Brands Under Pressure

Brands Under Pressure

The Meeting Where Brand “Didn’t Scale”

You've been in it, I've been in it. Here's what's actually happening.

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Kara Redman
Jan 03, 2026
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Just for Fun


The Meeting Where Brand “Didn’t Scale”

First, a story:

“Brand doesn’t scale,” he murmurs, pulling the zipper of his Patagonia a little higher. He takes a slow sip of his Intelligentsia, letting the bitterness linger as though it proved something.

“There’s no attributable ROI,” he continues, eyes locked on the new CMO. “Customers buy from our ads. Brand is irrelevant here.”

He checks his Rolex. The car should be out of the shop by now. It’s *always something* with the Audi. He has to pick it up before his 3pm meeting about migrating the org off Microsoft Office, even though he’s been living in Teams for years and the thought alone exhausts him.

He exhales. Leadership is heavy, just like Steve Jobs warned it would be.

“Let’s circle back on this later,” he says, already standing. He grabs his Bullet Journal and heads for the door.

My Observation

A pattern I’m seeing across companies right now.

We’ve all been in this meeting. Something in the business is in crisis or change, and no one can convince leadership there’s a brand problem. Usually one of two things is true: the business outgrew the brand, or leadership doesn’t really get brand and focuses only on short-term numbers.

This is one of those brand moments I talked about last week, a structural inflection point where the company has crossed into a new phase, but leadership is still operating with decisions made in an earlier one.

When that happens, brand starts to feel abstract, optional, even annoying. People across teams start resenting each other, decisions get stalled because everyone is covering their asses and keeping receipts instead of building something together.

So leadership reaches for what feels controllable:

  • Performance channels

  • Attribution models

  • Short-term ROI

Brand becomes the thing you “circle back to” once the chaos settles. So instead of updating the brand to match the stage they’re in, they try to out-execute the misalignment with more campaigns, content, measurement (shut off what doesn’t perform ASAP!), and what I call “prove it” meetings. It feels like discipline and control to leadership, but I call it avoidance.

What This Signals

Why it matters, and where things are headed.

When leadership starts calling brand “irrelevant,” it’s often because the business crossed a threshold, and no one updated the decisions that once worked.

Common signals:

  • Performance is working, but everything feels uphill

  • Teams are simply producing, not collaborating on big ideas

  • The CMO has to prove brand has value beyond paid campaigns

  • Brand conversations get postponed in favor of “real work”

  • The org has become more complex than the original brand story

  • Sales, marketing, and product are working in silos (and fighting)

This is the tell: Brand has stopped functioning as a shared operating system. People (internal and clients) no longer know what the brand stands for, they aren’t excited about it, and things are starting to feel disjointed and high volume rather than clear and powerful.

That’s a Brand Moment that usually happens when demand grows (scrappy teams have to scale fast and be intentional) or there’s some sort of capital event where a once unified “mom and pop” feel team has to suddenly adapt to complexity and act like a grown up company.

Your Decision Model

A simple framework to apply in your work.

Every Brand Moment forces a choice whether leadership names it or not. In its simplest form, you have 2 options:

Option 1: Optimize Around It

  • Double down on paid

  • Demand tighter attribution

  • Treat brand as overhead

Result:
Short-term stability with long-term drag. Everyone ends up miserable here while brand debt quietly compounds. Bail outs may happen later. Reputation stinks. (Examples: Casper mattresses, Tropicana, Gap)

Option 2: Rebuild for the Stage You’re In

  • Acknowledge the business is no longer what it was

  • Re-clarify what the company stands for today

  • Evolve the brand with the current market state

Result:
The brand stops being a meeting topic and starts being infrastructure, and it’s clear how the company is growing up with the times.

Most companies believe they’re choosing Option 1 temporarily to get out of a bind, but its hard to get out of and more often than not becomes the permanent state of affairs. Churn happens internally and externally. Have you worked for a company that chose Option 1? I sure have.

Inside the Work

How I’ve handled it with a client + the template we used.

Before Casper ever struggled, they nailed brand in a way few companies ever do.

They didn’t just sell mattresses online. They rewrote how the category showed up.

Early on, Casper ran some of the smartest brand-led activations in DTC:

  • A sleep-focused content engine (podcasts, books, research) that reframed mattresses as wellness (you could call their help desk and have them read you a bedtime story)

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