Transforming a Business w/ Gemma Cipriani-Espineira

Episode Thumbnail
This is a podcast episode titled, Transforming a Business w/ Gemma Cipriani-Espineira. The summary for this episode is: <p>This week, Gemma Cipriani-Espineira of Chili Piper joins us to discuss being a leader in Customer Success and how to transform while running a business.</p><p><br></p><p>If you want to join the discussion with thousands of other customer success leaders, join Gain Grow Retain: <a href="" rel="noopener noreferrer" target="_blank"></a></p><p><br></p><p>This podcast is brought to you by Jay Nathan and Jeff Breunsbach...</p><p><a href="" rel="noopener noreferrer" target="_blank">Jay Nathan LinkedIn</a></p><p><a href="" rel="noopener noreferrer" target="_blank">Jeff Breunsbach LinkedIn</a></p>
Ensuring There is Transparency in the Metrics
01:13 MIN
Ensuring Alignment Between Customer and Departments
01:12 MIN
The Ability to Lead When Change is Occurring
00:27 MIN
Running the Business While Transforming the Business
01:27 MIN
You Need Good Data, and Storytelling
00:37 MIN

Jeff Breunsbach: Welcome to the Game Grow Retain podcast. Okay, so we're here with Gemma Cipriani- Espineira who's the VP of Customer Success at Chili Piper. I was very nervous about that name intro. I'm not good at pronouncing, so hopefully, I nailed it. But Gemma, really excited to talk to you today. Thank you for coming on.

Gemma Cipriani-Espineira: Thank you, Jeff. And you had perfect pronunciation there. Thank you very much.

Jeff Breunsbach: Like I said, I was going to crosstalk-

Gemma Cipriani-Espineira: Now, I've got to try your name thought.

Jeff Breunsbach: Okay.

Gemma Cipriani-Espineira: Breunsbach. Breunsbach.

Jeff Breunsbach: So, it's German. You're close. I say it Breunsbach. My dad says Breunsbach.

Gemma Cipriani-Espineira: Oh, okay.

Jeff Breunsbach: So, I don't know why I could never get on the C- K even though it's a C- H ending, but he probably knows the pronunciation better than I do, but I'm a stubborn son, so we always go back and forth on that one. But you're close. And I think there used to be like an umlaut and like a tilt and umlaut over the U, and you say that in a certain way in German. But, I appreciate you trying, it's good to put yourself out there.

Gemma Cipriani-Espineira: I appreciate you trying with both our names. I think you did you did a great job. But no, honestly, really happy to be here. Thank you for having me on the series.

Jeff Breunsbach: Well, I always like to start with a fun question, and since I was just on a little tropical vacation with my wife, my fun question for you is what's your go- to frozen cocktail? Like do you love a Daiquiri? Do you like strawberry? Is it coconut? Is it banana? If you were on a beach and dreaming about just taking some time off, what's your go- to Daiquiri?

Gemma Cipriani-Espineira: That's a great question. There are definitely many that I would add to the list. One of my favorite things to do, by the way, if I'm hosting an event is to name the cocktails, like give them crosstalk-

Jeff Breunsbach: Like fun names?

Gemma Cipriani-Espineira: Yeah.

Jeff Breunsbach: Yeah.

Gemma Cipriani-Espineira: I love doing that, but right now, if you're going to take me to the Virgin Islands where you just went, I'm probably going to ask for a piña colada with dark rum.

Jeff Breunsbach: Ooh, dark rum. I like it.

Gemma Cipriani-Espineira: Yeah, yeah.

Jeff Breunsbach: I'm a big fan of mango. I did a lot of mango when we were down there. I don't know, it's just my fruit. I like that a lot. All right, cool. Then I'm going to a second follow- up question, just so the listeners can get to know you a little bit better. You have a bunch of squares it looks like on the back of your wall, or rectangles.

Gemma Cipriani-Espineira: Yeah.

Jeff Breunsbach: Is that just an art piece? How did that come about?

Gemma Cipriani-Espineira: Yeah, so my wife bought me a painting set, like an easel and a bunch of different paints, like acrylics, oils, watercolors, and that was a project that we did one weekend. I said-

Jeff Breunsbach: I like it.

Jeff Breunsbach: I

Jeff Breunsbach: need to get on that because my background as you can see is just a blank wall. My wife talks about it all the time, so I'm looking for inspiration. So, your background, for those listeners out there, very nice bookshelf, very tall, and then you've got your great photos next to it. I appreciate it. Well, I know one thing that we were just chatting through and I think would be a perfect starting point for us is just kind of that question, I think the inevitable question that you get asked when you're a customer success leader, which is hey, how do you know you have the right team size, or how do I know when I need to add to my team? And you've got your finance leader coming to you, you have your CEO coming to you and sitting there saying how do you know you have the right team? How do you you're doing the right things? How do I know that if I give you this budget that you're going to use it in the right way? kind of insinuation. And so where do you start with that kind of question as you do start thinking about it from a leadership standpoint?

Gemma Cipriani-Espineira: Yes, it's a big one, for sure. And I think what actually happens is you don't get asked whether you have the right amount of people in the team or whether the budget's been used properly. I think it's actually another question that's asked which is what does customers success do? And then when you get asked that question, the first piece of advice I would give anyone is check your impulse, right?

Jeff Breunsbach: Yep.

Gemma Cipriani-Espineira: Take a breath because it can be quite triggering to be asked that, particularly when working in customer success you're involved in so many things and it's like, " How could you ask me this question? What do you mean what do we do? We do everything." But I think over the years what I found really helpful is not only making sure that there's absolute transparency in the metrics, both liking outcomes that customer success impact, like retention, or inaudible adoption, but also, ensuring that there's clarity in the customer journey. Because when you have that clarity in the customer journey across the business, you then can say, " Well, we take our customer through these different phases in order to help them achieve their desired outcome, whatever it is, by a used case, inaudible product, so on and so forth. And in order to do this, these are the kind of activities that we do with them." And once you have that kind of visibility, the only other piece to really get a good handle on that I think not many people do in CS, but we will see more people doing is the amount of time that it takes to complete those activities. So, if you compare it to professional services as an example, professional service teams who may be focused on one very particular thing like an integration project, they're usually very good at tracking hours because they come from the project management world. There's always out tracking hours and then giving an estimate if you're going to be behind on the project and so on and so forth. But in customer success because we've kind of spun out of sales, you could argue, the way that teams have been built in customer success is by looking at their carrying capacity in terms of like a volume of customer, or an ARR number, or a volume of users. But, actually, to really to think about the hours that they're spending, right?

Jeff Breunsbach: Yep.

Gemma Cipriani-Espineira: Because there's nothing worse than being a CSM and feeling like you don't have enough time for your customers, and that is what as a leader, that should be your biggest priority, ensuring that the CSMs that are in your team feel like they do have enough time for customers. inaudible

Jeff Breunsbach: Yeah.

Gemma Cipriani-Espineira: Well, long answer there, but ...

Jeff Breunsbach: No, it's good.

Gemma Cipriani-Espineira: crosstalk.

Jeff Breunsbach: Like you said, it's a deep question, right? You can go to somebody for directions. But I like that approach that you're talking about because I think sometimes people think of their renewal just as an event in and of itself, it's just like, hey we just have to get the renewal done, when really, the renewal is just one point along the customer journey, and we've had all these other moments and touchpoints that are really just solidifying that the renewal is already pre- done. Like that's the way that we need to be thinking about it. And so, I think going back to your point though, at least back in some of our consulting days, I think the thing that we noticed a lot with customer success leaders who were growing and moving very quickly was they just got caught up in the cycle of not looking at the totality of the activities that we're doing. How do we start putting time against it? How do we start thinking about different models or different engagements for different types of customer? And it just started to become a kind of fire drill, " Oh, this customer's talking, you need to go to them. This one's talking, you need to go to them." And then, all of a sudden, I think you get to this point where back to your original point about what does customer success do, I think you get to this point where it's like, well, now that I'm thinking about it, I'm actually just doing a lot of these reactive things and we're just kind of making sure that everybody's a little bit happy. We're kind of pushing everything up a little bit at a time, and then it's like, oh, the renewals there. And so then we have a moment of time where it's like, the renewals here, are they going to be happy? Are they going to renew? We don't know. What can we start forecasting? But I think going back to that piece though, how can we start proactively looking at if we have a customer, what does that journey look like? How do we start thinking about it? Just some specific and key moments. How do we start associating time? And it's not going to be perfect. You have to adjust. You have to be able to go on the fly. But if I have at least three or four moments across that customer journey where I know, hey, I'm going to be spending this much time doing X, Y, and Z, and we can start associating that and start putting that expectation in, and I think that just where you start maybe it's just with a couple of those key activities.

Gemma Cipriani-Espineira: Yeah, absolutely. I mean even if at a very high level you could say it takes as many days to onboard customers, and these are the kind of meetings that we have to do with them, and this is the prac time that it takes for those meetings. You can come out and say, " Well, it's going to be 20 hours per new customer." So, that is so much more powerful than just saying that the CSMs can look after a inaudible business of this value. It's they can look after this many customers spending this many hours with them. And you know what? If we need to reduce headcount because there's some other kind of initiatives happening in the business, then that's okay, we're going to have to invest in other ways to reduce those hours that we're taking for customers. So, maybe it's both a deeper investment in the product or in the digital aspect of the customer success, which a lot of people talk about like I talk about it, is this your customer success?

Jeff Breunsbach: Yeah. I love that point too because I also think about that when you start using data to your advantage in that way, it really opens up a lot of possibilities where there's not really a given answer, where it's like, hey, this takes us 20 hours today, there's no real set... Like you said, it's hey, maybe we specialize that role and they become really good at it and that specialization-

Gemma Cipriani-Espineira: crosstalk.

Jeff Breunsbach: us time back, so maybe that 20 becomes 18, or 20 becomes 15, or maybe we tell that to a software engineer, and the software engineer says, " Hey, I notice you're doing a bunch of manual stuff that we could help provisionally account with, so let me go create something." And it takes them 20 hours to code it, and now it saves us five hours every single time. So, I love that point though because that is where you also as you start forming relationships around the business and you start saying, " Hey, here are some of the key metrics we're looking at, it's taking us 20 hours to onboard. Hey, we're trying to have an executive business review with tier- one customers, and it takes us 20 hours to pull data just to have that one meeting, then all of a sudden that re- frames the question, of okay, how do we get data quicker? Is it in the tool? Is it through dashboards? Is it that we have automated reports set up?" So I think to your point, like that can be used in such a good way across the organization to really start framing up some of the right conversations to say, how we drive kind of efficiency for our business internally while still driving the impact and the value, and the outcome that the customer needs to happen or is looking for.

Gemma Cipriani-Espineira: Yeah, totally. I think just to add on your point what you said about specialization, what's really beautiful about bringing in specialized roles is that you can then say to these specialized roles that your job is to reduce this by this. You know what I mean?

Jeff Breunsbach: Yeah.

Gemma Cipriani-Espineira: And if you're measuring everything from a somewhat effort- hours perspective, it becomes a lot easier to really manage progress and process and improvements. So I think about how fortunate our friends in sales are to have had revenue ops for so long. When you think about it, there's been sales ops roles and revenue ops roles out there for really, really long time. Well, not really long time, but I don't know, what would you say? Like five to 10 years probably?

Jeff Breunsbach: Definitely. Oh, yeah.

Gemma Cipriani-Espineira: Whereas you compare that to roles of customer success operations or digital customer success managers, these are pretty new things. Not many roles exist with that title. So, I think there's a lot that we could learn from them, optimizations that have been made on the earlier stages of the customer journey, and we need to apply them to further down in the funnel when they get to customer success.

Jeff Breunsbach: Yeah, it's like a natural maturation of our industry, right?

Gemma Cipriani-Espineira: Yeah.

Jeff Breunsbach: Like sales have gone through it. I think marketing has already gone through it. You're starting to see a lot more marketing ops types roles, and so I think it's like a natural evolution. I think one of the things that we've talked about a lot, especially since we started Gain Grow Retain is this sense of feeling confident walking into the boardroom or the executive meeting, so to speak, and sales feels really confident because they have things like how many calls are we making? What's the pipeline look like? What's our opportunity that we're closing? What's the deal rate or the close rate that we have? What's the average revenue that we're making? Like, they have these formulated and systematic ways because they've, like you said, they've been able to refine, and then there's methodologies that have taken hold in the industry that people believe in, that people have been schooled in, that there's trainings that you can get around, and I think marketing's going through that same thing, so I definitely see a very similar evolution, but I think we're still in the midst of maybe being on the beginning curve of that evolution for customer success to kind of get that same mindset. Especially around the digital piece. I think we're noticing that tons of positions are starting to open up around not only customer success ops, but now this customer marketing role or digital customer success role that I think you mentioned earlier where it's like part of it is you need to come to the table with a mindset of hey, I'm building a series of programs or series of campaigns that I need to engage customers with, and then part of it is that you're probably doing things directly with some of the customers, and then part of it is that you need to have kind of this technology and ops type of mindset where you're what's the data telling me? How am I making the right decisions? And so it's kind of this position that's coming in, it's sitting between marketing and customer success, but really, I think the intent and the outcome starts to be how are we driving digital engagement with customers, and how are we starting to push that further and further? Because, I think people are starting to realize that no matter how much it opens back up, I don't think we're ever going to go back to traveling the way we probably used to-

Gemma Cipriani-Espineira: Absolutely.

Jeff Breunsbach: And we need to start thinking about ways to engage with our customers. And frankly, our inboxes are flooded more than ever from emails, from webinars, from all these different things, so how do you create the right approach and the right system to engage those customers. And so, I'm curious from your standpoint, how have you approached that? How do you start thinking about that digital customer success role and kind of that engagement that you're trying to get from those customers?

Gemma Cipriani-Espineira: Yeah. So, I mean we've made a lot of progress since creating a position for additional customer success director. She's awesome. We can't live without her, that's for sure. And her capacity is really focused on getting the metrics in place. So, measuring everything, but then coming up with ways to improve the efficiencies across the team. So, there's the obvious stuff that digital customer success provides to the customer, so the on- stage stuff would be triggered automated emails when you notice some kind of definite option or a guided cadence through onboarding whether it's in the product or in some other kind of portal for the customer. And those are obviously, what the customer sees, and that improves the on- stage experience for the customer, so they're not waiting around the speak to someone, to get set up, or to get trained, or to achieve whatever they're looking to do with your product. But backstage, what digital customer success is doing is flying the flag for operations, and really kind of empowering the leaders in CS who are looking after the human side of things, to do so with more data. So, to make data- driven decisions. And I think you talked about the relationships in customer marketing as well, if you've ever been a CSM, which I know you have, one of the most annoying things is not knowing what's going out from different departments. It could be marketing. It could be product. It could be whoever is messaging customers, asking time from then, giving them an update on a feature that you kind of want to know about and you want to manage that messaging. So, another piece of digital customer success is really owning everything that goes out to the customer, so ensuring that there is a really clear alignment between all of the different messages a customer could be receiving. Because they don't see us as different departments, they just see us as inaudible. Right?

Jeff Breunsbach: Yep.

Gemma Cipriani-Espineira: So, that's another aspect of it, ensuring that we come across as one process.

Jeff Breunsbach: I'm smirking over here because we are going through that same thing. So, we created a mechanism internally that we call our customer communications clearing house, we call it inaudible for short, but this clearing house mindset is just what you mentioned, which is essentially, how do we centralize all the communications that are going to a customer? So, kind of every department now has to essentially flag it, or put it through this clearing house so that we at least just have an idea of what does this calendar look like? How can we make sure everybody in that company knows what's going out to when? Who's it being communicated with? We're kind of working through kind of some bumps in the road of just trying to make sure how do we visualize that? How do we help easily tell that story and send it out kind of company- wide? So, we're kind of working on that second piece, but at least, we've kind of got the teams rallied around that first piece because I think just like you said, we've kind of gone around everybody being like, " Hey, product team, doesn't it really suck when you don't know that we're sending something out about marketing, or hey, customer success team, doesn't it really such when this happens?" And so I think going around tell those stories, people have really kind of bought into that idea of like, yeah, you're right, we are sending more digital communication than ever, and we are one company, and so we can't really have this idea that we're sending somebody four emails in one day all from different things, all about different topics, and the customer's sitting there saying, " Wow, do they even talk to each other and they work at the same company?"

Gemma Cipriani-Espineira: Right.

Jeff Breunsbach: So, I definitely believe that for sure. And I love that approach. I'm curious, this digital customer success role that you have, do you also have customer success operations role as well or do you see those as one and the same?

Gemma Cipriani-Espineira: So, for our sized business and given the maturity that we already had in revenue ops, we see it as the same, but I think in time, as we grow, we might spin out ops as separate thing. I think it depends on the stage of the company and the maturity of data, consistency and transparency.

Jeff Breunsbach: Yeah, it goes back to that specialization, I think you mentioned earlier too, where it's like right now as that digital customer success kind of persons in that role starting to understand what are the activities they're doing, what are the things that they're doing, and then like you said, as you grow and scale, where does it make sense to specialize, like what makes the right sense to pull off of that plate to give to somebody else and say, hey this is a specialized role for you to do know because there is enough work to be done?

Gemma Cipriani-Espineira: Yeah, absolutely. Another one that is really inaudible and I is enablement as well, right?

Jeff Breunsbach: Yep.

Gemma Cipriani-Espineira: So, CSMs often don't have someone managing enablement because you kind of can get by with what is coming from a sales inaudible person. But I know it's a rule of thumb when your team's getting over 50 people, then you need that additional enablement person to support the directors. Yeah, there's other directions that I feel digital customer success could also look to encompass because there's a digital success for your customers, but then all of that backstage stuff, I like to talk about things as onstage and backstage, gives clarity to what we're fixing or improving. And a lot of the backstage stuff does come down to enablement, right?

Jeff Breunsbach: Yeah.

Gemma Cipriani-Espineira: People not doing things not because they don't want to just because they don't know how.

Jeff Breunsbach: Yeah. Man, this is great. This is providing some self- confidence and validation because I think we are in that same spot right now. So, last year, we brought on somebody to do enablement for our customer team, and so she's working closely with the directors of the teams to try to understand what their teams need, if we have upcoming releases or upcoming things that are happening, maybe from product, okay, do we have the right the training for the teams? Do we have everything into FAQ documents? How's the rollout going to happen? What's the communication look like? And so she's helping to prepare all that internal documentation, so that at any given moment, anybody on our customer- facing teams can sit there and say, " Hey, I'm prepared. I have all this stuff at my fingertips to be able to consume, to talk to customers about." And so, we actually have both of those roles just like you mentioned. Right now, we have a, we call it a CS ops analyst and who's doing a lot of that digital customer success, and then we've got the enablement. And right now, we're in the midst of hiring that third person to kind of pull off some of the duties from the analyst to look a little bit more into some of the messaging, and some of the digital programming, and things like that. And so we'll have somebody that's focused on metrics, somebody who's focused on enablement, and somebody who's focused on kind of the messaging side of things as well, to kind of round out that CS ops team. So, this is validating for me. I appreciate it.

Gemma Cipriani-Espineira: Yeah, yeah, it sounds like you've got a really good setup and ready to grow quickly through acquisition crosstalk.

Jeff Breunsbach: Yeah, yeah, right. That's very true, yeah. It is tough though, you know-

Gemma Cipriani-Espineira: Congrats on that by the way.

Jeff Breunsbach: Thank you. Yeah, we're excited. A big opportunity since we're going to be taking Vanilla and acquiring them and bringing them into the fold, so it's going to be really fun. But maybe another question that I have for you too is one of the things that I think a lot of our members are struggling with or talked about, I've heard come up constantly is this you're always going through change. I think change is the constant when you're working in a B2B SaaS business, I think that's what people have to be prepared for, but how you bring people along in that change I think goes a long way. To me, I think the sign of the true leaders are the ones who understand hey, we're going to be going through change. Here's how we need to bring the people along. It's not necessarily like people can think about the strategy. People can think about the execution, they can think about all those things, but how do we communicate it? How do we bring people along? And so, I'm curious, just like the route that we were going down and talking about having these different roles, being prepared for scale, I don't know if there's anything in your mind throughout your career maybe that's helped you as you've thought about, like how do we kind of bring people along in this change management process, especially as we're kind of always growing, we're always scaling, we're always thinking about the next thing? How have you done that maybe with some of your teams?

Gemma Cipriani-Espineira: Yeah, I think this has been a huge learning curve for me over the years and it's true, the only thing that is constant is change. I know it's a cliché, but it is absolutely true, so you just have to be comfortable with change, I think is a first learn. Something that I find very difficult is dealing with my impatience. So, if I know that something can be improved, if I've got the data to prove it and research the best practice, and so on and so forth, my go- to would be to just try and do it straight away. And I think one thing that I really was able to be better at this time round leading a team at Chili Piper was the change management piece, by recognizing that you have to continue to run the business while you're transforming the business. You can't just stop everything and say this is the new way that we're doing it. I mean, by the way, you can, but you might end up paying for it down the road when people aren't really sold into the reasons why the change is happening or aren't really enabled on how that's going to change their day- to-day. So, I think a much better approach and what I've learnt is to constantly remind yourself and remind those who you're employing into that, I'm trying to transform the business, but I'm also trying to run the business. So, there's certain things that I can do to transform faster, like bring in specialized roles that are maybe not directly supporting customers, but for instance, digital customer success or bring in director- level people who can be an additional support to the team. That's going to help me transform faster, that's going to help me run faster, but still, we have to keep things going. Yeah.

Jeff Breunsbach: I love that distinction because I think that also is as you become a leader in the business you start understanding how that has to happen, that you're either working in the business or on the business, right? And I think it's another analogy of that similar vein where you're trying to make sure that the team is supported and things are moving in the direction, and that the day- to- day stuff just continues to happen, but over here on the corner, you kind of have to be thinking about the future and working on the business. One of the things I always like to think about too is I always think that it's really hard for people to hold two truths, and so I think that's also something that I've had to wrap my head around too is that, just like you said, you have to be really, I think just thoughtful or methodical about how you introduce change and introduce what's going to happen because it's really hard for somebody to say, okay, this is true and I need to go do this, but then this is also true and I need to go do this, and so now, how do I hold these two truths in my mind? And so I think about that a lot too is if that's going to happen, how do I test it on a cohort first? Or, how do I do something on a small show to make sure, like you were saying earlier, like we can show it works, maybe we get some data behind it or something that can happen-

Gemma Cipriani-Espineira: Exactly. Yeah.

Jeff Breunsbach: ...that helps us say, hey this is working, and then we can start to kind of move the message along? The last part that I loved that you mentioned as well was this idea of getting them involved in that process too. I'm very much like an activator. I am like as soon as I hear if you told me like if Gemma's like, " Hey, Jeff, we have a problem. We need to go get a new CRM." Cool, I'm going to go get the CRM. I'm going to install it. I'm going to do everything. I'm just going to do everything. I'm just going to go, go, go. Like I start activating in my mind, like immediately when you say something, and I've really had to as a leader, understand that I need to activate through people. Like I need to influence and activate through other people. And so I just think, like you said, like sometimes bringing people along in that and helping them feel like they're part of the process or maybe they're helping with the ideation of it that's going to get them so much more involved and bought into, okay, we need to go do this and this is going to help us transform, or this is where the business is going. And so I think that also rang true from what you mentioned as well.

Gemma Cipriani-Espineira: Yeah, totally, totally. I think something Chili Piper as an entire company does really well is makes decisions quickly that are data- led, and we actually have a decision- making template that everybody in the company can use. So, if you want to propose something new, there's a whole template of doing it and you have to bring your evidence, put forward your options, and then everybody in the business has a chance to comment. So, it's a very Amazon- style approach.

Jeff Breunsbach: Yeah, yeah. I love that.

Gemma Cipriani-Espineira: What's funny is we're on Scheduling and we ROOT meetings, and we schedule meetings, but we actually do not meet unless we have to. Which is crosstalk-

Jeff Breunsbach: Very intentional. I love it. Yeah.

Gemma Cipriani-Espineira: Yeah.

Jeff Breunsbach: Yeah, that's so funny.

Gemma Cipriani-Espineira: It is pretty funny. We still have a lot of meetings, don't get me wrong. But we don't go to a meeting without having that really prepared. And it's very effective for sure. I would also say, something I learned from my friend Sara who is head of beta at inaudible but I had a beta transformation, I think it's inaudible. She came in to do a seminar for my old team at my last place, my old leadership team and it was all about change management. And that whole concept of freezing something that is already in place before you unfreeze it and then freeze it again to the new way of working I found to be like so, so helpful. So, even if you know what you want to do to unfreeze something, for instance, if it is say an advocacy process, like how do we ask customers to provide references? What is our current way of doing it? If there's 20 million ways that we're doing it, we better document all those 20 million ways that we're doing it before we then start to propose a new way of doing it, train everybody on the new way of doing it, and then freeze that new way into place.

Jeff Breunsbach: I like that a lot too. Yeah, it's kind of like getting a map or getting the lay of the land. Like we need to know everything that's happening today and getting it documented first. Because I also think that just reminds of this... I'm trying to think of the quote. I can't think of it right now, but I saw recently somebody was talking about this where they were talking about how people were solutioning before they even knew the totality of the problem of what was happening, and so it's back to your point, this person was already solutioning but maybe they didn't even know all the other ways that were happening. Maybe there was an entire wing of ways that people were submitting advocates that nobody had any idea about, and so then their solution only took care of 25% of the problem and it was, therefore, mute by the time they tried to roll it out, and so I think that goes hand in hand. I've been trying to do this a lot with our teams. So, I have a similar brief that I've been using recently, but mine is it sounds very similar, but it's like what's the hypothesis? What's the metric that we're going to use to prove whether the hypothesis is true or false? What's the business impact? So, outside of just the core metric we're going to use to tell whether it's positive or negative or true or false, what's the core business metric we're going to impact? Like you said, what are the possible solutions? And then what is the key next step, if you picked one of those solutions, like pick what's your recommendation, and then what's the one next step that you would have to go take on that? And so, like those kind of five things make up one slide, and everything should be presented on one slide that says, okay, here is this, I can read through it and use some accompanying stuff if we need it, if there's more data analysis, if there are things that go behind it. But I love that concept of like what's the data we're bringing to the table? What's the hypothesis we're bringing? Like, my wife is a doctor and so I always think about the scientific method of hypothesis and what's the route? And I feel like there's so much we can learn in the business world of like taking that mentality. Because I also think that at least me, it leads me to believe a lot of times too, I can test on a cohort first. I can test on, hey, my hypothesis is that I'm going to drive these 10 customers to go do X, and I'm going to use this metric, and the business impact right now is really small, but if I prove that it's true then I can roll it out to thousands of customers, and then the impact is big. And so it's just to me, it also gets into this mindset of iterating on small cohorts before we go test it on all of our customers at once.

Gemma Cipriani-Espineira: Yeah, absolutely. And you can build that confidence in testing and maybe failing on those tests by stating what you're doing, right? It's so funny, my wife also works in medicine, by the way, but she is not my inspiration for being hypothesis- driven, I have to be honest. It was my time at Decibel where I was working with them to service like a huge brands like Sony, LEGO-

Jeff Breunsbach: Oh, my gosh.

Gemma Cipriani-Espineira: ...inaudible, British Airways, and we were giving them recommendations on how to improve their website. So, as a customer success team, we had to be specialists in presenting insights, and then recommending actions based on those insights. Because it's so funny, I still talk about insights and actions with my team today because I think there's nothing worse than a hypothesis that's only backed by gut, right?

Jeff Breunsbach: Yeah. That is so true.

Gemma Cipriani-Espineira: Yeah.

Jeff Breunsbach: I feel like we're more similar than I knew because I worked in digital marketing for 10 years, and so I got to work with Bridgestone Firestone Tyres and Lenovo computers.

Gemma Cipriani-Espineira: I worked with Bridgestone at my first Saas job.

Jeff Breunsbach: And so we were helping them with their digital marketing campaigns, but it was similar where we were-

Gemma Cipriani-Espineira: How awesome.

Jeff Breunsbach: ... andwe were looking at millions of dollars of spend, and we were telling them where to direct it, and what is more effective, and how do we do AB testing, how do we look at the website and the conversion funnel that we have? Like all these things, and so we used to have to do similar reports where you'd put hypotheses, actions, insights that were happening, what's the final recommendation. So, yeah, I took that from my digital world as well.

Gemma Cipriani-Espineira: It's so funny because I think what we're both talking about here is what makes you a good CSM, some people say a good CSM doesn't necessarily become a good leader, but sometimes it does. There is some skills that you can apply to be really successful with your customers that also are really successful in how you apply yourself to your team and leading your team.

Jeff Breunsbach: And the other point that I'll tack onto this idea, just like you were mentioning, where like charts really don't do it justice when you are trying to defend or accept a hypothesis, it's like this art of storytelling is becoming so much more important. Like, the data visualization tools like we were talking about Looker, those tools are all great, and they help us aggregate data, they help us transform, they help us visualize it, but there is the human side of that is like how do I architect the story of what the data's telling me? What are the inputs? What are the outputs? How do I bring that hypothesis to life? And I think that's something that I've always tried to think about for CSMs is in your day- to- day role, it's not just taking your report and sending it to a customer, it's taking a report and understanding it because you understand their business, and if you can understand their business, and you can take that report and say, " Here's what this report means for your business, and here's some of the recommendations, or here are some of the things I'm noticing," that's where you become a really valuable part because you're bridging that gap. And that's the storytelling piece that I've been really infatuated with myself just the last couple of months is I actually picked up a book about how Amazon does a bunch of stuff, especially about storytelling, and some of that internally. And so that's another piece. But storytelling just popped into my mind as you were talking about that.

Gemma Cipriani-Espineira: We are really similar, Jeff, by the way. So, you keep saying the art of storytelling. I have a book that I've just finished, it's called The Science of Storytelling. It's by this chap called Will Storr, S- T- O- R. And I guess he's like an expert in helping writers understand how you can write better stories-

Jeff Breunsbach: Oh, my gosh.

Gemma Cipriani-Espineira: And I read the whole thing in a weekend, and I just found it really useful because when you are a leader and particularly when you're working in a high- growth company, it's not just having a handle and data measuring everything, having the best practice experience, it's selling the story. It's getting people bought in to why you're going to do something, and why you're going to test something, why you're going to change something. So, yeah, I totally agree with you. But you need good data. You can't just be a storyteller. crosstalk.

Jeff Breunsbach: Yeah, yeah, you need both, right? You need a balance.

Gemma Cipriani-Espineira: It needs to be an equal balance for sure crosstalk-

Jeff Breunsbach: I haven't read, but I picked up this book, it's called-

Gemma Cipriani-Espineira: Oh, Storyworthy. Cool.

Jeff Breunsbach: Storyworthy. So, here's this guy, Matthew Dicks, he's a 36- time story slam champion which is like this small place, I think it's in... Oh, I'm going to butcher this. This is bad. Connecticut, maybe? So, there's like this competition that they have at this place up in Connecticut where they come and they just write stories and it's like a poetry slam type thing but it's a story slam, so you tell a story-

Gemma Cipriani-Espineira: So, is it like a short stories?

Jeff Breunsbach: Yeah, so you create a short story and you do it. So, he's won this thing 36 times. And so I just bought this because somebody else had told me about it, but they had said how good it was. It's not really business- related, it's more just about the art of storytelling, so I'm excited to dive in. I also need a name afterwards-

Gemma Cipriani-Espineira: Yeah, that's awesome.

Jeff Breunsbach: ...but I'm excited to dive into that because it sounds similar. He's-

Gemma Cipriani-Espineira: This is the one I was talking about.

Jeff Breunsbach: Yeah. I just looked it up. I'm going to get that one on Amazon too.

Gemma Cipriani-Espineira: Yeah, it's a great crosstalk.

Jeff Breunsbach: I like to read. But yeah, that's similar. I think this guy is just basically just talking about how he thinks about creating, and engaging, and persuading story, no matter what it is, and so I'm excited. But, man, this has been fun. We are here to the last couple of minutes. So, maybe just my last question for you is what is one thing that is top of mind for you that you're working on here over the next two weeks, four weeks, next six months? What's something that you're kind of in the back of your mind that's something that you know you're going to have to do?

Gemma Cipriani-Espineira: Oh, gosh. Scale all my team.

Jeff Breunsbach: You just have to pick one.

Gemma Cipriani-Espineira: Okay well-

Jeff Breunsbach: Scale the team.

Gemma Cipriani-Espineira: Scaling the team is a given for Chili Piper and the growth that we're receiving, but something that I am going to be honing in on this quarter in particularly is our customer health story. So, ensuring that we have all the right metrics in place to bring more predictability to customer risk and customer opportunity.

Jeff Breunsbach: Very cool. Yeah, we're not quite that far. We're close to that stage, but that's something that's on our roadmap for a little bit later this year. So, I'll be interested to pick your brain after you do that and go through that process.

Gemma Cipriani-Espineira: Yeah, happy to.

Jeff Breunsbach: Yeah. I also don't like the word, I don't like pick your brain, so I need to get that out of my vocabulary. I need to think of a better way to share insights or-

Gemma Cipriani-Espineira: Share insights. Share input. crosstalk.

Jeff Breunsbach: Be a sounding board.

Gemma Cipriani-Espineira: Yeah.

Jeff Breunsbach: But Gemma, this has been really fun and I'm excited. We got to talk through a little bit about how do you start approaching that question of do we have the right resources in the team? Starting to think about what are we really doing? What are the right activities that we're starting to track? And then got to talk through a little bit about digital customer success and thinking about some of the roles just on customer success operations that are really helping kind of for growth and scale. So, I'm excited to put this one out there, but for anybody out there, where can they find more of you or more of Chili Piper? Where do you like to spend your time digitally so that people can find you?

Gemma Cipriani-Espineira: I'm a big LinkIn user, so that is the best way to get through to me for sure.

Jeff Breunsbach: Awesome. And I can definitely vouch for you in terms of being on LinkedIn. I'm right there with you, and I know you're there all the time too. So, it's been fun. I'm excited because I think I mentioned earlier about customer success kind of maturing or evolving and you know what we're doing, and I think there's a lot more people that are coming out and kind of sharing stories and sharing insights, especially on LinkedIn, so I've found it a lot of fun to network and find new people who are doing stuff. So, I'm excited.

Gemma Cipriani-Espineira: Yeah, absolutely. And I'm looking forward to sharing kind of more of our journey at Chili Piper on how we're scaling the customer success team, so we have some things coming out on our own blog, like success stories that we've ran, and we will also be continuing to gather as much best practice as I can from the getting through-

Jeff Breunsbach: Awesome.

Gemma Cipriani-Espineira: ...inaudible community.

Jeff Breunsbach: Oh, well, I'm going to hold you to that. I can't wait for those to come out and we can make sure and share those with the audience because I know there's a ton of people out there looking for this type of stuff, so it'll go a long way.

Gemma Cipriani-Espineira: Awesome.

Jeff Breunsbach: Cool.

Gemma Cipriani-Espineira: It's been a delight, as I knew it would.

Jeff Breunsbach: Thank you so much. I appreciate you doing this. I feel like we're probably going to have to do it again. I feel like there's probably more topics that we can go through, so we'll have to wrangle another hour from you at some point and get you on here again.

Gemma Cipriani-Espineira: Yeah, be happy to. Thanks, Jeff.

Jeff Breunsbach: Hey, guys, thanks so much for taking the time to listen to the Gain Grow Retain podcast. If you liked what you heard, please take a moment and share the podcast with your friends and colleagues and subscribe, we really appreciate it. Talk to you soon.


This week, Gemma Cipriani-Espineira of Chili Piper joins us to discuss being a leader in Customer Success and how to transform while running a business.

If you want to join the discussion with thousands of other customer success leaders, join Gain Grow Retain:

This podcast is brought to you by Jay Nathan and Jeff Breunsbach...

Jay Nathan LinkedIn

Jeff Breunsbach LinkedIn

Today's Host

Guest Thumbnail

Jeff Breunsbach

|Director of Customer Experience at Higher Logic
Guest Thumbnail

Jay Nathan

|Chief Customer Officer at Higher Logic

Today's Guests

Guest Thumbnail

Gemma Cipriani-Espineira

|VP Customer Success at Chili Piper