Q&A With Top Women in Retail Honoree Orlena Yeung, Former Chief Brand Officer, Chewy.com

Women in Retail Leadership Circle (WIRLC) recently released its 16th annual Top Women in Retail report. The valuable resource highlights female executives who impressed our Editorial team as well as colleagues from across the industry. One such woman is Orlena Yeung, former chief brand officer, Chewy.com. Here’s a sampling of Orlena’s interview featured in the report.

Women in Retail Leadership Circle: You oversee a brand that blends e-commerce, pet care services, and customer loyalty ecosystems. How are you leveraging brand strategy and customer experience to deepen engagement with pet parents, and what strategic priorities are you focusing on to scale those efforts over the next year?
Orlena Yeung: I’m fortunate to lead a brand built around a singular mission: to be the most trusted and convenient destination for pet parents and partners everywhere. Our promise is to make it easy to get everything you need — from food to pharmacy — to keep pets happy and healthy and to keep our customers happy with great prices, delivered right to their door. To truly fulfill our mission, we need to understand the entire pet parent experience and provide support and services across crucial moments. We’re building a connected system, from everyday products to vet care, that puts pets and the people who love them at the center.

Over the past few years, we sharpened our focus on retail fundamentals to ensure we’re winning on the basics. That foundation allows us to expand how customers understand Chewy: not just as a retailer, but as a brand recognized for our care and full ecosystem offering. A great example is our “For life with pets, there’s Chewy” campaign, grounded in the insight that every order is a window into a pet’s unique personality and needs. More importantly, it signals our commitment to be there through the comedy, chaos, highs and lows of life with pets — from new adoptions and puppy wins to 2 a.m. worries and end-of-life care.

Looking ahead, we’re focused on deepening personalization, further integrating health and wellness services into a seamless experience, and scaling Chewy+ and other mechanisms that celebrate loyalty and community. Our strategy is about showing up consistently so pet parents have a trustworthy partner to navigate any part of “life with pets.”

WIRLC: Your career spans brand strategy, consumer insights, and global marketing. Looking back, which skills or experiences proved most essential as you moved into executive-level brand leadership? Why?
OY: The willingness to stay curious, question the status quo, and continually innovate to solve consumers’ problems has been essential throughout my career. I’ve relied on those skills to translate human truths and needs into deliberate strategy and execution: what we say, how we show up, and where we invest.

Throughout my career, I’ve woven together customer patterns and needs with business opportunities and capabilities. My roles across entertainment, media, digital health and fintech taught me how to connect brand building to performance, long-term value, and the holistic customer experience. That balancing of insight, impact and prioritization has been critical in moving into executive leadership.

Equally important has been learning to lead through influence in cross-functional environments. A platform like “For life with pets” only works if product, CX, operations, and finance see themselves in it and execute against shared goals. Finally, building diverse, empowered teams and giving them clarity of direction and real creative runway, while embracing a try-fail-learn mindset, has been a powerful amplifier. Brand leadership today is less about being the loudest voice in the room and more about being the connector who brings the right resources together with a unified vision and strategy.

WIRLC: What bold leadership move has had the biggest impact on your team and/or organization in the past year?
OY: Elevating “For life with pets” from a campaign line to the organizing principle for how we show up for customers and for each other every day. We deliberately moved beyond purely transactional considerations to ask: What does it really mean to support pet parents emotionally and practically through every chapter — the silly, the stressful, and the heartbreaking?

That shift led us to put the real ups and downs of our customers’ pet parenting journeys at the center of both our storytelling and our road maps. We leaned into moments like welcoming a rescue, managing a chronic condition, or saying goodbye, and connected them directly to the breadth of Chewy’s ecosystem (e.g., telehealth, Vet Care clinics, pharmacy, insurance, and Autoship) as an integrated, always-on set of services.

Internally, it meant reorganizing priorities and success metrics around long-term trust: multiservice engagement, repeat use of health offerings, and brand love, and balancing that with delivering daily results. It required teams to embrace a more holistic, emotionally anchored vision. The result has been a more unified brand and, more importantly, more customers telling us they felt Chewy was truly there for them when it mattered most.