Hello and welcome to Modern CEO! I’m Stephanie Mehta, CEO and chief content officer of Mansueto Ventures. Each week this newsletter explores inclusive approaches to leadership drawn from conversations with executives and entrepreneurs, and from the pages of Inc. and Fast Company. If you received this newsletter from a friend, you can sign up to get it yourself every Monday morning.
When Sumit Singh left Amazon and joined Chewy as chief operating officer in 2017, the then-privately held online retailer was growing quickly. Fiscal 2017 net sales topped $2.1 billion, more than double the prior year’s, but Chewy was still losing money. Singh says he initially thought of the company’s customer care operation, which reported to him, as a cost center.
“That’s entirely the wrong way to think about it, particularly in a category where empathy matters,” says Singh, who became CEO the following year.
Some retailers create stickiness primarily by operating efficient supply chains that result in convenience and low prices. Chewy earned loyalty by layering on great customer service, with reps who would famously send handwritten sympathy cards or flowers to customers grieving the loss of a pet.
“When you invest in good care, you end up building relationships,” Singh says.
The ’empathy at scale’ advantage
Chewy, which was founded 15 years ago this week and had its initial public offering in 2019, operates 18 fulfillment centers and five pharmacy hubs. That makes it the third-largest direct-to-consumer e-commerce network in the U.S. It’s also become profitable. The company reported adjusted EBITDA of $718.2 million and net income of $222.8 million on $12.6 billion in net sales in fiscal 2025. (Earlier this month, Chewy told analysts it expects net sales of $13.4 to $13.55 billion for fiscal 2026, down from the previously expected $13.6- $13.75 billion, reflecting softer consumer spending.)
To continue offering high-quality customer service as the company grows, Singh plans to use artificial intelligence to help deliver what he calls “empathy at scale.” He says, “That’s a vision that AI can help accelerate.”
Chewy’s approach leverages its existing customer data—pet profiles, purchase history, shipping preferences, etc. Then, it uses AI that follows the company’s guidelines on how to represent the brand and delight customers to generate responses that are accurate, fast, and, yes, empathetic. Singh says Chewy plans to roll out a self-service tool that can provide personalized responses to a customer’s prompt. In one early example, a user asked the tool to write a haiku, and the bot immediately wrote a poem featuring the names of the customer’s pets. “We’re not taking the empathy away,” he says. “We’re making sure that context is interpreted through brand guidelines and data.”
Creating ‘wow moments’
Singh recognizes that many customers may still prefer to connect with a human customer care representative, and those folks aren’t going away. Singh says they’ll continue to have a high degree of freedom in the way they interact with customers. He adds that Chewy does not track average handle time or number of calls answered. The company’s care metrics emphasize speed to answer, empathy and accuracy of response, proportion of problems solved on the first contact, and employee retention.
“We try to hire people who are generally happy, healthy pet lovers, and we lightly train them,” Singh said. “We give them some basic guidelines around courtesy and empathy, but then we let them be themselves.”
The results are “wow moments,” such as a gift box that Chewy sent a customer who’d relocated to Texas after being displaced by California wildfires. The package included a Welcome to Texas candle and a hand-painted portrait of her cat, Tofu.
Beating the bots—for now
I asked Singh if he’s worried about agentic commerce, which many analysts believe will favor deals and transactions over differentiation and brands. He acknowledges that AI will change shopping but maintains that Chewy has several advantages: It already boasts some of the lowest prices, which should make it a favorite with shopping bots. Chewy also has a robust health business, including telehealth offerings and prescription drug sales, which are governed by regulatory and operational requirements that make it harder for bots to disintermediate.
And Singh continues to believe customer care is an edge. Pet owners, also known as pet parents, are guided by trust and emotional attachment that extends to the companies they patronize for their pets.
“A retailer like Chewy that combines low price, dependable fulfillment, embedded healthcare, and deep customer relationships is not disintermediated,” Singh said. “It is advantaged.”
How does your company incorporate a human approach?
Chewy’s emphasis on empathy is positioned as a competitive edge. Does your company use a human-centered approach? How does that help your brand? I’d love to hear about the ways you’re incorporating a personal touch. Send me an email at stephaniemehta@mansueto.com.
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- Why are so many companies getting customer service wrong?
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