S03 EP01 with Jared Webb - Welcome to Season 3: Good Data, Wrong Story

Season three of The Habit Architect opens with a shift. Michael Cupps has spent two seasons talking about personal habits and individual time management, and now he's turning the lens toward teams, companies, and what it actually takes to grow in an AI-accelerated world. The first guest in that conversation is Jared Webb, a customer success leader with nearly 15 years of experience inside SaaS companies, most of it in health tech and fintech.

The episode centers on a problem most SaaS leaders know but don't always say out loud: the data exists, and the boardroom still isn't acting on it. Webb breaks down why that happens and what CS teams can do about it.

Cupps and Webb dig into customer health scores, where the data lives in early-stage companies (usually in inboxes and personal spreadsheets), and how to build a scoring system that actually reflects what's happening in the customer base versus what the team feels is happening. Webb makes a distinction that shapes the whole conversation: feeling isn't a metric. The companies that protect revenue are the ones that make customer signals visible, trackable, and defensible.

They also get into what AI is changing in the CS world. QBR prep that used to take three days can now take three hours. That freed-up time is not just an efficiency gain; it's an opportunity to have the conversations that only a human can have. Webb's view is that CS teams that figure out how to pair their relational instincts with better data will outlast the ones that get replaced by forward-deployed engineers or automated agents.

The episode wraps with Season 3's new closing question. Cupps asks Webb what he would hand off to AI tomorrow and why it's been sitting on the list. Webb's answer: the sales-to-CS handoff. It's where the most context gets lost and where the first 90 days of a customer relationship either get built on a solid foundation or start with a gap that never fully closes.

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Connect with Jared Webb: linkedin.com/in/jaredwebb

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Transcript

Hello, and welcome to season three of The Habit Architect. I had a few posts about this. Florencia, our producer, posted about it as well. We ended season two, and then I went on a little vacation, which was fabulous, and now we're back and we're starting season three. And we thought a lot about season two. Cupps: 0:35

We really had some great guests. We had some great topics. It was really engaging. We had more subscribers, people watching the videos. Also, more people commenting in the, on the live stream, which is what we really like. So we wanna keep that going, and we wanted to keep the name going, but we wa- we also recognized that we had so many conversations about personal habits, personal time management, personal priority management, that we wanna start shifting into the age of AI a bit and how that's impacting both individual and team productivity, what that means to companies, what that means to the individuals involved in those companies, things like that. Cupps: So the topics are gonna shift more towards the, what's happening in business and what these same principles that we w- that we talk about for ourselves, how they apply to teams, how they apply to companies that are

trying to grow, that are trying to do new things, maybe raise money, maybe exit. All of those things are happening, and AI's accelerating that, so we're gonna talk about a lot of topics. Cupps: 1:35

Today, however, we're gonna talk ... We- we've got a customer health expert. He's ha- built a career, a very impressive career helping companies manage through customer health. And what I mean by that, it means churn. It means customer success, all of those things, and we're gonna talk de- deeply about that because there's a big movement in the market today, particularly around SaaS companies, and churn is happening big because p- companies can replace them with an AI native company, or they start doing it themselves. Cupps: So customer health and customer scores, customer growth, things like that are absolutely essential for especially that mid-market that are trying to thrive in the new AI landscape out there. So we're gonna bring Jarrod Webb on. We're gonna talk to him. F- I do encourage ... While we bring Jarrod on, I'll say we'll introduce Cupps: He'll introduce himself, but we also are we want you to subscribe to the podcast, so wherever your favorite player is, Spotify, Apple, whatever. We're proud to have another sponsor on. We have

Time Bandit, as always, as our sponsor. We also have Enterprise Diagnostics. We'll talk about that later. Cupps: We also are on all the same channels, so you don't have to re-subscribe if you already have, but please do encourage a friend to comment, like, all that stuff that makes the podcast go. So thank you very much for that, and welcome to season three. Good morning, Jarrod. How are you? Jared Webb: Morning. Good to see you. Jared Webb: How's everything going? Cupps: 2:35

Good to see you too. D- why don't we start with the background on you so people know who they're talking to? Jared Webb: Yeah. I'm Jarrod Webb. I'm a seasoned seasoned leader of success teams here in SaaS world, and really with a focus in health tech and fintech. Been doing this now for close to 15 years and learned a ton about just customer health and how customers behave and things, the signals and things that we need to be able to be paying attention to, and I'm excited to talk about it. Cupps: Yeah, that's fantastic. And what struck me when I first met you was your on your LinkedIn profile you had the metrics right at the very top. It's like customer churn, et cetera,

GRR, which is a common term in SaaS, and NRR is another one, and you just mentioned it right off the bat, which, which indicated to me that you know your business and you've studied it. Cupps: You're a pupil of the business and you know what leads companies that way. So that was... That, that's what really attracted me to your profile as well. I'm glad to have you on the show. I really wanna dig in deep to the experience. Tell people where you're from. I'm in Austin today, I'm not in Dallas, but where are you t- dialing in from? Jared Webb: 3:35

Yeah. So I'm outside the DC metro area here in Maryland, Yeah ... hailing from my new home. I just moved into my new house a couple weeks ago, and- Cupps: Nice ... Jared Webb: in Montgomery Village, Maryland. Excellent ... really getting settled in and getting to have a new conversation here, so excited for that. Cupps: And you're, and you don't have to carry anything wi- on this call. At least no, no more boxes. Jared Webb: Oh, thank you. Cupps: All right. Let's talk about the customer lens first, because I think this is an interesting topic. I've worked for a lot of SaaS companies, software companies and due to the gray hair, I've seen a lot of iterations of what the latest trend is, and AI is an interesting one, and we'll talk about that in a minute. Cupps: But what's interesting to me

is that- ... that there's a lot of marketing about what software does and should do, and I think, p- especially in the executive leadership team, they start to believe their own hype, right? But then there's a group in every organization that deals with that customer that's having either an issue or they need it to do something differently, or they need a new feature, et cetera. Cupps: 4:35

W- how is that vantage point different? Because it's not the marketing hype anymore, it's actually in production and they're using it. What's the biggest challenge with that disconnect? A- and I don't... Maybe disconnect is too harsh of a word, but what a customer's feeling and what we thought we were shipping. Jared Webb: I, it's a great question. There's tends to be a ton of assumptions taken when you're thinking about your customer base. And really what the biggest thing that I've seen and that I try to bring to light as soon as possible is what are we really hearing? Jared Webb: What's the real understanding of what customers are actually saying? So things today, like we're very fortunate to be able to use tools like Gong, tools like that r- Teams and

anything that records our calls to be able to kinda look back and actually read transcripts now and use AI to, to summarize them. Jared Webb: And really what helps there is you're really getting an understanding of what they're actually talking about. There's a lot of hidden signals. There's a lot of hidden signals for both growth and churn- Yeah ... that help to be able to close that customer loop, so to speak, as quickly as possible- Yeah Jared Webb: 5:35

so that the people that are talking to customers every day can get that information- Yeah ... to the people that can either code it or we can take a new approach or have a good strategy discussion with the customer. Cupps: Yeah, that is interesting. The systems have changed dramatically since you started your career 15 years ago, clearly. Cupps: ... The, and those signals are there with what your conversation is, but just in generally, how does... it seem, seems to me like if you were taking calls from frustrated customers or happy customers that just want more, how do you not always take their side, it's got... Cupps: You gotta walk that line in customer support, I think, because you wanna help the customer, but you also, you're a member of the company that produced that work.

H- how do you take the customer story forward w- in the right way? That pe- you know, a product person probably built, thinks they built the best product. Cupps: That's just, and that's good. That's what you want out of product people. But it doesn't always work out that way, right? Jared Webb: 6:35

No, absolutely. I think you're really hitting on something that's a trait that, I've had to learn over the course of my entire career, is how to best balance the conversation of we're doing great, but..." And really you gotta fight that with data. There's only way to fight that is with data because it, and customer data is, usually speaks the strongest. Jared Webb: The more customer data, the more trends you're seeing in what the needs are or the gaps or the successes. Like at an example i- is, you, at one of my former companies, we had, we were talking a lot about specific types of features that, that were, we thought that weren't really impactful, and ended up being something that we actually put around a whole roadmap feature around that ended up being new sellable

product. Jared Webb: So those type, that's the type of hidden signals that I'm talking about, is that without the data to be able to show the trend in a couple of the customers, and especially the smaller customers. Everybody tends to know their big customer needs and wants, right? Sure. You have a customer that's in your to- in your top 80%, you're probab- of revenue, you're probably gonna know a lot of what's going on there. Jared Webb: 7:35

But your top, your bottom 20% of your revenue is probably telling you signals about new markets that you can go attack and cr- and move that bottom 20 into that top 80% now. And- Yeah ... with that like I said, following trending, following the data of conversations, of emails, of interactions within the software, all important in being able to tell that story and helping show to product that, hey, that's something that we need or need to be thinking about. Cupps: Yeah. Yeah, that makes sense. It's interesting because I think most perceptions are that customer service is a cost center. It's just there to make the customers happy. But what you just

described is it's, it can, it's also a big revenue center because there's renewals involved and there's potential growth signals that you're identifying. Cupps: Absolutely. That's fan- Yeah, that's fantastic. When we th- a lot about what we talk about on the podcast is building systems or habits and approaches to things, and I think you and I were talking in the pre-show about customer health scores. Can you tell us a little bit about why somebody needs a customer health score? Cupps: 8:35

And then how do you start to assemble that? Because if you... I think if you're a SAS company and not of a big size, you probably don't have systems that automatically do that for you. Jared Webb: Let me start with the problem and why health scores- Yeah ... are important first, and then kinda talk about how to assemble them, right? So really the problem that health scores solve is all about visibility, right? It's not on- it basically gives you what's ca- what we would consider in SAS or in CS is a 360 of your customer, understanding those signals. Jared Webb: And so the frameworks that you develop, they

don't transla- they don't always translate from one company to another. The hierarchy and the idea o- of each of those does translate, but the specific signals, the specific things that you're looking for all come from whatever company it is you're at, r- history of churn, history of upsell. Jared Webb: 9:35

And so you're looking inside of those triggers, inside of your conversation data, inside of your product usage data for the s- for the specific signals and from the history of your customer base of what they've upsold or what they've churned from. And so that, that's how you end up developing a real health score that's truly meaningful. Jared Webb: As early stage companies, so a lot of my experience comes in series A, B, and C companies. Early stage companies, you're really starting with a more broad perspective, and then it becomes more narrow as you get more data as you grow, right? So it's really important to when ... The frameworks that you build might have signals from your value add, your

deployment, your engagement, your customer success conversations themselves, but they also might have things like your CSAT scores or your traditional NPS scores. Jared Webb: All of that together should make ... And you weight, you would wanna weight them and make them different, but that should, that's really how you make a true health score that's impactful for your business. Yeah. And from there, you're able to tell and take action on your risks, your growth opportunities, and to see where your customers are truly just steady or- Yeah Jared Webb: 10:35

you need to take more attention to. Cupps: And so what you described there is y- you've got a- customer health as an aggregate of your entire book of business, and then you've got a health score by account, i- is what I'm hearing. And based on the number of signals- Yeah ... you've got the veracity of that score is higher or lower, of course. Cupps: But it, it sounds like you, you d- really don't worry about a health score in the heat of things. Your team, your CS team, is doing what they need to do on a daily basis, so the scoring kinda comes downstream from the work, it sounds because of what

transpired in those interactions. Is that fair to say? Jared Webb: I would say it's a piece of your prep, it's a piece of your renewal and stuff that you ... it's a signal that you're looking at as you go. It can be a lagging indicator, but it can also be a leading indicator if you're thinking about it in terms of how your action that you're going to, right? Jared Webb: 11:35

Yep. So it's really ... It's supposed to be ... What it's truly meant to be is a snapshot of how that customer is doing today, the signals they're giving to you in the moment based on recent, most recent communications. Yep. And based on the history of the rest of your customer base to help you predict where you're going. Cupps: Yeah. Yeah. And you mentioned s- Series A, B, and C companies, and some ... obviously there's a level of maturity that comes with time and more money. As you raise more money, you can implement more, systems and things like that. But where is a ... And typically, let's say take a Series A company. Cupps: Is it all in the CRM system where this data lives, or is it in databases, spreadsheets? Where ... how do you start consolidating that mess?

Jared Webb: Great question. It really depends on the company, but the majority of the time when you're looking at the ... My experience in the Series A and early B companies, it's usually within people's heads, or in their own personal inboxes, or within their own personal sheets that are starting to get shared, or are starting to have impacts elsewhere. Jared Webb: 12:35

But really that's the challenge that early stage companies have, is how do you consolidate your data so that everybody can use it? Yeah. And the earlier you can put those pieces into play, the better information you're gonna have later on when you're trying to continue to grow, because you don't wanna be fighting yourself to get the data that you probably could've been gathering from the beginning, right? Jared Webb: Yeah. It's really important to try to link those things earlier and often. Cupps: Yeah. And now it's gotta be, it's gotta be getting somewhat easier, and not necessarily easy if it's like you said, in email boxes or on a spreadsheet. But it's gotta be ... A- AI's l- lending itself in a, in workflows and agentic kind of calculations and things. Cupps: It's gotta make it

easier. But before, before AI, what ... how would you come up with a customer score in that scenario you just painted? There's spreadsheets, there's email, there's a CRM, like a HubSpot or something like that. How would you physically go create the health score? Jared Webb: Yeah. Jared Webb: 13:35

So from before AI even with AI, honestly the key, the first thing you gotta do is really understand where you're at. So you have to have tons of conversations with people internally have individual executive level conversations with your stakeholders at each customer that, you can, as many as you can, to understand what truly their value is so that you're measuring the ROI, if people are getting ROI. Jared Webb: 'Cause that's tends... is today's world, value i- is gonna translate into are you gonna renew, are you gonna not? And that's what people wanna know. Yeah. I'm getting the value we're staying. But you'll, you also need to make sure that you understand the contract data, understand what you're supposed to be delivering, what you're not delivering, what you are delivering. Jared Webb: Gather all of those different things together from your support

tickets as well even, and put that all into one aggregate spreadsheet and weight it. Cupps: Yeah. Jared Webb: And then that's kinda how I built it back in the past. But today with AI you can connect a lot of those data places if you have them- Cupps: Yep Jared Webb: or those data lakes if you have them, and then pull it in that manner. But you still have a lot of, you still, you're still gonna have a lot of different places to pull from, so- Cupps: Yeah ... Jared Webb: it's important to try to figure out how you're gonna get that all aggregated, right? Cupps: 14:35

Yeah. It's interesting because you said something there that I think most people don't... Cupps: I'm, I shouldn't assume, but the, I wouldn't... I, when I traditionally think of customer service, you think of somebody that's just helping you work the technology, right? And so people call in because feature A is not working, so your CS team is helping 'em with that. But you said that what really matters if they're gonna renew is are they getting the value they were promised, right? Cupps: And that's a different thing altogether because somebody that's just having trouble turning it on versus did the company, are they willing to pay you again for what they got because it delivered value is a, that's a harder measurement, I would think. Cupps:

Yeah. Jared Webb: Yeah, I think the way that the mar- the way that the industries are all shifting, right? Jared Webb: And so your AI native companies are all about value. You're about volume. Are you getting the va- traditional SaaS company, you're looking at seats or usage data, right? Just like- Yeah ... are you putting enough people in the software? So when you're looking at your CRM, for example, like 10 seats equals this much. Jared Webb: 15:35

AI is changing that. So all S- even if you have a traditional SaaS model, you have to start thinking about when you're a CSM, when you're a CS leader, when you're a post-sales leader at all, are you delivering the value that they came here for? And how are you showing that value? You really need to be a true integrated piece into someone's data to, into someone's tech stack. Jared Webb: Yeah. 'Cause everybody's trying to vie for your business to, to use my tech. But- Cupps: Yeah ... Jared Webb: you have to make sure that you're re- relaying that value in the right way to keep

that customer knowing that you are extremely irreplaceable, Cupps: yeah. Yeah that's a great point, and I- it's interesting because I was thinking while you were talking that there is a lot of self-bias in the conversations around customer health I would think. Cupps: 16:35

'Cause I wor- the, one of the last software companies I worked for, they had a relationship management team, which was essentially CS in the field, and then they had a sales team, which was looking for new opportunities of growth and things like that. And I vividly remember many of the quarterly business reviews and things like that, there were a lot of words like, "Oh, they love us," they think the world of us. Cupps: We have great relationships. We went to dinner," things like that. I and all that's good, right? But, "They love us" isn't really a metric, right? It's a feeling. So how did you manage through that when you're doing, when you're in a room with your other executives and you're trying to think about your business and the health of that business, and you're there to advocate for the customer, how do you talk through those kinds of things to make sure that you're doing the right delivery, right?

Jared Webb: It's a it's a phenomenal question. It's something that has to get to- tuned e- every place you go, I think, that everyone's looking for a little bit of different things and your audience is a little different. But when I'm talking to other executives and trying to make sure that people understand I need a feature to keep a customer or I need a feature to be able to have opportunity to sell I I turn back to the data. Jared Webb: 17:35

I say, "It's not just this customer. I see this customer, these five other customers might have an opportunity here, and that's equating to a certain amount of revenue." And if it's a new product or a new feature, it, you're saying, "Hey, this, these customers are- Equate to this market share and there might be opportunity here for us to be able to make something new and really take something out to market that's different and could be a separator. Jared Webb: The number one thing that I have I always kinda come back to, right? And I've con- I've come back to a few times now is being visible under the data. Seeing the trends in the data and being able to argue it based on what people in your

customer base is truly saying and not just using feeling. Jared Webb: Yeah. Using feeling is part of that score and part of the things that we're looking for, but it's not all. And if you're relying only on feeling for your customer health, I can promise you that you're probably missing a lot of key signals that could equate to lost opportunities or- ... Jared Webb: Worse churn, and that's something that we want to avoid at all costs, Cupps: 18:35

Yeah. Yeah and that churn number is rising for SAS companies. It just is. And then, I, from my experience being part of some exits and things like that, you have to have a real defensible customer health story because if churn's coming out the back end, your ARR's dropping unless you're really selling on the top line you're, there, you really can't hide those numbers. Cupps: Do you have any stories or interesting anecdotes about, that, that account that got lost and it was just too late? I, it just seems like that happens more than anything, the customer has made a decision- No ... and you're learning about it af- well after they made the decision. Jared Webb: Yeah, many times. There's a

customer at one of my previous companies that we'd been working on deployment for an- one of their new pieces of software for, I don't know, six, seven months, and things had been going well. We met every week. We were, The attitude in the room was great. Jared Webb: 19:35

Open conversations every week. I was able to call that customer at whatever time of day. Ended up churning because we didn't have the signals and the right, They really needed in that timeframe. They were trying to, they were trying to move forward with some pieces in their business. Jared Webb: We weren't able to get the piece that we thought, that they really needed. They thought it was only a sliver of what we actually needed to do. Really important for us to be able to see those trends and to read those signals better and, that's something that we had to learn unfortunately, Cupps: yeah. Yeah and by the way, Nora on LinkedIn said, "Season three great, it's great to be here." That's awesome. Thank you, Nora. The the ... Let's talk about AI and what that does now. I know you

were collaborating on a product that would help CS leaders, help really SaaS leaders, the ex- entire executive team. Cupps: Where do you see AI being the biggest opportunity in this kind of area that we're talking about, from health scoring to customer service in general? Maybe th- think about some of the mid-size SaaS companies that you've worked with that maybe don't have those big investments in big CS platforms. Cupps: 20:35

And a lot of people think s- AI and CS is just a chatbot, but I think there's more to it than that, right? Jared Webb: Oh, absolutely. AI, AI has been talked about a ton in SAS right now, actually. There's every CS group I'm in right now, someone's trying to figure out the best ways to deploy their agents, the best ways to deploy their internal team, and understanding how to get people to learn and use it. Jared Webb: And I'm of the thought process that AI could be used in almost every piece of CS to be able to enhance and give people more bandwidth. Things like QBR prep, things like handoffs

call summaries is pretty standard, right? But, like, all of those different things can actually go ahead and combine into a health score, and that's really valuable of being able to pull the health score quickly, get those connectors in quicki- quicker than ever before, and create a health score and one that you can move with and grow with- Cupps: Yeah. Cupps: Yeah ... Jared Webb: 21:35

very quickly. So I think that those are some really big areas, and then what that does is it'll allow for the CS team take that information and have conversations with their current customers to see where opportunity lies and where risks are, and take out the... Jared Webb: i've, I heard some people preparing for a QBR for two or three days straight. Like- Wow ... that could be cut down to three hours maybe, with AI, and that's critical time that people can get in front of people and and bring back the human part of what we're doing and re- and build that relationship and allow us to have the true conversations around the uses of the products and things that we can help solve. Cupps:

Yeah that's fascinating. Yeah, I just, it just, I just connected a dot. So if you saw me blink, it was probably my brain churning back on. But the... I had lunch yesterday with a lady that and her business is helping executive teams manage board expectations and board meetings, and one of the things she does- is she says, "Don't go to a meeting that you don't already know what you're talking about." M- And, a- and so does the other people. So this is a... You c- you can actually change the dynamic of a QBR, where you're not just coming in and talking about in general, "Here's our business," but you're talking about very specific things. Cupps: 22:35

If the executives can see that health score that you're gonna talk about, you can actually talk about what are the recommendations to take action versus the history lesson, right? And I think that's a fundamental change. Absolutely. You're saving time on the prep and you're saving time in the meeting. Cupps: You're actually more productive in the meeting. What do you need to get done in that meeting? Not just, like I said, play back the history. So that's a huge thing. Absolutely. I hadn't connected that. Yeah. Yeah. What a different QBR that is, right? Jared Webb: Yeah. No, that's- Yeah Jared Webb: and frankly, that's Exactly. And that's where the true value is

for the CS world right now. I think that the leaders that are gonna be able to leverage AI in the way that allows them to do the thing that they are best at you're seeing a lot of companies go to things like forward deployed engineers or possibly it's even getting rid of CS teams altogether. Jared Webb: 23:35

And the thing that CS teams do really well is, or should be doing really well, is helping identify and reading the room in ways that an engineer couldn't, and helping find that opportunity and building that executive relationship that would carry on from the pre-sale. So- Cupps: Yeah ... Jared Webb: I think that's, as a CS leader my, my teams and people that I, I mentor with to, to be able to remember Jared Webb: That's a lot, where a lot of the value is. But also to fine-tune your technical chops because if you can leverage- Cupps: Yep. Perfect. Perfect. By the way, there's a little shakeup. I don't... It could be my

Wi-Fi here in the hotel, but you broke up there a little bit, but we'll just to, just just to s- mention that. I don't know if it's me or you or somebody else, but we're back on now. I can see you clearly now. Cupps: 24:35

Yeah, so that that's fascinating. I love that concept because there are a lot of the, y- the conversations that can change and it I'm thinking historically, I'm sorry, I'm thinking out loud here, but it's it's CS always seemed to be the l- the other thing when I was thinking about growth of the company, we weren't literally thinking about the CS team being a lead generation tool, but it certainly can now because the data's there, and it's just a matter of getting the connections to the signals that say, "Hey, we can grow this account if we act quickly," or, "We can save this account if we, do certain things." Cupps: And pe- a lot of people I think, at a fault, don't think of it that way, but what you're describing, it is a, it's part of, a vital part of the team. So Cupps: Hopefully you can hear my, hopefully Jared Webb: you can hear me

Cupps: We can still see you and hear you Jared Webb: Oh, me? Still got me? Okay, great. Sorry about that. Cupps: No worries. No worries ... Jared Webb: might be my Cupps: in-house Jared Webb: internet. Cupps: Let's talk... yeah. It could be this hotel internet. I don't know how it all affects. But the, let's talk about the storytelling stuff because I think that's a, that's an important part. Cupps: 25:35

So a CS leader could have been promoted because they were really good at their job. They could have c- they could come in from the outside, helping an, a CS team mature and grow. But what is the responsibility and the ownership of telling that customer's story? Do you have any tips for people that are saying, "Hey, here's what I'm seeing in the customer signals. Cupps: I need to convey that to the company." Do you have any tips on how they position those either weaknesses or strengths and just the overall customer story? Jared Webb: Yep Sorry, Cupps, can you repeat the question? I'm sorry. Cupps: Yeah, no, no problem. You are back now. So the the storytelling aspect of it, CS leaders that

maybe have been promoted, they haven't been in a leadership position or they're coming in new do you have any tips for how people can tell at the aggregate what's this customer success story, and then individually if there's some advice you have for people? Jared Webb: 26:35

I'm sorry. Hold on. I'm trying to check my internet here. I think it might be me. I'm not sure. Cupps: It may be. Florencia, in the background, do you, My Jared Webb: back? Cupps: Are you seeing the same issues? You're back. You're back Cupps: Let me see if I can chat the, through the, a question here Cupps: So Jared, there's a the question is in the chat if

you can see it. I don't know if you got that or not. But we can see and hear you. I j- I think you just can't hear me Cupps: All right. Florencia, I think we probably have a bad connection. Maybe we should- Cupps: Yeah, go ahead. Go ahead, Jared Jared Webb: 27:35

Yeah. So I guess the, if the que- like the questions around like how do I tell the story to other executives I think talked about this a little bit earlier, but I think the story that I, that tell around customer health and what, what's been going on and how to best utilize AI and utilize things for us in customer signals is really around like Opening up visibility, opening up the understanding of our customers because we can only talk to so many people. Jared Webb: You only have what, four CSMs maybe on a team. And so with that little of people on your team, you're not gonna be able to talk to

all your customers every day like you want to, especially if they're... Especially if your software is something that they interact with every single day. Jared Webb: How are you gonna get the true feedback of how they're utilizing where they're going every day if you don't utilize some type of AI or some type of form of work to help understand those quiet signals that they're giving you when they're in the software, when they're using and u- understanding where they're going and where they might be leading to? Jared Webb: 28:35

I think that's so important to be able to gather the data and then I tell the story using just repeating what my data tells me what people are doing. And then I make sure that story is aligned with, where I wanna go, or if it's not where we think we need to go or where we have to go, like maybe I have to do some rethinking and retooling and then s- come back and say, "Look, this is what my data's telling me, and I see that we need to be attacking more of this mid-market, for example. Jared Webb: The mid-market in our company makes up, 5, 10% of our new target area, and,

maybe that is something we need to take a look at. Or, hey, maybe it's not something that's so important that we might have thought was important because it's only such a small number." Yeah. Just depending on the movement and how things are going there. That's how I would read it and look through it, and represent that back to the executives. Cupps: Yeah. And let's talk a, take a hard conversation that... Yeah hopefully you can hear me again. Take a hard conversation. Cupps: 29:35

Maybe it's time to fire a customer because they're not profitable or they're not, they're churning through your CS teams. Maybe they're for any number of reasons, when you spot a customer that says, "Hey, this is not the kinda customer we need to because it's a distraction to our broader mission," how do you handle that discussion? Jared Webb: Those are much harder. Yeah The ones that you wanna... there's a metric that I use that I think CS teams need help on getting, but really can start- at least start the conversation. It's all around cost to serve. ... And if your cost to serve is way higher than what you're looking at, you really need to understand, is that customer really worth it? Jared Webb: Are they a key

customer that's in the market that you need to keep them around, or are they a customer that is just taking up a ton of time? Very often what I've seen is that the earlier customers tend to have had a different perspective on how and what they could get at whatever time. And it's those are the more difficult customers, either the smaller... Jared Webb: 30:35

especially the smaller ones at that time, 'cause th- they take up a lot of time, but they don't take up a ton of your ARR and NRR books. As you grow, those customers with the smaller numbers tend to get less time. And so it's actually a great place to be able to leverage your AI in any agents that you're using to be able to give them the touch level and the need from your team that they could get to be able to help save them. Jared Webb: And then where where it's needed, you can put in the human in the loop to be able to go attack that and help them out. Cupps: Yeah. Yeah, that's fantastic. Thanks for that. Co- the cost to serve is a good metric. If you were gonna give somebody advice they're out there and they're managing a CS team of a, let's say, a Series B company which is getting some

scale, getting some, you've got some revenue coming in. Cupps: Where would you start today if you say... If they're, they just feel overwhelmed, they've got, some level of systems and not, where would you say to start? Jared Webb: Very first place is you've gotta start with those conversations and the data around what customers are saying about you. Jared Webb: 31:35

Start taking it piece by piece. You start with the easiest place where you have the most data available, which tends to be tickets. How is, how are tickets trending from your top segmented customers all the way down to your lowest segmented customers? Do that same exercise with your conversation data if you have it. Jared Webb: If you don't have it, have very intentional conversations with your team that's been on the ground l- talking to the team. Or talking to the customers, excuse me, and understanding, gather that data, aggregate that data as best as you can, and then you'll, you will likely start to see trends. You'll start to see that a specific type of issue is popping up that's causing pain for a larger segment of customers. Jared Webb: You might see that there's, people are asking for certain things that

we, that you might not have seen before, and you might didn't even know was there or was an opportunity. Once you start getting into a couple of different segments of conversation data and interaction data, you're gonna start to see trends. Jared Webb: I would that's where I would start, because like I said earlier, the customer's voice speaks the loudest, and it's our job as CS leaders to be able to translate those needs of the customer back to our business and to help either the customers or help ourselves and ultimately really help both of us grow together. Cupps: 32:35

Yeah. That's fantastic. And by the way, we've got Jared's LinkedIn cl- scr- crawling on the screen if you wanna reach out to Jared. He, I know he's open to talking to s- other CS leaders and team members, et cetera. Check him there. So Jared we w- in the previous seasons of The Habit Architect, I always ask about personal habits, but now we're gonna change up the question a little bit. Cupps: So you're the first to have to answer this question, but, ... if you were to hand something off personally or professionally to AI that is always on your to-do list, always on, that something that's always there, what's

the number one thing that you've either handed off or plan to? Jared Webb: Oh, the number one thing I'm working on handing off is all of the handoffs, to be honest with you in between teams. Jared Webb: 33:35

I think that a lot of things get missed from... I'm gonna use the sales handoff to implementation and to go live. But those, there's a lot of things that get missed in those conversations that the sales team has, and that they kinda come over to us, and I think that it's important that as a customer, you're, have a continuity of service from all the way from pre-sale into sale, because the most excited you're gonna be and the most crucial time of any, That's right Jared Webb: relationship is that first 90 days after you've signed a contract. And so- Yeah ... the less repeating we have to do about value add, about things that you were looking for, and the more that we can have informed discussions right off the bat, the better the relationship will be from the start. Cupps: That's fantastic. Cupps: That's a good observation. Thank you for that. That is true. That is true. You can fail in those first 90 days, or you can

over- you can overwhelmingly gain a customer for life, so to speak. So awesome. Absolutely. Awesome. Good conversation. Sorry we had the Wi-Fi problem, but that's not the end of the world. Cupps: We can clean it up on post and that way the, for people that wanna catch the full version again. Congrats on the new house, too. Cong- that's a big ev- evolution as well, so hopefully- Thank you ... that's going well. Thank you so much for sharing your insights on CS and really what I'm excited about is what the possibility of agentic workflows can do, and all of those things that you talked about. Cupps: 34:35

Look forward to circling back with you soon on that and see what kind of progress you, you've made with it, with the AI stuff and the handoffs. Jared Webb: Absolutely. I'm really excited, and thank you for having me. It's been a great time. Cupps: Yeah. Thank you, Jared, and for everybody else, we'll be back next Thursday as well. Cupps: Do check us out on your favorite podcast channel share, all that stuff that we ask you to do. And do stay in touch and let us know if you've got other guests that you would like us to interview people personally that you would s- you would suggest, or you wanna you wanna join us as well. Cupps: If you've got an interesting topic, then please do DM myself or Florencia. We- we'd love to hear from you. So thanks everybody, and have a great day.