AI Fluency in CS: How to Build a Team That Actually Adopts AI with Cassie Vaughn

Anika Zubair: Today I am joined by someone whose career is proof that customer success is one of the most powerful launchpads in SaaS and if you treat it like a true revenue function, your role will grow. Kassy Vaughn has spent six years at Monday.com starting as an enterprise CSM and working her way up to Regional VP of Customer Success in North America and Latin America. And before that she spent time at LinkedIn and App Annie, building her CS foundations from the ground up. And today Kassy is Head of Growth Strategy at Clay, one of the fastest growing go to market platforms in the market. She is also an expert at Primary Venture Partners and advising founders and investment teams on um, what great customer led growth actually look like. And we are talking about a topic that I feel very strongly about which is AI fluency within your team in customer success. So not just whether your team is actually using AI, but whether they are actually adopting it in a way that drives results. Kassy has seen this from both sides, leading large CS organizations and now sitting inside of one of the most AI native companies in the space. This is going to be a conversation to take notes on, so let's get into it. Hello everyone, I'm 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 destiny nation, 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 um, Cassey to the podcast. I'm super excited, honored, like ready to have this conversation with you today. I feel like you've made this big career move and it's so Exciting. And I just. I want to dive more into that. But before we kind of get into the topic, please can you tell my listeners just a little bit more about yourself, how you find yourself at Clay right now, what your role is, kind of what your career trajectory has been up until now.

Cassie Vaughn: Yeah, sure. And you're catching me at such a crazy point, first of all. So happy to be here. Thanks for having me. But, um, I'm day four at Clay right now, and I took no time in between. So last Friday, I was still a Monday.com employee. So there's a lot of, um, identity crisis happening in my brain at the moment and needing to shift and unlearn and relearn. So I'm very much in the middle of a unique time of my career path. But, um, I left Monday leading the customer success function for the Americas. So I had. Most of my team was based in North America, and then I also had a team based out of Brazil with a presence that we just opened in Mexico City. And, um, I was there for six years. So it was an amazing journey. I had the best time. It was really like, I. I caught Monday also at the perfect moment where they were right at the. The crux of hitting their hypergrowth a year before they IPO'd, and then the rocket ship just continued after that. This week, actually, the week after I left Monday, they just launched their new AI agents. So it's also a hugely pivotal time for Monday. Um, and I left the team knowing that I was leaving them at another influx point. So it was good for them to get a fresh start with new leadership, new perspective. But, uh, I will always love that team, and I will always miss them. And that growth that I had at Monday, I went from being a CSM to then managing a team, ultimately leading, um, a segment which was enterprise to start, and then ended up leading the entire region. So the growth that I had there, I'm forever grateful for. And it was, uh, an amazing journey, like I've said a million times now, but it's really the people and the product that made it for me.

Anika Zubair: Yeah. And Monday's. It's a great product. I'm like a great team as well. And I love your career trajectory. Truly love it. You started, like you said, CSM at a point at a company where I'm pretty sure Monday was mostly known, but I'm sure even six years ago, it was still, you know, breaking into the market. People were trying to understand what a Monday tool did. Great claiming, by the way, Monday. But, um, aside from that you had great trajectory into, ah, SVP of a region of the whole, of the whole sector of customer success, which I know a lot of people listening are amazed by, want to aspire to. But now you've moved into this new title, which again, from when we last talked even till now, it's been such a quick turnaround. And I would love to know, but I'm sure my listeners would also love to know, what is your position at Clay? Kind of, what are you building? What's the team company like so far? I know it's day four. What are you kind of being held accountable to? Tell us a little bit more about what's happening at Clay.

Cassie Vaughn: Yeah, happy to share. So Clay is, interestingly enough, at the size that Monday was when I joined Monday, both from like a people and a revenue perspective, and also about to grow at probably an even bigger clip. Um, but I first spoke to Clay a few months ago. I was doing some research and then I had reached out to this woman named Jess Bergson, who I think she reached out to me first, actually. And we were planning coffee. We kept missing each other, but it stayed in my head for a long time. And then I started listening to Clay podcasts about Clay, following their founders, looking into, like, more details about the company. And then ultimately I reached back out to Jess a few months later and I was like, hey, I just want to chat. Like, as CS leaders understand how Clay is doing this thing and you know that you have this, this concept of growth strategist, which is a different title for customer success than I've traditionally heard. So I came to the Clay office, we had a coffee. It was meant to be like a peer to peer conversation, or like a conversation that was like me learning from someone who's doing something differently in the space. Um, and from there she was like, actually, what if you just joined? So we started the process and everything moved very quickly. But the thing that really intrigued me about Clay, other than the product and the way that they're really a category defining product and creating this role of a go to market engineer and then also creating the value for that role. Um, the thing that really intrigued me was this growth strategist function. So the customer success function at Clay is called growth strategy. And they, um, really own everything end to end for the customer journey. So they take everything post sales, meaning from onboarding through adoption and then renewal and expansion, and they truly own the expansion motion. It's not a, you know, tee up the expansion M and hand it over to the accountant. It is they are driving the commercial deal as well. Um, and I have a sales background as well, and it's something that I missed from my CS role at Monday. So that was really what deeply intrigued me about this team. And the team and the culture and the energy is just so good. Like, the way that I can describe it is hungry. People love working here. They throw everything at the job. They're coming up with creative ideas, they're solving every customer problem they can. They never want to say no to a customer. And that kind of energy and passion and it's hard to. It's hard to resist wanting to pursue it.

Anika Zubair: Yeah, very much. It's like, it's so much like, oh, yes, I want to be part of that energy. I want to. I want to catapult to the next level with them, which, again, Clay is doing such amazing things. I think it's so early in its growth, but also you look at their

Cassie Vaughn: growth and you're like, wow, how are

Anika Zubair: they doing all of this? It's, it's amazing to see. And I love the title growth strategist. I love that your team is accountable to everything because, uh, truly I think that's where customer success did come from. But I think over the last decade it's kind of split in different directions. Whether it was like, looking after, like you said, onboarding, implementation, whether it was talking about a renewal, but then handing it off to an ae. I feel like a lot of companies have like really evolved customer success out of what the true function has been, which is end, um, to end customer growth, management accountability, whatever you want to call it, but it from end to end. And I love that you, you know, also have a sales background and you want to tie that back in. But I do love that you've really double, double down in like, revenue within customer success, growth within customer success. I do think that's like a pivotal moment we're having in 2026 in CS in general. And I'm. I love that you come from sales, but what inspired you then to move away from sales into customer success? I love hearing how people break into customer success.

Cassie Vaughn: Yeah, it was a bit of a ping pong, actually. I moved into customer success first, then did a little stint in sales, then move back into CS. But, um, I joined CS for the first time at LinkedIn. At the time, I was part of LinkedIn's talent acquisition team. And LinkedIn, their bread and butter product, still is a talent acquisition product. So I was using the tool that we were also selling every day, which meant that I could empathize with, um, the buyers on the other side. So ultimately I wanted to work closer with the buyers and my team was the programs for the talent acquisition team. So we would own things like the TalentConnect conference. And I went to the Talent Connect conference for the first time, met a bunch of these customers, and I was like, I want to give. That's the relationship that I want. Like, I want to connect them more to LinkedIn and the company and the mission and the product. So ultimately I decided to move jobs. And then I also moved from San Francisco to New York when I did this. And then while I was in customer success, I was like, you know, there really isn't a reason why I shouldn't be owning the entire relationship and also helping them drive growth and think about new strategies for their team. So that's why I moved into sales. Um, but what I missed from the sales aspect was just like the altruistic nature of the relationship. Like, it was much more focused on the revenue as it has to be, and that's the sales work and not necessarily anchored to the value, at least at that time. LinkedIn has done a much better job now in doing more consultative sales. Um, but I wanted to anchor back to the value for the customer. And I think that's why now we will see so many CS roles merge into these growth strategy or more account management roles. Again, because as we enter AI and as consumption becomes one of the more leading, um, pricing models, value is expansion. So the more that you're driving value and the more that you're driving adoption of a product, there's natural expansion that comes from that. So it's really cool actually to see that customers don't have to. It's not as transactional of a relationship where they have to think like on a skew basis, like per se equals this amount of money. It's. If I am using it this much, it's probably because there's something that's working for me here. If I want to explore using it more, it's probably because I think there's more value I can extract from the product and it's more organic the way that these products are growing. So CSS positioned itself uniquely in the place where they drive value. And therefore now in the future, they will also drive revenue 100%.

Anika Zubair: And I love that you just said it's like we are connecting the dots there. It's not inherently obvious. Like, yes, using the product more. Yes. Tapping into different use cases. Very natural for customers that are really loving and using a product. But it is part of our role to connect the dots and really show that value piece. Because again, when you show that value, you're then able to grow revenue, whatever it's by seeds, consumption, AI tokens, you name it. The pricing change that's happening in SaaS right now, it's going to be interesting to see in a few months and a year too. Um, but you've had some great experience, Cassie. I'm just thinking like, wow, what a powerhouse leader you are. Like LinkedIn sales, Monday.com all the way to SVP and now at Clay. And that's just, that's amazing. I love your career journey and I think that right now a lot of CS leaders are also having this moment, um, where they're really thinking, what's next in my cs? Because, like, there's so much happening right now. There's like AI saying AI LED layoffs. Right? And then there's also even the, I guess maybe identity crisis that's happening right now with am I a revenue leader, Am I a CS support leader? And I think a lot of people are questioning what's next in their career journey. But I'm curious, I know you've just stepped into a new role kind of what is next for you? Like, what is your CS career dream or ambition or what are you thinking about next as well?

Cassie Vaughn: It's a good question. Um, I think I want to really expand on this, um, ownership end to end of the customer journey. And what I'm most excited about is redefining the customer journey. So Clay has done an amazing job growing this team and the wins that they've had and the way that they're achieving their results and hitting stretch target and hitting extra stretch targets. It's an amazing group already and there's a lot of drive there. Um, but it's running like, uh, the second level, um, evolution of a startup. That's what it is. And what is missing is some of that storyline. So what is the actual customer journey that wants to be followed or should be followed to drive the value that I keep talking about? And I'm really excited to reimagine that. Like the traditional customer journey I think has been, let's call it 80% similar in most CS functions. And now we can rethink what that should look like. And where you insert, insert things like services or where you insert touch points for use, case development and expansion in a different way. Like the flywheel notion is probably still very much alive, but it's really rethinking how Customers want to engage, especially with AI tools. So, um, for me, the AI, it's redefining that and then also leaning into the AI knowledge side of things. A lot of customers that I worked with both at Monday and I haven't spoken to any customers yet at Clay because I'm on day four. Um, but I imagine the conversation won't be too different. They're excited about AI, they're nervous about AI, but most of them feel that they need to be farther than they are on their AI journey and they're looking for anyone to help provide some of that guidance to them, even if it's on just one small part of their workflow or one small part of what they do on the day to day. It's really about how do you create a relationship that's centered on learning together and driving confidence and helping navigate the unknown. And, and I think that's where the confidence that a CSM or a growth strategist has in the AI field in general and what's happening in the broader ecosystem, other companies and other tools and other ways of doing work, they can bring, uh, a certain level of consultation to the customer relationship that never existed before and help them navigate this really uncertain time. Even just as like a thought partner, as someone who is like, I don't know where the end goal is, I don't know what this journey looks like personally, but I'm navigating it with you and here's what I'm learning and we can share some of these learning on the day to day and this can be a safe space for us to bounce ideas back and forth, for us to experiment, for us to try new things, dip our toe in the water with agents and figuring out how we bring better productivity to your team. That's the kind of relationship that I think is so sought after by our customers right now. And I'm really excited to see how that evolves and how we can bring that to life as customer success leaders.

Anika Zubair: So just a quick pause from the podcast. Here's the thing about AI in customer success success. Right now, everyone's talking about it, leadership is asking about it. But most teams are stuck in this awkward middle ground right now and a few people are experimenting with ChatGPT or Claude on their own. And maybe someone has built a prompt for summarizing call notes or building a dashboard with more customer insights with Claude Cowork. But there's no real strategy behind AI right now. And meanwhile your team is still buried in the manual day to day work. They're Spending hours prepping for calls, writing follow up emails, putting together QBRs, or even connecting all the tools together with an AI piece, that all of this should actually be doing more work for them. And they know that they should be doing more high value work. Every CS team knows this. But unfortunately the day to day keeps swallowing customer success professionals whole. Now imagine your team actually has the space and time to do the strategic work that actually moves the needle.

Cassie Vaughn: They're not drowning an admin.

Anika Zubair: They're walking into every customer conversation prepared, proactive and focused on outcomes. Not because you hired more people, but because your existing team is finally operating at a level that the business needs them to be with AI. Now that is exactly why we have workshops at the Customer Success Pro. And the one workshop that I think would really help your team, if you really are feeling the pinching point of doing more, is we have a workshop of, uh, delivering high value customer experience at scale. And we built this workshop to basically work through how your team can realistically do more meaningful, higher impact work across a large book of business without burning out and without just doing more. And of course this workshop would not be complete if we did not also have AI part of it. So we train your team on how to basically use AI as a co pilot as well. And here's the thing Cassie and I have been talking about today. It's all about AI fluency. That's the piece of the puzzle, that's the real unlock, is knowing what high value actually looks like. So your team knows where to focus on the time that they're getting back. And if that resonates, the link is in the show notes. Let's talk about bringing this workshop to your team so that they can focus on high value impact rather than daily busy work. All right, let's get back into the podcast. I love that and I love that you are just talking, talking about not just the evolution, but like what it is we can actually provide for our customers, uh, and how we partner with them. Because I think the term, for example, trust and advisor has been thrown around left, right and center in customer success. But like, what does that actually mean? And like you just said, being exploratory, really planning out growth and really understanding how their business is going to break into a new market or challenge this new status quo or whatever it is. But it is being that business partner or business advisor to your customer. And yes, you're going to be trusted. But I think sometimes we overuse that terminology in customer success and it almost leads to us saying like, oh, but to be a trusted advisor, I can't push them or challenge them. I have to kind of just meet them where they're at and tell them what they want to hear. But like you said, it is that freedom, that ability, as we kind of move into this next era of SaaS around AI, it's like how do we work together to challenge what your growth trajectory looks like and how do we then make that happen with our product and service as well? So I love that you're kind of at the forefront and building all of that. That's super exciting. And I love that you're also at uh, what I consider an AI native tool. Now I know that that term is being thrown around left, right with every SaaS product right now, but you are truly at an AI native product right now. And you've also built a lot of AI fluency within your customer teams and the teams you've run at Monday. And for the audience, just to be super clear, we're not talking about how your team like just uses ChatGPT or Claude. We're actually going to talk about how you get your team to adopt with AI, use it as a copilot, really just make it part of your everyday. Because I think that's where we're missing. The conversations that are on AR are just about like prompts, use cases, this kind of stuff. But I want to, I want to dive in deeper, Cassie. I really want to get into kind of like what it is your team was doing at Monday to be AI fluent. But what is it that you're thinking about now? Moving into clay and making sure that your team is truly AI fluent when it comes to again, using tools, building agents, you name it, I'd love to hear it.

Cassie Vaughn: So it really stems from this idea of trusted advisor that you just mentioned. I think there's a lot of, uh, false ideas around what a trusted advisor is. And the core of that idea is that people think that a trusted advisor is someone who has all of the answers and guides their customer or their advisee on how to get to those answers. The reality and the reason why I use the term thought partner now is because that's the world that we live in. Nobody has all of the answers, Nobody knows what the ultimate outcome is. And I think that with the reason why I anchored on AI fluency for this piece is because that is the most unknown area of everyone's world right now. And it's about how you feel comfortable less with your consultative skills of getting someone from point A to point B and Getting them to the answer and more with your creative problem skills and more with your, uh, assessment and thinking and learning skills. So what I found was that AI fluency, it really meets people in different places. Some people are more open to leaning in and learning and experimenting, and some people are hesitant and waiting for like, what is the right way to do this and then I'll follow that path. But what is needed is this ability to self learn or self empower. So, um, what I really wanted to accomplish here is the ability to give them like a very loose framework for how they could do this. So on Monday, we started to develop this AI fluency program. Before I left, that was three layers. The first step was just developing the ability to self educate. So do you know good sources to follow, good podcasts to listen to voices in the space? Uh, companies that are doing very cool and iterative and, you know, experimental ideas, um, different types of AI language and terminology, like the difference between, um, you know, an LLM and an agent. These are things that are at the basic and core level, but the skill there is giving them the tools to start to self educate. So for me, it started very simply. I challenged myself for three months to listen to two different AI podcasts a day. Once on my commute to work and once I can commute from work. And it changed everything. Like just getting exposure and access to the conversation helped me feel, let's say, 40% more confident in my ability to talk about it. So that's the next level. The next level is how do you actually communicate about AI trends, what's happening in the space? How do you take what you're learning from your self enablement, your self education and contextualize it. Start to form an opinion, start to feel confident contributing to conversations or throwing out like a, uh, contrary idea or, you know, trying to figure out, like, how do I find my voice in this space and what is my opinion and how do I bring that to the table? And then the third layer is where everyone thinks that they need to jump to immediately, which is the building, like actually getting your hands on the tools, building agents, experimenting. And no, I'm not talking about to your point, just prompting ChatGPT or prompting Claude, although prompting alone, I think people have overestimated their skills.

Anika Zubair: I think we underestimate how powerful a correct prompt can be because AI is only going to tell you exactly what you ask it. And sometimes we really underestimate how a powerful prompt can make all the difference between a correct answer and then just, uh, something that throws at you it's

Cassie Vaughn: funny because I heard, uh, one of the growth strategists here at Clay, I was listening to one of her calls to educate myself on the tool yesterday, and she said artificial intelligence is artificial. And we have to remember that it's not just intelligence. You have to give it native human intelligence for it to work appropriately. And the more that you give it, the more that you prompt it, the more that you structure those prompts and help guide it to where it needs to go, the better it's going to work with you.

Anika Zubair: So love that, the reminder of artificial because again, let's not outsource our brains. It's only as smart as what we put into it, essentially.

Cassie Vaughn: So that was the levels of fluency and the notion was that people should be able one. It's not mandated. It was supposed to be something that was incentivized and exciting in a positive way, like you can only gain points or recognition for doing it, but it should give you the framework for how you're going to learn and navigate this very, uh, you know, complex and unknown time, um, so that you can build confidence and ultimately become that thought partner not only for your customers, but also for your peers internally and help continue to raise the bar for everyone else as well.

Anika Zubair: I love that. And I love that you started with being a leader yourself and self educating yourself. Like you said, a podcast to and from commuting work, just really understanding and really figuring out what AI even means. Because I think that word is just thrown around so much and all of us, especially in tech, it's hilarious because I've said it, um, when I got my haircut, I said it to my hairdresser. Have you seen what Claude's doing? And she had no idea what Clawd even was. Right. Like, and yet we're in tech feeling behind because we're not constantly educating ourselves. But I love your first layer of self education, taking the time to listen to top voices within the industry. But I want to double click a little bit on the communication and build side of things because I think we're all trying to self educate. There's a lot of content out there right now, which is, is wonderful, but also overwhelming. So how did you kind of like move into more communication and building, especially with your teams? Because I think even as CSM start to go and understand AI and start using it, whether it's prompting it, uh, whether it's listening to something, reading something, I think that that second and third layer level that you just mentioned it, it really is really important to start to see that shift. And I'm curious, how did you get your mindset of your team to start working in these three levels and kind of how did you mandate all that and move them through those levels of not just self education, but communicating it and building together as well?

Cassie Vaughn: Yeah. So when I left Monday, they haven't launched the program yet, but we were still able to enforce the communication and the building through showing good examples of people who are doing it. So I think it's about reducing the fear or reducing the barrier to entry and showing them, look, your peer, who is not a developer, who has no coding background, who has, you know, mostly the same qualifications as you and does the same job as you day to day, built his own agent to give him an a daily prompt of like, here's what's coming up for you. Here's everything you learned from your customers in the past, you know, seven days. Here's what you need to make sure you're following up on. Here's your next steps and here's like industry news to keep you abreast. Like that's, that's a partner in your day to day. That's someone who's helping you focus and starting your morning with what do I need to do and where do I best spend my time? And it was a simple agent that, um, I saw one of our CSMs build. We were fortunate at Monday, that Monday was building an agent tool. So the barrier to entry was already removed because they could experiment in our own native tool where they were comfortable. But even still, you had to get past a certain level of fear and make it known that failure is okay. So for example, one of my directors, and if he listens to this, he's going to laugh. But we had a panic email one day where we were working with a customer through, uh, an escalation and one of his agents accidentally emailed the customer something that they should not have emailed them after a phone call. And yeah, he was like, oh my God, what do I do? I'm so sorry. Just wanted to let you all know I already handled the situation but that we had to laugh about it because that will happen. You know, these little things will go wrong. You're not going to get it perfect. There's going to be room for failure and room for like, oops moments. You just have to figure out what's catastrophic failure and how do you avoid that and what's an okay space where I'm like, maybe an email gets something. I don't want to go rogue, but if it's gonna help me gain so much productivity in my day and an ability to experiment. It's worth it. So, um, it was more about showing them and really putting on a pedestal the people who were leaning into the discomfort and leaning into just testing and experimenting, showing them also the things that could go wrong and laughing at it and making it feel like it wasn't so scary if something doesn't work the

Anika Zubair: way that you want.

Cassie Vaughn: But it's about creating that sense of fomo. Like, really, you should feel like you're missing out or you're not doing enough. I like the feeling of paranoia that everyone has right now where everyone feels behind on AI. That's good, that fuels growth, that fuels curiosity. So I want to feed into that in a way that's healthy and not debilitating or paralyzing.

Anika Zubair: Yeah.

Cassie Vaughn: And I think that that goes a long way just by showing the people who are doing that and continuing to reward them.

Anika Zubair: I love that. And I think it's so important for any leader to realize that you have to give your team, like, time and space to experiment and try things. And I think in customer success, we probably do it the worst of all other departments, if I'm honest, because we just go, like, from meeting to meeting with customer. We're just like, let's just go. There's almost very little prep time to these meetings because we're all very busy. But also, we don't get to experiment how we're gonna position our new product, how we're gonna actually talk about growth. We don't get to trial it. But I love that at Monday. But just your philosophy about, like, hey, I wanna lead by example of giving safe space to actually try something, to actually feel like you can build something. And okay, yes, you made a mistake, but let's laugh about it. Let's actually just learn from this, move forward and grow. And I know there's a lot of other companies that are across the globe right now that are doing, like, test environments or even, like, just dummy data in AI, where it's like, hey, like, go build something. Go break it. Go try something. Here's some test tokens. Like, you're not going to spend too much money. Just figure it out. Because even me, um, personally, I had to learn the hard way of running out of tokens, where I'm like, oh, my gosh, I have to prompt more precisely or I have to make sure that this project is very, very specific so I don't hit my clog limit on a daily basis. So experimentation is Just is so important. Like you said, we're at a time where we're fueling curiosity, which I think is only going to level us up as humans. So I love that. But I also love that you guys started building AI agents. And I want to talk about that because I think not everyone's there yet. I think a lot of companies are in the space that you and I just talked about where they're AI curious, they're doing some education, they're trialing using AI tools or prompts and stuff. But they're not at uh, the real case where they built an agent that's a true co pilot to their day to day. And I think you guys have built some amazing things. And you had a family of agents the last time we talked. So can you walk us through kind of how you structured these agents, what problems they're actually solving for for your CSMs? Like what does that all look like, having a family of agents?

Cassie Vaughn: Yeah. So the family of agents really, it's owned by. And I'll give her a shout out. Her name's Kim Landau. She runs the medium, um, Touch Motion at Monday. But she originated a lot of these agents, um, just to serve the role of a CSM in more of a scaled way or a digital touch way where we don't have a full time CSM there. But when I saw what she was structuring, I was like, oh, a CSM could also be using that to help them scale their own touch. So for example, um, the family of agents she was creating was a number of different agents who did specific jobs with specific skills. So there's a discovery agent who does a lot of the, you know, validation and requirements gathering and needing to understand the pain that the customer has, but then also figure out what exactly they're looking for out of the product, synthesize all of that information and serve it up. Then there's the build agent who takes that information and actually builds in the product the configuration that the customer wants. And then from there there's an optimization agent who can chat back and forth with, um, the customer on, you know, how do you want to continue to tweak this or improve it over time. And I'm simplifying these. But that family of agents can roll up into being one digital CSM really for a lot of these customers who weren't getting the live touch. Um, and it works great for a PLG motion, but it helped me to really think about and break down this notion of. Because I think originally everyone is in the same space where you think of an agent and you think of a super agent who you're supposed to train to do everything. And really you should think of an agent as like different skill sets or families of agents who do different things roll up to one centralized owner or manager of all of those agents. So another one that I'm thinking of building even now at Clay, we're doing a lot of hiring. We're growing very quickly right now. So already I can see on my people's calendars and, um, on my calendar packing out how many interviews we're taking every day. And it is so important that we remain aligned on what we're looking at for what we're hearing, different things that we're detecting. And, uh, you know, every interviewer knows filling out a scorecard is the last thing you want to do. After you have a conversation, you need to move on to the next meeting. So I'm trying to figure out, like, can I build an agent one to join me on calls and help me prompt. Like, you didn't dig into this yet. Remember to ask these questions or it feels like you've covered this. Here's a good example of this. Now you can pivot and move over here. So it's there with me as like, ah, the person who's helping guide me through the flow. And then there's another agent that takes the, and synthesizes this information. And this is where human in the loop becomes important. Because I don't want an agent to score this person for me. I don't want agents interviewing my candidates. I think a human touch there is so important. So I want the agent instead to say, okay, here's what we think you would score the scorecard as. Tell us where you disagree. And if you want to add things like you thought they were particularly good at framing the pain, we can actually, as ah, the agent, go back to your recorded conversation, whether it's in notes or whatever, and pull the snippets where they did really well at this and put it into the scorecard, which means that someone else can reference. Okay. Cassie's view of what it means to qualify pain or define pain. And anchor to pain means this. Like, this is how it actually looks from a candidate. Here's what they're saying and here's what it means. That level of context, I would never have put that much effort into my scorecards, which meant that actually the information passing between interviewers was so minimal. And now we can make this like a very souped up group brain where we all know, like this is what good looks like. This is what is not passing the bar right now. And we're all very aligned without it taking massive amounts of effort from our end. So it's not something I've built yet, but it's something that I'm starting to tinker on that I think can help us stay.

Anika Zubair: But I love that you found a problem and you're like, hey, how do we address this? How can I, like, duplicate or triple myself? Because, again, you're one human. But, like, there should be a family of agents or other little things that are being ticked off. And the one thing that I absolutely love that you just said is that you don't need to have one, like, super agent doing everything. And I feel like that is the narrative that's being very misconstrued right now in not just cs, but, like, tech as a whole. I think everyone thinks you need to build this powerful, like, one, one and done agent, whatever you want to call it, but that it's going to, like, almost outsource an entire human, which maybe someday, you know, the pace AI is moving up. Maybe there will be at some point. But right now, it's like you had a very niche problem that you were solving for, and your CSMs needed some help, someone else to lean on, and you guys built a little agent or a few agents that, like, did little parts of the process. But I think the one other thing to call out that everyone listening I hope you take away is that, like, it's a copilot, like, you are still in the driver's seat, or it's, you know, it's someone else driving next to you. It's not the person that's doing all the work. You still wanted to have the human, um, part of even interviewing. You're like, I still want to have that assessment because I think that ultimately stays human. But there are little tasks to make sure that we're uniform, that we're structured, that we're achieving things the same way, no matter if it's you interviewing or three other people on your team. And I think that's really important to call out, because we are so, so, so, like, tied into this perfect world where AI is going to do everything that a human does. And again, coming back to the artificial piece that you said earlier, AI is only as intelligent as what we train and do with it. And it is a co pilot. And you don't have to just have one copilot. That's the other thing. You can have 10, you can have 15, you can have 20 doing all these different things. So I really love that you're calling that out. And you are just so into the AI space. I'm already learning so much from this, and I think a lot of CS leaders who are listening are feeling a bit overwhelmed. Like, AI has truly become both exciting and exhausting all at once. And some leaders that I speak to, they just don't know where to start. Honestly. They don't have someone on their team who's naturally an early adopter. They're not an early adopter. They're just feeling very stuck. But they're being told by senior leadership, hey, we need to be AI first or AI native or whatever, and they're feeling really, really stuck. Do you have any tips or an advice for anyone that's, like, just either starting off or trying to figure out where they even need to go when it comes to embedding AI?

Cassie Vaughn: Yeah, I have so many tips on this because I've been trying myself, and it's. It's. It is really difficult. As much as you say that I'm ingrained in this, I feel like I'm on the outside still. Like, I don't think I've gotten to the level of, well, that's good.

Anika Zubair: We all have, like, AI imposter syndrome.

Cassie Vaughn: Everyone has AI imposter syndrome, the most common disease right now. But, um, I think for me, it really did start with just hearing other voices talk about it and not. I wasn't so fixated on trying to find my level of understanding first. I was just like, you know what? I'm gonna listen to these same three podcasts week over week over week to hear how they develop their thoughts over time and how trends are emerging. And then hearing how they talked about it made me more confident. But beyond that, I think it's really like, you need to get your toe in the water there by exposing yourself to the conversation. But the opposite is almost even more important. I think this is a piece that people are losing. The limiting factor most of the time in AI is our human ability to be creative. Meaning we have to think about what are the creative ways that AI can actually solve this problem? Where should the line be between what AI is doing and where the human is starting to be involved? That all requires creative problem solving, creative thinking, and the creativity is something that we haven't had to stretch ourselves on in a very long time and incorporate in tech, for example, at least in what I do. Um, so it's almost more important to do the opposite, like, touch grass. I hate to say it, but it's like go outside, do something creative. I don't have any creative hobbies and I've realized it. Like I don't do any art. I don't like, I don't, I'm not musical. I don't, I don't have anything that's stretching that side of my brain. And I feel it like when I'm really thinking about how to creatively tackle what AI can do or prompt it to do something. And I see all these other people thinking of these amazing agents or these amazing ideas or even with clay, the way that they're using clay to solve problems for customers with insane questions like things that I didn't think were even possible. Today we learned about a customer who wanted to use clay to find out, you know, which businesses had two dumpsters outside of the business they knew to target them with certain campaigns. I would never know how to even tackle that.

Anika Zubair: Interesting. So niche.

Cassie Vaughn: Yeah, but it's not the AI tool can do it. It's my lack of creativity to figure out how do I make AI do what I need it to do or what is the bounds, what is the art of the possible as everyone says it. So I'm now I've stepped. I'm still listening to the podcast and still staying involved in the conversation and testing tools, but I'm more focusing on how do I stretch the creative side of my brain so that I can develop that muscle to be stronger. And then the other piece of all of this that I would say is, is something that I'm seeing a lot of CS leaders do that I think is working. You need to carve out budget for people to be able to expense and use different AI tools, even if it's basic tools. Like I use granola every day as my AI note taker. Starting to test like Whisper Flow, I also use. It's not really, I don't see it as like, you know, the most game changing AI tool, but it's such a

Anika Zubair: fun tool like Whisper Flow really just opens up a world of creativity. To your point, things that I'm easily, I can talk about and then it can just, you know, give me a space to start from because it's way easier to talk than to actually sit down, type write all that. Uh, yeah, exactly.

Cassie Vaughn: Low risks, low effort. So giving people budget to say like you can expense $20 worth of app subscriptions every month and just like start to figure out, you know, what you want to do with it or buy more. Here's like I'll let you expense A certain amount of token, uh, increase that you need to do. Giving people the ability to experiment freely. That's also a way to be creative, you know, so it's developing the creativity muscle that I think is the most important.

Anika Zubair: I love that. And I love that you call it out because it's so true. Like, I mean, I think I'm somewhat creative, but as you just said, my limits on AI too are how far my brain is willing to stretch to think about the problem I'm trying to solve. I know there's a problem, but how can I do it creatively? And AI is only going to build it if I'm able to actually tell it what to build and what format or structure or outline that I need it to do something. And so I love that you just mentioned that. Yeah, it is a little bit touch grass, but it is true. We have to remember that AI isn't the silver bullet. It's not going to come up with solutions for us, but it can be a partner. But we need to be the leading partner in that conversation to really help it understand what we're trying to build, how we're trying to execute, what we're trying to do faster, better, whatever. And it is so important, um, uh, to be creative. And I love that you pointed out because I think sometimes we do get so caught up in tech doing the same over and over and over again that we forget to try something new or try to challenge ourselves creatively. So I do love that. And, um, I have one more question before we jump into Quick Fire. And I think this is a great, timely question because you built some amazing things with AI fluency and the whole program you built at Monday. And I know you're starting over and starting from scratch again. So I guess since you are starting from scratch again, what would you maybe do differently or try differently now that you're at clay when it comes to building AI fluency within your customer team now?

Cassie Vaughn: Yeah, I feel like what I, uh, have learned from the model is that it doesn't need to be in my head. Originally it was a pyramid. Like it was sequential. The steps that you had to take, almost like maslow, those hierarchy of es. But I actually think it's just three, like simultaneously occurring buckets. Like you can be self educating by experimenting and building. So those things, you don't have to self educate and then develop an opinion and then experiment with building. Like those things can all be happening together. And that motion happening at the same time simultaneously is actually developing your fluency in an even more accelerated way. So rather than treating it as, like, levels and step by step, I think I would just make it like an open a la carte menu of, like, here's all the different activities you could do to increase your fluency. Some of them have different weightings. Some of them are going to be more time investment, some of them are going to be harder, some of them are going to be more expensive. But you choose where you're going to start. And it's like a choose your own path, choose your own journey type of situation. It's more just about making it like an open, playful space for experimentation. And I think that's something that I would have shifted about the narrative there.

Anika Zubair: I love that. I love that. I think all of us should just be more open, fluid, creative. Insert adjective here about how we actually decide to embed AI within our teams, but also encourage teams to continue to use it and level themselves up, too. I love that. So many takeaways. Cassie, we could probably talk about AI forever, which in this world right now, like, AI is everywhere and I'm kind of exhausted by it. But there's so many cool things that you're building. And I just want to say thank you so much for, like, sharing everything you built. Um, but I'd love to jump us into our quickfire questions where I challenge all my guests to answer the next few questions in a sentence or less. Are you ready to take on the challenge?

Cassie Vaughn: Okay. Yeah. I actually did read these, if you send them in advance. So this is going to be, like, real fresh.

Anika Zubair: Okay. Amazing. She is not prepped at all. So my first question is if you could predict the future and what do you think customer success is going to actually focus on next year?

Cassie Vaughn: I would say value leading to consumption, leading to revenue. So it's that connection of the day to day to driving the revenue, like we said.

Anika Zubair: Love it. Music to my ears because that's everything I preach. It's like, the more value you show, the more revenue your customers grow in. So that's amazing. Next question is, which app or software do you use every day or every week? And it can be on your phone and. Or your laptop, doesn't matter.

Cassie Vaughn: I say granola, and I'm sticking with it. It's, uh, especially when you're learning and you're in a new job, it's got to be your right hand. It takes everything that you're learning and synthesizes it down when your brain is melting. And then you can just ask it, like, remind me what was talked about in this conversation again. Or, like, help me synthesize the overall summary of what I learned this week. So, granola.

Anika Zubair: Love it. Love it. Amazing. And what is something cool that you are doing with AI but in your personal life?

Cassie Vaughn: So I'm trying to build an agent right now to own my family's life schedule. I have a daughter. She has many activities every week. We're traveling in the coming weeks, so I want it to give me, like, uh, start of the week. Here's all the classes your daughter has. Here's the things that you have to set up for her, like, next doctor's appointment, et cetera. You need to remember to do your grocery shopping on Wednesday. Here's some recipes for you. So, like, almost a house manager.

Anika Zubair: Yes. I'm about to say the TikTok house manager that I keep saying everywhere. I was like, you're building an AI house manager. Which sounds amazing. You'll have to tell me, because I want the details on that.

Cassie Vaughn: That's what I want.

Anika Zubair: Oh, my gosh, that's so funny. As you were describing that, I was like, oh, my God, Cassie's building a house manager.

Cassie Vaughn: I see the TikToks, and I'm like, uh, one day I need to afford one of those. And now.

Anika Zubair: Exactly. I was like, oh, my God, I bought a house manager. That sounds so amazing.

Cassie Vaughn: Exactly.

Anika Zubair: Love it. Okay, next question. If you could change one thing about customer success, what would it be?

Cassie Vaughn: I think it's the imposter syndrome. I think so many CSMs feel that they aren't commercial or salesy, and being commercial or salesy doesn't have to be commercial or salesy. It's actually just a good relationship and having good conversation and understanding what is meaningfully impacting someone's life and how you're shaping an impact for them for the better. That's the root of everything. And if you can anchorage that value, that is what drives revenue. And I think it's that notion. I know so many CSMs who are terrified of this idea of becoming more commercial, and I'm like, there is nothing for you to be fearful of. It's just about, like, different communication skills and different ways of framing what you're already doing.

Anika Zubair: Yeah, I love that. Oh, everything you're saying has just music to my ears. I'm like, yes, I agree. I agree, I agree. Amazing. Okay, my last question is, who should be my next podcast guest?

Cassie Vaughn: Oh, great question. Um, okay, so I'm going to dinner with a bunch of CS leaders tonight, so maybe I should text you later.

Anika Zubair: But, yes, Please do.

Cassie Vaughn: Yeah, I would say. I mean, my former boss@Monday.com, tom, is like my CS idol, Tom Ronan. Uh, but at Monday, there's a lot of amazing CS leaders there, I would honestly say. And I think we dabbled in this before, and I know you have a lot of CS leadership on the pod, but bringing in one of the CSMs who was built agents for themselves to show how they've infused today, that is where I would start. Like, I would focus on one of them because I think managers also are in a position where they're learning more from the field right now than vice versa. So hearing from someone who's in the field, working with customers and the agent that they built to do that, and then other leaders being able to inspire off of that idea, I think I would do that.

Anika Zubair: Yeah, I love that. I would love to have more of your old Monday team. I think they've all built some amazing things. And also, you're a former boss. If anyone wants to be on the pod, I would love to have you on. But thank you so much, Cassie, for your time, your honesty, your transparency about everything you've built and what you continue to build. I'm so excited for your next chapter at Clay as well. If my listeners have anything more or any questions that they want to follow up with you, is there a best place to get a hold of you?

Cassie Vaughn: Yeah, LinkedIn. I am a LinkedIn alum M and I still love LinkedIn. I live there, so don't, uh, hesitate to reach out out. I think this is the best time for conversations. And thanks so much for having me.

Anika Zubair: Thanks, Lassie. I'll make sure to put Cassie's LinkedIn down below. And thank you so much again for sharing all your knowledge. I really appreciate it.

Cassie Vaughn: Thank you.

Anika Zubair: 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 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 top 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. And hey, if this episode 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.