Category: Show Notes

Most B2B CEOs never spent time in marketing. Fewer than one in five ever held the title. Which explains a lot. From undervalued budgets to misaligned expectations, marketing often gets boxed in as a support function instead of the growth driver it is. If marketing is going to lead, CEOs need to understand what it can really do and what to look for in a CMO who’s built to deliver.

To set the record straight, Drew taps three marketing leaders, Rebecca Stone (Cisco), Grant Johnson (Chief Outsiders), and Jan Deahl (Drake Star), to reframe how CEOs see marketing. It is a strategic engine built to shape markets, guide buyers, and drive growth. Together, they make the case for what’s possible when CMOs are empowered to lead. 

In this episode: 

• Rebecca on why CMOs need to think and act like a CEO 

• Grant on how mismatched expectations set CMOs up to fail 

• Jan on aligning marketing’s role to company stage and goals

Plus: 

• The key questions every CEO should ask their CMO 

• What to fix when marketing is stuck in order-taking mode 

• How smart onboarding sets CMOs up to lead 

• Why growth depends on more than just demand gen

Tune in for signals that shift how your CEO sees marketing. 

The CMO role is not for the faint of heart. Growth targets loom large. Every dollar and decision gets second-guessed. MarTech keeps stacking up until it threatens to topple over. Drew calls it the coldest seat in the C-suite. It is also the most dynamic, the one that rewards clear thinking, fearless collaboration, and a readiness to shake up the playbook. 

In this episode, Drew sits down with hosts Alec Cheung and Barb VanSomeren of The Marketing Share podcast to share wisdom from his own career and from hundreds of CMOs inside CMO Huddles. Together, they talk about the collision of growth pressure, evolving executive dynamics, and constant change. The conversation gets to the heart of how CMOs can simplify their strategies, earn influence across the leadership team, and lead marketing with focus and courage when the demands never let up. 

In this episode: 

• Drew shares how CMOs can stay focused when everything feels urgent 

• Drew explains why a peer network is essential for clarity and solutions 

• Drew reveals the mindset shift that turns growth pressure into momentum

Plus: 

• Building alignment with your CEO and CFO on marketing’s impact 

• Finding the confidence to defend your strategy 

• Lessons from leaders who kept brands moving in tough markets 

• Why bold marketing still wins when others play it safe

Tune in for a look at the CMO role today and the mindset, moves, and alliances it takes to succeed under constant pressure. 

It started with a 90-day challenge: make a GenAI-powered video promoting the 2025 CMO Super Huddle using only off-the-shelf tools. What followed was equal parts ambition, frustration, learning, and editing. Along the way, Drew got a crash course in prompt writing, script timing, voice cloning, and the realities of working inside tools that promise automation but still require a certain level of finesse. 

With GenAI coach Samantha Stark of Phyusion guiding the early stages and Steve Mudd of Talentless AI stepping in for post, the project quickly became a real test of creative endurance. Each step surfaced a new set of tradeoffs. The tools were powerful, but stitching them together was anything but seamless. What came out the other side is something Drew’s proud to share, along with lessons from two expert AI collaborators and a few fun reveals they brought to the table that show just how weird, clever, and unexpected GenAI production can get. 

In this episode: 

• Samantha shares how GenAI tools spark ideas but still need human direction to shape tone and story 

• Steve explains how editing brings structure and emotion to GenAI content for a more watchable result 

• Both guests highlight the importance of adding context to make GenAI output resonate with viewers

Plus: 

• What GenAI tools need from you upfront to deliver useful output 

• How multi-tool workflows impact timing, syncing, and storytelling 

• Where to focus your time during GenAI production for the biggest payoff 

• When expert editors can step in to shape flow, tone, and polish

Tune in for a behind-the-scenes look at GenAI video and audio creation, guided by the experts who know how to make it all come together. 

Every customer reaches a turning point. Something’s not working the way it used to. And now they’re ready for change. That’s when your product appears as a possibility. But if you lead with features or force-fit personas, you’ll miss the real energy behind their decision. That’s why Bob Moesta starts with struggle. 

In this episode, he joins Drew to discuss how demand forms through struggling moments, not random needs, and why nobody buys any product randomly, ever. As the author of Demand-Side Sales 101 and a longtime builder and educator, Bob shares how to identify that momentum, map the forces behind a decision, and reframe sales and marketing as tools for understanding what buyers are really trying to solve.

What You’ll Learn:

• Why buying decisions start with struggling moments 

• How to ask questions that surface energy, not just answers 

• The four forces shaping decisions: push, pull, anxiety, habit 

• How to spot what customers switch from and why 

• Why the buyer vs. user distinction matters in B2B

Tune in to hear how demand really forms and how to spot it when it does. 

Synthetic research is rewriting the rules—and Jon Lombardo is here to explain how. In this Huddles Quick Take, the Evidenza co-founder breaks down the three biggest misconceptions marketers have about AI-generated research, from assumptions about accuracy to the myth of average insights. 

You’ll hear how synthetic research can help you test messaging, uncover clear audience insights, and even rewrite jargon so sales and buyers actually understand it—all without waiting months or spending a fortune. 

What You’ll Learn:

• 3 misconceptions marketers have about synthetic research 

• Why AI can surface insights that are better than traditional methods 

• How synthetic research unlocks deeper audience understanding at scale 

• When to use synthetic over human research (and how they work together)

For the rest of the conversation with Jon—including B2B use cases, segmentation examples, and a deeper dive into category entry points—visit our YouTube channel (CMO Huddles Hub) or click here: [https://www.youtube.com/watch?v=k4S_Ib-SmZY]. 

Get more insights like these by joining our free Starter program at cmohuddles.com. 

Penguins spend 75% of their lives in the water, actively positioning themselves exactly where they need to be to hunt and survive. It’s intentional placement. Strong brands do the same. They know where they belong and commit. Too many don’t. They drift, hoping the market finds them. You’ve got to stake your spot and give your marketing something to stand on. 

In this episode, Drew brings in Marni Puente (SAIC) and Sara Larsen (Wolters Kluwer Health), two marketers who’ve learned that positioning only works when it’s clear, repeated often, and owned beyond marketing. They get into how to break the cycle of repositioning, earn internal trust, and lay the groundwork for durable growth.

In this episode: 

• Marni shares how a tight positioning strategy anchored SAIC’s rebrand and became a decision filter across the org 

• Sara explains how to drive clarity in a matrixed enterprise, aligning stakeholders without watering down the message 

• Both guests reflect on the power of internal alignment as the real test of a strong position

Plus: 

• How to test positioning with internal and external audiences 

• Why simplicity is your signal when it comes to clarity 

• What positioning unlocks across marketing, sales, and culture 

• How to build buy-in that lasts beyond launch

Tune in to learn how focused positioning gives every team a north star and puts your brand strategy to work across the business.