For years, B2B growth felt predictable: run the demand-gen playbook, crank the funnel, and expand into new segments. But the moment you try to scale upmarket into enterprise? That deal is off. Or gets very, very tricky at best.

What worked in SMB and mid-market stalls out at the top of the pyramid. Sales cycles balloon. Brand trust matters more than tactics. Buyers suddenly have committees. And the old “demand gen on repeat” playbook doesn’t just break, it collapses under its own weight.

That’s where (and how) Ryan Nelsen built his career with huge success with Qualitrics, among other gigs. Ryan has lived through the transition from tools to platforms to revolutions. He knows what it takes to reinvent the playbook when your market shifts underneath you.

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Your playbook is cracking, bruh

On this episode of Playbook Broken, Ryan and I get into it:

* Enterprise is not just “bigger SMB.” Moving upmarket requires a new sales motion, brand positioning, and organizational muscles.

* Category beats features: Winners aren’t just building products, they’re reshaping industries. HubSpot didn’t just sell software; it created inbound (errr, Loop?). StackAdapt is doing the same at the intersection of adtech and martech.

* Consolidation is coming: AI isn’t just another tool, it’s collapsing the Martech stack. CMOs don’t want 12-point solutions. They want unified ecosystems.

StackAdapt’s growth exposes a hard truth: you can’t enterprise your way with mid-market tactics. What worked yesterday won’t get you there tomorrow.

“There’s power in making sure you own a category. Double down on why it’s working, why there’s value, and stay consistent in your story.” - Ryan Nelsen

Forcing yourself

Five weeks into his new CMO role, Ryan shattered his femur in a wakeboarding accident. Onboarding while relearning to walk became an unexpected metaphor: leadership is about forcing yourself through reinvention, even when the playbook you relied on is gone.

Every marketer clings to the illusion of timeless playbooks. But Ryan’s story is proof: disruption doesn’t schedule itself around your strategy off-site. It hits, it breaks your playbook, and it forces you to rebuild in real time.

The real job isn’t running the play. It’s knowing when to burn it.

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Around the town, notes and musings:

* The latest season of “Only Murders in the Building” is a gas and features some wildly funny cameos.

* I dragged myself up to Washington, DC for #GTM2025 and met some incredible people. The highlight for me was Will Guidara’s keynote. If you haven’t yet read “Unreasonable Hospitality,” do yourself and your team a favor and read it ASAP. I wrote about the keynote on LinkedIn.

* I’m having fun experimenting with LLMs and came up with a pretty slick “Focus group idea,” check it out here.

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