Name: Breaking Silos: The New, Dual Realities of the COO Role
Uploaded: 2026-06-01
Duration: 16 min 37 s

Silos that once defined the C-suite are collapsing—and no role is changing faster than the COO. Today's operators sit at the crossroads of finance, strategy, technology, and more. Scott Roe, COO and CFO of Tapestry, and Kelly Esten, CMO and COO of Enterprise of Toast, are navigating this evolution firsthand—balancing overlapping mandates in the luxury goods and restaurant and retail technology industries, respectively. Toast is ripping up traditional playbooks even further by having multiple COOs inside the organization. Join this candid conversation about how these leaders are operating across traditional boundaries, managing competing priorities, and what it takes to succeed when the C-suite is expected to be more aligned than ever. 

Kelly Esten, Chief Marketing Officer and Chief Operating Officer of Enterprise, Toast
Scott Roe, Chief Operating Officer and Chief Financial Officer, Tapestry
Moderator: Phil Wahba, Senior Writer, Leadership, Fortune; Co-Chair, Fortune COO Summit

Breaking Silos: The New, Dual Realities of the COO Role

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Let me ask you, what's your typical day like? Is this two jobs or is it really two that have melded into one? Sure, I'll start. Uh, hello everyone. Uh, you know, I think it's one job, Phil, and with two minds you got a little devil on each shoulder, at least from my perspective. So I'm CFO and COO, and I don't think you can really separate your mind, right? You bring different aspects and different points of view to bear, but in the end it's, you know, I, I view my job as an amalgamation of both of those. I'm gonna go 2 jobs um for me I really run two separate departments with 2 separate operating rhythms with two separate leadership teams and so I cherish those moments when they come together when there's a marketing program for our enterprise business and all of a sudden I. Get to use my full brain on one thing, but for me it's about how do I make sure these two different departments get the right amount of attention, the right amount of time, and, uh, the way I set up my operating system, some days are all one, some days are all the other, and you know, the best days you get a little bit of both. Well, let's talk a little bit about the, like each of you, your other job is, is different, um, I mean we've seen I cover leadership at at Fortune and sometimes you see, uh, somebody will be COO and then they'll have the CFO or they'll have the CMO, they'll have something else. And so at this moment in time, what's the rationale at Toast for you having CEO Enterprise plus CMO and offer at Tapestry and mixing with finance? So Kelly, why don't you go first? Yeah, you know, I grew up on the marketing side of the business and a handful of years ago we were really starting up our enterprise business at. So I left marketing for a few years and went all in on making sure this kind of new segment had what it needed to be successful and what that meant was I went around all the operations of the company, whether it was customer support or customer success or even tools and systems to figure out how does it need to change how we operate to serve larger customers. And then when I came back to marketing, uh, it's hard to take those hats off sometimes and, um, what I, we found was there was still a need for a leader to pull together the segment thread and so one thing we've done at Toast is actually have multiple COOs. I know we're gonna talk about that. Um, who each lead different parts of the business who have a different operating model and so as I've brought them together what like the time in the enterprise business rearchitecting how we operate for large customers brought a totally new perspective to how I do marketing. Both how I lead the team, the context I bring to the team about the broader, um, ecosystem we're working on within Toast, as well as just being super close to customers and bringing that perspective back to the marketing team. So it's, I'd say it's probably something that's not a forever but it's more about the maturity of the different businesses that Toast and where we are now and what executives can bring those tool kits to bear. Yeah, I think that I, I would, uh, agree with your comment. I think organizations are fluid and it depends on the current, you know, what is the mission of the, of the, of the enterprise and what talent do you have within the organization. So when I came, uh, 5 years ago today, my anniversary, anniversary, thank you, uh, into the company, I, I had strategy and was the CFO and then and more or less a year later. I took over the CMO role and you know one of the things that we were looking to do is reduce the space between so as you reduce the leadership, the senior leadership team, if you bring together, uh, you know, fewer people to make decisions, it makes you more agile, it makes your ability to pivot and, uh, make quick decisions just easier. There's fewer people at the table, so I think from my back. Background which I had a back in a background in tech and a strong experience in supply chain, it was a natural for me to roll up those functions and and really think about integrating the business and and be a little more seamless. So you talked earlier about having two figures on your shoulder, one an angel, one a devil, which is which? Do you ever in the morning look in the mirror and start. Arguing with yourself with your COO guy saying, hey, I need upgrades to my CRM system. Coach, by the way, which, uh, the bulk of tapestry sales come from that brand, has been killing it 30%, uh, comps last quarter, and a lot of it is because of how good they are at getting market insights. So they spend a lot of money on marketing, but also on all the data, so the market is very targeted. And then does the CFO side of you say, whoa, whoa, whoa, we just spent a lot of money on CRM and all this tech just cool your jets, you know, we don't wanna freak out Wall Street, you know how they get when you start to spend money and, and so do you ever debate yourself in the mirror in the morning? And then I don't think I'm gonna answer that question. No, I, you know, so what we did, Phil, is if I go back is we really remade the business model because we had it started with a key insight which was. You know, we need to reach a younger customer, and that customer we know has a lot of noise in her background, right? We, we hear that Gen Z is kind of the point of market entry where we focus our efforts and a lot of people would say that consumer is more fickle. I would argue that's kind of lazy analysis. She just has more choices today. So if you look at her closet, yeah, there's more brands because she has more choice. So we realized in order to reach that consumer we had to break through. In order to do that, I wish Wall Street would give us a pass, but they won't, so we had to remake the business model. So we've quadrupled our marketing investment and our operating, uh, our operating margin is up 600 basis points over the last 5 years, right? So without the hard work that comes finding efficiency, driving gross margins, all those things, we couldn't afford the marketing capacity, the reach that we need in order to execute our strategy, which is. Opening the aperture, looking redefining the total addressable market and not just try to trade share, which is the traditional way that people looked at it in our category, but actually how do we grow the market and, and to do that we had to reach a lot more people so there were two sides of it, right? What do we do in terms of executing the marketing and what are the investments, but also what are we gonna do as a company to um. Allow us to do that and still have our investors stay with us. Not easy. Yeah, well, they're staying with you. Your market cap is at an all-time high, close to it. It is, yeah, yeah, we've, we're, we've gone up 4, uh, 400%, 4 times, yeah, in the last 5 years. So, um, a question for, for, for you, Kelly, is one of the things that's interesting about Toast is that you're not the only COO in the company. Um, and a couple of years ago I did a, uh, um, in-depth piece on Costco and I went back to their leadership website. 8, members of the leadership team at Costco also have COO in their title, so like the chief merchant, which would, which is the title you would have at another retailer. Uh, it's called the person's called the title is EVP Merchandizing COO, and then the head of the Canadian business is COO, and so there are 8 people out of 30 that have the COO title. You guys have something similar. So what's the rationale? Is this a way to tell, you know, for the CEOs to be, they want the whole leadership team to be thinking like operators no matter what you do? Is that the point? Yeah, absolutely. You know, for us, first of all, I think the COO title is really flexible, right? We probably, if we went around this room and asked everyone. What scope you have a COO we'd get a pretty wide range of answers from people who are running all customer facing teams to people who are more technical focused to people who have supply chain like there's a really wide range of what COO can mean but for us it is about who has responsibility to operate this part of the business. And um we've really put COOs around our growth bets at Toast. So if you think about toast strategy, we've been traditionally an SMB restaurant business and that's our continues to be a growth engine for us and it's absolutely our core business. But as we look to future growth, we're really looking for some new areas for us to expand international being one where we have a COO and of course enterprise where we have a COO. And so the idea is this person is operating that business and has the authority to change how we operate. To make sure we're meeting the needs of that new business opportunity and not being held back by, you know, interacting with how the core business operates, which is now a very well tuned machine, um, but we have the ability to kind of break that model and rejigger it whether it's systems, whether it's processes, whether it's people, and make sure it fits the operating model needed for that new area of the business. Well, speaking of scope, maybe can you just give us, uh, an idea of what the COO part of your job includes? Yeah, sure, I, I, uh, oversee all tech, so that includes digital technology and AI. My boss jokingly calls me the AI czar, and I said, as far as I remember the czars, it didn't work out that well for me. And uh and then I have all the supply chain and then uh financial functions and and before I turn it over I'd just like to build on what you said I think that's really interesting you have so many COO titles because the way we talk about and think about leadership is um you know everybody earns their seat at the small table from somewhere you're you're a marketer. I have a financial background. You know, supply chain, whatever it is, but at that table we're all business people, right? And so you gotta get out of your functional, uh, orientation and that's why I answered that earlier question, Phil, that you asked is I think you gotta bring your whole self, uh, to the and and think like a business person and not like a functional leader when you're at these, these kind of jobs. Absolutely. You know for me it's the entire customer journey, so everything from sales to on boarding to customer success and support as well as our product investments to make them successful and it's really about um when we thought about what's the scope we need for the COO role in these new growth areas that we wanna operate differently it's about where we wanna cross the businesses and where does the model need to change, uh, and that might be different for the international business than it is for the. Enterprise business, for example, um, and so that's OK and let's make sure those roles are really about how do I have the freedom to operate and make the right decisions on behalf of my customers. I'm gonna come to the audience in a minute for, so if you have questions, uh, put your think caps on and then we'll, we'll have somebody come and visit you. But, um, for now, um, can you tell us, uh, when would it not make sense, do you think for An executive to not have uh dual roles. I mean, that's sort of the standard usually people have one, but you know there are obviously benefits. But uh what under what circumstances would you say, yeah, no, one title is enough. I'm not sure if I'm exactly answering your question, but as I think about my two roles, Phil, it'd be, uh, I mean you could make an argument having the CFO independent and not having other, you're a little bit, you know, the fox fox watching the hen house if you, right, if you don't play that role properly. Um, the way that I think about that and the way we try to do it is I have very strong lieutenants who I empower and I ask them, challenge me, right? If I ever get over the line or if I lose my objectivity, you gotta make sure you have an organization and a culture that's allowing you to call out if you see something that doesn't make sense. Hopefully I won't do that. But you know sometimes we lose our perspective. You see something, say something, as they say in some way. I, I think it's also about never being the bottleneck, right? Your point about really strong lieutenants, to me, how you manage a broader scope is you got the right leadership team in place. You have the right operating system in place. You know where you have to weigh in, where you've got lieutenants who can go do that, and I think as you. You the faster decision making benefits like I can discuss with myself whether a marketing campaign should be SMB focused or include enterprise, but I don't need, so I don't need to bring someone else in. But when I become this kind of bottleneck across the business, that's when you've got to think, OK, there's not enough overlap here for this to make sense for the business. I think we had a question in the back. Yeah, I guess you can just say uh your name and affiliation and sure, yeah. Hi, it's uh Christoph again from, from Wise uh and uh the question is, uh, probably for Kelly Mora, but in the multiple CEOs set up, I'm curious how you make sure that you don't, that these different CEOOs don't operate in silos because there are certain things like processes, tools, etc. where it's worth overlapping or using the same technology, same processes and Yeah, just curious how you make sure that this, you don't generally duplicate work and become too inefficient over time. Yeah, absolutely, you know, two things. One is there are absolutely times where we don't want to duplicate efforts, so we have, you know, very tactically we meet monthly and we talk about what's going on in our segments, decisions we're making, things we're pulling out, etc. but we've also made an explicit decision that sometimes that's OK. Like if I wanna go put in a project management tool for example or a new AI thing for enterprise and there's a duplicate effort going on in another part of the business we've actually accepted that the innovation and the closeness to the customer, the decision making we're making close to the customer is worth having some duplication across the business that's an explicit trade off we're making at this maturity. For these businesses that will ultimately change as the businesses mature, but right now the point is go fast, be close to the customer, make those independent decisions. Yes, check when there's obvious overlap, but we're making that trade off a little bit in the business as well. I think we have a question over here. Yes, uh, hi, I'm Shweta from Cognizant. So first of all, nice to have a conversation which was not about AI. You're welcome. But let me, yeah, don't worry, but we'll, I'll bring AI here and I'm gonna go back to a conversation that was my, my with my CEO of the last session where interdisciplinary skills are becoming so much more important. Do you see this kind of, you know, leadership crossing over our traditional boundaries and taking multiple responsibilities becoming a lot more common because of AI, especially like I think you said, you're also the AIs are in the company. Well, so AI is a tool, it's an enabler, but it doesn't override your, your fundamental, uh, outcomes you're trying to achieve and the way we think about it is I, I, I like the way you said it right. Where are the red lines? Where are the degrees of freedom, and, and I'll tell you, I'll give you a specific AI example. So we have what we call enterprise initiatives which are. Have a large AI component so they require cross uh cross function or cross brand or cross region or maybe all of the above coordination and we manage these as enterprise projects so you'll have a project manager and you'll have somebody looking across the common thread because when you start touching different organizations you don't want people moving at different speeds or having different. Uh, you know, approaches and the fact that it's AI enabled just opens the aperture on what you can do at the enterprise level, but to me it's about the outcome, not about the technology, you know, AI can be a hammer looking for a nail, um, and then on the other hand we have, um. General uh uh capabilities that we give to, uh, um, all of our employees, frankly and say go crazy within your areas of responsibility as long as you don't cross a functional boundary or where we've set those red lines then we give people autonomy to innovate and within their areas. Yeah, the only thing I'll add is we are seeing some blurring of functional lines, right? like. I think about sales and marketing where the SDRs and the marketing funnel we think that's gonna compress with AI or the line between product marketing and product management might blur and so there is some kind of looking at those boundaries and rethinking how different executives might lean further up funnel or further into product or product further into marketing so that's the one place where we're starting to see those shifts happen as well. Great. Well, thank you guys for joining us, and I'm told that for your 5th anniversary at a new job you can buy a coach, a briefcase. Oh, is that right? Get yourself a, a store discount. But join me in thanking Kelly and Scott for being here with us today.