Most CEOs talk about growth metrics, market share, and quarterly targets. Sumit Singh, the CEO of Chewy, talks about empathy. Not as a buzzword slapped onto a PowerPoint slide, but as the actual operating strategy of a multi-billion dollar pet retail company. Wild? Yes. Working? Also yes.
From Amazon to dog food, with feelings
According to Fast Company, Singh made the leap from Amazon to Chewy back in 2017, initially joining as chief operating officer before eventually taking the top job. If you know anything about Amazon's notoriously no-nonsense, metrics-first culture, you'll appreciate just how much of a philosophical gear-shift that represents. He essentially traded one of the most data-obsessed companies on earth for one that wants to send you a handwritten card when your cat dies.
And that last part is not a metaphor. Chewy is genuinely famous for doing exactly that - sending flowers and personal notes to customers who've lost pets. It's the kind of thing that goes viral every few months because people cannot believe a corporation did something that human.
So what does 'empathy at scale' even mean?
Here's where it gets interesting, and a little philosophically thorny. Empathy is, by definition, a deeply personal, one-to-one human experience. Scaling it sounds a bit like bottling lightning or mass-producing a hug. But Singh's bet is that you can build systems, culture, and customer touchpoints that consistently feel personal - even when millions of customers are on the other end.
Think of it like this: your local independent pet shop owner knows your dog's name, remembers that Mr. Biscuits is on a grain-free diet, and checks in when you haven't been in for a while. Chewy wants to be that, except for every pet owner in America, online, 24/7. No pressure.
Why this actually matters (beyond the cute factor)
Pet owners are not a casual consumer demographic. These are people who genuinely consider their animals family members and will spend accordingly. Building a brand that earns that level of emotional trust isn't just nice - it's a serious competitive moat. It's very hard for a generic retailer to replicate the feeling that a company actually cares about your guinea pig's wellbeing.
Singh's leadership approach, as outlined in Fast Company, suggests that chasing empathy isn't some soft, feel-good distraction from real business. It IS the business. And in a world where most companies are racing to automate every human interaction out of existence, that's a genuinely countercultural bet.
Whether you think it's brilliant strategy or extremely ambitious idealism probably says a lot about whether you've ever received a sympathy card from a corporation and actually cried about it. No judgment. We've all been there.
