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Sumit Singh
Chief Executive Officer & Director, Chewy

Customer-Obsession, Curiosity, Moonshots with Sumit Singh | Shared Table Episode 6

📅 Feb 26, 2026 Shared Table 40 MIN 2994 VIEWS 61 SEGMENTS · 2 SPEAKERS
For millions of pet parents, it's more than just a delivery; it's a symbol of convenience, care, and a deep connection to their beloved animals. It reflects a powerful trend: pet subscriptions now drive 40% of pet care dollars, with omnichannel consumers spending 30% more annually. This powerful customer bond was at the heart of the latest Shared Table conversation with @Chewy CEO @Sumit Singh. Sumit's journey is a masterclass in leadership, taking Chewy from $2B in revenue to a remarkable $12B. His secret? A relentless customer-obsessed mindset, a spirit of curiosity, and a willingness to t...

Questions asked in this interview

12
  1. 4:10Do you have one of those?
  2. 6:51What's your vision if you're talking to future talent that's considering past going forward?
  3. 11:07And how are you reinventing yourself, Sumit?
  4. 16:11You've got to do that authentically, right?
  5. 20:05How do we go deeper as an industry?
  6. 25:39In any talent at any age right now to be in a position of strength in 2030. What's it take?
  7. 29:09Tell me what's the myth in that?
  8. 33:33So why, whether you're an investor or a veterinarian, why is Chewy getting into the vet clinic business?
  9. 36:34And if you were in my role, where would you be leaning in?
  10. 38:13Tell me what's inside Sumit's household. Where are you?
  11. 39:15What would be up near the top?
  12. 39:25And then I got to ask, what's your favorite animal protein?
Jeff 0:08 ↗
It's an honor, Sumit, to just have time with you, to share a table with you in a conversation. I've admired you. I think you came into this role in 2018 about the time Elanco went public and have been kind of side by side admiring and watching you. You came in a couple billion dollar size of Chewy. Now it's 12 billion. It is probably the most known brand in the American household when it comes to pets. I know that box is on my front porch probably once every week. There's something coming for my wife with Chewy and our Labradors. But I want to go right to you, Sumit the Man, and I'm going to grab a graduation speech you gave a couple years ago at University of Chicago and you concluded that speech. And I think that's a powerful time with a message is, hey, factors that affect your life are always going to be there. What I love though is you kind of said, hey, stay grounded, stay humble, be grateful. I really resonate with this. Always learn. You've created this just presence around you about being curious. That's what I learn when I'm around you. And optimism, you say, is the ultimate recipe and factor. So with that, hey, you want to give that message to graduates that says a lot about who you are. Tell me who is Sumit and what is the story behind you that maybe people don't know.
Sumit Singh 1:31 ↗
Wow. Thank you for having me. It's nice to be here. Great to be talking to you. When you put it that way, it makes me think, Jeff. I was born and raised in India and so I've had the unique privilege, I guess, to have appreciated both cultures. I moved to this country when I was a very young man, early 20s, and so I've grown up here and I've come to love the country and everything that it has to offer. When you're fortunate enough to have gone through this type of a journey, it gives you perspective to appreciate life from all different angles. And you know, growing up in middle-class India, middle-class values of hard work, humility, respect, and priority to education have always sort of stuck with me. And when I came to this country, it really helped me learn how do you create opportunity? How do you give opportunity to others? How do you collaborate? How do you innovate? And so, but ultimately we're all human beings and we face ups and downs in life. And these are qualities that have helped me kind of stay humble, that have helped me sort of manage stress better. That have helped me stay grounded.
And so I think it's important to talk about them because while successes get celebrated a lot and a lot of people get made heroes out of it, there's also days when those heroes are down and in those days it's helpful not to self-doubt. And on the other side there are many people who are trying to make it who don't, but also in those instances it's even more important to not self-doubt and to continue to just stay grounded and keep working your way to your goals. So I think that's really kind of the core message of it. The curiosity, I think it really comes in. I have a 10-year-old and when I look at children interact with the world, they interact with the world unencumbered. They're not worried about the other person judging them. They're not worried about what somebody might think of them. They're just asking questions and the questions that they ask are phrased in the most simple manner. So the ability to keep to look at something complicated in a simple way and to ask your way or to learn your way through it using the simplistic methods, I think is just powerful.
Jeff 3:58 ↗
And life takes that out of us sometimes. Right.
Sumit Singh 4:00 ↗
It really does. It's a spark that I feel all of us need a little bit of reminding sometimes. And you look at kids and you look at pets and you're always like, well, great, they've got it.
Jeff 4:10 ↗
Yeah. Is there a moment that you go back to and say, boy, that changed a trajectory? I remember sitting in an FFA convention in 1985 and there was a moment where I said my life went a different direction. I mean, the India to the US and your story is very layered with a lot of... is there a moment where you say, boy, that's a moment? I think moments really matter to leaders. Do you have one of those?
Sumit Singh 4:34 ↗
Yeah, I think if I recall or if I take stock, there are three really important decisions from a personal professional career intersection point of view that when I look back that have really created these step function changes in life and profession. And so before I go into them, they all sit at the intersection of opportunity, self-confidence, and in some way naivete. And by naivete I mean not knowing enough about the risks that lie and being comfortable with the failure that those risks might bring you. So again, intersection of opportunity, self-confidence, and naivete. And so the first one was when I took a leap of faith and really said to myself, born and raised in India but I want to build a life in the United States. Okay, how do I charter a path? Middle-class family, not too much financial support. I arrived in this country right at the point when 9/11 had happened, so a pretty bad time to arrive and to build a life for yourself, to seek the opportunities, etc. So that was one. The second one was when after nearly 12 or 13 years I decided to leave Dell where I had worked for so long to go to Amazon. And that was a pivotal change because culturally these two companies were very different. They were also very similar in the notion that they had pioneered in their own way large shifts in industry, deal with e-commerce and just-in-time and free cash flow and so forth and so on. And Amazon with kind of, well, Amazon's Amazon, we know about what Amazon's done. And so that was the second one. And the third one was leaving Amazon to come to Chewy. And so these are in some way moonshots because you sort of build your career... most people build career linearly. I've built my career nonlinearly. You know, two degrees in engineering, not formal training in sales or marketing or product management. Yet have always found myself at the intersection of consumer tech. I think again just opportunity, self-confidence, and naivete.
Jeff 6:51 ↗
The nonlinear is really in contrast to a lot of what we're kind of training the next generation is. Hey, develop mastery, deep expertise. Know your area really well. You went to the contrast. What's your vision if you're talking to future talent that's considering past going forward? What...
Sumit Singh 7:10 ↗
I think given the world that we are about to step into and some would argue we're already living in with AI and with the disruption that we're facing, it's hard not to bring AI into a conversation these days. I think nonlinearity is going to be even more important. See, nonlinearity is not about taking random jumps or testing and trying random stuff. It is about skills that you gather which may not immediately be clear as to how they form the entire picture or the puzzle but these are pieces of the puzzle. If you can generally be thoughtful about the skills that you're gathering then I think a few years down the line or separating the forest from the trees, the picture actually looks quite beautiful. And so today, look, I think there is a tremendous need and will always be a need for skill and vertically holistic knowledge base, right, so depth. At the same time the ability to go broad and be flexible with your mind and have the agility to learn new things. And to tie them back with what you know and understand what you don't know, I think is going to be a very important skill set.
Jeff 8:31 ↗
I agree, the learning agility also the jumping as I even study your story. I mean it builds a capacity for courage. Right. To say, look, I've done it before and boy, I made that jump and it worked. And I look at the next generation of talent and say, I need more of a risk profile and more learning agility. This life is full of ambiguity. You got to be able to be in the center, helps develop judgment, help develop pattern recognize, a lot of helpful skills.
Sumit Singh 9:00 ↗
Yeah. I ask this in most of my discussions. What's your why? They always say, you know, it's more important than what and how. It's why, what drives you? If I could say in an essence of a few words, if I got close to the people that are close to you, what drives this guy?
Jeff 9:16 ↗
Yeah.
Sumit Singh 9:18 ↗
I think personally I've just always been a restless individual. And I've found it hard to stay... so stasis really scares me. I'm kind of claustrophobic in a static world. And that continues to push me to either understand or learn the next thing. I really like connecting skill sets to produce or to amplify the output and I feel like at Chewy scale a lot of times that's the role I play where I'll take a person who's a really good builder and a person who's a really good perhaps a scaler or a thinker and a builder and get them together and say, okay, come up with something beautiful. But why do I do it? I really like moving agendas forward. To say I like moving humanity forward is too pompous because I don't think we're working on, you know, we're not designing rockets. But at the same time to be able to create something unique that can touch the lives of people or the hearts of people, which we've tried to create at Chewy and try to scale at Chewy in the way that we go to market or in the way that we connect with our customers to leave them with an impression of what an empathetic company could feel like. That's a pretty good motivation to keep customer obsession in front of you. The other motivation is it provides a really good defensive mode around the larger players that may have come at it from a different way or they might have used their capabilities in a different way. So yeah, I like it.
Jeff 11:07 ↗
So how I opened with this curiosity that I get from you, if I had a word cloud, curiosity would be definitely one I would put for you. How are you reinventing yourself? You know they kind of say you can today really judge the age of a person, not physically but mentally by their level of curiosity and how they act on that. And how are you reinventing yourself, Sumit?
Sumit Singh 11:34 ↗
Yeah, I appreciate that question. I try to... I read a lot and so at any given time I have multiple books going on in parallel. One of the books that I'm reading right now is I went back and picked up the biography of Benjamin Franklin that was written by Walter Isaacson. And Ben Franklin is the patron saint of self-improvement if you would. Another one that I'm reading is a book called Loonshots. Not Moonshots, Loonshots. We'll talk about it afterwards. Really interesting book. So I read a lot and I try to really process what I read and I try to live in a loop of a self-created loop of plan, do, check, act. And so it's the self-enforcing loop where I do sort of spend some time reflecting on my actions, reflecting on the decisions, and the impact that it has to me or people around me. Two, I am constantly busy with learning new things. So 6 months ago I went and got myself a tennis coach and so I play tennis now 3 days a week before I come to work and it's actually been a wonderful addition to my repertoire. I am recently trying to learn more about watches for no other reason. A few years ago I was trying to learn about sake for no other reason, just because. Cognacs was another one I got into. So it's just a passion to create. AI, you know, I stepped into the world of AI and I looked at myself and I found myself to be remarkably unprepared to tackle the world that was in front of me because we haven't been students for 20 years and yet AI requires a very student mindset per se. So I have the mindset and I said great, I'm going to lead AI for Chewy and I'm going to make myself worthy of leading AI for Chewy. And so that's the process that I'm in right now. So in some way I'm reinventing myself to learn this disruptive technology that's in front of us.
Jeff 13:48 ↗
Let's see, one other one and then we'll jump to Chewy is what is your... you know you run a manufacturing plant or you run Chewy's warehouses with an SOP, a standard operating procedure. We know that is a system and a process that optimizes. What is the PSOP of Sumit? What is your personal standard operating procedure? What are the rhythms in your life that make you sustainable? I believe you and I know the world's going to get faster, more complex, more ambiguity. And sustainability of self is vital. What are a couple rhythms that you say, man, this is what makes me five years from now, I'll be as competitive and as sustainable as ever. Beyond the reinvention you just mentioned, what's your PSOP?
Sumit Singh 14:34 ↗
I think the one quality that at least when friends and family members talk about me in what's unique in this guy versus some of us, I think it's the level of self-discipline that I have. I'm an early riser. Wasn't an early riser. Trained myself to be an early riser and that's just become the way of life for as long as I can remember. When you're disciplined, you're able to compartmentalize your time in a manner where you don't have to get into academic debates of let's say work-life balance. You are able to integrate work and life in a manner that it just sort of comes together for you in a holistic manner. That discipline also allows me to ensure that I spend some time working out, I spend some time reading, I spend some time with family, I spend a lot of time working. I think self-control, discipline, and commitment to a purpose. You started this conversation a few questions ago with the why and with the purpose. I've been at Chewy now nearly 9 years and I'm still dancing into work. And the thing with me is if I get bored, if I feel like I have stopped learning, if I feel like the curve of bureaucracy overshadows the curve of learning and growth, that's generally my disembarkment point from any activity. It's not just profession, it's any activity. And that's kind of when I sort of say this one's not fun anymore. Let's move to this. So it's just a great thing between that and between the closed loop of feedback.
Jeff 16:11 ↗
Yeah, that helps. Well, you can... the casting the shadow of a leader dancing into work as you say. I mean, you bring energy to a room and you can't do that artificially. You've got to do that authentically, right? And yeah, I can feel that. So, hey, tables matter. There's some stuff on this table, you as I opened up, you have created a brand, you and your team, that blue Chewy means something to everybody. I mean, when I drive in my driveway after a long day at Elanco and I look and there on the porch is a Chewy box, you know, there's a feeling, there's an emotion, and just take me a little bit to, you know, what's on this table, what's here on this set, just to give me a sense of what's behind this brand, what's the essence of Chewy.
Sumit Singh 16:56 ↗
So, what you're seeing around us is all of the ways that we surprise and delight customers in very human and very direct kind of tugging at heartstrings. Sort of old school classical ways of building connection and building memories and driving towards loyalty. So, what do I mean by that? You have a bag with a cat's picture on it. This is somebody's cat and the bag was shipped to a customer, you know, who was probably our first customer. What's behind you are a series of pet portraits who are drawn by local artists. And you cannot buy these from us. You cannot coerce us into giving you one. These are surprise and delight. Our customer service agents or customer care team is trained to, you know, pull these out from moments of interactions that they're having with customers. Somebody had a first child. Somebody's parents were sick. Somebody got a first job. So, it's these moments of highs and lows that...
Jeff 17:59 ↗
You have artists on staff.
Sumit Singh 18:01 ↗
You have local artists on staff.
Jeff 18:03 ↗
Tell me more. So, these are...
Sumit Singh 18:04 ↗
Hand-draw these portraits.
Jeff 18:06 ↗
Wow.
Sumit Singh 18:06 ↗
Of someone's pet.
Jeff 18:08 ↗
Or someone's pet.
Sumit Singh 18:09 ↗
And it's a gift.
Jeff 18:10 ↗
It's a gift to you to delight.
Sumit Singh 18:12 ↗
Yes. And it's our way of... many companies think of customer relationship management. They acquire a customer and then money is spent to retain customers and to get them to upsell. This is our CRM, right? These organic ways of making a connection are the greatest word of mouth advertising that we could ask for because I promise you if when we send a hand-drawn portrait to a customer of their beloved pet, we have them for life. It gets talked about at dinner tables. It gets talked about at parties. You get noticed, you know, when you're wearing a Chewy jersey and walking through an airport or a Chewy hat and walking through an airport, you get called out for how much people love your brand. That doesn't happen with other brands. And so, this is the core essence of... we started as an e-commerce company. In many ways, a majority of our revenue is still e-commerce, but now we're steadily moving into services and physical experiences delivered via vet clinics. We'll come to that in a second. But an e-commerce company living in the world of other larger e-commerce companies, you have to have a moat, a differentiation in this category. When we talk about pets, and you know this equally or better than anybody else, this is an emotive category. And so if we are able to put this ring fence around us, it gives us immunity in some way. It boosts our immunity and it gives us a protective moat, right? Because these memories will fuel long-term recollection and loyalty towards our brand that drives repeat purchase that fuels the revenue flywheel. It's a very business-centric decision, but taken from the heart.
Jeff 20:05 ↗
Yeah. So go deeper because we throw out too often I think in our space. Oh, the human-animal bond, the pet bond. I mean, you... I come in and see this black and yellow lab. I have Lily and Lake and I've had four generations of labs and when I see my kids come home from college and what happens there, there's something very indescribable, right? I mean, it's the emotive piece. Take that layer and go deeper on that because I think you've unlocked that better than anybody else. And that's probably what drives these letters that come in here. How do we sustain that? How do we go deeper as an industry? I mean, this is... there's a lot of people listening that are part of this spectrum globally.
Sumit Singh 20:54 ↗
I think it's a misunderstood concept that good service costs more. So first of all, I think business leaders perhaps if we reorient our thinking to saying good service costs less over the long term. That will change the mentality of service centers being cost centers to engagement and revenue centers. That mentality will then drive a two-pronged approach. And I'm speaking from a business mind because ultimately I'm assuming that unless you're a nonprofit or charity, you're doing this because you believe it works for your customers, for your team, and for your shareholders, right? Or you won't be here, right? We wouldn't be here if we didn't know this worked for us. So how do you change the mentality? So if you have this mentality of this is an engagement driving center, this is a revenue generation center. And I'll tell you why I say that. See, over 30% of our calls that come into our care centers are not for customers that are disappointed or that have questions around general merchandise. These are customers that are calling to learn more about their pet. They just brought home a puppy. They don't know what to feed it. They're going through a tough day and they want to pick up the phone and call somebody. And we pick up the phone in two rings or less. And so our care team is trained to stay with you and have conversations about you and your pet as long as you want to. But I just recently... a customer posted on LinkedIn. She lost her cat 3 years ago. We sent her a pet portrait. It made all the difference to her. She hasn't had an animal for 3 years or maybe it's a dog. She brought home a new animal, a new pet, cat last week. And she came back to Chewy and posted on LinkedIn that moments that create joy and delight matter and loyalty lives on and it has been 3 years since my last pet purchase but when I'm back in the market I'm back with Chewy. And so how do we do it? You have to embed it into the mentality of the company, the DNA of the organization. So you have to hire people accordingly. You have to develop people accordingly. You have to encourage them. Give them the autonomy. We don't have a strict hard playbook for our care agents. You can't train for empathy. You cannot train for spontaneous moments in response to an empathetic situation. It has to come instantaneously if it is embedded in the DNA and the culture of the team. So that's a very important one. And number two, you use technology. So by going empathetic it doesn't mean that it cannot retain the human touch. The human touch is in the creativity and the recognition of the situation to take the action. Everything else can be automated. Right? So our agents now understand, we have... they've been given tools that allows them to quickly process and submit for requests and curate these asks, etc. And we're able to respond to them.

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APA

Singh, S. (2026, February 26). Customer-Obsession, Curiosity, Moonshots with Sumit Singh | Shared Table Episode 6 [Interview transcript]. Shared Table. CEOInterviews.AI. https://ceointerviews.ai/interview/734058/

MLA

Sumit Singh. "Customer-Obsession, Curiosity, Moonshots with Sumit Singh | Shared Table Episode 6." Shared Table, 26 Feb. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/734058/.

BibTeX
@misc{singh2026_734058,
  author       = {Sumit Singh},
  title        = {Customer-Obsession, Curiosity, Moonshots with Sumit Singh | Shared Table Episode 6},
  howpublished = {Interview transcript, Shared Table. CEOInterviews.AI},
  year         = {2026},
  month        = {feb},
  url          = {https://ceointerviews.ai/interview/734058/},
  note         = {Speaker-attributed transcript with timestamps}
}