Derek Yarbrough
Derek Yarbrough is a chief marketing officer and CEO advisor with nearly 30 years in fashion, specialty retail and digital commerce. He has served as CMO of Old Navy, J.Crew and Madewell — three of America’s most recognized lifestyle apparel brands — and was on the founding team of Walmart.com in the first wave of ecommerce. He has led businesses from $80M to $8B, teams from 20 to 200, and marketing budgets from $30M to $300M+.
Named one of Business Insider’s most innovative CMOs, he works where brand and performance stop being separate budgets: architecting brands that can’t be substituted, building customer growth models that compound, and rebuilding the teams that have to run both.
He founded Rare Root Advisory in 2024 because the best strategic thinking he saw in three decades mostly didn’t get executed. Not because it was wrong — because nobody had asked whether the organization could carry it. Corporate inertia isn’t stupidity. It’s a merchandising calendar locked nine months out, a headcount plan approved last October, a CFO who already committed the number to the board, and four functions with genuinely conflicting incentives. A plan that ignores those things isn’t ambitious. It’s unimplementable, and everyone in the room knows it by page four.
Rare Root takes a small number of clients a year and works across brand, customer and team rather than one slice of the problem. Derek is the senior person on every engagement — there is no bench, and no partner who appears once, in the pitch.
Let’s chat about your brand, your customer, your team.
Tell us what you’re trying to achieve and what’s getting in the way. The first conversation is free, and useful either way.