Moving upmarket. Several companies in the $10M to $100M range are trying to shift from SMB or mid-market into enterprise sales. That changes everything: the messaging, the GTM motion, the sales cycle, the content.

Multi-product GTM. Another stage-specific challenge. Companies that grew on a single product are now trying to figure out how to message, position, and sell across multiple products. The messaging and GTM complexity compounds fast.

Structural misalignment after acquisition or reorg. Teams getting folded into larger orgs post-acquisition, losing autonomy, dealing with role confusion and layered processes. One leader described it as “a lack of accountability because processes and roles are overcomplicated.”

I’m not going to pretend we have all the answers. But that’s kind of the point of getting 100 of these leaders in the same room this week. We’re going deep on every one of these topics in Arizona. I wish I could have everything recorded for you and share, but that would get me in big trouble since the whole point of this event is to be off the record. So this is the best I can do for now.

If any of these land with you and what you’re dealing with right now, I’d love to hear it.

If you’re looking for a peer group, consider joining us in Exit Five’s CMO Council.

— Dave

P.S. Which of these challenges is the biggest one on your plate right now? Hit reply and tell me. Maybe you can come to our next MLR if this one is a big hit and we do it again in year two.

Golf yesterday with Colin #foundermode

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