How Toast Uses Data To Drive Hospitable Moments With Emmanuelle Skala

Sean Lane: Hey, everyone. Welcome to Operations, the show where we look under the hood of companies in hypergrowth. My name is Sean Lane. Every customer success team ever will tell you that they want to become less reactive and more proactive. But few CS leaders will tell you the truth, that it's a journey to pull off that type of transition. And it's even more challenging to balance improving the efficiency of your organization with the experience of your customers during that journey. Luckily on today's episode, we're talking to someone who is not only a CS leader at a hypergrowth company, but she works in an industry where her customers have understandably high expectations, the hospitality industry. Our guest today is Emmanuelle Skala, the senior vice president of customer success at Toast. If you don't know, Toast is the restaurant technology juggernaut that's trusted by tens of thousands of restaurants for their POS system, online ordering, payroll and more. Toast hit$ 900 million in total funding earlier this year, when they were valued at 4. 9 billion. And Emmanuelle, she oversees the entire post- sale operation. In our conversation, we talk about the evolution of CS and CS operations, how Toast creates hospitable moments for their customers through data, and how the CSMs on her team are measured. And we're also going to talk about Emmanuelle's unique career trajectory that started in operations, then onto sales, and ultimately now into CS. And that journey, that trajectory, that's where we're going to begin. Because what started as a career in factory operations at Intel has given her this really unique perspective and unique set of experiences that still influence her approach today.

Emmanuelle Skala: So I actually came out of school with a degree from Carnegie Mellon in industrial management, which is sort of a fancy business degree. Pittsburgh was historically steel factory kind of center, and they created the degree for factory managers. So it's kind of a business degree, but with a real heavy operations bent. And yeah, I started my career in factory operations. I worked for Intel. And so factory operations is a lot of process and a lot of data. When I pivoted away and started working in software, I kind of moved my way into that sales ops role. And this was, I mean, pre- SaaS, but very beginning of sort of the software industry thinking about sales as less of relationship responsibility, or less of a relationship career and a bit more of an optimization game. And so finding my way into sales ops was really interesting. So this was right at the beginning of actually when they founded Salesforce. com. At Endeca, we were one of the very first Salesforce. com users. So it was the beginning of a data oriented sales process. And it was really cool being at the forefront of figuring out how to use data and how to track data, and how to optimize process to get a better sales outcome. So that's where I really started to blend my operational background in sales. But I also knew that I needed to actually sell. Because I personally feel like if you're just on the operational side, and you've actually never done the job, that you're not going to be as effective as if you've experienced both. You can look at the numbers, you can look at the process, you can optimize, but you also actually have sold yourself. You've been there, you've done that. And you also get more credibility, frankly, from the sales teams. So after about five years or so of being more in a sales ops role, I felt like I needed to actually be in a bag carrying role. And so I pivoted to carry a bag. I actually didn't really love it. I did it because I like it was, like I said, a good milestone and good credibility. And I was probably doing it more as a researcher than doing it as a profession. Because I wanted to understand it. And I do think that that really set me up for sales leadership. Because I had the process piece, and I had the strategy piece, and now I'd actually experienced being a closer and being on a quota as an individual contributor. And so from there, I was able to move into sales leadership, and lead a variety of different sales teams. And this was probably at the rise of the whole inbound and BDRs, and when that whole phenomena started. Salesforce again, being kind of a pioneer in that area. And what I was finding was there was a lot of effort going into how do we optimize the sale, right? From specialized roles to being really data- driven. Highly optimized that funnel. Every piece of the funnel, every minutia of the conversion through the funnel, there was a lot of effort into doing that. And that was really exciting. And I loved being a part of that. Maybe a few years later, CS started to become a thing as sort of the continuation of the funnel. And when SaaS, when recurring revenue models and monthly subscriptions, and even no contracts started to be in favor, it was important that you had a team that was focused on retention and growth as much as that was focused on the new sale. But the retention and growth teams were almost early days, or almost the sales function was early days. It was all about relationship and lacked some process. It was all relationship and firefighting. Lacked process, lacked numbers, for sure. Other than retention, there was really no way to measure CS. And when I had the opportunity to take on... First, I took on a role that was a blended CS sales role, which was really interesting. And then took on a role that was solely CS. It kind of gave me the opportunity to apply a lot of that process orientation and operations orientation to a new function that really hadn't seen it. So that's been my journey. My journey from factory operations to sales operations, to sales leadership, and then to CS leadership.

Sean Lane: It's amazing to see this clear pattern emerge throughout Emmanuelle's entire career, as she's describing it. From sales ops to sales leadership, and now in CS leadership, she always found herself at the forefront of an evolving role or function. The common thread that I see, though, is this infusion of data- driven processes and search for efficiencies in every single phase of her career. She was always seeking out new ways to apply the skill sets that she was developing. Now I promise we're going to come back to the CS side of things and CS ops at Toast. But before we do, I had to go back to what Emmanuelle was saying about her decision to try her hand at being an individual contributor in sales. She explained her belief that carrying a bag was important to her to someday becoming a sales leader. And it's easy in retrospect to see how that ended up working out for her in her career. But in the moment, she couldn't have had any idea that that was actually going to happen. So I asked her, was that a risky choice at the time? Was it scary?

Emmanuelle Skala: I mean, like you said, in retrospect it sounds a lot more planned out than I think it was in reality. So what was happening was, and I think part of it is just I'm a little bit bifurcated in I get equal amount of personal satisfaction and energy from being in a spreadsheet trying to figure out what a data trend is telling me as well as being in front of customers. Those both light me up pretty equally. And what was happening when I was in sales ops is I was finding myself getting further and further and further removed from the energy that I would get from having those performance moments that you get when you're in sales, or when you're training, or when you're on stage speaking, et cetera. And I was spending too much of my time in the operations and I wanted a balance. And so I sought it out for two reasons. One was because of that balance. And two was because I started hearing from sales managers and sales leaders that I was working with that they were kind of treating me as the spreadsheet person, the systems person. And I felt like I had more to offer. And so there was a little bit of a I can do this, and maybe something to prove. And then there was also a desire to just have more of that kind of interaction, more of that selling interaction. And I've never been personally afraid of pivoting and trying something new. I always have confidence that sort of you can go back to the thing that you're good at, is number one. And why not? Life is too short. Why not try something new? Worst case, it doesn't work out, and a year or two years down the road you go back, or you change again. I do think personally it makes for a more well- rounded leader. If your ultimate goal is to be a leader of some type, it doesn't have to be a sales leader necessarily, but as leader of some type, you're a much more well- rounded leader when you've done a handful of different roles. That's why big companies have MBA rotation programs, right? Because they want people to experience different roles, and they're breeding them for leadership. You're a better ally at the board table or at the executive table when you can really understand where different leaders are coming from. And you're going to be more collaborative and you're going to shoot for better outcomes. The motivation for me was I don't care if I fail. And frankly, I wasn't that good. To be honest, I wasn't that good at being a bag carrier. I was okay. I wasn't the number one rep kind of person. I was okay at it. I didn't love it. And I was fine at it. I'm definitely a better leader than I am a rep. But it was just something that I felt like I had to try. And also I didn't want to lead from an ivory tower. I wanted to lead a place of experience.

Sean Lane: And a lot of it I feel like is perception, right? How you are perceived by all the folks that you are trying to lead or influence. But also what you were saying about having actually been in their shoes, right? That is what true empathy is, right? You were actually able to say, I've done this job. And so looking out from behind my spreadsheet, I actually get it, right? I know what I'm asking of people.

Emmanuelle Skala: Right. And I wanted to have the war stories too that everybody else had. Sales has a lot of failure. That's just part of the game in sales. There's a lot of failure. And so I think it's through that that you learn. And so, yeah, I don't regret it. Like I said, it was a couple of years. I didn't do it for very long. And then even though I wouldn't say it was the highlight of my career in terms of achievement, it was an important step on the journey.

Sean Lane: I find Emmanuelle's perspective to be so refreshing. In a world, particularly the tech world, where people jump from gig to gig or company to company so frequently. And oftentimes they jump at the first sign of challenger or any struggle. She's just said that this two year stint wasn't really that long of a time. Because in the context of an entire career, it isn't. And that experience was important enough to her to make that stop along the way. Okay. So let's jump ahead to present day where, as I mentioned, Emmanuelle is the SVP of customer success at Toast. As she said, customer success and customer success ops currently find themselves in this same evolution of process improvement and measurement that sales had found itself in earlier in her career. So to give us some context, I asked Emmanuelle about the motivation to join Toast in the first place, and where in that evolution they have been as a CS org during her three years there.

Emmanuelle Skala: There was two motivations for me to get into CS. One was, as I said before, I noticed it was pretty nascent as a function. And so there was this cool opportunity to not only help Toast build this function, but also just being part of the nascency in the industry. Very similar to I was part of the nascency of the more data- driven sales industry. So that was kind of cool. But also what I was seeing was that software companies, SaaS companies in particular, were putting a ton of effort into optimizing go to market and then optimizing growth. But a lot less in optimizing retention. And I think it really burned a lot of companies, especially in the time when capital was pretty easy to acquire. That tons of startups were acquiring capital easily, putting that into their go to market motions, hosting really big bookings number, and then had a massively leaky funnel, and ultimately led to their demise. And so as a sales leader, I started to see that this is, sure, I'm hitting my numbers, but if the company's not going to be successful, it doesn't really matter. And so I really wanted to solve for the how do you not just sell to a customer, but how do you make sure that customer is around for life, right? And how do you make sure that you're optimizing the customer experience so that your attention rates are high and expansion rates are high. And then referrals, so it comes full loop back to referrals, referrals are high, which then fuels the sales team. So when the opportunity came at Toast, it was pretty exciting because Toast is a really strong go- to- market engine. But CS at the time was kind of plugging holes and it was responsible for every customer facing function post- sale, from onboarding through kind of more account management through also the technical support aspect of it. But it was reactive, fairly firefighting, and plugging a lot of holes. And very reliant on the human. There was a bit of an inconsistent customer experience. Because when you're relying on the human, and not on sort of factory standards in terms of consistent processes, then you're going to deliver an inconsistent experience. And so when I got there, we'd have some customers that were just absolutely delighted with every bit of their experience with Toast. And you could have a very similar customer who was absolutely angry at us inaudible experience with Toast. And so my goal was, all right, how do I create a very consistent, scalable machine, right? In the same way that many companies for the 10 years prior, including some that I was part of, created consistent scalable sales machines. I wanted to create a consistent scalable CS machine. So I mean, it starts with a lot of what are your playbooks, what are your best practices? How do you train your team to those best practices? How do you put the systems in place so that you can audit and manage to those best practices? And then how do you measure, and how do you get the data in place and the milestones and the metrics in place until you can measure every step of the way to see how you're doing? You can look at where your bottlenecks are, and then you can adjust based on where the challenge is in your overall funnel and your overall customer journey is. So we've been working on that. I mean, that's been a three- year journey. When I got to the company, there was very little metrics that we would measure CS on, very little diagnostic data. We had sort of outcome data. We had enough outcome data. So I mean, obviously we knew what our retention rates were, and we knew what our onboarding rates were. We knew our book to live ratio was, and we knew what all the outcomes were, but we didn't really have a good sense of what the inputs were in order to achieve the right outputs.

Sean Lane: I was just going to say, one of the things I think is helpful for people to understand about some of those inputs and that process that you're describing at Toast is that for a lot of SaaS companies, this is a technical implementation of a cloud- based tool that people are using on their desktop, or on an app, or whatever, right? And you guys certainly have a component of that, but there's also just this very physical in- person and hardware- based aspect to what Toast does as well. And so everything that you're talking about about this being very human based and tough to make it truly scalable, that's a whole different layer of challenges when it comes to post- sale and realizing the value that people bought Toast for in the first place. So I imagine that was a whole nother layer for you as you're trying to not just measure the business, but also figure out how to make it less so based on that individual human.

Emmanuelle Skala: Yeah. I mean, I think that the tricky part for Toast is that we're not just a software company. Software, hardware, networking payments, but a lot of complexity. Our buyers are also restaurant owner- operators generally. And so they're not tech savvy, and they also have a million things to do. They wear a million hats. And this is not like they're only... It's not like if you're a Salesforce and you're selling, and the person who's implementing it is the sales [ inaudible 00:18:06], that's their job. This person's job is to run a restaurant, not to manage a POS system. Then there's a physical nature. And then there's also the expectations of people in a hospitality industry, right? In the hospitality industry, people expect a human interactions, right? That is just part of the relationship, is a really big part of why they buy and why they stay around. And so one of the biggest challenges for us has been how do we maintain a deep relationship oriented sort of mentality, but at the scalability and cost structure of some that's more... Inherently, you think of a factory as probably the least human, least hospitality think you can think of, right? So it's how do you blend, how do you get factory- like performance, and both from an efficiency standpoint as well as from an output standpoint, but blended with hospitality, which is inherently very human based. And I just like solving hard puzzles. So to me, that is just really cool, is can you get hospitality- like experience, but in a factory predictable low cost way?

Sean Lane: How do you balance factory- like performance with hospitality- like experience? Talk about a tricky balance to strike. Emmanuelle's customers are held to such a high standard in their restaurants every single day. So why shouldn't they hold their vendors to the same standard? I'll never forget. I used to work in restaurant technology as well. And a restaurateur once told me that running a restaurant is like hosting a massive dinner party at your house every single night. Except your guests are going to call you out when they don't like the art on your wall or the colors of your chairs. I love how frequently Emmanuelle's first job in factory operations comes up in the way that she describes her business now. She's constantly seeking out those factory- like standards and efficiencies. But what I think is most impressive is that she does this in a way that doesn't ignore the customer experience. She's not putting efficiency over customer satisfaction. She's focused on both.

Emmanuelle Skala: Part of it is also finding ways of using data to drive hospitable moments, right? And when I think about the engine and the factory, I think about, okay, some parts of that factory line are high value added activities. And some part are really low value added activities. And we've been on a journey to automate all the low value stuff, which then frees up the humans to do the high value stuff. So we can have the same cost structure in terms of the number of humans that we need for every implementation, or the number of humans that we need to manage an account, or to answer the phones in our care team. But we're now adding real hospitality value because we've freed them up from doing the low value work.

Sean Lane: Can you give me an example of a high value hospitality moment?

Emmanuelle Skala: Oh yeah. I'm going to give you a couple. And I can give you examples of some of the lower value ones. So buying a replacement printer. There's no reason inaudible someone to do that. I know what I need. This printer is fried. I need a new one. That's it. That's something that you should just go online and buy. We did not have that previously, right? That was something that actually you had to talk to a human to do previously. Now, the way to transition that into a high value, is the customer goes online, buys the printer, right? The care agent, 24 hours after it's been delivered, calls the customer, and says," How's everything going with your printer? Do you need any help setting it up?" It's the same amount of work for the human in terms of the hour spent placing the order and et cetera versus the hour spent calling them and asking how it went and seeing if they need any help. But it's a significantly better experience for the customer.

Sean Lane: That's amazing. And as you've changed that lever, you've ridden this wave of digital adoption. You've separated these activities into high value and low value. That has also enabled you to completely change the model as well in terms of how you service your customers. And the fact that I feel like most CS organizations, when they start, start with a very simple, okay, one human being for every account type of model. But obviously as Toast has seen the hypergrowth that it has seen, you've needed to tweak that.

Emmanuelle Skala: Like I said, I mean, this is a journey. We're not complete with it. inaudible, right? So I'd be lying if I said that there wasn't still low value work that the humans are doing today, right? We're knocking things down one at a time to get to this ultimate place where all the low value work is automated. But yeah, what it does is it definitely has allowed us to pivot our model, right? And so I have three teams. I have our onboarding team, our customer care team, and we call them restaurant success managers, or CSMs. And all three of those teams have been able to go through their own transformation in how they perform those roles. But as an example, the CSM team used to be kind of an extension of support. Where they were firefighting. They would be quarterbacking churn threats, things like that. And they were covering every account in a very reactive way. Now the CSM team is covering our top accounts, and they're measured on how many business reviews they're doing with their accounts. And they're talking about the roadmap, and they're having these strategic business reviews, and they're building deeper relationships. Now, are they still quarterbacking if there's a churn threat or something? Of course. That doesn't go away. But they have the data to be able to focus on the customers that have the most need. We have data around things like adoption. So we know which of our customers have high adoption scores with our products and which of them have low adoption scores with our products. And so now a CSM, instead of just waiting for whatever fire's going to show up that morning when they show up to work, now they can look at, okay, which customers might need me today because which customers in my portfolio are showing low adoption. Which customers can I proactively reach out to and help them through that adoption curve. So it's just a game changer in the way that they perform their job. I would probably say we're maybe two thirds of the way on the journey. But we're on this journey from, let's say, reactive button pushers to proactive consultants.

Sean Lane: But I'm so glad that you call it this journey, and you recognize the fact that you're part of the way there. Because I feel like every CS leader anywhere will tell you that, yeah, we're trying to be less reactive and more proactive, but the journey for how to actually flip that switch is a pretty tough one. And you're probably never going to be at a situation where you're going to be 100% proactive.

Emmanuelle Skala: Never. Yeah.

Sean Lane: I'm curious, you talk about some of these different product based adoption scores and information that you are giving to your CSM team or your restaurant success team, and arming them so that they can be more proactive. For people who are listening and want to do something similar within their teams, what does that actually look like if I'm a CSM? How does that information surface itself to me? And how do I use that to then plan out my day, right? Because it's one thing to have the data, it's a totally different thing to get your restaurant success team bought in on the fact that, okay, this is how you can actually become less reactive because we're going to give you this crystal ball of information ahead of time.

Emmanuelle Skala: So that's also a journey. I'll tell you where I want to land, and then I'll tell you where we are now. Because we're not all the way where I want to land. But where I want to land is, and I've actually done what I'm about to describe, I did it at DigitalOcean for only two use cases, but it was probably our most important two use cases. So I know this is possible. It's just a decent amount of work, especially for an organization as big as Toast. But where I want to land is that all your data is orchestrated. All your product usage data and your behavioral data and your demographic data is orchestrated in your systems. And this is a heavy partnership with BI. So there's a data layer that you have to basically get all your data in one place first. Then you have to orchestrate, especially the product side, in order to actually identify trends in your usage data. So once the data is orchestrated, then there is sort of a layer of business rules that says, okay, when this happens, do this. And so a lot of if then statements essentially, right? And next layer on top of that, once you sort of orchestrated all the business rules, is the actual events, right? The activity or the trigger. Which can show up to a CSM in the form of a task that they have to complete in Salesforce or in whatever system that they're using. Or it can show up as a campaign that's going to go out through a marketing automation system, as an example. Or that potentially even can show up in a trigger that's direct to customer that just bypasses the humans altogether, like an SMS. Why bother telling a human to alert a customer to something when you can just alert the customer to something immediately? And so that is exactly where we're going. I'll give you a couple examples of some that we have today and some that we don't have today. One that we don't have, but we're working on actually right now, is as a customer is going through their onboarding, onboarding Toast is complex. They're likely to hit some snags or they're likely to get distracted potentially, or not complete a task, or not complete a task fully. If we can orchestrate the product and we are. We're dead smack in the middle of this. This one's actually going to go live pretty soon. If we can orchestrate the product to know, oh, look, this customer has stopped, or hasn't completed a task, or it's been X days they've gotten stalled. It's been X days since they've worked on their onboarding. That can notify an onboarder to reach out and say," Hey, can I help? It looks like you're stuck." Or it can notify, and again, we're working on both of these, or it can notify the customer with an SMS that says," Look, you haven't completed this task yet. Here's a video in case you're having problems. Here's a video that shows you how to complete that task." Right? So really, it's nudging the customer, giving them the right content exactly when they need that content and/ or a human, when they need the human. That's an example that, like I said, we're smack in the middle of, and definitely will be done this year. Some examples of ones that we've already done are, because we're a hardware company, we have device logs, and we can tell when a hardware is failing. And so we can push those alerts to our care team who can then proactively reach out instead of waiting for the customer to call us and say," Hey, my card reader is failing." We can call them and say," Hey, it looks like your card reader's failing. Do you have a few minutes to troubleshoot now?" And then maybe process an RMA if we need to process an RMA. So that's something, again, that we can do now. In the ideal world, to answer your question, a CSM comes in on Monday morning and all of these triggers have created their to- do list for the day. In the interim, when you're not all the way there, yeah, it might mean that they have to go to a separate place or a separate dashboard because it's not all orchestrated together to be able to get that. But you can measure it through the comp plan, or you can it through just your expectations on metrics. So let's say we want every CSM to do five adoption calls a week. Yeah, maybe it's not all orchestrated and perfectly tasked out for them. Maybe they have to look into two or three places to get the data. But you can still measure, did they do five adoption calls a week, even if it's a manual process to do that. So that's sort of what I mean along the journey, is, yeah, it's not fully orchestrated, but I can still drive the right behavior and then make it easier over time.

Sean Lane: Before we go, at the end of each show we're going to ask each guest the same lightning round of questions. Ready? Here we go. Best book you've read in the last six months.

Emmanuelle Skala: Oh geez. I would say, oh God, probably not best, but I would say a books that I've read. No, I've actually read a book in the last six months. I'm trying to think about business. I've actually been reading a lot of fiction lately just because-

Sean Lane: That's fine.

Emmanuelle Skala: ...summer. So I really enjoyed American Dirt.

Sean Lane: As did I. It was really, really good. Really, really good. All right. Normally we have people who are in ops. So I ask them their favorite part about working in ops. So you can either do something from when you were in ops or working with ops. Favorite part.

Emmanuelle Skala: Oh God, definitely favorite part is when you have a hypothesis, and then you go grab a bunch of data to either prove it right or wrong. I'm pretty curious. And I love manipulating data and asking the why 17,000 times until I get to the answer.

Sean Lane: All right. Flip side. Least favorite part about working in ops.

Emmanuelle Skala: I would say least favorite part is it's hard. It takes a long time. I mean, especially in a business as complex as Toast, it takes a long time to orchestrate all your data and your systems. I kind of have a high sense of urgency. So least favorite part is things take longer than I'd like.

Sean Lane: Someone who impacted you getting the job you have today.

Emmanuelle Skala: I would say probably Mike McGuinness. Give a shout out to Mike, I'll make sure he listens to this, so he knows we're inaudible. But he was my boss at Sophos. He ran sales. He was one of those leaders that gives people their space to really flourish and puts a lot of trust in people. And he gave me a ton of responsibility in some cases where I was ready for it and other cases where I wasn't. So he believed in me and really just helped launch my career.

Sean Lane: All right. Last one. One piece of advice for people who want to have your job someday.

Emmanuelle Skala: I would say, like I said toward the very beginning, don't be afraid along the journey to try something different. Even if it's a lateral move, even if it's a pivot, even if it feels like even a bit of a backwards move, you're always going to learn something. So think about your career, instead of a career journey, think of it as a learning journey. Can I learn some thing from this, even if it physically feels like a step backwards? If you can learn something, you're on a journey, and you're on a path towards something bigger.

Sean Lane: Emmanuelle, this has been awesome. I really appreciate it. One last bonus question for you. You work with restaurateurs every single day. It's been a tough year for restaurateurs. How can all of us out there who love going to restaurants and love restaurants support them during this time?

Emmanuelle Skala: So two things. Buy gift cards, maybe for the future that you can save, or gifts to your friends. So this holiday season, it's a good time, instead of buying someone the latest iPhone or some electronic, buy them gift cards at their restaurants. And order take out. Even if you're not comfortable going to a restaurant, especially as it gets colder, order take out. And just remember that when you do order takeout, to go directly to the restaurant's website because some of the third parties charge fees, and the restaurant ultimately makes more money if you go direct to their website or call them for your takeout.

Sean Lane: Thank you so much to Emmanuelle for joining us on this week's episode of Operations. Also a special shout out to Mike Lemire at Toast for helping make the introductions. Thanks so much, Mike. I want us all to take Emmanuelle's advice and seek out the restaurants that are near us, places that we love, and buy a gift card for somebody, or order take out. It's obviously been an incredibly tough year for restaurants. And so anything that we all can do to support the restaurants in our area goes such a long way. If you're going to do that, I want you to let us know. Tag me on LinkedIn, tag me on Twitter, tag Drift, tag Toast, tag Emmanuelle. Let us know the places that are local to you that you are buying from as a result of listening to this episode. If you like what you heard and you want to hear more stories like Emmanuelle's, subscribe to this podcast. We put out a new episode every other Friday. Subscribe so it automatically shows up in your feed. And if you really liked what you heard, please leave us a six star review on Apple Podcasts. Six star reviews only. That's going to do it for me. Thanks so much for listening. We'll see you next time.