543: Marketing's Long Game in Enterprise Deals

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