The Customer Success Pro Podcast · 2026-07-01 · 52 min
Key moments - from our scoring
Substance score
63 / 100
Five dimensions, 20 points each
Andrea Kayal brings an unusual perspective to the CRO role at Help Scout: she spent most of her career in marketing (CMO at several tech companies after starting at major brands like BMW and MasterCard) before transitioning to full revenue leadership. Her team of 20 covers everything from marketing to partnerships and customer operations. At Help Scout, serving 12,000 mostly smaller companies (under 500 employees), Kayal manages a 12-person C Team split between reactive customer support (about 7 reps handling inbound queues), success managers for onboarding and complicated issues, and account managers dedicated to Pro customers ($25k+). The secret to this efficiency: Help Scout's product design allows users to get running in 15 minutes and reach power-user status in a day, dramatically reducing support volume. Kayal makes a bold argument that gross retention and churn targets belong on the product team, not CS - because no CSM can overcome a fundamentally flawed product. She recently implemented a new segmentation framework to serve the 12,000-customer base, and advocates for human-led support as a revenue driver, not a cost center. She also emphasizes the importance of deep team tenure (her VP of Customers has been there 10 years) and cross-functional alignment through frameworks like RACI.
The company achieves this through intuitive product design that allows users to get running in 15 minutes and reach power-user status in a day, dramatically reducing support volume. They also segment customers into tiers with different service levels: baseline SLAs for all, fast-track onboarding for mid-market, and dedicated account managers plus CSMs for their highest-value Pro customers.
CSMs focus on onboarding (with fast-track and white-glove options) and handling complex support issues requiring a phone call rather than email. Account managers are assigned to Pro customers ($25k+ annually), focus on identifying expansion opportunities, run quarterly business reviews, and manage renewals while advocating for the customer's needs to the product team.
Andrea argues the Chief Product Officer should be accountable for gross retention, with the VP of Customers and CS team as participants and responsible partners. If a company has a leaky bucket problem, it's typically a product issue, not a sales or CS problem, so fixing retention requires product investment first.
Gross retention shows pure customer retention without factoring in expansion revenue, while net dollar retention includes additional revenue sold into the existing customer base, which can mask underlying churn. Andrea recommends checking gross retention rates when evaluating any company.
Because at some point customers get frustrated with generic answers and templates - they want a human to have a specific conversation tailored to their use case, integrations, and unique setup. Human support, especially when handled by experienced team members like Help Scout's 10-year VP of Customers, becomes a relationship management tool and revenue driver.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode contains solid operational insights around customer segmentation, tiering frameworks, and the use of AI as a support tool rather than replacement. However, it relies heavily on broader SaaS principles (ARR-based tiering, AI tooling) that are increasingly well-known, and spends considerable time on philosophy (e.g., product ownership of churn, humans vs. AI) that, while valid, lacks novel depth. The segmentation framework using Hex and Claude is concrete but not deeply explained.
We use a technology called Hex...you can just query this and say, can you show us where natural splits would be for our customer base based on how much their contract value?
30% of our new revenue coming from this [customer support-driven referrals]
The core argument - that support is a revenue driver and that AI should augment rather than replace humans - is increasingly mainstream, not contrarian. The 'forward deployed engineer' concept borrowed from engineering teams is interesting but underdeveloped. The positioning of support as a referral engine (30% of new revenue) is noteworthy but presented anecdotally without methodology, making it hard to assess if this is genuinely novel or simply well-executed execution of known playbooks.
Because we're like, sometimes actually the better experience for the customer is to just immediately get their question answered if, if they can. Yeah, but if immediately it's not answered, we immediately want to connect you with somebody who can get that done for you.
AI first, there's just...it stops becoming AI first very quickly. It's like, nope, human to the rescue here.
Andrea is a strong operating guest: she is a CRO with direct P&L responsibility, has meaningful tenure in the role, manages a revenue-generating organization, and oversees the specific function (support/CS) being discussed. Her background spanning marketing to CRO adds credibility. However, she is not a household name in the CS community and Help Scout, while solid, is not a high-profile scaling success story (12k customers, $500-person customer profile, mature SaaS not hyper-growth). She speaks from real operational constraints, which is valuable.
Currently the Chief Revenue Officer at Help Scout, I, uh, have a team of about 20 people, um, that is everything from marketing to sales, partnerships and then the customer's team.
I've worked for varying stage companies, 5 million to 50 million, um, really just taking companies through each phase of their growth.
The episode includes some concrete specifics (12,000 customers, 12-person C team, $25k+ = pro tier, 30% of new revenue from support referrals, 15-minute setup time, power user in a day, use of Hex and Claude for segmentation). However, the support-as-revenue-driver claim (30% figure) is stated without methodology - how is this measured, tracked, or validated? The segmentation framework described is high-level; actual tier definitions and staffing recommendations are vague. Missing are KPIs, timelines, concrete CSAT/NPS numbers, and details on how the forward-deployed engineer concept actually works in practice.
30% of our new revenue coming from this
Everybody at a baseline...we have four tiers
The host asks competent, relevant follow-up questions (e.g., 'how do you serve 12k customers with 12 people?', 'where does support touch revenue?') and shows familiarity with the guest. However, questioning lacks sharpness and pushback. The host rarely challenges vague claims - e.g., the '30% of revenue' assertion goes largely unprobed (how is it measured? self-reported?). The host frequently validates rather than interrogate ('I love that,' 'I completely agree'). There are long stretches where the guest lectures on AI philosophy without friction. The conversation is friendly and coherent but leaves many empirical claims untested.
I love that you have uh, account managers as well. I feel like that's kind of the new trend
I love that. So that's how you directly trace it back
Computed from the transcript - who did the talking, and the words that came up most.
Transcribed and scored by The B2B Podcast Index.
Speaker A: This episode is brought to you by RevUp Academy. Hi CS Pros. I just wanted to quickly jump in and let you know that if you are enjoying the podcast but wondering how you too can become a revenue focused customer success professional, then I have the answer for you. Some of you might not know this, but I run a cohort based coaching program that walks you through step by step on how to align customer success strategies with with revenue and it's called RevUp Academy. It's my complete step by step coaching program that helps you elevate your skills and your mindset to focus on driving revenue for both your customers and your company. And it is a live coaching program where we open doors for enrollment only a few times a year and the next time we're opening doors is in September. So if you want to end up on our VIP wait list and get in before doors open in September, head head over to thecustomersuccesspro.com RevUp uh, go over to thecustomersuccessPro.com RevUp or check the show notes for more information. Hello everyone, I'm um, your host Anika Zubair and welcome to the Customer Success Pro Podcast. Your go to space for real talk, expert advice and actionable insights in the world of customer success. I'm a CS executive leader, award winning strategist, CS coach and customer success fanatic. I help CSMs, UM and CS leaders build the skills and the confidence to become revenue driving pros and scale world class CS teams. So whether you're brand new to CS or a seasoned leader, this podcast is here to support your growth. Because customer success isn't a destination, it's a journey and I'm here to be your guide and navigate every step of your journey. So join me every Wednesday where you'll get fresh CS tips, tricks and strategies you can actually use. Some weeks I'll share my own insights and best practices from working in CS over the last 13 years. And once a month I'll bring on expert guests to dive into the most relevant and pressing topics in customer success today. So if you're ready to level up, hit, subscribe on Apple Podcasts, Spotify or wherever you tune in and let's make your CS journey a little bit easier together. Welcome back to the show. My guest today is Andrea Kahle, Chief Revenue Officer at Help Scout. We're marketing customer success, customer support and every commercial team reports into her. What makes Andrea's view so interesting is the path that she took to get here. She came up through marketing serving as a CMO before stepping into her full revenue remit. So she really sees how post sales side actually contributes to growth in the way most revenue leaders might miss. And the company she is currently working out is called Help Scout. And Help Scout currently serves around 12,000 customers, mostly companies of 500 employees or below. And Andrea recently led a full resegmentation of that customer base. And today we are getting into how she pulled that off with a small team and why she is convinced that human led support is a revenue driver, not a cost. Andrea, welcome to the show. I'm excited to have you. Let's jump into this conversation. Welcome Andrea, to the show. Before we get into today's topic and really get into it today, I would love for you to share in your own words who you are to my listeners a little bit more about yourself, how you started at Help Scout, where you found yourself, now kind of your role, your background. Just give us a little bit of insight into your career.
Speaker B: Sure, happy to. And also thank you for having me. Um, so currently the Chief Revenue Officer at Help Scout, I, uh, have a team of about 20 people, um, that is everything from marketing to sales, partnerships and then the customer's team. Um, but my current role wasn't always my role. I started my career on the marketing side for big brands like BMW and MasterCard. Had some really fun jobs. The BMW art cars which were painted by for example artists like Andy Warhol, and then worked uh, on big brand events like uh, the 2006 FIFA World Cup. Um, so had a lot of big brand experiences in my background and it really showed me kind of like how marketing helps endear consumers to uh, the brands. And so I fell in love with marketing, um, and then got into tech very early on after that, uh, and stayed in tech ever since. I've worked for varying stage companies, 5 million to 50 million, um, really just taking companies through each phase of their growth. Um, and most of my career wasn't on the marketing side as cmo, but most recently in the last five years I transitioned to CRO. Uh, um, I have obviously marketing is near and dear to me. Uh, but as the Chief Revenue Officer now I focus on all the commercial um, work that we do. So that's from the very beginning of the journey on marketing side all the way through to how we support our customers. So that's been a very um, exciting transition. And then just as far as Help Scout's concerned, I, um, was on the board of Help Scout for two years prior to joining and the real um, impetus for me to move from board member to CRO was how Help Scout really treated their customers. Uh, we have very low churn at Help Scout and I think it's because Help Scout always, um, did a great job of treating every single customer, uh, with importance and urgency and really thoughtful way to care for them. And I think that's carried through and I know that'll be some of the topics you talk about today. So, yeah, thank you for having me.
Speaker A: Of course, of course. And also for everyone listening, I was ages ago once a Help Scout customer. Um, that's uh, what made me smile when, when we decided to have this conversation. But in my very first Head of Customer Success role, uh, I was a very small startup and Help Scout was the tool of choice, uh, that we decided to go for, for my support team to actually look after tickets, you know, managing the queue, managing all that stuff. Help Scout was our, our documents and also our help docs. Everything was in there and uh, it was really seamless, honestly, from onboarding and everything. So it's awesome to see how much the company's changed and grown and also your career as well. Seeing going from CMO to CRO, you don't hear that very often, if I'm honest. It's like, it's not that usual jump. But it's also interesting to see that you went from such big logos down to a true nimble team that's running full end to end and looking up to a very large customer, uh, base where it's over 12,000 customers, which we'll get into a minute. But I'm super curious, what does the breakdown of the team look like? Especially let's call it the customer facing team. What does that look like at Help Scout? Is it mostly Support Success onboarding? What does that all look like?
Speaker B: We call that team C Team. Um, and it is comprised of, um, customer, uh, success managers, a small group of customer success managers. Um, but primarily C Team is customer support. And that's the reactive support that our customers get. Um, if they have a question or they're writing into their queue, obviously we, uh, use Help Scout as Help Scout to support our customers. Um, that team is comprised of, I would say like levels, for lack of a better term, of people inside that organization where, uh, depending on how complex or sophisticated the question is, it gets routed to somebody who could be more technical, um, you know, in areas of that. But every single person on C Team has been, I think, uh, everybody is definitely over two years at Help Scout, but some, as many as, you know, five and the head of customers, uh, our VP of customers, Abigail Phillips, has been at help scout for 10 years. So yeah, a lot of like really deep tacit knowledge about the product and how we support our customers at Help Scout is, I think benefits from the fact that there's so much tenure.
Speaker A: I love that. Ten years at any, any given tech company is a long tenure. That's amazing.
Speaker B: We really benefit from her experience, um, with the product. I don't, I mean I, I know tech has like, you know, turnover and like go to market in particular. I don't know, like two years is like a long time.
Speaker A: Yeah, it is. I think two years is a very long time in, in any sort of go to market role.
Speaker B: Totally. So, um, but you know, every time we have a question, a question mark, relying on kind of like the historical information about like, did we try this? Why, why aren't we doing it this way? It's just nice to have somebody who's like this historian of facts. Um, so yeah, we're um, so that's how the C team is kind of.
Speaker A: I love that, I love that. And you have a pretty, I mean, I'd say split of like you said, success versus support, which uh, being a support tool yourself, it's interesting to hear how you guys kind of decide to uh, support and service your own customers. What is the difference? Like what do you, what are they held accountable to? What's the KPIs or what does support do versus the success team? At Help Scout?
Speaker B: Support is the reactive. That's anybody who, any of our customers writing into the queue. That team of about, I would say I think it's seven customer support reps. Um, they have, they have KPIs, like SLAs, um, you know, how many uh, how many times does it take to like respond to or you know, answer the question fully? Um, you know, the quality of those responses all measured by like csat, you know, customer happiness. That's obviously like something we're, we're tracking. Um, and uh, customer success is focused on onboarding. So for some of our larger customers, just making sure that from day one they're set up for success. We have two onboarding types. We have one that's basically like a truncated or like fast track onboarding where like maybe the customer isn't massive but they still like want, you know, some support when they need it. That's more of the on demand, um, you know, getting them up to speed. And then for pro customers, which is, you know, are like sort of this enterprise plan we have an account manager who gets dedicated to that account. Um, we have a customer success manager onboard them and then after that they actually have an account manager and that person is responsible just for their overall success, the renewals, you know, making sure that they know about all the products and, and product adoption and those kinds of things. They do QBRs with the customers. So it's just like white glove service for.
Speaker A: Yeah, I love that you have uh, account managers as well. I feel like that's kind of the new trend or. Yeah, I don't know. I was an account manager in a previous life too and I just think that it's interesting to see how within tech and software we're kind of doing like a 360 on the CSM versus account manager role. Because I was in account management before, I guess customer success manager title even exists. But now it seems like a lot of companies and it sounds like Help Scout is doing the same exact thing too where it's like focus on adoption, onboarding, value delivery, uh, outcome, uh, delivery with a customer success manager. And I'm guessing the account manager is looking after the commercial or uh, either growth, opportunity identification or renewals or something like that.
Speaker B: Exactly right, yeah. Account managers are really focused on for the larger customer. So that's for US today it's $25,000 or more. That's basically, you know, those are the, you know, the pro customers. They get an account manager because there's just more opportunity for ah, like white space we call that, which is, you know, they may not know of all the products that they could use or adopt. So you know, we want a human being to facilitate that process. And then certainly on the renewals we want to make sure our customers feel heard. Um, is there a gap in the product features? You know, do we, do we actually need the account manager to go to the product team and say hey, this customer matters to us. I mean all customers matter to us. But like you know, they're investing in Help Scout, you know, to, to X degree. We need to build this feature for them. We have a monthly go to market alignment meeting that where we use that time for the account manager to come in for our VP of customers to come in and talk about all customers no matter their size and say like hey, this is what we're hearing from the market. This is how we're prioritizing our roadmap to make sure that like, you know, especially for the higher value customers are heard. And so that's where I think a person is really important. That's like, that's the relationship management side of it, where somebody, you know, seen and heard, um, the csm. There's a CSM focused on onboarding. There's another CSM focused on the entire base M. Because we have, you know, we, as you mentioned, we have about 12,000 customers, um, making sure that if someone writes into the queue and maybe the question is like more complicated or it deserves a conversation, a phone call, not like some asynchronous emailing back and forth, that CSM will get on the phone with the customer, no matter their size, just to make sure that they can handhold them through that problem. Because, uh, sometimes you just want to get a person on the phone, you
Speaker A: know, 100%, you just, you want to have a conversation. And I have said this in multiple podcasts before. I know you and I have talked about it, uh, before and we caught up. But truly, like, humans want humans to one degree. Like, yes, you can troubleshoot via chat bot or AI or something along those lines. But at some point you are, like you just said, you're going to get frustrated or you're going to be tired of a, uh, generic answer and you want to get very specific, very niche to the problem you're facing and very much into your use case and your integrations and your whatever you're building with your product and service. And sometimes no matter how much you train or build or have an AI bot agent or like, you know, templates to, to reach out to customers, it does require, like you said, human intervention where you're able to actually have a conversation where it's very interesting how you've kind of like split up the team and how it all looks as well. Because I think a lot of people are getting nervous that having account management means that CS is no longer relevant because account management is just going to manage the account. But there's so much more, like you said, that the customer sales manager is doing outside of just the renewal conversation. And I also just think it's not fair to say that they have to do all of these things. I personally feel like the CSM role has been given every title under the sun, meaning literally, it's the kitchen sink of you do something for the customer and then you also do everything for the customer. And which means it's really hard for CSMs mostly to really be proactive and be able to showcase value without having to run from like, pillar to post to figure out what to do with each customer. But it's interesting how you have a mix of almost like, like you just said the C team, the whole team, interacting with the customers based on again, what part of the journey they're on, what kind of frustration they're feeling, what, what's their engagement level like? All of that seems to. To factor into your. Into your journey, which is really interesting. Quick pause. Before we get back into our podcast episode, I want to talk about something Andrea and I keep circling around, which is seeing revenue risk before it's too late. And as we're heading into summer, which means Q4 is closer than ever. And in SaaS, Q4 is where the bulk of your renewals are and expansions close. And here's the thing most teams are missing. They are working to save an at risk renewal landing in October, November or December. And they have to start at least 90 days out to do that. Guess what that is right now. So if your team only learns to forecast and run renewals in September, the revenue is already going to be slipping and then you're going to be acting way too late. This is exactly why I train customer success teams to do in half day workshops. We end up doing forecasting of renewals, spotting at risk accounts early, and running the renewal conversation that protects your end of year revenue. This is a workshop that you're going to want to book with your team before the summer ends so that your team can walk into Q4 able to see the risk while there's still time to actually figure something out and protect the revenue of that client. If you are interested in helping your team identify risk, grow revenue within your existing client base and land Those renewals before Q4 ends, go ahead and go to thecustomersuccesspro.com team event and book a call with me so we can grab some time to talk about a workshop for your team. All right, now let's get back into our episode. I want to talk about 12,000 customers because that's a lot of customers for you said 20 people in your full Org, but only how many in the C team?
Speaker B: Um, there's 12 people on C team.
Speaker A: 12 people and 12,000 customers. That's wild. Clearly there's something that you guys are doing when it comes to either segmentation or breaking down how you're serving these 12,000 customers. Can you talk to us a little bit more about what does that look like? Because there's no way you could be serving them all the same way with a thousand of them.
Speaker B: Um, a big, big kudos goes to the product for, um, the user experience, being intuitive.
Speaker A: Mhm.
Speaker B: Because of that, the questions we get are solvable quickly. Um, again there's a definition. It's always great.
Speaker A: It's always great to have a great product I know to actually use.
Speaker B: This is why maybe this is a controversial point. Um, this is why I do truly believe that the retention target, the churn target, um, should be on the product team because at the end of the day it isn't going to be a human being that can save someone even the best CSM or the best account manager on the planet. I like this someone realize value in the product if it's falling down in certain areas. And this is precisely why I joined Help Scout. It's because that doesn't tend to be a problem for us like this leaky bucket where people are like getting in, they're like, I don't know how to use it. It's too complicated. It needs very long implementation times. Our stats basically show that you can get up and running in 15 minutes and power user in a day. But because of that I think it allows the questions for us to solve with humans to not overwhelm the queue. We're not getting hundreds of thousands of inquiries every day about how to use a product or why isn't this working or this is broken or this is confusing. By design the product was built for people to really understand how to use it. So I think for that reason that the team has always been a manageable size. Uh, we obviously like everybody gross margin is a um, critical like input to you know our key metrics and you know we want to be 80% or better that that and, and because CS uh sits in cogs, we have to like keep an eye on like how big the team is to support that. So but from day one I think the product played a big role in that and the yeah ability I would agree.
Speaker A: I know you said it's controversial but I, I think it's valid. Like I'm sorry you could build the best product but then if you don't have good salespeople to go out and sell it or even marketers to go market it, you're going to be building a product for no one and vice versa. You can have the best sales marketing customer team try to be selling everything but then if you don't have a product to back it up, that's actually going to hold up when it comes to their user experience and how they're, how they're seeing value out of it Again you, you're not going to save it if it's just, if it's everything's falling apart. So I agree that there is a uh, I wouldn't just say product and engineering, but I think there's like a universal understanding that churn retention is a company wide problem. Like it has to be. Otherwise there's no way like no one, no one perfect product can continue to sell itself because otherwise then we would never have sales. And uh, as we know there's billions of salespeople out there. Yes, but, but vice versa. Like even with the best salespeople, if the product doesn't hand up, it has to work in tandem. Which means that retention churn all of these metrics as much as we own them in the commercial teams.
Speaker B: Yes.
Speaker A: Something that should be shared, it's something that should be owned because uh, it will never work. One doesn't work without the other. To your, to your point, if you
Speaker B: were to like put this through like an ARPA framework, we use that at Help Scout which is, you know, accountable, responsible, participant, advisor to determine ultimately like who owns what. Yeah, I do think that the A in that, in that for that KPI should be product. I think that you could make the VP of customers and the C team participants and responsible for this to like help improve the number. But at the end of the day it's the chief product officer who has to stand up against whether or not somebody's going to vote with their dollars. And um, this is sort of tangential comment to this but like for any other, like maybe go to market or commercial leaders who are listening. If you are interviewing for a job, the first question you should be asking that company is what their gross retention rate is. Because gross retention doesn't obfuscate net dollar retention which is like what else did you sell into the customer base? It's purely like how many dollars are leaving every year.
Speaker A: And if you have a big problem there, I wouldn't want to be a part of that organization because it just tells you everything about your product if you have that many customers leaving.
Speaker B: Yes. And the first place companies go when they have a problem there is to want to shut down sales and marketing because they're like we have a leaky bucket. So if you're a customers leader, you're like uh, maybe it's a problem I can help solve. But I would really be like pointing to the product like what's up here? Or is like marketing driving all these like non ICP customers and it's just not a fit, like where's the problem? And then if you're you know, a sales and marketing leader and you have a gross retention problem. You're like, gosh, I really need to dig in here because I don't think my teams will be funded to drive more in if they're all going out the back. So that's why I think just, um, you know, you were asking, your original question was like, how did. How do. How does such a small team support so many customers? I do think it's because the product just works. And because of that, the questions they have to answer are, yeah, super simple.
Speaker A: But also to the point, like, you are able to continue to grow and continue to keep such a large number of customers with such a nimble team because the product does what it does on the tin, which is perfect. Um, but again, I don't think you're serving them all the same way, even though you have this wonderful product, which, again, I can attest. I evaluated it back in the day in my first head of CS role, and it was wonderful. And again, we brought it on board. It was great. But I would love to understand what does customer success look at that 12,000, how you guys even, like, serve that many customers? Because there's no way they're getting calls every. Every month. That's like, it's impossible.
Speaker B: We just rolled out a new framework for how to think about this. So every customer at a baseline, we make sure is, like, taken care of very Simply by, like, SLAs to get back to them when they have questions. So you're going to get a great baseline level of support. At Help Scout, the question for us was more like, we do have customers that could be more valuable to us because they have either an expansion opportunity. So we thought about it, like, in terms of, like, tiering the customers and then basically like, what does the support overlay look like because of that, based on where the white space is. So expansion opportunities, like, they're not using these products. They should. We should go tell them. Or product adoption, meaning, like, this customer actually may feel a little unhealthy to us. We need to, like, get them using more product features because they're, uh, not getting the most value out of Help Scouts. So then there's this, like, health score overlay. So we basically said, let's break the customers down by total revenue. Let's see where they fall in terms of tiers. For now, we have for. And by the way, this is work we only recently just did.
Speaker A: Okay.
Speaker B: Um, as, um, as an exercise, we. So we use Claude for this, obviously. Uh, we have. By the way, I was about to
Speaker A: ask, like, how did you start? Because that's a lot of customers where you use AI. What kind of tool will you do to really break this all down?
Speaker B: We use a technology called Hex. Um, I. Big fan of this technology. A, ah, big fan of our data team also because they basically, they just made sure that every data point we could possibly capture about our product, our internal data points, you know, like our salesforce, our HubSpot, every piece of data we have is connected all through Hex. And now we can, you can go in Hex or you can go into Claude because you know that that's connected. And you can just query this and say, can you. So we, we just started out by saying, um, can you show us where natural splits would be for our customer base based on how much their, you know, based on the contract value? Where would be natural splits for us to think about a customer support model with these overlays, white space and customer health. And it was great. Like just there were so many data points that we did a lot of
Speaker A: white space analysis for you essentially to really analyze. Uh, love that.
Speaker B: Yes, yes. And it's an, it's an overlay just to say, like, how do we want to put people on that? Uh, either on proactive support or on white space or customer health, which is this like product adoption. So that was the um, framework we used. But really I think the best thing to say about that is because this would be nuanced for every business. Like some customers may not have 12,000, maybe you only have like 100 or 500. I would do a lot of prompting to understand like what, where your analyst thinks there could be, um, natural opportunities inside of your organization. You need to get that all connected first. But it did. I broke it up into four tiers and then it basically inside of each sell, it said, if you're looking for expansion, here's how I would put people in each of these buckets, both CSMS and account management in support of white space or in support of proactive customer support. And then it gave us like a number. It's like I would recommend, you know, or you're, you're appropriately staffed for this. This is how people should be spending their time. And it was awesome. So I think it was work for us.
Speaker A: Yeah, yeah. And like, if I was a leader, like doing this for the first time, because I bet you there's a lot of people listening right now where they're like, that sounds so cool. Like, I know I need to segment my customer base. I know I should probably segment like you Said into different tiers. And one is probably like, what's my growth bucket, what's my maintain or my okay bucket? And then what's my at risk bucket? Which is what normally comes to mind. But I love how you've kind of layered number of things there. You've layered like what resource do I have to put behind this uh, tier of customer? Where's the growth behind this tier of customer? There's different layers here. So if I was just starting off, and I know that you mentioned prompts and really like, like, you know, asking it to do more and refining those prompts, but can you walk us through like practically where did you actually start? And if someone was starting from scratch today, where would you guide them or tell them how to kind of do this level of analysis where it gives you those kind of layers of segmentation.
Speaker B: The first step to that is to determine which variable do you think you should be breaking your tiers by to start? Ours was ARR. Uh, I think that that's the most reasonable way to think about your customers. Not because you want to think about them as a number, but because you, uh, are at the end of the day, it is a customer support model. You're trying to find out which customers need the most support and then where is your tolerance economically to actually provide that level of support? So ARR is a good natural break for deciding, okay, Everybody in tier one is, let's just say $5,000 annual contract. And below tier two is whatever between 10 and 5, 20 and 15 and then 30k and above. Right. Like you can, you would just, you should have some idea for how you think about the.
Speaker A: You generally do anyways. Like, I think most of us exactly have like the top 20, the middle 50, the bottom 30, whatever. It is. Like we have different, at least mental math of what we think our customers all fall into.
Speaker B: Exactly. The second piece of this is then the overlays. That was the second piece for us, which is like, what are we really trying to do here? Well, obviously we want to move customers up ARR bands. Right. So the second overlay to that is white space. So we're like, okay, where are the product adoption opportunities? For example, we have a product called AI Answers. This is the basically AI Answers helps with tier one support right now. Um, it's like if somebody went to the website and they get to the beacon, which is the chat window, they have a question like, um, what's my password? Or whatever, or password reset, I don't know. That's obviously very basic. But they could chat and figure out how to do that with AI answers. That is a product we build by consumption. So you buy Help Scout with seats, and then you buy by consumption. But there's a bunch of customers like not using that right now. Where is that white space inside of the tiers for AI answers. So that's like one product overlay for white space.
Speaker A: Yeah, but did you tell it that product or did it kind of just understand. Okay, you did. Okay, so you were really clear, like, I want to do white space analysis, and these are our product lines. Essentially. That's what you. Okay, got it exactly right.
Speaker B: I said, I said show me the WhiteSpace opportunity for AI answers. And that's where this is amazing. It just goes in and it's looking at all the, you know, product usage or whatever. And it's like in each tier, this is how much revenue opportunity is available for whitespace. And then we're like, okay, well then how would we staff against that? You know, and it determines like where you, you know, you'd put people. And then the second is on product usage. Um, like these companies aren't using workflows they should because they're not getting the most value out of Help Scout. And so how would we staff for that by tier? I love that those are just two examples, but, um, those are what I would call overlays on the tiers.
Speaker A: Yeah, but I love that you're using AI to do that level. Because I think again, in traditional ways of SaaS and the way we've always segmented customers has been what you've just said. ARR. Very. I don't want to say easy, but it's almost like, what are our highest revenue customers? Those are the ones that get the most amount of resource time, et cetera. But there is usually, and I always say this whenever I do talks or workshops with teams, is that usually a lot of revenue is hidden in the middle chunk of your customer segmentation. But it takes a lot of time, brain power, energy, whatever you want to call it, for someone to go and do the analysis of their book of business of that middle tier to really understand, hey, what are they not using us for? What could they be using us for More? And usually again, CS people are the most time poor people, I think in SaaS and technology that they have all the intention to do all that, but more times than not they're just kind of rushing it and they're just kind of thinking, oh, maybe this account's kind of, uh, like opportunity for growth, but they're not Actually doing that level of analysis which is so interesting that you've been able to get AI to do that and split it all up. But I want to talk about something that you've told me before which I find even more interesting, which is once you segmented, you told me that you have revenue generated from your customer support team. Not success, but the support team is actually helping one of those tiers of customers and then they're generating revenue which is again amazing. But I don't think we hear that enough. We always hear as support as like oh, they're just there to answer the question. They're there to technically get the customer across the line. But are they actually having commercial conversations? And I would love to hear how now that you've done all this segmentation, you now have your support team who's mostly tickets and triage is their job, is now generating revenue for you guys. How did that even start? Where did you even go? Or how did that even happen?
Speaker B: Totally. Um, um, there's, there's two ways of thinking about how they were driving revenue. The, the, the part we were talking about before this call that I think is the most important way this shows up for us is in the percent of revenue that people self select to say I've used Help Scout before or I was recommended by Help Scout. The reason that's happening is because I do think that the product is easy to use, an easy setup. But our customer support is top, top notch. Our customer support team is thorough, kind, funny, helpful, like on top of it and technical when necessary. Um, because of that I think it's a differentiator and I think, and I know in our data that that's what's driving the referrals. Customer support. Being great at customer support.
Speaker A: The human beings is there because of support.
Speaker B: Yeah.
Speaker A: They are now getting more inbound for you essentially. That's what you're saying. Like referrals of brand new customers. Not just growth of the existing customers, but new customers.
Speaker B: New customers. Yeah. It's 30% of our new revenue coming from this.
Speaker A: Wow. From just support being amazing and then how you, you're marketing too. But I was just about to say marketing must love you support.
Speaker B: They do love the support team. Again, like uh, okay, is it like you know, are they writing in to say like Chrissy specifically is the reason I refer like you know I'm making the tie. I'm saying because I think our support is a differentiator. Obviously we, we care deeply about support, it's the product. But because ours is so Excellent. And which shows up in CSAT and NPS and everything else. And people are just telling us, I was referred to Help Scout by a friend or colleague. That referral is happening because I think our support is so great.
Speaker A: I love that. So that's how you directly trace it back is when you, when you like ask them, hey, how did you come across us? Like, oh, we were referred to and they were said that you guys had great support. That's amazing. I love that.
Speaker B: We hear that all the time. Yeah, but.
Speaker A: But that means that you guys aren't using AI for support, which could be another. That could be another thing. Or maybe you are using a bit of AI, but it sounds like you have real humans on the front lines driving real interactions with your customers. That's then resulting in, like you said, 30% of your inbound referrals. But what are you guys doing with. Because that's the other thing that I think is controversial right now is I think all companies are like, let's throw support out. It can be an AI bot agent, whatever. We don't need to have humans answering basic questions. What do you say to something like that? Because clearly your humans are driving sales for you guys.
Speaker B: I would agree that the AI can answer basic questions and ours does. We have a great product for this. It's called AI Answers. We use it. Somebody comes to the site, they have a basic question, like they have a question about our Doc site that you were talking about, like, what is knowledge base? You know, how do I, how do I. How easy is it to deploy Help Scout's knowledge base? We have amazing answers to basic questions that do not require a human being. What that allows though, is for the human being interactions to be awesome, very thorough, very timely, you know, gets the answer right and done faster because they're not worried about the nonsense stuff that you don't need a person for. So I would say that it is because we have AI answers and AI on the easy stuff. It's totally accelerated and amplified good customer support to like exceptional customer support, because that's what their time should be focused on. Because you do.
Speaker A: I love that.
Speaker B: Yeah, we're still, um, we're still not at the point where like every possible. I would call them Tier 2 and Tier 3 questions, which is like maybe very specific account data related to like a custom field or something that AI is just not focused on answering right now. Um, that's where a person really does better and we still continue to invest there. That's very important to us.
Speaker A: Yeah, I love that. And would you say the main differentiator there is, like you said, the more complex answer, like where do you draw the line? Because I think that's where everyone is getting confused of. This is what AI can do for customer support and this is what humans can do. And like you said, because a human stepped in at the right time with the right answers, it's resulted in you guys generating revenue from that interaction. You clearly aren't driving people away. Which I hear that also quite often is like, because customers are so frustrated with how much AI first a company is doing that they're so annoyed that they're like, okay, I'm gonna go somewhere else because there's no human here.
Speaker B: Exactly. I mean it could make or break, you know, your brand. Maybe some brands are big enough where like it doesn't, you know, they're needed and maybe they just don't care to put as much effort into like how a customer is supported. That's just not our philosophy. But the way at that answer to that question is we have AI, uh, answers on helpscout.com right now. And if you go there and you had a question, the first thing you're served with is the, what we call beacon and you can ask your question right there. It looks like Claude, you know, in the bottom right. It's like ask any. Ask me anything.
Speaker A: Yep.
Speaker B: If you are not satisfied with that answer, you are given immediately the option to connect with us. Mhm. Connect with a human. That's what we call no dead ends. Because we're like, sometimes actually the better experience for the customer is to just immediately get their question answered if, if they can. Yeah, but if immediately it's not answered, we immediately want to connect you with somebody who can get that done for you. So it's a self triage situation. Um, and that tends to happen when the question is just more complex where AI answers isn't looking into the soul of the account. The human will have to do that. Um, and then they can work with them on the solution. So that's a big deal.
Speaker A: Yeah, I completely agree by the way. And I think coming back to your earlier point about how AI is doing some parts, but then there's always human intervention or there's something a human's doing that's just going to land better. I just think that right now everyone in tech and SaaS is saying AI first, AI first, AI first, especially in support. And I really feel like it's causing more harm than benefit at the moment. And also it's just, it's Annoying because we're just not at the stage yet. Is AI evolving? Of course. Are, uh, there tons of agents being built? Of course. But can AI replace your support head for like with an agent right now? Can you cut someone in support to then replace with an agent? No, because at the end of the day, you are getting 30% of net new revenue because there's a human interaction happening there. And I will always say it that humans buy and sell from humans. It's just how it's gonna be. I really doubt even 50, 100 years from now someone's gonna wanna buy from a robot or anything because how annoying do we get? Even when we have to wait and talk to, like, the automated voice, uh, like when you call your bank and it's not actually anyone, it's just an automated voice that's been around for decades. And I still get annoyed every single time I have to get a hold of a human. And I just think, again, there has to be human intervention. Because there's almost like working with AI as a co pilot rather than replacement, which I think everyone is just. Yeah, it is 100%. It is a tool. It's a tool.
Speaker B: You know, when Excel came out, they weren't like, replace the accountants, but they made sure that every accountant was using Excel as a tool to accelerate their work. And that is no different here. AI first, there's just. Sure. There's, uh, a caveat to that though, which is until it doesn't work for
Speaker A: you, or until it frustrates someone that they leave or whatever the case is,
Speaker B: it's like, okay, sure. Well, we'll. We agree. Sure. Try to help yourself first because it could just be faster, better, easier for you. The minute you are not happy with that, though, it stops becoming AI first very quickly. It's like, nope, human to the rescue here. So, um, the idea that AI is replacing customer success and customer support people right now, it is not the right picture of what's actually practically happening from an operating standpoint inside of companies. We want it to accelerate their work so that the support gets better. But there's still no way that AI is able to answer every customer support problem right now. And that's just the spectrum of where we're at. And I recently just heard, um, the founder of, um, Thoma Bravo, it's one of very large, uh, venture capital firms, uh, they've invested in some of the largest tech companies on the planet. Orlando. Bravo was, you know, because there was this whole idea about SaaS apocalypse and AI is, you know, just taking over everything and tech companies are in trouble. And he's like, the SaaS apocalypse is over. What we're finding is just that, like it is an accelerator for these companies, but it is not, you know, by no means just like a replacement everywhere, you know, clear, clear across the board. And, and I, I, I, I'm happy that that's being shared more broadly now because like, I'm seeing that as an operator. So yeah, no replacement to definitely like faster, better, you know, more efficient support is the goal, 100%.
Speaker A: And I think, I'm so glad that that narrative is coming out as well as you said, because again, the narrative I'd say at the start of this year was like doom, gloom, AI is coming and taking all of our jobs. But I do think that like you said, it is a tool and it is something that's going to help your teams, whether you're in support, sales, product engineering, whatever is a tool designed to help exchange, accelerate your productivity, your execution, your insert something here. But I think in general what's happening is people are seeing it as like, oh no, it's going to do the work for me. But how many times have you asked whatever AI tool you're using, whether it's Gemini, Claude, ChatGPT, whatever it is, how many times have you asked it? And it was perfect. Like, I would love to see that stat really, because it's never been even the ones, even everyone who trains. It's so much left, right and center. It's still not perfect because it's just a tool and it's only as smart as the humans that put in data into it. And like you said, accountants still exist, even though there's Excel and all these accounting software and everything in between. And again, bank, banks exist with bankers in it. Even though we have automatic machines to give us cash if we want cash, it doesn't matter. Like, there's always going to be tools that help support humans, but it's not going to replace. So I'm, I'm so glad you agree on that point as well. And we talked about so many things today, but I'm really curious to hear one more thing before we go into our quick fires is if you were speaking to like a CS or support leader that takes like one practical thing away from this episode, whether it's segmentation, whether it's revenue from your support team, whether it's like, you know, really being, making sure you're tiering your customers and layering in the AI piece, what do you think would really help change the trajectory of their business in the next quarter or next few quarters. What do you think that they should be focused on?
Speaker B: Uh, two things. First, I think think of the role in terms of outcomes. So like are you, you know, how are you focused on churn, compression, expansion, whatever that thing is, and then how are you using the tool now? Because it's automating questions you don't need answered anymore. How are you getting more efficient at uh, like supporting the impact of that outcome for your company? So just get good at always making sure that you're tied to something that is providing like measurable impact, but using the AI to do more of that work to give you leverage where you're like, I'm a, I'm a like a super CSM now because I am using AI to support the strategic work, not the, you know, like the, the easy answers that AI is solving for me. So you know.
Speaker A: Exactly. To give you the brain space to really level yourself up and be trul. Strategic. A business partner of like someone who can analyze and help customers grow, rather than just someone who answers.
Speaker B: Answers, exactly. Yes. Is I think that's where. I think that's the best benefit of AI at the moment. The second thing is, um, there's uh, an interesting happening at least at Help Scout where. Because the speed at which engineering. I think the biggest team's getting affected by what's going on with AI right now is obviously epd, engineering, product design. They're the ones that are like having the biggest reckoning right now because they're going from like shipping from a month to a week or like a week to a day.
Speaker A: Crazy. I mean, I'm always amazed. I'm like, I'm building things. I never code something and I'm like, what is this? If I was actually someone who did code for a living, what would this accelerate to my brain, you know?
Speaker B: Right. Uh, because of that there's this like role that's emerging called like the forward deployed engineer. And that I think is a very interesting concept for like CSM or like customer support team to think about when your customers have a question that traditionally you'd have to put in a queue or a linear card and wait or.
Speaker A: Yeah, wait till a product design or someone gets back to you. Exactly
Speaker B: what's possible now if you could deploy that for the customer in a day, like how do you start thinking about your role as more of like um, a product manager?
Speaker A: Mhm.
Speaker B: Because building is faster. That could just be one dimension, I think, to CSMs that continue to evolve because we're not waiting. We don't have to wait anymore for like customer impact. So that just may be one other area that I would think the two leverage points for AI as a CSM would be just like, yeah, what strategic initiatives can you use AI for that? Uh, like increase your impact and then how you think about product and how what can get built and deployed for customer impact, like more instantaneously. How do you become more of a partner in that way to the customers? Is, is that. That's the other dimension I love.
Speaker A: That I uh, love. And it's so true. It's so true. There's so much more power and like you just said, we can deploy something or maybe even the CSM can do something as well because it's so it's possible because it's at our fingertips now rather than waiting for like you said. Oh yes, it's on the roadmap for. I still remember saying that like 12:30, like, oh, we've, we've added it to the queue. I've created a ticket. Yeah, we've got to wait until the product manager like, you know, uh, like decides that that's priority and then the engine layers are working on it. We don't have to say those things anymore. You know why? Much more in our power.
Speaker B: You know why? Because there's less risk now. Because building doesn't take months and years.
Speaker A: Years. Years. I would say years.
Speaker B: Like, who cares? Prioritize it right now because who cares? Everything takes a second. And I'm not trivializing it, but like.
Speaker A: Yeah, but it's true though. It's like we don't have to like, of course be mindful of what you're building and uh, prioritizing things. But at the same time the build portion of that does not need to take like a three week sprint to actually get 10 engineers to like, you know, build out this part of the platform.
Speaker B: Right.
Speaker A: It's an engineer and maybe a week and AI.
Speaker B: Uh, absolutely. You have to make sure that like, you know, you know, inside of that obviously there are guardrails for like, you know, making sure that the quality of the product stays, you know, but like, you know, there's no longer. I just think that like, as a csm, I would be like really excited about the opportunity to um, to deliver more value and impact to my customers more immediately. And then you really become like a trusted.
Speaker A: Yeah. And indispensable because, you know, so. And you have that, that authority, that power, that knowledge. Uh, it's like a trifecta of information that a CSM Then becomes because you're able to up level yourself with AI in that way. So I love that. Amazing. Okay, I would love to move us forward to the quick fire questions where I challenge every single one of my guests to answer the next few questions in a sentence or less. Are you ready?
Speaker B: Yes.
Speaker A: Okay, first question for you is if you could predict the future, what do you think customer success or customer support will focus on next year?
Speaker B: The forward deployed engineer mindset. How do you deliver more impact to customers?
Speaker A: Love that. I love that. I always love seeing everyone try to answer these in one sentence or less. They start realizing, whoa, I can't seem to do things in a sentence. It's okay. You're not the first to struggle. The next question is, which app or software do you use every day or every week? And it could be on your phone or laptop. And why Hex?
Speaker B: Because it's an analyst in my pocket.
Speaker A: Love it. Amazing. Okay, next question is, if you could change one thing about customer success or support, what would that be?
Speaker B: Move the accountability for churn to the product team.
Speaker A: Love it. And my final question is, who should be my next podcast guest?
Speaker B: Well, I will give you a very biased answer here, but our VP of customers, Abigail is, she is a wealth of, of knowledge so I, I recommend her.
Speaker A: Amazing. Abigail, I'd love to have you on the show in the future. Thank you so much Andrea for your energy, for all your insights, for everything that you shared with my guest and my uh, listeners today. I would love to continue the conversation but as we wrap up, if any of my listeners have further questions want to continue conversation, what is the best way to get a hold of you?
Speaker B: I'm on LinkedIn so just Andrea Kail, if you find me on there DM me, I will be happy to chat.
Speaker A: Amazing. I will make sure to put Andrea's link of uh, her LinkedIn down in the show notes. Thank you again so much much for coming on the show.
Speaker B: Really appreciate it. Thank you.
Speaker A: Thanks for tuning in to the Customer Success Pro podcast. I hope you picked up something valuable to take back to your team. If you enjoyed this episode, it would mean the world to me if you took just 10 seconds to leave a review on Apple or Spotify. It helps more CS pros like yourself discover the show. And creating new episodes takes a lot of of work. So leaving a nice review keeps me motivated to keep creating. And don't forget to hit subscribe on Apple, Spotify, YouTube or wherever you listen to podcast episodes. I drop a new episode every Wednesday packed with practical tips and if you've got a topic you'd love for me to cover or want to be a guest on my show, send me a message. All the details are in the show notes. I'd love to hear from you.
Speaker B: You.
Speaker A: And hey, if this episode, uh, helped you share it with a fellow CSM or CS leader, remember, sharing is caring. Cheers to your CS journey and I'll catch you next week for our next episode.
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