Redefining The Future of Stuart Weitzman
Chief Marketing Officer of Stuart Weitzman, Kaisy Mae O'Reilly, brings dynamic change to the well known brand.
For Kaisy Mae O’Reilly, chief marketing officer of Stuart Weitzman, every step is a statement. A dynamic leader with over two decades of experience, O’Reilly has proven that blending data-driven insights with creative storytelling can drive extraordinary transformations in the world of luxury branding. Her journey to the helm of one of the most iconic footwear brands is as compelling as the campaigns she’s crafted.
Born and raised in the Philippines, O’Reilly grew up with a deep appreciation for hard work and education. Her parents, who emphasized the value of academics, instilled in her a drive to excel. Initially envisioning a career as a doctor, a life-changing graduation trip to Hong Kong opened her eyes to the possibilities of the global stage. This spark of inspiration led her to Procter & Gamble, where she spent 19 transformative years shaping global beauty brands like Olay and SK-II. Her ability to adapt and innovate was evident as she navigated the transition from traditional advertising to pioneering digital platforms, ensuring these brands resonated with a new generation of consumers.
Her Start at Stuart Weitzman
In 2022, O’Reilly joined Stuart Weitzman as senior vice president of Digital, Strategy and E-Commerce. She was drawn not only by the brand’s legacy but also by its alignment with her own values: empowering women to stand strong. Her initial projects focused on understanding the mindset of the modern footwear consumer, leading a survey of over 4,000 participants to identify key opportunities for the brand. This data-driven approach revealed a simple truth: Stuart Weitzman’s customers seek stylish yet comfortable footwear that empower them to navigate their multifaceted lives with confidence.
On the up and up
Promoted to chief marketing officer in 2023,O’Reilly’s influence at Stuart Weitzman has been nothing short of transformative. Her first major initiative, the “How Lovely to Be a Woman” campaign, exemplifies the brand’s ethos. Featuring global ambassadors like Christy Turlington, Issa Rae, and Lucy Liu, the campaign celebrates the strength, resilience, and beauty of modern womanhood. “We challenged ourselves to go beyond the traditional fashion campaign,” O’Reilly explained. “It’s a celebration of what it means to be a woman today — balancing careers, families, and passions, all while stepping forward with confidence.”