Author: Melissa Caffrey

Company-wide AI adoption needs a flock leader. Marketing may already have the job. 

Marketing has a few advantages here. It hears customer friction early, touches nearly every corner of the business, and has gotten pretty good at doing more with less. That makes it a natural proving ground for new ways of working, with a chance to test what works, prove the value, and give the rest of the company something worth scaling. 

In this episode, Drew talks with Thalía Diedrick (GoTu), Allison Breeding (Direct Travel), and Lauren Boyman (KPMG US) about how marketing can lead company-wide AI adoption. Across three differently sized companies, they compare what sophisticated AI use looks like, how workflows start to change, and where build-versus-buy, governance, and training enter the picture. AI moves fast. Companies have people, processes, budgets, systems, and guardrails that take a little longer to turn. These marketers are figuring out how to bring the whole company along. 

In This Episode:

• Thalía shows how GoTu built a bespoke AI project manager into the team’s daily workflow, helping marketing model a more AI-native way of working
• Allison shares how Direct Travel drives adoption through business-problem hackathons, a central owner for new ideas, and regular wins shared with leadership
• Lauren on how KPMG uses marketing as “client zero,” pushing beyond basic adoption to test AI approaches the wider business can learn from

Plus:

• How to make smarter AI build-versus-buy decisions
• How to scale AI experimentation without creating agent sprawl
• Why organic traffic can fall while buying intent rises in the AEO/GEO era

Listen in for how CMOs can lead company-wide AI adoption and turn experimentation into new ways of working. 

Some of the most expensive friction in B2B marketing starts with one question. Can I trust this? 

The buying process already comes with enough hesitation. Add a message that burns extra brain calories, a brand promise that shifts depending on where you meet it, or outreach that feels suspiciously automated, and the trust tax starts piling up. Every extra layer gives buyers another reason to pause. 

In this episode, Drew talks with David Horsager, author of Trust Matters More Than Ever, about how trust gets built into the message and the experience around it. David puts clarity and consistency right into the machinery of growth, including what it takes to earn belief again after trust breaks. AI turns the volume up on all of it, giving buyers more reasons to wonder who, or what, is behind the message. David’s advice to marketers stays wonderfully uncomplicated. Say the thing clearly enough that people can remember it, repeat it, and act on it. 

Three Ways Leaders Get Trust Wrong: 

1. Underestimating the cost of low trust
2. Not fully understanding how trust gets built
3. Not knowing how to rebuild trust once it’s lost

What You’ll Learn: 

• How to make messages memorable, repeatable, and actionable
• What builds trust across remote and hybrid teams
• How small, consistent actions build trust over time

Listen in to learn what makes a brand easier to trust, and how clearer marketing keeps the trust tax from piling up. 

How do you know whether the brave move is to go for it or plant your feet? 

CMOs are making that call with short runways, incomplete information, and teams being asked to adapt fast. Comfort can delay the hard decision. Pressure can push leaders toward false certainty or speed for speed’s sake. Brave leadership is more measured, and it gets stronger with practice. 

In this episode, Drew talks with Todd Henry, author of The Brave Habit, about building that practice into leadership. Todd shows how clarity and agency help teams move when the path ahead is still taking shape. The superhero cape can stay home. This is bravery with judgment, habit, and a much better read on what makes your team tick. 

Three Ways Leaders Get Bravery Wrong: 

1. Trying to manufacture certainty in an uncertain moment
2. Equating bravery with action
3. Motivating the team through the leader’s own lens

What You’ll Learn: 

• How to turn brave leadership into a weekly habit
• Why separating true risk from perceived risk matters
• Why AI works best when it amplifies expert thinking

Listen in for how CMOs can build bravery into their leadership, lead with clarity through uncertainty, and give their teams the agency to move. 

Before you ask for another leadership tip, check the glasses you’re already wearing. 

Ty Hammond doesn’t do tips anymore, which slightly complicates Drew’s plan to grab a few quick leadership nuggets. Good thing. When leaders already know the move they need to make and still keep avoiding it, the blocker is often the assumption coloring how they see the moment. If the glasses say “nice guy,” accountability can start to look like becoming the bad guy. That’s the kind of lens Ty wants leaders to notice first. 

In this episode, Drew talks with leadership coach Ty Hammond about the hard moments CMOs tend to label as problems to fix. Some need a tactical solution. Others are adaptive, asking leaders to build the capacity to sit with the discomfort long enough to see what’s really going on. 

What You’ll Learn: 

• Why leadership tips fall short without awareness
• How blind spots shape the moves leaders avoid
• Why some hard moments are adaptive, not tactical
• How to spot the story making accountability harder

Listen in for a quick way to spot the assumption behind the leadership move you’re avoiding, and decide whether the challenge in front of you is tactical, adaptive, or both. 

PE-backed CMOs have to make marketing make sense at board speed. 

The questions come faster. The comparisons come from portfolio companies that look nothing like yours. And no budget line stays “just marketing” for long. 

In this episode, Drew talks with Kevin Ruane (Precisely), Julie Kaplan (Higher Logic), and Alan Gonsenhauser (Demand Revenue) about what it takes to succeed as a PE-backed CMO. They explain how to learn the investment thesis, build CFO trust early, use customer success as a signal source, and make growth more predictable, explainable, and easier for the business to back. 

In This Episode: 

• Kevin shows how to make brand and demand credible with PE sponsors by tying every investment to a clear business story
• Julie explains why CMOs need to understand the PE firm’s thesis, exit story, and pressure points before adapting the marketing plan
• Alan shows how PE-backed CMOs make growth more predictable by owning outcomes and translating marketing into financial language

Plus: 

• Why PE-backed CMOs need a business point of view fast
• How marketing becomes the glue across the business
• Why CFOs need to see customers, not just line items
• How to use board meetings to sharpen priorities

Listen in for how PE-backed CMOs can turn the investment thesis into a stronger marketing agenda, make every bet easier to defend, and show the business exactly how marketing creates value. 

Change only looks sudden when you missed the signals. 

Rita McGrath gives that idea teeth for CMOs leading through AI, org design changes, and markets that refuse to sit still. The signals are usually there. But in businesses wired to confirm what already happened, they get drowned out by revenue, pipeline, CAC, and other lagging indicators. Those numbers still earn their seat, but left alone, they can keep everyone staring backward while customers and competitors move ahead. 

In this episode, Drew talks with Rita McGrath, Columbia Business School professor and author of Seeing Around Corners, about how CMOs can build the muscle to spot change early enough to act. Rita connects weak signals, leading indicators, arena thinking, and strategy-led AI to a bigger job for marketing leaders. Help the business move sooner, then make sure new efficiencies fund the next bet. Because as Rita says, you can’t shrink your way to greatness. 

What You’ll Learn: 

• How strategic centering helps leaders make stronger bets
• Why the next threat may not be the rival on the battlecard
• What separates AI users from AI-powered thinkers
• How to balance the core business with future growth options

Listen in for how CMOs can read the signals sooner, put strategy before AI, and turn efficiency pressure into fuel for the next bet.