Culture, curiosity, and the human skills AI can't replace at J.Crew: Lessons from Gena Smith

When Gena Smith joined J.Crew as CHRO, she stepped into one of the most storied brands in American fashion. She also stepped into a blank canvas. For Smith, who spent 14 years at LVMH leading people strategy through rapid global expansion, that kind of opportunity was exactly what she was looking for.

In this episode of the Skilled, Smith talks us through how she thinks about values, accountability, AI adoption, and what it means to build an HR strategy that actually serves the business.

Why employee experience has to come before customer experience

J.Crew is a brand built on making people feel something. 

Smith argues that this makes the internal employee experience non-negotiable. You cannot ask employees to deliver an experience they are not having themselves. There has to be coherency between the values a company espouses publicly and the way those values show up internally, in how people are managed, developed, and held accountable.

This was true at LVMH, and it is true at J.Crew. In both cases, Smith found that shared values around creativity, collaboration, and entrepreneurialism were what made the culture work. 

When those values are clear and consistently lived, the customer experience becomes more authentic because the people delivering it are genuinely engaged.

The difference between values on a wall and values in the work

One of the central threads of this conversation is the gap between companies that list their values and companies that actually operationalize them. 

Smith is currently leading a bottoms-up process at J.Crew to define exactly what each value means in practice, not just in principle.

Take creativity. In a fashion company, creativity can mean something very different for a senior creative director than it does for someone in finance or HR. Smith's team is working with employees across the organization to define concrete behaviors for each value: What does it look like? How do you demonstrate it? How do you cultivate it in others? And critically, what happens when someone is not living it?

That last question is where many organizations stop short. Smith is clear that you cannot claim to be a values-driven organization if you are not willing to hold people accountable when they fall short of those values. Accountability is not at odds with a people-first culture. It is part of it.

Once the behaviors are defined, they get embedded into every HR process: performance management, leadership development programs, hiring, and 360 feedback. 

The values become the common thread that runs through everything rather than a separate initiative sitting alongside the real work.

AI adoption starts with mindset, not tools

J.Crew is in the early stages of a company-wide AI adoption push, and Smith is leading it with a clear framework: mindset first, skills second, tools third. 

The instinct at most organizations is to roll out tools and assume adoption will follow. Smith argues that this gets the order of operations wrong.

In her previous role, Smith and her team ran an AI task force specifically to understand what was blocking employees from engaging with the tools they already had. What they found was telling. 

Some employees felt fear about job security. Others felt that using AI was a form of cheating. Both responses pointed to the same root cause: the wrong mindset. The answer was not more training mandates. It was communication, framing, and psychological safety.

At J.Crew, Smith is applying the same logic. Employees are being organized into cohorts based on where they are in their AI journey, and the program is designed to meet them there rather than assume a uniform starting point. 

The goal is to normalize experimentation and help people see AI not as a replacement but as a capable collaborator that still needs significant human direction and judgment.

Creating momentum without leaving anyone behind

How do you push performance momentum forward in a world where every employee is at a different spot in the AI-readiness spectrum? 

Rather than setting a single standard, she focuses on making people feel that wherever they are on the journey is exactly the right place to start. The message to her teams is consistent: it does not matter if you are just beginning. Just start.

J.Crew has also leaned into storytelling as a tool for driving adoption. 

When employees share what they have built or figured out using AI, those examples get elevated and shared across the organization. The CIO sends a weekly newsletter that surfaces external AI use cases alongside internal ones, creating a steady stream of reference points for employees who are still finding their footing.

The paradox of AI: human skills matter more, not less

Asked what she would tell her younger self about leadership, Smith returned to a theme that ran throughout the conversation. 

At the end of the day, it is about the people. Every strategy deck, every transformation initiative, every AI rollout comes to life only because of the humans behind it. 

And in a world increasingly shaped by AI, Smith sees a paradox taking hold: the more intelligent the tools become, the more the fundamentally human skills matter.

Critical thinking. Judgment. The ability to assess an output and know whether it is right. The courage to give honest feedback and have hard conversations. 

These are not soft skills. They are the skills that determine whether any of the rest of it works.

Smith also pushes back on the idea that a people-first culture is incompatible with high performance. Compassion and accountability are not opposites. 

Being honest with people about where they are falling short, being clear about expectations, and having the courage to act when someone is not in the right role: these are acts of respect, not harshness. That combination of warmth and rigor is, in Smith's view, what separates organizations that talk about culture from the ones that actually build it.

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