A founder recently told me their “dream hire” for a Head of Design had slipped away. They had found the perfect candidate. Seasoned. Visionary. A leader who could transform their product and brand. They threw in a great salary, equity, and all the right perks. The candidate nodded, asked thoughtful questions, seemed engaged. And then? They disappeared. Not a rejection. Just silence.
It wasn’t an isolated incident. I’ve heard this from multiple founders, and from design leaders on the other side who say they’re tired—tired of fighting for influence, tired of being hired as a “strategic partner” only to be handed a checklist.
So who’s right?
The companies struggling to hire and retain great design leaders? Or the design leaders who feel undervalued and unheard?
Both.
Design leadership today is stuck in a paradox: CEOs want innovation, but they also want predictability. Design leaders want autonomy, but they also want to be part of something bigger than themselves. Both sides walk away when they feel the balance is off.
And that’s the real problem: everyone wants design to lead, but no one agrees on what leadership actually means.
Design Leaders Want Ownership. CEOs Want Business Impact. These Shouldn’t Be Opposing Goals.
Companies that truly leverage design grow revenues twice as fast as their competitors. That’s not a guess—that’s from repeated studies on market leaders. But most companies still underutilize design leadership, confining it to aesthetics instead of using it as a driver for strategic decision-making.
That’s why so many great design leaders ghost job offers. They can tell, almost immediately, if the company sees them as a partner or a polished slide machine for stakeholder meetings. They’re not going to waste their energy fighting for influence in a place where every decision gets overridden by gut instincts or the loudest voice in the room.
At the same time, let’s be honest: design leaders aren’t always great at meeting CEOs halfway.
A founder hiring a Head of Design doesn’t just want a visionary. They want someone who understands business constraints—timelines, engineering realities, financial trade-offs. A leader who doesn’t just push for “better design” but can tie that push to measurable business outcomes.
Great design leaders don’t demand a seat at the table. They prove why they deserve it.
Why Design Leaders Walk Away (And When That’s a Mistake)
Some companies just don’t value design leadership, and no amount of money or equity will make up for that. If you’re a design leader being hired to “shake things up” but every idea needs five layers of approval, you’re not a leader—you’re a high-paid production artist.
But I’ve also seen design leaders walk away from great opportunities because they expected total control instead of collaboration.
A startup I advised had an incredible design hire lined up—someone with a history of driving major product transformations. But during the final conversation, the candidate said, “I need the freedom to own the entire product experience.”
The CEO hesitated. “You’d work closely with product and engineering, of course.”
That was the dealbreaker. The candidate wanted full ownership. The CEO needed someone who could lead, not dictate.
So they walked. And that company? They hired someone else—a great design leader who knew when to push and when to align. Someone who didn’t just ask for trust but earned it by showing how design could impact retention, revenue, and long-term differentiation.
And now? That design leader has full ownership—because they built credibility first.
Why Companies Struggle to Hire Design Leaders (And When That’s Their Fault)
Some companies say they want a design leader, but what they actually want is a design executor with a fancy title. They don’t want to be challenged. They don’t want design involved in strategic conversations. They just want a department that makes things “look good.”
If that’s your company, just be honest about it.
Call the role “Lead UI Designer” and hire accordingly. Don’t bait-and-switch candidates with talk of vision and leadership if they’re not actually going to have decision-making power.
But if you do want a real design leader, then set them up for success:
- Give them decision-making power. If every design choice requires executive sign-off, you don’t have a design leader—you have a design service team.
- Stop measuring success by output. If your only metric is “how fast they ship,” you’re undervaluing the real impact of great design. Measure retention, engagement, and revenue lift from design-driven initiatives.
- Pay for the business impact, not the title. The best design leaders increase customer satisfaction, drive conversions, and strengthen the brand. Their compensation should reflect that.
- Invest in design culture. If your designers feel like outsiders in product and engineering conversations, your culture is broken. Design leadership isn’t about one person—it’s about integrating design thinking into every part of the company.
The Companies That Get This Will Win. The Rest Will Keep Wondering Why Design Feels Like a Cost Instead of an Advantage.
Look at the companies dominating their industries today. What do they have in common?
They don’t just “hire” design leaders. They build environments where design leadership thrives.
Because here’s the thing: design isn’t just about making things beautiful. It’s about making things work. And that requires partnership. It requires trust. It requires both sides—design leaders and executives—to understand each other’s language.
If you’re a company struggling to hire a Head of Design, ask yourself: Are we hiring a leader, or just looking for someone to execute decisions we’ve already made?
And if you’re a design leader frustrated with the hiring landscape, ask yourself: Are we looking for autonomy, or are we willing to build credibility within the business first?
The best teams figure out how to meet in the middle.
The rest just keep losing each other before the first real conversation even begins.
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