In this podcast, Prob Deep Singh, head of Enterprise for Uber Eats, discusses how Uber preserves startup agility despite its corporate scale. He emphasizes that speed, experimentation, and a culture that celebrates failure are ingrained in the company's DNA, largely due to hiring entrepreneurial individuals, many with no prior corporate experience. Uber Eats' innovation journey began with a flawed model of mass-producing single dishes, but through relentless experimentation—such as testing bike deliveries and adjusting for ice cream—it evolved into a global three-sided marketplace. Scaling poses challenges, particularly balancing centralized technology hubs in New York and San Francisco with regional teams that provide local customer insights. Singh highlights the importance of strong leadership that is clear, candid, and attentive to individual team members' motivations, as well as building diverse teams with complementary backgrounds. He stresses that customer feedback must be actively captured and integrated across the organization, especially from restaurant partners. When launching new initiatives, Singh advises transparency with customers about experiments, as they value innovation and will tolerate risks if the brand is honest. To manage cultural gaps between new projects and the core business, he recommends involving internal talent, continuously demonstrating value, and humbly sharing lessons from failures. Overall, Singh notes that innovation is now a leadership imperative, enabled by technology that makes rapid change and data-driven decisions easier than ever.
Welcome to the Innovation Roundtable Insights Podcast. This episode was recorded at an Innovation Roundtable Workshop hosted by IBM in New York in October 2018, where our colleague Leonard sat down with Prob Deep Singh, head of Enterprise for Uber Eats. Prob Deep explains how Uber kept the flexibility and the agility of a startup while being a corporation. Furthermore, he brings us through the innovation journey of Uber Eats, starting from the early experiments to its commercialization, scale, and growth. Prob Deep, thank you very much for your presentation and thank you for joining me in my little pop-up studio. Maybe we can start the interview by you just briefly explaining who you are, what company you work for, and what role you have at the moment. Sure, my name is Prob Deep. I work here based in New York City for Uber. I actually work for Uber Eats, where I lead our enterprise business in the US. Maybe you can give us a bit of an overview about kind of innovation or product development within Uber and how that framework looks like and how Uber Eats fits into that. Yeah, well, you know, Uber is a company that hasn't been around that long. And so we've sort of been innovating since the beginning. And so, innovation is very much tied into the DNA of everybody at the company where we're constantly thinking about what's next and what's new. And a lot of it has to do with, you know, the founding culture of the team. We were very much an entrepreneurial group. We moved incredibly fast. Some people know probably the fastest growing startup of all time. And so speed is a big part of our DNA. So anytime we come up with something that we think is interesting, there's a natural inclination to move very fast. So it's a big part of the culture and has a big impact on how we think about innovation too. How is it possible, because you mentioned it yourself, Uber has been growing quite quickly over a very short amount of time. How is it possible or what are the challenges of keeping that flexibility and agility that a startup has while Uber is almost can be described as a corporation? Yeah, it's very tough. I think I talked a little bit about today my talk, but a lot of it comes down to the people to be honest. A lot of young people who are very entrepreneurial and that DNA helps us not get stuck in corporate culture. There's a lot of people whose first job is at Uber and so they don't have a lot of preconceived notions about maybe working at a big, big Fortune 500 company. I think that helps the culture. We celebrate failure. A big thing about a company like Uber is testing things as a big part of how we learn and very okay in our culture to try things and to learn from them. Maybe you can give us a bit of an overview of how it is organized from an organization perspective and also physically where the team working because it is something that is also globally. So Uber Eats is all over the world now we're in over 300 different cities and so I would say you have a lot of the core technology teams split across New York and San Francisco and those people are in global roles. You also have a lot of people that are doing more global functions based in the US. And then across the world you have teams that are managing the businesses remotely or from those places. So for example, I have a team in Amsterdam that's managing the European market. And so I would say at one point in time we had people everywhere. In the last year we have started to bring that in a little bit and have centers. So we have our hub in Europe is primarily in Amsterdam and the UK. Our hub in America is both in New York and San Francisco. So the vast majority of Uber Eats employees are there and kind of similar across other regions where we have a hub. You mentioned milestones and also funding connected to milestones which is really something that is very common and the standard in the startup world. Maybe you can talk a bit about how you are dealing with those kind of fundings that are really tagged or really closely connected to some of the milestones and how you manage that. Yeah. I would say that with Uber Eats we were lucky enough to have a lot of support. And so while we did have milestones we hit growth KPIs, things of that nature. The initial focus was very much just grow and grow fast. And so actually initially we didn't have a lot of milestones. It was really a way where the leadership team let us grow and encumbered because I knew that was the best way for us to really get to some level of scale. Answers from really tough questions about the model, things like that. And then I would say now as a business given our scale and size we really do have a milestone approach. But again, given the strong support from Dara and the leadership team for Uber Eats, it's not a let's make this thing incredibly profitable. This lets build the best business possible and if that means growth, if that means leaning into supporting restaurants more, then let's do that and let's not worry about just having a really healthy P&L. Maybe you can take us a bit through the journey kind of with the early experiments of trying to get it right. And now more recently really trying to commercialize scale and grow. Yeah, the early journeys always the fun part. We, when Uber Eats started it was actually a very different business model. It was basically a restaurant would make a lot of the same dish. So if it was like a burger place they'd make 100 burgers or 50 burgers in the morning, it would give them to one driver and that person's trunk and then you would be able to get lunch in 15 minutes. Not a scalable business model at all, but we learn how to talk to restaurants, we learn a little bit about food. That led us to our marketplace model that we have today. And you know, honestly, even till now there's just a ton of experimentation again back to the culture of saying, okay, well, you know, can we use bikes? Okay, well, if we use bikes then we can't have pizzas on those bikes because how do you have pizzas on bikes? So maybe like we have to block that pairing. Small things like, you know, when you have ice cream you can only deliver it so far. So let's make sure our algorithm accounts for ice cream. Let's try new stuff. And so we're just constantly thinking about what's the future of food delivery, what's the future of food and we're trying new things in the model. So I would say a big part of our success has been that culture again of experimentation. In terms of where we are today in scale, I'd say, you know, it's not easy to take a business that three years ago didn't exist. Now like I said, it's this massive global food delivery company and run it in a very, very central way. So I think a lot of what you might feel is a bit of a push and pull between central and decentral. So the questions we have to face are, you know, how many regional teams do we need to have and how many teams do and how much of stuff can we run centrally. You need the regional teams because of the insight locally and the ability to innovate and be connected to your customers. But at a certain point in time you have to make a decision about whether you bring that back. So that's an example of a like a tough scaling question we're wrestling with. And I guess let me ask you a question about kind of the parallel, you know, if they're any parallel, between kind of there are many, but especially when it comes to kind of the taxi service or the people delivering service that Uber started with and the food delivery, I guess the people delivery is more homogeneous across the world rather than where it's very local and specific to users that are very different and in different parts of the world. How much could you learn from the core business in terms of that and how much did you actually have to probe and experiment yourself? Yeah, it's an excellent question actually. And it's something that I don't think Uber initially thought about enough. But what we really need is a restaurant engagement model, right? Because restaurants, you know, so riders and drivers, that's two people, that's a two-sided marketplace. Eaters, restaurants and drivers, that's a three-sided business model. And also to your point, you know, a burger from here and here, it could be very different where it's a Toyota Camry here and here is the same thing always, you know. Or a Honda Civic and a Toyota Camry are pretty much the same thing. So this is why we are spending so much time and money building B2B business for Uber Eats where we have sales managers, account managers actually going in and building relationships of the restaurants for the sole purpose of keeping them happy but also so that we have the best selection. Because the way to do what you're talking about is so if I open up the Uber Eats app and any city in the world, I have a good pizza place, a good Chinese place, a good sushi place, et cetera, et cetera, so that I get what I want. And so that's a lot of what we spend our time taking about now. Let me ask you about, come almost a bit of a leadership question, is about killing projects or small initiatives. It can be like larger projects which would be Uber Eats as a whole. But also within Uber Eats, it's many different kind of ideas and initiatives. How are you going about really stopping things when you see that they are not working? How do you deal with the people that were involved and so on? Well there's a lot to do with Uber so I think one of the good things is you know, again so number one we celebrate failure. So people that are doing those things, if you fail that doesn't mean you're fired and you have to leave the company, it just means we're going to put you onto something else and it's not going to be a bad thing, right? So number one, you put the right people in those roles and they feel comfortable about their job security. Number two, we have so much to do that there's unlimited amounts of opportunity at Uber I think and so people don't feel like they won't have a job afterwards. And then in terms of killing projects I think you know, this is sometimes a place where we might even kill things too fast. We are such a fast-paced company we're growing so quickly and sometimes it's hard to think long-term because you're going so fast every day. So sometimes you see something not working and you say well maybe we should check that out.
that down. So I think actually our problem is the opposite that some big companies have, which is maybe we're killing things too quickly. Let me ask you kind of a very related question about teams. What is a good performing team? And what are some of the qualities or personalities or the composition of it? What do you see in your work? Yeah, it depends obviously on all sorts of things, but I would say generally speaking truthfully any team needs a great leader. The leader sets the direction, the culture, they allow people to be where they are, they manage people well. So at the end of the day, the leader is the one who's going to set that, right? And it's not that the team is important, but if you don't have a great leader, it doesn't matter how great the individuals are. So I do think really good management is important in any team. The other thing I'd say is you want to find people that are complementary and different from each other. I think it's not a good idea to have people that are all the same. You end up with group thing problems. Sometimes you don't have people to challenge you as much. You don't necessarily need to mandate it, but I like the idea of having people with different backgrounds, race, gender, sexual orientation, whatever it is because they're going to experience a world in a different way and they're going to see things you haven't seen. And so you do it that way, you bring people from different industries, and then you get the best answers. You have everybody the same, like you might not get the best answers, especially as you grow and scale in your business becomes more complex. What is then important for that leader? What are the leaders, the kind of qualities or traits that leaders should have? Again, it just depends on the situation, but I would say as a leader, I try to be clear and candid all the time. There's no point in sure-according things. Sure-according, I mean, you can be nice and sympathetic and empathetic to people, but you have to be clear and direct. It doesn't help someone to not give them feedback. It actually hurts them in the long run. So I always take that approach with people that I manage. I also try to really understand what makes individuals, what motivates them. Everybody's different. Some people are motivated by money, some people are motivated by pride and success and recognition and other people other stuff. And then some people don't like to be managed. And sometimes that's okay. But if you don't know enough about the person, then you're not going to manage them well and then they're going to leave or they're going to get unhappy or they're not going to do good work. So it's really just about knowing every individual that you manage well. Let me go back a bit with the attention towards really figuring out customer needs. And this was really true in the beginning and it is of course an ongoing process all the time. What are some of the methods, especially also uncovering that more latent needs or unspoken either of your stakeholders in the equation? So I think it's really important that the people that are talking to customers, oftentimes sales teams, account management teams, customer success, it depends on how it is in different companies. On the B2B side and then on the B2C side, maybe it's more the product itself. It's really important that that voice of customer has a direct feedback loop to every part of the business. So when you see problems is when people aren't listening to their customers and they aren't getting to know their customers. So it's not that customers will pretty much tell you everything and they will tell you more than you want to know. But the problem is people aren't listening to them and they aren't listening to them enough. And so it's about making sure that you are really capturing as much customer insight and then it's coming back to the entire organization. Now how do you do that well? The people that do that need to be a very important team. They can't be like the customer service arm that no one talks to. It can't be a sales team that's in a different office and no one talks to it. It has to be an important team that people actually want to hear from. Because otherwise customer insight gets lost. You don't get the real time good information and you build the wrong product or you do the wrong thing. Let me ask you about then if some of the ideas and user insights are not clear but there's a good idea about it and then you start experimenting with some of the solutions or solution propositions. How do you do that with a quite a valuable brand that already has some quality connected to it and some how do you start experimenting like the typical minimum-valve product thinking with a brand that has value and can potentially be damaged? It's a good question and here's how I would hear so first of all sometimes there's no easy way you have to do it because part of what you're selling is your brand. So I think to a certain degree you can't hide behind you can't you have to put your brand in front of the center and I think it's about being really clear and transparent with people always. You can't pretend it's something that's not. If it's something new you have to tell customers that it's new and that you're trying it out. So I think what ends up happening sometimes is big brands are afraid to try things because they're worried about what their customers might think. But customers like the fact that you're innovative and if you're solving a pain point for them they'll be happy that you're solving it and they'll give you some slack especially if you build a good relationship with them. And so I don't I think tight I don't think that's as big of a concern as people think number one and then number two would just be that at the end of the day like if you're really really worried about what you're putting in front of your customer then maybe there's a reason for that and you should reevaluate what it is because fundamentally in my opinion like you should be very happy to say to your customer here's a new thing that I believe is valuable. What's wrong with that? I think that's a great thing. You should accelerate it. You're talking about cultures in the beginning and culture being important and then also in your talk you talk about kind of different cultures especially in the early beginnings when you want to do something new and there is already a big core business that you need that separation in one of your buckets of called structure. How do you manage kind of those different cultures and especially also how do you bring those might be diverting cultures back together? That's really hard. Part of the way that you do that like I said is you have to you want to make sure the business is connected to the it's not like you're putting someone on an island right? The number one you want to bring people who are already part of the business because they're going to know the existing culture and they're going to already have some of that in their DNA so you're not going to be so far away from it and this is why I suggest don't just bring in outsiders and have it be completely outside driven because then you have that bigger cultural gap. The second thing is I think you have to do a really good job of managing up and managing sideways and managing downwards meaning you have to constantly be showing the organization the value that you're bringing once you get to a certain scale and level because they so that they understand what you're doing and why it's important and so one of the thing people fail at is they want to be stealthed for so long and they want to be this cool thing that no one cares about but I think you got to be careful with doing that too much and then I think the last thing is is like you have to be humble about your failures because people like an underdog and so you know you have to when you make a mistake and a new initiative you have to talk about it and talk about how you've learned from it. You don't want to be the school starter person that wears jeans and everybody wears suits and like you know you're never you never make a mistake like that's not true because if you're not making a mistake you're probably not building anything valuable. Last question, broad a question. How do you think innovation is changing? Has changed the last 10-15 years maybe? Well there's a couple different elements to that. I mean one is that I think everybody's being disrupted right? Everything is being disrupted the technology has provided an environment where like the whole world is changing and so the Fortune 500 is going to look different in 20 years and 50 years and 100 years. So I think just like innovation it's a concept is no longer a small small thing like everybody thinks about it. If you're not a leader and you're not thinking about your business model innovation you're probably not a great leader. Another thing I'd say about innovation and how it's changed is just that like you know it's a lot easier to do things than it was before. I mean you can change things quickly you can you have more access to data and insights you ever had before and so I think being able to do things and move your business and change it is actually easier than I ever was. And then you know look one of the other things that I've noticed when it comes to just like innovation as a concept is that it's more we're definitely at a place in our sort of like history where people are understanding that the way that we did things for 100 years in business is maybe not exactly the right way to do things and so there's more appetite for people to say for example you know the way that we people work should change and so working remotely, wearing different clothes like all these other things that create a fun work environment. People are finally adapting to that being important and being okay and then I would say also on that note you know the the people that are going to be the best leaders of tomorrow are people that I think have this what I call like a frontier skill set. There are people that have been in these changing and fast changing environments. There are people that are comfortable with that type of level of changing disruption. They're not the people that necessarily are going to be extremely risk of versus just want to stay at a company for 50 years. And so I think you're going to see a different type of profile emerge and be CEOs where maybe those people wouldn't have been CEOs before. So I think all those things are going to happen in the next next number of years and it's just going to change the whole business landscape. Thanks a lot once again for your presentation and thanks for that interesting and pleasant conversation. Okay, thanks, I know, I appreciate it. Thanks. [Music]
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Podcast Summary
Key Points:
Uber maintains startup agility through a culture of speed, experimentation, and celebrating failure, driven by entrepreneurial employees.
Uber Eats evolved from an early, non-scalable model (mass-produced single dishes) to a three-sided marketplace (eaters, restaurants, drivers) through continuous experimentation.
Scaling challenges include balancing centralized operations with regional teams for local insights, and managing a complex B2B relationship with restaurants.
The company kills projects quickly when they fail, aided by a culture that normalizes failure and offers abundant internal opportunities.
Effective teams require strong, clear leaders who manage individuals based on their unique motivations and ensure complementary, diverse team compositions.
Customer insights are critical; they must be captured and fed back into the organization through respected teams like sales or account management.
When experimenting with a valuable brand, transparency with customers about new initiatives is key, as customers appreciate innovation.
To manage cultural divergence between new initiatives and core business, leaders should involve internal talent, communicate value, and share failures humbly.
Innovation has become more accessible and necessary, with technology enabling rapid change and data-driven insights, making it a core leadership priority.
Summary:
In this podcast, Prob Deep Singh, head of Enterprise for Uber Eats, discusses how Uber preserves startup agility despite its corporate scale. He emphasizes that speed, experimentation, and a culture that celebrates failure are ingrained in the company's DNA, largely due to hiring entrepreneurial individuals, many with no prior corporate experience. Uber Eats' innovation journey began with a flawed model of mass-producing single dishes, but through relentless experimentation—such as testing bike deliveries and adjusting for ice cream—it evolved into a global three-sided marketplace.
Scaling poses challenges, particularly balancing centralized technology hubs in New York and San Francisco with regional teams that provide local customer insights. Singh highlights the importance of strong leadership that is clear, candid, and attentive to individual team members' motivations, as well as building diverse teams with complementary backgrounds. He stresses that customer feedback must be actively captured and integrated across the organization, especially from restaurant partners.
When launching new initiatives, Singh advises transparency with customers about experiments, as they value innovation and will tolerate risks if the brand is honest. To manage cultural gaps between new projects and the core business, he recommends involving internal talent, continuously demonstrating value, and humbly sharing lessons from failures. Overall, Singh notes that innovation is now a leadership imperative, enabled by technology that makes rapid change and data-driven decisions easier than ever.
FAQs
Uber relies on a culture of entrepreneurial people, many of whom have only worked at Uber, and celebrates failure to encourage testing and learning without fear.
Initially, restaurants made bulk dishes like 100 burgers, gave them to one driver, and customers got lunch in 15 minutes. It wasn't scalable but helped Uber learn about food and restaurants.
Uber celebrates failure, so people aren't fired; they're reassigned. The company sometimes kills projects too fast due to its fast pace, which is the opposite of many large companies.
A great leader sets direction and culture. Teams should have complementary, diverse backgrounds to avoid groupthink and generate better ideas.
They ensure a direct feedback loop from customer-facing teams like sales to the entire business. Listening to customers is key, but many companies fail to act on insights.
Be transparent with customers that it's new and experimental. Customers appreciate innovation and solving pain points, so brands shouldn't fear trying new things.
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