
How AI is transforming customer success, retention strategies, and feedback analysis—plus why better conversations drive better outcomes.
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Nathan Isaacs
Welcome back to Insights Unlocked. In this episode, I'm joined by Josh Schachter from Gainsight to talk about how AI is transforming customer success from scale and feedback to redefining retention, and why strong relationships and better customer conversations still matter more than ever. We also dig into agencic workflows, common pitfalls, and what top teams are doing differently. Enjoy the show.
Podcast Host / UserTesting Narrator
Welcome to Insights Unlocked, an original podcast from User Testing where we bring you candid conversations and stories with the thinkers, doers and builders behind some of the most successful digital products and experiences in the world, from concept to execution.
Nathan Isaacs
Welcome to the Insights Unlocked podcast. I'm Nathan Isaacs, principal Content marketing manager at UserTesting, and our guest today is Josh Schachter. Josh is the senior Vice president of strategy and go to market development at Gainsight and host of the Unturned podcast where he digs into what's changing in customer success, especially as AI transforms how teams understand and keep customers. Welcome to the show, Josh.
Josh Schachter
Thank you, Nathan. I'm excited to be here.
Nathan Isaacs
Before we dive in, I'd love to start with your background. What drew you into the world of customer success? And can you tell us more about the work you're doing now?
Josh Schachter
I didn't know what customer success was five years ago, Five and a half years ago. People think that that's hyperbole, like, oh, it's just kind of your origin story that you're making up, you know, postmortem, etc. Nope, nope. Had no idea. Never even heard of customer success. Five and a half years ago, I built my career in product management. I've had some other startups and. And then I was in. I was working with Boston Consulting Group with the digital ventures, like an internal incubator for their largest customers in product management and taking companies from 0 to 1. When you're taking companies, you're working for a consulting firm, working with Fortune 100, taking them from zero to one, you don't really know what customer success is because you're more in the innovation incubation stage. And I won't go through, like, the entire journey of my startup that we sold to Gainsight. It's in. In the last summer update AI. But basically we followed the breadcrumb trail and we came across this thing called customer success. And we said, oh, wow, this group, like, this is who we want to serve as our early beachhead. I'm a big fan of Jeffrey Moore Crossing the Chasm, and we saw lots of pain points that I'm happy to discuss and and, and also really tight community. And we said, okay, this is where we want to start.
Nathan Isaacs
Well, I always love it when, you know, startups. And this is going to be. My next question is about the book you're writing. But startup founders start out with this idea of who their audience might be or whatever, and then all of a sudden they discover who their true audience is. Right. And if you can do that, and then all of a sudden everything starts going forward. Right. And all that, as we're talking about what you do and your startup and all that kind of stuff. I understand. And am I right or wrong about this? You are writing a book. Can you tell us more about that?
Josh Schachter
I am writing a book. I wasn't expecting us to go into this. This is like we're early days here, early innings. I'd say maybe we're in like the second to third, bottom of the second inning in writing this book. And it's around a concept I'm calling the. The relational founder. Founders who thrive by building exceptional relationships with all the different constituents that you think of when you think of building a startup, first and foremost yourself. That's actually the one thing that I've learned in this process of talking to other luminary founders is like the importance of the relationship with yourself, with your co founders, with your team, with your community, with your investors, and so on and so forth. And it's about. It's like little vignettes of talking to founders who have been very successful of stories, you know, what they've. They've done to build those relationships. So we're excited about it.
Nathan Isaacs
It's. I, you know, I, I'm not here to give you compliments, but I will say that I'm here to take them. Yeah, you can get it. You know, like, I, I'm not really a. My colleagues will tell you I'm not a BS Er. But what I noticed, I, I saw that post that you had gotten the domain for that, and you're announcing that you're going to be working on that. And I'm just, I was looking at the comments and those comments. That's. I mean, it's kind of proof that you are one of those relational sort of founders where you've developed relationships with other people and it, it shows up in places like that on LinkedIn where people are making true comments and not just click clicking a like button. So, hats off to you for, for doing.
Josh Schachter
I won't take my hat off. Nathan, I'm.
Nathan Isaacs
I know. I'm not asking.
Josh Schachter
You're in My hats on.
Nathan Isaacs
As soon as it was coming out of my mouth, I was like, oh, he's wearing a hat and he may not take it off for me.
Josh Schachter
And my hat's my billboard. This is my unturned billboard. We got to get you a podcast billboard. For your. You know, for, for your.
Nathan Isaacs
I went, I went rogue a number of years ago and just had a T shirt made up and then got in trouble because I, you know, I did it off of like Canva, you know, their T shirt program and they didn't have the brand color and my, my brand manager came down from the top rope on me and said, you know, I gotta do this. I was like, I just wanted one T shirt for a conference or whatever. So.
Josh Schachter
Yeah, no, but listen, thank you for the compliment. It's uncomfortable for us to take compliments, right, to listen to those out loud. But, but I'll take it because it's something I'm actually pretty passionate about is building relationships. And you could argue that that was kind of my super strength in Update AI, there was lots of noise, or there still is lots of noise. Can you imagine in the note taking space, we consider ourselves conversational intelligence, you know, fancy version of note taking. Actually, I just found out this morning that Granola raised, I think $125 million Series C at a $1.5 billion valuation from Sequoia or Kleiner Perkins rather. But like building the relationships and being in the community with that presence, with that LinkedIn stuff and everything was, it's not moat, it's not defensible, but that was our way to rise above. And it's something that I actually took from my experience, my five years at bcg, because I observed all the managing directors and how they were able to orchestrate those deals and getting close to their buyers, the executives of these large companies. And it was all through relationship building. And so I said, okay, that's how we're going to cut through the noise here. So thank you for that compliment.
Nathan Isaacs
But I mean, it's one thing to have that as your, your strategy, your tactic or your plan or just who you are in your DNA. It's another thing to execute on it. Right? And I, I can tell you from a person who does a poor job of that, it's, it's, it's hard work and, and you can get caught up in the moment and there's always, we all have 50 hours of work that we're doing in a 40 hour week and, and you have to make time to, to have those sort of relationships. So hat tip.
Josh Schachter
Anyway, thank you. Thank you. You have to make time. You have to be very intentional. It has to come from a place of like your actual energy. Right. If you're not into it, you're not into it. For me, I was a product manager my entire career up until the point that I went to BCG, I became a GM, I had my own startup but like for 15 years I was a product manager. But guess what? I was never like naturally inclined to be so technical, to sit down and to do like the qaing and like the acceptance criteria and like my mind just never really worked that way. And so I've realized, call it later in my career that this is where my energy is. And when you have the energy that you know, when you're focused on that area, it makes all the difference. The other thing I'll say is that I was always petrified of any kind of public speaking. So the fact that I'm out here speaking these full sentences right now is a miracle. I mean there's. I posted about this on LinkedIn a few months ago. You can see in the background here, for those watching, I have an Emmy award. It's yes, it's real, but funny story behind that. I've never worked a day in television or anything like that, but I worked at the NFL. We won the award. Long story short, I was too afraid to go up on stage to accept the award from Michael Strahan and Joe Buck at Lincoln center because I had too much stage fright. So I've always just been petrified of anything to do with public speaking. And a large part of obviously like building the relationships and the LinkedIn and everything is getting your personal brand out there and becoming more and more comfortable with that part of that role. I guess the lesson is, you know, growth mindset, you can build these muscles if you just kind of practice makes
Nathan Isaacs
perfect type of thing and stay true to who you are. Right. If you are just adopting some other influencers strategy, it's not going to be authentic to you. You're not going to be able to go out there and do it. And this is not, we will transition here into customer success.
Josh Schachter
Sorry, I'm sorry.
Nathan Isaacs
No, but I think it's all this is true of companies and true of, you know, making your customers happy if you have a relationship with them and it's an authentic relationship. And, and so, you know, and that gets into my question like you know, from your, your time as a startup, your time last year over at Gainsight, what are the best Customer success teams doing today that others are not, especially when it comes to understanding and acting on customer feedback.
Josh Schachter
Every customer success program is kind of different. That's what we've all learned about customer success. It's a little different than sales where you've got these set playbooks, you know, medpic or Bant or whatever that just kind of apply for any organization you're in. So that's really the, the interesting thing about cs. It's also the really difficult thing about customer success. What are the best teams doing to listen to their customers? Well, the way that we think about customer success, I'll give you a little bit of like the corporate.
Nathan Isaacs
Yeah, absolutely.
Josh Schachter
The way that we. First of all, we think that customer success, there's this, this movement of from SaaS to RAS. Now what is RAS software as a service? You know, companies are selling like user testing, like gainsight, selling software as a service. But at least in the customer success space, there's this movement to retention as a service. Everything that we do as a customer success post sales organization, it will be incredibly outcome driven to really make sure that we're driving people's successful retention. And the way that we think about the CS model is really three different segments. You've got your higher touch, your more strategic enterprise accounts that are, are much more human led. You've got kind of the, the ones that are. Well, you got the ones at the long tail, which is where you're seeing all kinds of benefits of agentic and autonomous types of motions. And then somewhere in the middle is maybe pooled accounts and those things and that's where you're, you're using like the, the digital types of, of touch points, community and education. User testing is using those types of motions, I know, to kind of, to be able to interact with those groups as well. And yeah, and so through each of those different. It kind of depends on the segment, right? Like through each different segment you can, you can get the voice of the customer in different ways. I think a really cool use case right now we have this ATLAS agent, you know, Agentic basically renewals. And I don't know that we're actually doing it. So this is me like kind of riffing and opining right now. But, but one thing that I, I think they may be doing it, I'm really looking forward to is so, so ATLAS is a way to autonomously have email exchanges and phone call exchanges with your customers at the long tail as they come up for renewal. Whereas before you just didn't have capacity to manage it. At all. And you thought things would just kind of auto renewal. Now you're able to have the bots and agents, you know, help you manage that end to end. And what I think is the coolest thing is in part of that we're doing that, you can start to collect feedback from the customers that you're calling. Oh, tell me, you know, like, how are we doing? If you had a magic wand, what would you be doing better? What is your likelihood of renewing? And now you can start to collect your recording all these right through the agent experience, you can start to collect those recordings at scale and synthesize and see the trends of the voice of the customer in the long tail. That relates to my old startup of what we were doing at Update AI with conversational intelligence. So that's why it's an interest to me. But like to me that right there is super cool because I think it's been very tough for companies to understand in the past Long tail customer sentiment.
Nathan Isaacs
And it's a gold mine, right? All this data about the relationships you've had with your customer during the time that they are a customer or when they're not a customer and they've come back and all this and using AI in all of its different formats, it can be that, that way of doing it. Right. I know that, yeah, we've had programs where you're like, let's have a 90 day check in with our customer, let's have a six month check in. I mean this is that idea. Right? But at, at a, you don't have to, you don't have to do.
Josh Schachter
Yeah, yeah. And so, so in the higher touch models where you've got customers that, you know, have a higher, higher, higher ACV ARR, the best teams are, they're conducting more value, value conversations with their customers. AI has allowed folks to more easily generate value narratives. You know, call them QBR, EBRs, but just decks that are able to really, to show, you know, here's what your goals were when we started to onboard you, here's how those have evolved. We've got all the phone call recordings and all the different information that we synthesized from all the data sources to know what those goals are. And here's, you know, the value that we've driven to you today. And so when you think about the skills that a lot of CS leaders are looking to bring on in their CSMs, it's those CSMs that are able to articulate that value creation, that value narrative. And it's something that we're doing at Gainsight. One of the, it's mildly different, but one of the initiatives that I am sponsoring that we've recently launched is identifying our instance reviews. So when you think about, you know, a platform that has lots of capabilities like keensight over years, it's possible that there's like this instance drift, right? Like things, you know, you've had lots of configurations. And, and, and so we're now identifying the ability for a CSM to go back to their account leaders or their accounts and say, here's a look at your account, here's how it's configured, here's the scope that you have entitlements to, here's what you're using, here's what you're not using, here's the value you're deriving, here's where you could be generating more value. That entire presentation, soup to nuts, is based on uploading, you know, exporting and uploading a configuration file or usage file and just pressing go and getting that spit out to you. And then it's the matter of the CSM being able to orient that in front of the customer.
Nathan Isaacs
You've talked about the process of building out that workflow here recently on LinkedIn and a couple posts on your newsletter, Unturned newsletter for the rest of the tech world were all being challenged to think about building agentic workflows or at least mapping these things out. And one of the things that I think you mentioned was like you had an idea and then there was a reality like what we learned along the way. What advice do you have for other teams as they start doing this? As they, whether they're in product or marketing or wherever it may be in the organization, as they start thinking about building out their agenc workflows. Oof.
Josh Schachter
Okay, so there's so many different angles that we can go with here. We could talk about build versus buy if you want. I personally am an advocate of build and then ultimately figure out what you need to buy. I think if like even within customer success, I talk to lots of leaders who have folks that are building different modules and whatnot and you could say, oh, do you feel threatened by that? That they're trying to, you know, anthropic and all this, they're trying to take, take it out, take, take out these platforms, CSPs. No, these, like I want these companies to be building those modular superpowers. Some of them will be off to the races and they'll continue to maintain on their own and iterate and improve on forever. But for the Most part there's going to be a certain point in which they're going to realize that they don't want to become the maintainers and iterators of this software. And so they're going to come back to us or to any SaaS company that's out there listening and they're going to be more educated and informed buyers of our software. So I love to encourage people to go build and to learn by doing as. As we've gone about that. So in the instance review project that I spoke about, you know, a couple things we had had the help. Unbeknownst to us, when we first started the team I was working with, there had been another group at Gainsight that had been doing some heavy lifting of kind of clearing the way with, with access to data. So that basically to give us the foundation of what we needed for this thing. So make sure you've got the right data folks involved. Right. Make sure you're at that IT level, you know, working with that team because that'll be the biggest hurdle and that's kind of an obvious thing. Data hygiene is also something that you hear of all the time. Right. So you have to have like, right data in to set the foundation. You've got to also create a blueprint for the workflow that you're trying to AI ify or identify. If, if you don't have that, that service design. Right. That blueprint in place, you're not really going to know like what you're trying to, to improve or disrupt through identification or where you're going. So we also encourage that.
Nathan Isaacs
Yeah. And I think doing something like that you'll find out maybe you don't need to create an agenic workflow that you can just do just a good old fashioned automation. You know, it's like actually writing down the process of what needs to happen, you know, and the different steps and all that kind of stuff.
Josh Schachter
That's also where the voice of customer can come in too because you know, you, we just used to do this at BCG a lot like a lot of design thinking and service blueprint designs. And so you'd lay out the workflows and the customer journey and then you talk to customers and you would map out the highs and the lows of where people feel in pain and where are they feeling good, you know, red dots, green dots and then from there that's what you try to solve for or amplify in the case of things. So just to go back to what you guys do and to your ethos like that's where you overlay the voice of the customer onto those service designs and then you can, you know, figure out which part of it you want to build. The next thing I'll say is. Find the right folks within the organization outside the IT guys that, you know, can really kind of help clear the way. Find the right, find the right folks to. To work on as. As the. The kind of the ground troops of this. To create that groundswell engagement that ultimately you hope becomes contagious and spreads within the organization. And it's not necessarily who you think it might be that are those folks. It doesn't have to be the most technical person in the room. It's generally the people that have the most natural curiosity to learn that are excited by this whole AI thing as opposed to of course the folks that are a little bit more eerie of it. And so give those folks the bully pulpit, the stage, let them shine, showcase their work, try to clear their calendars as well. So we had one guy in our ops team and our rev ops team and I said to him I was able basically to clear. He doesn't report into me, but I said, you know, Stephen, can we, can we get your entire next week blocked out? And so with that you, you know, 90 of what you do is just vibing and just learning to, you know, on. And he did it and he came back midweek and he's like wow, like I've completely crushed my entire work plan for the week and it's. And I still have half the week left and somehow I can get farther ahead schedule. But it was because he was given that ability to be heads down and to get into kind of the flow state with. With what he was doing.
Nathan Isaacs
Hmm. With. I think you had a. A recent episode. I hope this is a case I'm remembering correctly where and. And we're going to still talking about AI but on the other side of the coin where you have so many AI sort of businesses and they. They talk about all their o. We got so much ARR. But the customers are turning after their three month sign up and, and I think you guys called it the, the. What do you call it? The apocalypse or retention apocalypse.
Josh Schachter
Yeah.
Nathan Isaacs
What. What you know, in. In that sort of world where, where that's a real thing, you know, what should customer teams be thinking about or doing or managing with the data to make sure that they can help move through all that and succeed?
Josh Schachter
Yeah, there's a lot of companies out there that are experimenting with their AI enablement. I mean even at Gainsay today we, we're subscribed to multiple LLMs and we're, and we're starting to consolidate is the, is the point. And I think a lot of companies were like that. They're like, they're, I mean, shiny object syndrome. It's all so, it's all been so exciting of what you can do with AI, but now we're starting to get a little bit of like, category confusion, of like, okay, what's the difference between all these different tools? You know, like, there's slight nuance but not step function differences. And so I think we are in a world here where there is going to be more. I don't know if consolidation is the right word, but you're going to be choosing one. I guess it's consolidation. You're going to be choosing one out of all the different tools that you've been experimenting with for each of the different areas. And there's actually a VC who I admire very much. His name is Brett Queener. He's a managing director at Bonfire Ventures and his thesis. And a little bit of our CEO Chuck Kanapati. Actually. They worked together at Salesforce. So it makes sense that they both come from this, this background of product marketing, which I know is your background as well. But, but Brett's thesis is that, you know, a really important driver of retention and sales in this age is your product marketing. Because when all the products feel kind of similar and people have been experimenting and testing stuff out for three to six months, but now they're going to, you know, cancel some subscriptions, it is, can you get the message of your value prop across effectively. And then of course it's the relationships. And then of course it's also the, you know, efficacy of the product as well.
Nathan Isaacs
Right. You've, you've have these relationships, you've, you know, 180 plus or so episodes of unturned. What are the, you know, what's the one belief or what are the, the handful of like, big ideas that all these guests have shared with you that kind of, there's some common ideas there. And, and what, what can you share with us? Like what, what have you learned after 180 episodes?
Josh Schachter
I mean, CS leaders, they all have different, slightly different playbooks and operating systems, but they all think the same. They're all trying to figure out AI, everybody in customer success, and I think across the board feels like they're behind. The truth is that not many are, only the people that are, you know, kind of really shying away from it. But the people who actually, you know, it's one of those things like only the paranoid survive. So the people that are paranoid enough that they're behind probably aren't so far behind. We're all kind of in it together. The folks that have been very successful again are the ones that have been able to identify talent in their organization and assign them to roles where they're really focused on building out AI as a dedicated function. So I'm a big believer in that right now. The folks that have been successful have also, they've led by example themselves. At the leadership level, they're in a gainsay, I don't know. Top three, maybe AI users and most knowledgeable people at the company is our CEO Chuck Kanapati. He writes emails to the company after the weekend of the different apps that he's vibe coded and the latest and greatest with Claude and cowork and code and all these different things. And you need leader. And then at the functional level as well, we try to lead by example and you need that in order to, to encourage the rest of the team. And then like I said before, for the folks that are kind of at the IC level on their way up, when you see those, those pockets of talent that are really do, you know, showcase their work and let them share it with others. We have a guy at Gainsight. His name is Brady Bloom and he's a product manager. He used to be a csm. He also incidentally was Billy from apartment Something in a Dumb and Dumber movie. He was the, he was the blind boy whose, whose parakeets head gets chopped off. But I digress. He's.
Nathan Isaacs
I am not promising that in the show notes. That's all I gotta say.
Josh Schachter
Not, not in the show notes. No, no. But he's become like just this impassioned Claude user and, and we had our RKO a couple weeks ago and we spent like two to three hours with him on stage. Again helps that he's a child actor, but with him on stage just preaching to the entire organization and showing us everybody whiffed out their laptops and showing us how to use these skills that he had set up for us in Claude and he had made at the organizational level so we could all benefit from them. So you know, finding that person in your organization is super important. So yeah, AI, AI, AI. I think like I mentioned before, SAS to ras, the, the, the customer success world is starting to understand that, you know, it's become outcome based and a lot of leaders are seeing their teams as value architects, that their goal is to really make sure that, you know, if, if AI can do the note taking and all that kind of stuff, then it becomes the roll up in CSM in these conversations with customers to get the best stuff out of the conversation to feed the AI. Because the AI can only do the synthesis on the information it has. So it's dependent on CSMs and these professionals to really know how to run those conversations in a very kind of value value framework. And then there's a question of, you know, will CSMs be generalists or, or specialists? And there's different schools of thought on that as well. I, I, that was a little winding. I don't know if I answered your question directly.
Nathan Isaacs
Absolutely, absolutely. It's also interesting as. You know, many years ago I used to be a newspaper reporter, crime reporter, and it seems like every episode I'm bringing this up and the thing is like it was a certain skill set you had to do to do that that really carries over into all this other stuff I've been doing ever since. And you're getting into the AI is only good as you can give the data, you can give it. So don't ask yes and no questions, ask open ended questions. Right. Dig deeper, ask follow up questions. That popped in my head as you were talking about getting your CS team to really deepen that relationship with, with customers.
Josh Schachter
Yeah, yeah, I am.
Nathan Isaacs
It's not just that, you know, we can say, oh, the, our retention levels not hitting our desired target and it's the CS's CS team's fault, but it's not right. It's, it's everyone, everyone's on this boat together and we're all kind of like, have some responsibility. What's your advice for all those others? The, you know, the, the people who listen to this podcast? Designers, product leaders, UX researchers, what can they do to directly impact customer retention?
Josh Schachter
What can they do? Well, sell products where the customer is a good fit for the product, not oversell. That's the foundation of it.
Nathan Isaacs
Solve a real problem.
Josh Schachter
Solve a real problem. You know, there needs to be a, a connective tissue between customer success, their relationship with the customer, their ability to get feedback from the customer, to get feature requests from the customer, and then closing the loop on those feature requests. You know, the relationship of the cus of CSM back to product, back to design, to prioritize based on what they're hearing and then once those things are improved and are released, making sure that's communicated back to the customer, particularly those that have asked for that improvement in the first Place that's an area where I see that's often dropped for good reason. It's a tough loop to close, but to the extent that your CS can stay really tethered to the product team, I think that that's always a good thing.
Nathan Isaacs
I think then, you know, and especially in our. I can fake a lot of things, but I can't fake being an engineer. But in this world where you can use Claude code or something like that to spin out a fix. Right. You know, your customers aren't, they're asking for the big things, but they're also asking for little things. And the little things may not have been valuable enough to spend resource time doing in the past. Right. But now you can knock it out. You could, you could get that knocked out in a sprint and then be able to kick it back and have that communication back with the CS team that they can share like, hey, we're working on this big thing that's going to happen. But we also heard you and, and where we knocked out this, you know, we changed the color of a button or something like that. Right. And able to do this. And so me as a customer, right. I think of all the technology platforms that I, you know, Nathan Isaacs is a marketer, you know, the recording platform we're using and stuff like that, when I hear and I see those little things, I'm, I feel like they're appreciating what my problems are on a day to day basis.
Josh Schachter
Yeah, they're listening to you. We, we, we just did a, a pilot with notion for their note taker and we, we had feedback, I had feedback for them specifically about some button that you press and oh, if that button had a drop down to give you. And then I look two weeks later and lo and behold, the button now reflects the request that I made. Now they didn't close the loop and tell me that, but nonetheless they listened to it and so that was, that was cool.
Nathan Isaacs
Yeah. And I think that's also a key lesson there is closing the loop. Right. You, you know, making sure give the, the team a little snapshot and you don't even have to write this. You can just have chat write it for you.
Josh Schachter
Yeah.
Nathan Isaacs
And, and say hey and pass it along to your team. So Josh, I really appreciated your time today. How can people learn more about you, your thought leadership and what you and the team are doing over there at Gainsight.
Josh Schachter
Yeah, I appreciate it. We're doing some cool stuff. If anybody wants to learn about Atlas, our, our agentic system, you're welcome to actually DM me on LinkedIn. I'm active way too much on LinkedIn, so if you message me I will see your message. Love to follow and connect with each other. And then yeah, listen to Unchurned. We've become pretty much the preeminent post sales podcast. And we have our substack now too@ Unchurned.Gainsight.com and there's some cool articles there. It's meant to be more behind the scenes. No corporate stuff. It's meant to be really valuable behind the scenes type of thought leadership that we produce. So we'd love to have folks following along.
Nathan Isaacs
Yeah, just a quick testimonial and researching Josh, and doing all that, I engaged with this content and I found it valuable. It's not a space I play in at all. And I was like, oh, there. I learned something there. All right, so I recommend that links to all that will be in the show notes. Go ahead and tell the team, like I'll go ahead and buy Atlas for user testing. Just tell them Nathan said it's okay. All right, done.
Josh Schachter
Done.
Nathan Isaacs
See how that goes.
Josh Schachter
Signed, sealed and delivered.
Nathan Isaacs
Yeah, I'll be looking for a new job next week. Josh, again, I really appreciate your time today. Thank you so much.
Josh Schachter
Thanks, Nathan.
Podcast Host / UserTesting Narrator
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Episode Title: From SaaS to Retention as a Service: How AI is Changing Customer Success
Date: May 11, 2026
Host: Nathan Isaacs (Principal Content Marketing Manager, UserTesting)
Guest: Josh Schachter (SVP of Strategy & Go-To-Market at Gainsight, Host of Unchurned Podcast)
This episode explores how AI is rapidly transforming the practice of customer success—from scaling interactions and capturing feedback to defining new models like "retention as a service" (RAS). Nathan Isaacs and guest Josh Schachter unpack what leading teams are doing to drive outcomes and loyalty, why relationships (not just technology) matter more than ever, and how companies can avoid common pitfalls as they build agentic workflows. The conversation dives deep into customer feedback, AI-powered workflows, actionable advice, and key lessons from dozens of customer success leaders and innovators.
[01:14]
Nathan introduces Josh Schachter, who shares his unexpected journey into customer success, having started in product management and working with startups and at Boston Consulting Group before finding his calling through his own company, Update AI.
[03:16]
Josh discusses his upcoming book, "The Relational Founder," which focuses on founders who excel through relationship-building—with themselves, teams, co-founders, investors, and communities.
Key Points:
Notable Quote:
"It's uncomfortable for us to take compliments, right, to listen to those out loud. But, but I'll take it because it's something I'm actually pretty passionate about is building relationships." (Josh, [05:36])
[09:37]
Josh explains that while every customer success (CS) program is unique, leading teams share common tactics—especially in leveraging AI and listening to the voice of the customer.
[10:11]
CS programs are segmented by customer profile:
AI Use Case:
"ATLAS is a way to autonomously have email and phone exchanges with your customers at the long tail as they come up for renewal....Now you're able to have the bots and agents help you manage that end to end." (Josh, [12:05])
Synthesizing Feedback at Scale:
Automated feedback collection from every long-tail interaction, allowing teams to detect sentiment and trends previously impossible to capture.
[13:34]
In high-touch segments, AI helps teams generate value narratives and QBR/EBR decks—demonstrating how goals have evolved, mapping value delivered, and identifying where customers are underutilizing entitlements.
[15:39]
Key Steps:
Memorable Moment:
"You've got to create a blueprint for the workflow that you're trying to AI-ify or identify. If you don't have that service design... you're not really going to know what you're trying to improve." (Josh, [17:41])
[19:13]
Overlay voice of the customer on service design maps to prioritize automations
Find champions in the organization—not always the most technical, but the most curious and motivated—and give them the space to innovate
Notable Story:
Josh recounts how clearing one ops team member’s calendar enabled rapid, transformative progress in building out CS automation ([20:23]).
[22:07]
Discussion of high churn rates among AI SaaS tools and how companies are managing through consolidation and product-market fit challenges.
[24:34]
[27:13]
[29:53]
Don’t oversell; prioritize product-customer fit from the beginning
Create tight feedback loops between CS, product, and design: capture requests, close the feedback loop when improvements are made, and communicate those changes directly to customers
Small wins matter:
In the AI era, small fixes requested by customers are easier to deliver—these quick wins boost perceived value and foster loyalty.
Notable Anecdote:
Josh shares the example of giving Notion feedback and seeing it implemented—illustrates the impact of quick action on customer delight ([32:17])
[33:16]
For more:
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