Category: Show Notes

One interested buyer can get an enterprise deal moving. Then the buying committee shows up, each with a question, an objection, or a reason to hit the brakes. 

That first bit of interest only carries the deal so far. Finance wants numbers, technical teams want proof, champions need help making the case, and priorities can take a hard left at the worst possible moment. So where should marketing stay involved, and how do you keep adding value without turning the whole process into one giant group project? 

Joining Drew are Michael Callahan (Salt Security), Brooke Ames (Q2), and Guy Yalif (Webflow). In this episode, they follow a B2B deal past the hand raise and into the part where momentum gets fragile. They get into where buying groups get complicated, what happens when interest starts to cool, and how much coordination it takes on the seller side to keep things moving. In enterprise, there’s a fine line between staying in step and stepping on each other. 

In This Episode:

• Michael breaks down how to build depth of contact across a buying group and give each stakeholder the proof they need to keep moving
• Brooke walks through the operating model she built to turn strong starts into strong finishes, with five initiatives, clearer ownership, and scorecards tied to what teams can influence
• Guy digs into what enterprise buyers need to feel safe saying yes, plus how LLMs are reshaping shortlists, reputation, and the story buyers hear before sales gets in the room

Plus:

• How to map a buying group without creating a thousand threads
• Where marketing should stay involved after the handoff
• What keeps a stalled deal warm without another hard sell
• Why the reps and sales engineers closest to the deal often have the best insight

Long enterprise deals rarely stall all at once. Tune in to spot where momentum starts slipping and where marketing can step in to keep the deal moving. 

Search visibility has officially outgrown your website. 

SEO still has a seat at the table, but now it has a lot more company. LLMs can build answers from sources scattered across the web, including places your buyers might never visit themselves. So where does authority live now? Which prompts are worth chasing? And how do you keep “everything everywhere all at once” from becoming your channel plan? 

Ross Simmonds, founder of Distribution.ai, has spent years obsessing over what happens after you hit publish. In this episode, he and Drew start where the money is, tracing high-intent prompts back to the sources shaping AI answers and showing why off-site authority suddenly matters a whole lot more. From there, the focus widens to something marketers can’t automate away. You still have to make something worth finding in the first place, then keep enough brand and humanity in the mix that people care when they find it. 

AI may be changing where brands get found, but boring the humans was never much of a growth strategy. 

Three AI Visibility Misunderstandings Marketers Have 

1. GEO is just SEO with a new name
2. Ranking number one is still the finish line
3. Your website is where AI visibility is won

What You’ll Learn 

• Why Reddit and YouTube are becoming major sources for AI discovery
• How to trace high-intent prompts back to the sources AI cites
• Which on-site SEO fundamentals still matter before you go broader
• Where human brand preference fits in an agent-driven buying journey

The internet got messier. Your channel strategy can still stay focused. Tune in for a smarter way to decide what to create, where to distribute it, and where the citation trail says to place your bets. 

You’ve got the experience. The interview is where you make it clear, memorable, and unmistakably yours. 

Years of stories, wins, lessons, and opinions are great raw material. Then an interview asks you to pull the right one out, fast. That’s where answers can sprawl, too much context can take over, and too much polish can make you sound less like yourself. So how do you stay specific, answer cleanly, and ask smart questions of your own? A little structure helps you do all three without sounding scripted. 

Joining Drew for this episode is leadership interview coach Dalena Bradley, who has spent the last nine years focused entirely on leadership interview prep. They get into tightening the stories you want to tell, handling everything from “tell me about yourself” to why the last role ended, and asking what matters most in the job early enough to shape the rest of the interview. 

Do that well, and the interview gives them a feel for how you think, how you listen, and how you’d actually show up as a leader. 

Three Interview Mistakes Executives Make 

1. Staying too general instead of giving a specific example
2. Rambling when nerves or context take over
3. Sounding robotic from over-rehearsing or memorizing

What You’ll Learn 

• How to interview the company while they interview you
• Handling layoffs, short tenures, and awkward questions cleanly
• How midstream questions make interviews more conversational
• Why mindset, body language, and your setup can work for or against you

Tune in for CMO interview advice on telling tighter stories, handling tough questions, and showing up in a way that makes your leadership easy to see. 

AI is rewriting the CMO playbook fast. And somehow, human judgment is getting more valuable. 

Start with what the machines do well. They can crank out content, make sense of scattered data, and turn repeatable tasks into workflows at ridiculous speed. That leaves marketers with a better problem to solve. What should they do with the room they get back? Could the bigger payoff be more time for judgment, creativity, relationships, reputation, and original thinking? If so, a few old-school strengths are looking pretty future-proof. 

For episode 540, Drew does what any reasonable podcast host would do and interviews himself. He pulls together what he’s hearing from CMOs and what CMO Huddles has been testing. From there, he gets into what separates AI experimentation from workflows worth keeping, why AEO is making PR and original research more valuable, and when a homegrown AI tool turns into a software business you never meant to own. 

He also gets candid about the hidden costs of AI and what happens when adoption outruns organizational discipline. If AI can clear the sludge, terrific. Just don’t let it take the humanity with it. 

What You’ll Learn 

• Why smart AI experiments start with a business problem and a clear baseline
• Where AI-generated content creates brand risk, and why original inputs matter
• What separates AI activity from actual AI maturity
• What a study of 13,000 CMOs reveals about tenure, company type, and career odds

Listen in for a clearer sense of where AI earns its keep, where marketers need to slow down, and which parts of the CMO playbook are still worth hanging onto.

Marketing has no shortage of good ideas. The trouble is, they’re all competing for the same budget, people, and attention. 

When everything looks important, something has to give. A big growth bet may deserve the full weight of the team. A proven motion might be better off with a template and a handoff. And a perfectly good idea might need to sit in the parking lot for a while. Somebody has to decide what gets the team’s energy before every good idea starts claiming it. 

In this episode, Drew is joined by Heather Adkins (Trimble), Will Meier, and Betsy Daitch (Canoe), three marketing leaders navigating the trade-offs between business impact, time, budget, and team capacity. Together, they wrestle with the judgment calls behind those trade-offs. 

How long do you let a new idea season? When has a strategy earned its retirement? And if AI gives you more capacity, where should it actually go? 

In This Episode:

• Heather explains how velocity, leverage, and time-to-value help decide what deserves marketing horsepower
• Will shows how tighter constraints across three brands can force better choices, including one low-lift fix that helped opportunities jump 10X
• Betsy shares how force-multiplier thinking and faster event follow-up helped move MQL-to-opportunity conversion from 30% to 55%

Plus:

• How to park good ideas without losing them
• Who needs a seat at the table when priorities shift
• How to push back when conviction is low
• Whether AI belongs on the org chart

Listen in to learn how B2B marketing leaders can make smarter strategic trade-offs, prioritize marketing budget and team capacity, and use AI to create room for higher-impact work. 

Urgency makes shortcuts awfully tempting. Find the problem, make the plan, get moving. But a little more work before the sprint can save a whole lot of fixing later. People, relationships, and processes all have to be ready to carry the speed. Get that setup right, and you can hit the gas with a much better chance of keeping the wheels on. 

In this episode, Drew talks with Anne Morriss, co-author of Move Fast and Fix Things, about what leaders need in place before they accelerate organizational change. They get into why the first problem you see can send you chasing the wrong fix, why the people you always turn to might be missing something important, and why CMOs have a particularly useful superpower when change gets messy. The same storytelling muscle used to move markets can help people inside the company understand where they are going and why the trip is worth taking. 

Three Ways Leaders Make Hard Problems Worse 

1. Solving the wrong problem
2. Relying too heavily on familiar networks
3. Under-investing in storytelling and change communication

What You’ll Learn 

• How to spot your trust wobble across logic, authenticity, and empathy
• Why curiosity can reveal what judgment misses
• How to make clearer people decisions when waiting has a cost
• Why repetition matters when leading through uncertainty

Hear how leaders can earn the right to move fast through organizational change.