Show Summary

Creative work doesn’t start with a brief—it starts with trust. And when operations and creative build that trust, the results go far beyond delivery.

In this episode, Kyle Wright and Brianne Gallagher—Creative Director and Head of Creative Operations at Wayfair—share how they’ve restructured the relationship between their teams. Instead of chasing speed at the expense of meaning, they’re building systems that protect space for strategy, storytelling, and original thinking.

We talk about what it takes to move from reactive execution to proactive collaboration: the tooling, the prioritization, the upstream conversations—and the mindset shifts underneath it all. What happens when ops stops managing projects and starts enabling vision?

This isn’t just about better workflows. It’s about building the conditions for better ideas.

Key Points + What They Made Me Wonder

• Strategic creative work begins upstream—so why do so many teams still wait for the brief to start thinking?
• “Thinking time” needs to be designed into the system—so how do we defend it without turning it into a productivity metric?
• Concepting works like an internal LLM—it learns from what we feed it—so are we investing enough in our creative inputs?
• The right tools reflect how teams think, not just how they ship—so what assumptions are baked into our current stack?
• Protecting creative headspace requires saying no with purpose—so how might ops lead the charge without becoming the bottleneck?
• Creative and ops teams shouldn’t just align—they should challenge each other—so what kind of trust makes that possible?
• Emotional resonance is a business result—so why don’t more systems measure for it?

About the Guests

Kyle Wright is the Creative Director at Wayfair, where he leads brand and campaign storytelling across channels. With a background in design, experiential, and brand systems, Kyle is focused on protecting space for intuition and human originality inside fast-moving creative ecosystems. Connect on LinkedIn

Brianne Gallagher is Head of Creative Operations at Wayfair, where she’s spent over a decade evolving ops from a delivery function into a strategic partner. She’s focused on building systems that enable great creative work at scale—without sacrificing soul. Connect on LinkedIn