 Hey, hey, this is Carlos. I'm the founder and CEO at product school and today I'm here with Caitlyn Quinlan, who is the general manager at Gainsight. Hey, Caitlyn. Hi, Carlos. Thanks for having me. Good to have you on the show. Love having people from your company like CEO Nick. I want to continue digging deeper into the conversation because you guys are building something really cool that has an interesting angle that connects customer experience, customer success with product. I haven't seen too much of that yet. So but before we get into that, I also want to learn more about you. General manager. That's a that's a big title. So how did you get started? Yeah, so I've been saying for years, like, let me give you the abridged version of my background. I feel like as the years go on, it just gets longer and longer. So I'll do my best to keep it short. But I will go back to the beginning. I started my career on the East Coast of financial services, doing something completely different and investment due diligence for private equity companies and VC clients. And I noticed in 2009, 2010, there was like a huge shift on the deals that we were working on and everything was software. So concurrently, my partner Matt and I moved back to California. He is going to get his MBA and I just started to get the foam of Silicon Valley startup life. So as I looked around, you know, at those clients, private equity companies, what are they investing in? And to me, like one factor emerged to be very prominent, which is if I'm going to go to a company, I really need to believe in the product. And the custom, the company's success is going to lie in that durable value of their product. So I made a jump to an operating role at it. What was then a startup of MongoDB and far and away, like the coolest thing for me was going from financial services where everyone had my same job and same role. We were all kind of doing the same work to working across all the functions with completely different disciplines. And it was my first time ever working in the weeds with product and engineering and sales leaders. So now in total, I've been at four software companies. MongoDB, Mixpanel, Nova, which is a spin out of DreamWorks and then arrived at Gainsight where I am now and had done throughout that time pushing to learn more about each part of it. Organizations function. So I've held various roles across the functions and leadership teams which have led me to my now current position, which is the GM for the PX product line at Gainsight. So for those of you that don't know, PX is what product and customer success leaders use to create the best possible experience for their customers in their software. And I'll just have to make a quick plug for on product school. We do have our micro certification for product like both using PX. So check it out. Yes. I was also looking at your LinkedIn profile. I saw you had no nine different roles at Gainsight. And that's really cool. Well, first of all, even before that, it's not a lot of investors turn operators. I've seen a lot of operators turn investors. So that's definitely like an interesting move. But then once you turn operator, you've been wearing so many different hats before you became a general manager. So maybe you can guide us a little more through that journey, especially at Gainsight. Yeah, totally. So I joined Gainsight focused on sales strategy and operations, which is a role I'd held at Mixpanel prior. And I think what drove the sort of like multiple roles and moving to different parts of the organization was one, of course, curiosity. But a lot of it was following the customer journey. So I started out really focused on just sales. And then as like the classic go to market story, there was so much of a relationship to marketing that it quickly bridged to be like, OK, it's not just sales analytic strategy. It's got to include marketing and marketing ops and that stuff. So it becomes revenue operations. And then, of course, Gainsight, you know, very focused on like customer and the customer journey. So, OK, well, you can't really just think about pre-sales. So then you've got to look at what happens after you close the deal and soon adding in CS analytics and strategy and putting this strategy together so that all of the functions are operating in the same way on the same cadence and executing on the same plan can really make or break the success of a product line. And so that's where I started to pick up other things. Like I started focusing on the strategy in particular for just the one product in PX because I was like, OK, I can follow decision making. The way that Nick phrased it to me was I need to know that when one team makes a decision in one function, there's somebody that cares about the results everywhere else in the organization. And so just sort of built up from there until I found myself here running this product line. The way I've seen your your career evolve within Gainsight is similar to the way I've seen product-led companies evolve. They typically started with a more of a sales-led approach. And at some point they started looking at, OK, but what drives the sale? And it's typically an excellent product experience. And then eventually it's like, OK, but what is driving an excellent product experience is actually engagement and usage. The users need to love it first, right? And that creating that motion obviously leads to sales. But it's really it's been interesting. And I haven't seen many sales leaders that are able to kind of branch out of sales to start getting a bigger scope for for an entire business unit. Yeah, I think you're so right. I, you know, for a long time, I think a lot of people thought as of PLG as and just sort of like a premium conversion from a free trial. And it was very new business focus and like very just on the the marketing or presale side. But it's been so true for me and especially like learning at Gainsight as the company has grown that a lot of PLG is focused on your post sale, what your users are using in your product and how they achieve their outcomes and grow with your product and find more parts of it. And then as your company grows and becomes multi product, that's what I call like the second funnel after the sale for cross-selling expansion. Your product is both the most effective and the most efficient version of selling that secondary product. And if you optimize the experience with good digital engagement, that is going to be the way that your customers interact and grow with you. And in a way, your product is very meta because one of the first movers are the evangelist in product-led growth. At the same time, you're building a product for product people. So so what is your your day today as a general manager? Yeah, and so sort of like zooming back out as the GM of PX, I'm responsible for setting the strategy of the product line. So this guides how our go to market and our teams go to market with PX. But it's, you know, that sounds like it's just from the sales and marketing perspective, but it's also about the roadmap for PX and how it's set and maintained with product and engineering. So a lot of my day-to-day can be unblocking decisions or managing, you know, sort of like escalated. How do we address this new thing that's come up? But basically, it's like I was sort of saying, keeping all the functions aligned around the same strategy so that we're operating towards our goals and the most effectively that we can. And, you know, do spend a fair amount of time with customers and prospects understand their first hand feedback and experiences. Which to your point on PX being very meta just sets the bar really high for how our own experience of in-app engagements and how people self-serve through a knowledge base, just how they interact with our product and how they make that journey easy. Because I like to say, no matter how hard you try and no matter how many human connections you make by default, your product is the most contact that your users and customers have with your company. So it's got to be a good experience. So as a GM, do you own profit and losses? So yeah, so there is a, I mostly focused on the growth of the product line, which is just the nature of the cycle that it's in. But I spend a fair amount of time looking at our full P&L, so profit and loss statement, for just that product line. So we definitely balance, like as we think about where we'll grow, we're balancing how the Cogs line up to that, for sure. It's a little bit, you'll have to tell me, it's my first sort of almost scratching the surface of what it's like to be a CEO running a mini company within a company. Well, I was just going to say, a lot of people used to define a Rova product manager as a mini CEO and kind of disagree. Actually, I think a GM is more like a CEO, mini CEO in a way, like you are the CEO of a specific business unit. I've seen a lot of product leaders become GMs. And usually the difference is that at some, at the GM level, you own P&L, product leaders don't typically own it. But I'm also curious to know, how is your relationship with your, with your product leader? How do you divide and conquer? Yeah, extremely close. And not just one product leader, but the whole like set of product leaders. It's one, I think it's just important to make sure that the strategy is aligned with the roadmap. So in this case, Maxime Oceanov is our product leader. And so his team owns like the full roadmap, right? But the way that we prioritize what gets built and what we work on is through like a really collaborative relationship with my, my role and the other general managers. So which is great because that allows us to really heavily influence the strategy, but always be operating in the same way. And there's continual sort of check-in. So based on this development that happened, how does that influence or not influence that they change in our, in our strategy? And I'll say that I think working with people who are product managers or product leaders is, is really helpful in this role just because the GM role tends to be extremely cross-functional. And you have a lot of stakeholders and there's probably not a lot of other roles in the organization that from the very first level, you're starting out with so many stakeholders across the business, like a PM has. I mean, like the PMs and audience can tell me, like, do you have loud stakeholders that all want different things? How do you reconcile what everybody wants? I feel like that's a very similar skill set. So it's always really great to be collaborating with that team. It sounds very similar. I always say it's, it's really a mindset more than a specific title. And in your case, like, just at a very high level, like, what is the status of the company? How big are you guys? How many products do you, do you have? Yeah. Um, so I lead the product experience product line, but overall, Gainsight is a platform with three primary products and growing. Um, so we have our customer success product, our digital hub, and then product experience, which all sit within a platform to have a cohesive customer experience. Um, uh, yeah, suite of products. Is that what you meant? Or did you have an additional pricing? So the follow up question is, okay, so you have a platform product that is supporting additional products. So I'm just thinking about your roadmaps and your interactions with a different product leaders. Like, as you think about growth, um, how do you ensure that there is some consistency, uh, to just to make sure that the way you are growing your different product lines, uh, it's, it's, uh, and their specific strategy. Yeah. Um, so I think we have some structural things in place. And then for me, I have some sort of like methodology or approach things that are in place. So structurally, um, each of the GMs, we work really closely together to make sure that we have an aligned prioritization. We understand based on how the business is doing, where the business is investing and growing, where do all of our, um, product roadmap investments fit relative to each other? So we are very aligned. So when we have those conversations with product leaders, we are very in lockstep with what the rank of prioritization is. So it's very collaborative in that way and, um, organized, but I think more than that for me, the approach and methodology is what are the use cases that our customers are buying for and more specifically, what are the outcomes they're trying to achieve and how do those relate to not only my product, but also the other products. And for that, you have to look at the full suite of products, not just your own, because a customer, when they come to you is not buying one product in a silo alone without thinking that everything else is disconnected. They think I have this goal and this problem. I think you gain sight, can solve it for me. And I don't care which product does it. I have just a problem and you just need to solve it. So when you think about the answer to that, it's more about the use case than it is the individual product. So that's sort of another way I try to stay aligned and make sure that I believe myself in the customer's shoes. So it's more about the use case than the individual product. I agree, because at the end of the day, that use case goes across different products in some situations. And one thing that I've seen in the product world as it evolves, like I started 10 years ago and when did gain sight start, by the way? Oh, that's going to test my knowledge. I believe it's 2012, maybe a little bit earlier. So over 10 years and we've had a couple lifetimes and had a different name before. So it's been a while. It's been a while. And, you know, but back in the day, there wasn't that much awareness around the role of product or customer success. And you guys have been at the intersection of it. I've seen different products that are also serving product managers that take different angles. Like that could be analytics, it could be road mapping, it could be prototyping. And I've seen gain sight of all kind of from the product, the customer success, but that now connecting with other functions such as products. So I'll be curious to know what are some of those key use cases that you've seen that can go across both customer success as well as product. Yeah. So maybe calling out the three big ones that are like top of mind a ton these days. So usage data or product telemetry in a health score to predict the performance of that customer and whether they're going to renew or not. So I think a lot of people right now, especially given the economy, would like, you know, a crystal ball of where are all their customers going to be? How happy are they? Are they going to renew with me and, you know, have 100% knowledge? Which is great. I think one key input to that is how are your end users using your individual features and the stickiest features? And are they completing the different paths in your product that make them realize value? So one big one is how you marry product usage with health scores and the prediction of like retained ARR and growth and net retention. And another one that has come up a lot is digital led onboarding. So you have this great product. This just been sold to a customer. You need them to onboard. A lot of that can be done manually in trainings, but that is not how we as users are trained on our iPhones today. It needs to be really intuitive in the product. And so I think that's something where CS has a huge investment in making sure that the customer on boards and has a good experience. But the product can bring a huge amount of that like guiding the user through sending them in app guides that say, hey, we've noticed that you did this or we know that your role is this. So we know you're going to use the software in this way. Let me give you a tip on how to, you know, move forward in learning this product. And then maybe coupled with that, the third one would be self-serve is really big right now. And so is you think about a user and I like to my example I like to use, which maybe will resonate with you. When you think about self-serve, it's not like I regular user have a help ticket that I need to log in, whatever it's like. Think about the executive using your product, which is the person you most want to be in there. It's like the CEO of the other company, but it's Thursday night at 8 30 p.m. And they have a question and they don't want to bother somebody on the team who probably know the answer. But you want to keep them in the software because they even just logged in. They're doing something great. You want to keep them in there. If you have like a knowledge tenor bot or you have a community that can answer their question right away. So they keep moving in your product. That's super valuable. So those are things that are company level strategies or their customer success strategies and well product strategies that those use cases really marry nicely together. And definitely to double click on customer success piece, because for the longest time it's been treated as the second class citizen, right? Like sales, marketing, engineering product would get usually more visibility and resources. And then you have this used to have this team in the corner where like really get a ton of value keeping the lights on trying to make sure that our clients are getting value from our product. And now they're definitely being elevated. They're really getting an AC at the table. We're seeing more companies that are appointing chief customer officers. That's that's huge. Like I was literally celebrating that a few years ago when I saw more and more companies appointing chief product officer. I think that's all news now. And I see the next wave of chief customer officer. So I'm curious for your perspective, like what are you seeing? And how is that relationship between a chief customer officer with that CPO to make sure that they are also getting enough partnership? Yeah, totally. You know, it's funny. I go back to my original work that I did in my very first job. And I think about because I'm very much like math science person. And I think about the logic of like why why why did the chief there was no chief customer officer? Why were CS like I had a smaller seat at the table or no seat at the table? And it didn't make sense to me because very quickly as you're growing as an organization, your customer base becomes way larger than your new business revenue that's being acquired. Like to the order of tens of millions or hundred millions of dollars, this number becomes their customer base because it's a lot larger. And I think that gets exacerbated in an economy right now where it's high customer acquisition costs to acquire new customers. And you sort of look at like, oh, where is our business? Oh, surprise, you know, 80% of our business is recurring customer base. And it really starts that conversation about where is your growth coming from? Well, it's actually coming from our customer base growing with our own products or cross selling to multiple products. And if you think of it from a product perspective, and you're thinking about where am I gonna invest my time and where am I gonna invest my roadmap? Well, one of your biggest parts of your business is that closed loop feedback from customers putting in their product insights across maybe angry NPS surveys. We've all had a couple of those. But if you put the dollars, purely the dollars in my brain just because way back in the day came from a finance background, it is a huge investment to focus on the customer side. So when you're thinking about as a product leader, who are my stakeholders that I wanna spend time with when I think about where I should invest time? Well, a whole bunch of your customers are under that CS part. And I think a lot of companies are seeing CS as way more revenue generating now than they did in the past. And as I was saying, I mean, there's a huge plug for your product being part of that revenue generating cycle. We like to call them product qualified leads, PQLs. PQL, definitely. I'm a huge believer in that. I think if anything, during this complicated economic downturn, we're seeing how product-led growth is just not a tactic. It's really a company-wide strategy and leveraging existing customers can lead to more lifetime value. Because obviously you can renew those customers. Ideally, you can upsell those customers. But on the other hand, those same customers can be leveraged to bring net new customers. And I think that is now, in times where you don't really have more budget for going out there and start just pumping ads or getting net new customers, thinking inwards and realize that, oh my God, the value is in house and it's more important than ever to treat our customers well. It's becoming more of a profit center. And I think it's elevating the conversation around why this team of customer success or even product deserves more investment than thinking of it as a just cost center because of course the sales team closed the deal and now we need to deliver something. Yeah, for sure. I definitely have to ask you about AI because it's one of the hot topics that is touching every single function of the organization. So for your product, what, how are you thinking about potentially integrating or leveraging AI? Yeah, so I think in general, like I'll be the first to admit that I certainly don't know everything about AI but it's something that's so rapid growth. Like it's on my mind. I'm trying to learn from smart people like, you know, X Amazon product leader, Polly Allen and Conviction founder, Vici Seriglo. So I'm like researching with, you know, content they're posting. But in general, I think, you know, when you think about the simplest answer is probably the best. Where generative AI makes a lot of sense is displacing low value human activities. So I think right now where, you know, we're focused on is how can you take things that already exist in the product and then for ways that you would configure in the product do have a generative AI start you on this. So if you, for example, engage site across our platform, you can have a journey where you take the user through and you have engagement that you make with them based on the steps and actions that they're taking in your product. So one thing that we just announced at our conference two weeks ago is investing in how we can generate what I say I wanna create, for example, because I already used it, a digital led onboarding journey with engagements. So having it be the starting base and then tweaking it based on the things you know about your business. So it's really about like, how can I use it to like make all of my PMs and my admins of the software? How can I make their time more powerful focused on the right activities versus the low value activities with starting something they've already done over and over again? One use case I saw as someone from Gainsaw actually gave me a demo, but it's really the difference between going from data into insights. So me, as I get access to Gainsaw, I have a lot of data points and I can access the data, but then it takes effort for me to make sense of that data. So leveraging that AI to automatically give me those insights in a unified view, it's really, really powerful. And I like that these new LLMs that are technically public and accessible for everybody can help, but I think there's a lot of value in connecting that with the in-house data. Yeah, so another thing we're investing in is taking product usage data or anything that you pulled out of your product data-wise and then using AI to pull out the insights. And especially somebody who spent a lot of time in business operations, like you don't wanna spend any of the time crunching the data and just getting to the answer. You wanna give yourself as much of an advantage to be like, okay, this is what I learned. Now, how am I gonna apply that forward to either inform my strategy, change it, compare it to other parts or double click and ask deeper questions. So it's definitely like, you could be quite a bit more efficient, but also it can take us into a much more rich conversation by taking some of those steps away. So super excited for that as well. And I think you're spot on. Well, now I have kind of a challenging question for you because I heard from multiple people at Gainset that takes writing being a human-first company and taking a type of approach. So how are you thinking about combining that human touch with superpowers that someone can acquire by leveraging AI? Yeah, so for those of you that don't know Gainset focuses a lot on its purpose of winning in business while being human-first. So really putting people at the center and understanding that first and foremost we're humans before we're even employees or customers or end users. And so, one, I think just keeping that focus in mind, it allows us to have much more empathy for what the user experience is going to be and keeping that in mind. But two, I think a lot of it is about, again, displacing low value activities to really take advantage of the human connection where it matters the most. So you don't want the people in your organization to do, for instance, like really menial tasks, like summarizing notes from a meeting they've had during they're doing a user survey or something that's gonna inform the product roadmap. You'd rather have something take all of the data that was recorded on a call and summarize it for you so that you can then make the smart decisions beyond that. And I think that is both the efficiency and scale part of it, but I also think it's sort of where people end up focusing as far as personalization goes, because, again, I think our standards of what we expect when we log into a software now are because of all the B2C consumer apps, they know me, they know so much about me. They're targeting me based on exactly whatever I've done and all of the history that they've aggregated. So when you log into a B2B software, you better have at least a similar experience of please know what role I am, why I'm logging in and also know what I've done in the product. And so if I've completed some steps, don't send me a pop-up that relates to something that I've already completed or already know or one example we like to use is if I'm logging in for the first time, don't tell me about a new release because I clearly doesn't matter to me because this is just the new product, this is not a new release, this is just your product to me. And so I think keeping personalization at the center of that is gonna be really important. I agree, that's what I see a lot of opportunities for product managers to add value through new technologies, such as AI, not as a way to replace the PM, but definitely like if someone can accelerate the creation of a PRD or simplified in a way that can be easier to digest if someone can help identify some of the different paths that can be created to provide a better experience for a new user versus an existing user, I take it. I think that's giving us superpowers and of course it still takes a human layer to edit and tweak the technology to make it more personal. Yeah, I went to a product conference recently and somebody used the analogy which I'm sure I won't get exactly right but if you think about humans and speed relative to all animals in the animal kingdom we're like at best in the middle of the pack but you put a human in a car or plane and now we're the fastest. So it's really about like that enablement of AI to just propel us forward in a way that we otherwise naturally couldn't but still with that human layer. I think PRDs is a great example who wants to do the first draft but of course it takes someone to go through it and be like, okay, the AI generated one doesn't quite get us there but now I have something to work with. Well, Caitlin, I loved learning from you. It's been a great time. Thank you so much. Yeah, thanks so much for having me, Carlos. Bye.