How one designer led an AI revolution at Pendo: The paternity leave epiphany | Brian Greenbaum

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I had tried cursive for the first time and what I was able to create just blew me away. I sent a message to my manager, my manager's manager, the CPO and then a few other folks that I knew were really interested in AI and I was like, "Listen, I had this really profound experience and I think we really need to uplevel the skill of our entire product organization, not just designers, but also PMs. We need to become more familiar with this technology. We need to understand how we can use it." This is actually the message that I sent while I was on paternity leave that definitely got my leaders really fired up. I didn't know exactly how this was going to go. All I knew was that I needed to get more folks paying attention to this AI stuff. >> If you were the first to raise your hand that says, you know what, I want to figure out how our team can use AI. I'm going to lead this organization. It's such a unique leadership opportunity to show crossf functional broad impact on teams. Welcome back to How I AI. I'm Claravo, product leader and AI obsessive here on a mission to help you build better with these new tools. Today I have Brian Greenbomb at Pendo and he's going to show us not only how he uses AI in his own product work, but his step-by-step plan for getting your product and design teams adopting AI as well. Let's get to it. This podcast is supported by Google. Hey everyone, Shishta here from Google DeepMind. The Gemini 2.5 family of models is now generally available. 2.5 Pro, our most advanced model, is great for reasoning over complex tasks. 2.5 Flash finds the sweet spot between performance and price. And 2.5 Flash Light is ideal for low latency, high volume tasks. Start building in Google AI Studio at a.dev. >> Ryan, thanks for joining us on how I AI. Happy to have you. >> Yeah, so excited to be here. Well, what I am excited about in our conversation is in a lot of our How I AI episodes, we've shown specific ways that you can use specific tools to build or do things with AI. And you're going to help us take a step back and say, you know, let's say you have all these tools and you want to start using them. How do you get a full team or a full organization, a full company actually adopting AI? And so this is a how I get everybody else to use AI episode. So I would love to start with what I call the inception phase which we all have gone through or are all in the process of trying to get our team to go through which is when you get people excited and sort of jumpstart the energy around AI and I think you approach this in a really interesting way. So I'd love you to walk us through what you did at Pendo. >> Yeah, absolutely. So to take you back, um it's the end of last year. So last July, I had uh my daughter Meer, my daughter Maya was born. Um you can kind of see the nursery in my background with this is sort of shared office uh nursery. Um and I was on paternity leave at the end of last year and I'm um sort of like a tech geek. I've been following AI for a while. Like my day job is a designer at Pendo, but you know, I've always sort of been into tech and so been following AI very closely. Um, I've also had some experience like building side projects and things like that. And I think it was back in November, cursor came out or maybe it was a little bit earlier than that, but cursor I had tried cursor for the same for the first time. And what I was able to create just blew me away. So I had like a side project idea, this hobby app in my in my mind about a music player where I can um play albums by scanning a QR code on on sort of like a a piece of paper. I was very jealous of people who had record players. don't have space for a record player in New York and they get to choose music by sort of flipping through through albums and uh I like having you know unlimited access to to music via Spotify but I sort of miss that sort of like tactile um experience. So I was like what if I create these sort of like laminated cards and I have this way of just being able to play the albums that are on that. Um so I had this idea of like what if I can create sort of a mobile app where I can scan like a QR code or I could recognize the album cover and I can print these album covers out and just be limited in in that way. And uh I I had no idea how to do that like on my own. Like I'm not an active developer. I can't sit down and write that application. And I pulled up cursor and like within a couple hours I had a working prototype. And like that just blew me away. I was creating QR codes. I was >> >> uh creating PDFs. I was like doing all this like really really really cool stuff. And um you know like I said my my day job is is a product designer. And I immediately understood that like, okay, this is really cool as a sort of side project. That's really fun, but I could use this to build interactive prototypes. Um, I'm I'm I consider myself pretty proficient with Figma, especially when it comes to prototyping, but I understand the limitations of using Figma for prototyping. Um, a lot of what I do at Pendo is sort of working on features that are analytics based. And so, when you're creating mock-ups and prototypes that are data driven, it's really hard to communicate what the, you know, how these things are actually going to work with real data. So having a prototype that is codebased that is working with even just fake data and interacting sort of in a more dynamic way is really useful. So I was like wow I we could really use this appendo. Um so I had the you know even though I am on paternity leave you know I had this idea and I was like I couldn't contain myself you know I had I wasn't going to come back to work until the beginning of January. So in December um I wrote a whole bunch of folks at Pendo. still had access to my Slack. And so I wrote, you know, uh I sent a message to my manager, my manager's manager, the CPO, um and then a few other folks that I knew were really, really interested in AI. And I was like, listen, I had this like really profound experience. And I think, you know, uh we really need to uplevel the skill of our entire product organization, not just designers, but also PMs. We need to become more familiar with this technology. We need need to understand how we can use it. I had already understood that like there's no playbook for how to learn this stuff. There's no class you can take. Um there's no book you can read. And the technology is evolving so fast that the only way to really know how to apply it is to become very familiar with how it works to kind of stay current with all the latest technologies and the tools and just sort of like see a bunch of examples and like selfishly like I wanted to spend more of my time at work doing these things, but I also wanted to um help my my colleagues and my company just be more successful because I I saw a clear path to that and just getting more pe more my peers, more of my colleagues like doing the same thing and sharing their experiences. is uh I know would help me learn and I think it would just sort of like you know uh rise all the boats and so this is sort of an example here not example this is actually the message I pulled it up uh that I sent while I was on paternity leave just to kind of give you an example um of what something like this looks like um and I wrote this like pretty long message I mean for folks that are um not watching this you know I just kind of said TLDDR in a similar fashion to uh you know there's an and there's an engineering focused uh sort of group uh that had that had been around for at least a here but nothing really focused on PMs and designers. I was like I'd like to lead um a group like that uh before a cross functional cross functional product team with design designers PMs and etc with two goals. Um Pendo's product team can leverage the cutting edge of AI tools to get more done in fewer hours and less resources improve decision-m and communicate and validate ideas more effectively. And then two, because Pendo is also sort of servicing a lot of product organizations that are going through similar transformation um to help position Pendo as a thought leader in the space because I knew it was going to be really important. And then I went through like a longer version of sort of like my my experience of like building this app and um and why I thought it was important. And um you know I'm really fortunate to be part of an organization that uh supports sort of initiatives like this. And so I, you know, that that definitely got uh my my leaders like really fired up. In fact, the CPO was like, "Hey, can you come to like all hands next Monday and talk about this this concept?" And I was like, "I'm on paternity leave. I can't do it yet." Um uh but I will start as soon as I come back. And so that that's sort of that's sort of what happened. So that was a catalyst for uh this idea. And I gotta say like I'm I'm the kind of person that uh you know sometimes I can be like type A and like really like think things through, but I also know that sort of committing to something or just like forcing myself to like throw myself into a situation um without knowing like how it's going to work out uh can also result in something really interesting. Um so I didn't know exactly how this was going to go. All I knew was that I needed to get more folks paying attention to this AI stuff, and I also needed to create time in people's calendar where everyone could just like focus on it and play or maybe um uh like uh hear a presentation on on something new. >> So, I have to call out a couple things here that I think are really important. one for anybody trying to, you know, give a a a justification if you if you need it for investing extra time, resources, and energy into this AI transformation in your organization. I love that you call out actually the two things that really matter. They're very similar things to um how I called out the value of AI transformation at Launch Darkly, which was one, our team's got to know how to use this stuff. like we've just got to know how to use these tools, get more done, be more efficient, just use the best of the best. The second one though I think is really interesting and there's still a lot of opportunity here. You know, you're on this podcast which is there's this opportunity for leading organizations to position themselves as thought leaders in how you get stuff done with AI in your vertical. And so for us it was like we have to be great AI engineers because we need to you know be great engineers generally. This is the next phase of how software engineering is going to get done. We need to be thought leaders in the space. And very similarly for you on the product side. I think it's just really important that you can create platforms for your company to be experts in the space if you lean in early into these technologies. You know, the other thing I want to call out is, you know, I try to tell people about this all the time. This is like promo making work. And what I mean is like this is the kind of initiative that doesn't come around that often as an opportunity. And if you are the first to raise your hand, like if you are the first designer that says, you know what, I want to figure out how our team can use AI. I'm going to lead this organization. It's such a unique leadership opportunity to show crossf functional broad impact on teams and like there's only gonna be one or two of you that get to be the leader of it. So I'm like really encouraging people to be like you raise your hand early to take on the initiative for the organization. One because I think it's the right thing to do for the team, but two, it's really great from a personal career perspective. >> Absolutely. And like you know I wasn't I wasn't going to focus on that. Um but I will but like what you're saying is absolutely 100% true. So um like this this sort of uh initiative has opened so many doors. We'll get into it in a moment but it's opened so many doors internally within the organization. Like I'm speaking with you. There's no way I think I would be speaking on such a high-profile podcast if I didn't start working on this and sort of build up a sort of the the body of work that I have over the last nine months. Um I get to work on some really cool AI projects. Um, I have folks throughout the organization that are not even in product and and and and design, folks I didn't even know reaching out to me and sort of like looking to me as a thought leader. And that wasn't my intent, but it's absolutely true. It's like there there are opportunities across um all organizations right now regardless of your level. I mean, I'm a senior staff um but I'm an IC. I'm I'm just a product designer like but I'm having an influence way beyond my my scope. And I think uh regardless of where you are like if you have the initiative and the energy and it does take a little bit of time like there is some nights and weekends that like I kind of put into it but I also love this stuff like I was kind of doing it anyway and so absolutely it is it is a career builder builder. >> Yeah. And then you know maybe my last reflection is do you know how many people I know that have gone on parental leave and in between rocking their newborn have been shipping stuff with like like cursor like every single parent I know. This just might be my my peer cohort. Everyone I know has been texting me from parental leave being like, "Claire, I've been vibe coding with my baby and I am so into it." So, if you have uh if you have somebody on parental leave right now, it's very likely they're going to come back um AI pilled for sure because that is what I have seen consistently with with some of my friends. Okay. So, let's actually get into this message, kick things off, but then you actually have to functionally make this happen. and you sort of had like a two-pronged approach to two things that were really effective in getting this going in your organization. So what were those two things? >> Yep. Yeah. Um so the two things um so I'm just kind of bringing up here um in case it's helpful. So this was sort of the first announcement I made within the organization had come back in January. Um we this is sort of like our private channel of the entire product organization. So within Pendo product the product team are PMs, designers, writers um and a few other folks. And so I was like, hey, I'm starting this initiative. And um in my mind, I I I was thinking that there's sort of a two-prong approach. There's an asynchronous and a synchronous. One thing that I um uh was very familiar with, like just in my own life, but also talking to other people, is that you'll typically hear something like, "Yeah, that AI stuff like I know it's important, but I just don't have the time." Like I don't have the time to like watch all the videos and you know, vibe code and lovable or whatever it is, right? And the crazy thing is like if you don't make the time for it, you're never going to learn it and at some point you're going to get behind, right? And so it was really important for not just there to be a place within Slack and encourage people to share on Slack asynchronously to do it at their own pace, but also to create time in people's calendars so that they can come um and focus on like whatever the topic is. And also within that session, it's not just about a presentation. It's also like it's really important for that presentation or that session to be interactive. So let me give you an example of that. So this was this was a this was a kickoff as well as an exercise about building apps. Um just to sort of give you a insight into how I start started this off. I was like hey AI is getting better. It's getting faster and it's evolving how software is planned, designed and built. And this was really meant to speak to not just us as builders but also sort of the the product that Pendo was building. And uh right around that time, Andrew Ing had a a really I thought thoughtful blog post about how he was thinking about how uh PMs need to position themselves sort of in the AI in in this AI future. And then AI is typically sort of in the space of sort of engineering and technical stuff and you know he was positioning AI as perhaps being uh or at least engineers being better positioned to sort of like take advantage of all this stuff because they are technical. Um but he's saying it was really important for PMs and I would also put designers in that camp as well uh to become proficient. And so these were the sort of five things that he was he really wanted to focus on technical proficiency um just iterating on the development like using AI in a sort of iterative capacity uh being very proficient with data skill and managing ambiguity and then ongoing learning. So like that was really sort of the emphasis I wanted to drive. Um and so again the structure of sort of like or at least the goal sorry the goals of the the product AI was around to uh uplevel and modernize the skill set of our of our product people to improve our comprehension and literacy and then because our customers are also builders to empathize and assist with them as well. And I wasn't sure if this technique again was going to work but this was how I was thinking about approaching it. just being more hands-on, getting our hands dirty, radical many to many sharing, being intentional, creating the space, and then identifying the patterns that worked, um, and then sort of turn those into reusable patterns. So, in this opening session, like I was saying, like it's really important to have an interactive session. And I'm not going to go through the slides of like how I talked about code building tools and the different, you know, the various types and some things that I had built. Um, but there was a section that was at least I think 10 15 minutes where I was like, "All right, everyone, you know, go to bolt.new." That was the app that we chose to use at the time and create an account if you haven't created an account. And then everyone go to Bolt and copy and paste this. So, this was just a prompt that I had created. Uh, it wasn't hyper optimized. It was about creating a to-do list, the most basic like little mini SAS app that you could possibly build. And I had everyone type this in. And then there was like a little enhanced prompt thing that I wanted everyone to use just to sort of see how like uh this this app could sort of take a very basic thing and and turn it into a more sophisticated thing and then let it rip and hit go. And I would say I wasn't expecting this when I did this the first time, but the thing that really stood out because it was sort of like obvious to me that this is this is what would happen. But the some of the feedback I got was like wow like we all typed in the same thing. We all clicked on the enhance prompt button and we all got different results. So like this was just sort of an example of like these were all the to-do list applications that the app created after running that that query and I think in in a third of the cases like bolt just came back and said nope like like like error whatever and then like so we immediately got into sort of the whole oh okay don't worry like if you get an error just to fix it blah blah blah and everyone sort of like got through it after two or three rounds. So that is like it was great to experience that as a team and not only just to like do it and see how it worked but also to see the diversity of like how like these applications um are built and how Genai is being used and then the other thing I had people do in the last like 105 minutes is experiment on their own and I told people just to do crazy stuff like we're not doing this for any like we're not really building a to-do list and the AI will do its best to um do as you say so you can give it like the most wacky you know instructions right like, you know, make it, you know, add a retro 8bit pixel art theme, you know, introduce a dark mode title, make it look like MySpace from 2007. And so that was sort of like an interesting thing, too. So, like people sort of like went nuts. They shared some things like I think there's a few examples here of like people saying, "Oh, you know, I tried. Yeah, here here this is what UI will look like in 20 uh 200. Here's my Tumblr style, you know, to-do list." Um, and like this was intentional to sort of like make it fun. These are designers, but there's also PMs and like we all know sort of like the there's a line between sort of like professional stuff and personal stuff. Um, but like what I really wanted people to experience is that uh this can be fun and just like to broaden their minds about how they can apply this technology. One thing I want to call out as a meta benefit to this slide that you showed and maybe we could go back to it of like now go wild or or optimize it is I think as designers and product managers in companies and you can tell me if you have a different experience but we have just gotten beaten by the scope creep stick so frequently that we have actually lost our muscle for like asking for the magic thing. We always start with the MVP. We always start with like what is the bare minimum thing I can ship to meet the user requirements that I know engineering can do and like we've lost this ability to imagine like what if it did this and what if it did that and it could be interactive or there could be voice and what I like about AI is one it makes those magic things a lot easier to build you know more efficient to build but two like it's going to let designers ers and product managers return to the craft of building the awesome product as opposed to like the viable product which is so like if you reflect on it it's so sad that we have put on a pedestal like minimum viability as just like such a low bar and now our bar can just be so much higher for what we build but you have to like reignite this muscle of like how to even think about what those things could be. So, I love the idea that you, you know, put these uh these iterations in categories like visual iterations, interactive iterations, entertaining or gamification iterations, and then like media again is something that's really interesting that you can do with AI. I know as a designer like how many times have you been like, "Oh, an illustration would be amazing here, but no one wants to spend the time to like draw a custom icon or a photo would be here, but like we don't have any stock photo budget for this project, so I'm just going to like erase that and put whites space." And so I just think like that piece is so underrated for AI is like getting out of getting us out of MVP mode. >> Yeah. And I got actually a really cool example of that as well. So like, you know, that was the sessions, right? But then there's also the channel and so um you know there people are constantly sharing things links to articles experiments that they've tried. I mean that was the whole intent of it right is just to sort of have a space where people can share things and I think there's an example in here where ah yes here it So Mark, you a he's a a product designer and I think this was right around the time that Midjourney um launched the ability to do animations or video and he was like, "Wouldn't it be cool to have, you know, sort of in this intro screen these little animated characters that sit there and just like wave at you, right?" >> And it's so cute. >> Exactly. Right. >> And that it wasn't that hard. I mean, like I think he, you know, he iterated on a couple of problems like this, this is not in the product. It's not in the product yet, but I mean, he was able to create an asset that not that hard to drop in if you have the right spot for it. Um, and like like you said before, it was, oh man, like really cool to have like an illustration or an animation, but I got to go talk to a professional or I got to go spend like nights and weekends working on it. It's like not worth the effort. And now we can bring a little more life into our applications. >> And that life of course turns into like what I just did, which is like, oh my god, I love it. Which is just like customer connection to your brand, to your product. um a little bit of sense of like this team actually really cares about the craft and is going to continue to invest in this product experience all that all the great stuff and then I I just want to call out for folks that maybe missed this in part of the transition. So the two kind of major pieces you put in were these sessions, these product and AI sessions, and you showed us the kickoff deck of what that looked like, both the why and then like let's actually get into it. Let's do it together. And then the second piece, that's the sync piece. Um, and you do those weekly, right? Or just >> we do them bi-weekly. I mean, we could probably do them weekly, but we've we've done them bi-weekly. >> Yeah. I um I I I put in a we put in a similar thing. um we called them like AI power hours on Friday and it was like every week we we would do that. And then the second thing is the async channel which like if you do not have it you should definitely have it where folks are just sharing and I like this bullet point that you had in your slide that was like radical peer-to-peer share. I forget what it said but it was such a good phrase. Yeah. Radical many to many sharing. And so one of the things that I think organizations often suffer from during this AI transformation is information hoarding and like secret AI. And I think it happens for two reasons. Secret AI can happen because people aren't sure what they can use and we're going to talk about that in a minute. And so they like kind of pretend they're not using AI or they use their like Gmail account, Gmail chat GBT account because they don't want to get in trouble but they're going to use it anyway. And so there's like secrecy because people don't know the golden path of using AI. And then there's like information and skills hoarding right now, which is like the dark side of being an AI agent or an AI change agent, which is people are like, well, I'm the only one that knows how to do this. So I'm going to stand out if I'm like extra good uh on these things or just get my work done faster or whatever. And so this like build in public many to many sharing is so important for a healthy culture around AI transformation. I cannot emphasize this this one enough. >> Absolutely. >> This episode is brought to you by Lovable. If you've ever had an idea for an app but didn't know where to start, Lovable is for you. Lovable lets you build working apps and websites by simply chatting with AI. Then you can customize it, add automations, and deploy it to a live domain. It's perfect for marketers spinning up tools, product managers prototyping new ideas, or founders launching their next business. Unlike no code tools, Lovable isn't about static pages. It builds full apps with real functionality. And it's fast. What used to take weeks, months, or even years, you can now do over the weekend. So, if you've been sitting on an idea, now's the time to bring it to life. Get started for free at lovable.dev. That's lovable.dev. You implemented this back in January, back from from uh leave. We're can you believe it? The year is like almost over. We're like we're like there. It's unbelievable. >> I know. >> Um and and you know, how did you actually measure? Did any of this matter, right? Like did we do this and was it fun and or did people actually adopt this and how did you how did you get there? >> Yeah. Yeah. So, um I think there's like there's several ways I can answer that question. The first is like, you know, I >> I didn't intend to have to implement a companywide transformation, right? Like I I needed to start uh somewhere or at least I wanted to really focus on my craft and the people that are around me. So that was product design, a little bit of engineering, right? And so product AI is intentionally focused on the area around creating products um using AI to um do design, product management, engineering, that sort of thing. It wasn't intended to sort of like branch out to you know how does revenue sell better or how does finance do whatever finance does better right? Um the channel so like it really it was really important for the channel to be public. We have like 200 plus people on the channel now. That is way more than the product organization. So the thing is like even if you're sort of focusing on a functional area um there's aspects of that functional area that bleeds outside of the organization. Um so just to kind of give you a perspective on like the sessions that we ran right so we started back in January we were doing it every two weeks and you can kind of see sort of like some of the the different topics. It wasn't just all about vibe coding. It's about prompting. It's about you know how do you take customer feedback and sort of make sense of it. Um there's sessions here on just like diving into just Gemini. I mean like we have access to all a whole bunch of Google features from Google that are AI related and they're spread out throughout their entire ecosystem. So it's like hey what's what are all the things that we can do to sort of take advantage of that and that was one where I intentionally made it not just about product and design because like you know the the finance people and the revenue people could definitely take advantage of things like deep research within Gemini or the AI function within within uh sheets. So sometimes like it makes sense to sort of like really promote these things outside but again it was like you know you kind of want to make sure that you stay within your group. And then separately there was an initiative uh an OKR in the first quarter of of this year. Our quarters begin in February. So I had started this. Yeah. What's it's so weird enterprise enterprise sales uh fiscal year right there. >> Yeah. It it it really confuses me because like we're in fiscal year 2026. Like I thought still >> 2022 and it's October. What's happening? >> Yeah, totally. Um so yeah, we're like a little like one month off. So our quarters begin in in uh in February. So I had started this and I think because you know to your to your point earlier about like how this this uh is also a good career move. It adds a lot of visibility I think to you if you sort of take the initiative. Like I had just started this a couple weeks earlier, but I was invited to be part of a crossf functional group that was responsible for a companywide OKR to improve um um AI AI leverage within the organization. And so um I can show you some of the things that we did but like I think the most important thing uh that we did was just measuring right just measuring sort of like what is the and we called it a sentiment survey because like we didn't really know what people's or like my colleagues uh feelings were about AI right like because you know you might feel like AI is taking your job or AI is creating slob or you might feel that like AI is such like a cool fun like incredibly transformational technology that you know is gonna solve cancer, right? Like I don't know what the the sentiment is. We weren't really, you know, you're not h you were never really hiring for the skill or this attitude, right? And so you have a group of folks and you know you're thinking about instituting a transformation on how they work and the technology they use. And so it was really important I think for us to get a temperature read on like how people felt about AI. But we also wanted to know other dimensions as well. Are they aware of the like for instance are they familiar with our usage policy? Right? There's a lot of shadow IT happening just like you said like people are using their Gmail their personal chat GBT accounts to do professional work and they're not sure is like is that cheating? Is that allowed? Um or even like what kind of data am I allowed to put into chat GBT? Can I put like customer transcripts in there? Like I don't I don't know what the answer is. And some people are just doing it because they know it's going to be helpful and some people are not doing it because they're worried that you know that's not that's not cool. Um, and the other thing too is like they don't know what tools are available because yeah, I mean like you have Salesforce, you have Gmail, but you don't like we at the point at that time we didn't have companywide licenses for chat GBT, right? So like no one knows what what is actually available to them. Um, and so what I'm showing here is like the beginning of the quarter. So like the idea was we would do some things within the quarter, but in the beginning of the quarter we take this baseline and we asked these five questions and we also got some uh some qual feedback as well. So it kind of gave us a little um an idea sort of like you know why things were trending in a certain way. Um and then one thing that we we we noticed and you're kind of looking at sort of like the trend of what happened be from the beginning of the quarter to the end of the quarter. Uh there was an increase along all of these measurements and the biggest ones were around this uh usage policy and which tools do I have available to me. I think the biggest gap was here because we didn't spend any time with it. So there was a lot of work done in that quarter um just by making people aware of what they can do and how they can request software. So here's a just a screenshot of an internal uh uh confluence document we call the AI knowledge center. And in this document um is all the information that an employee needs to know about which AI tools they have available to them. So, like if you were to scroll down, you'd get this like alphabetized table of all the products that have been approved to be used within our organization for security reasons, um, for for legal reasons. I mean, the the thing is that like AI is a is a vector for doing some really bad stuff. And even though you want to move fast and you want to use all of these really cool tools, you don't want to put your company and your customers data at risk. And so it's really important that you know you work closely with your security, your IT department, your finance department, your legal department. And like again I was very fortunate in to be in an organization where like those folks which sometimes can feel like friction and a barrier like they um I think they recognize that like this was also really important and sort of like prioritized um you know still doing all the the solid work but like adding uh I prioritize sort of like the enabling us to sort of like not just use these tools but experiment with different ones. like I found myself for like a month like every week I was submitting these like zip requests for new software that I wanted to to try out. Um and it would only take maybe like a week for me to sort of get the the okay and you can kind of see like it was really important not just to see which applications I had access to and how how that application could be used but what kind of data can I share within an application as well as if I want to get access to it like what are ways that I can I can get to that. And so when I you know I go back to this slide you know that was that was one of the the the tactical things we're able to get done in a single quarter that really made a huge difference sort of in this um in this metric of awareness about policy and tools. >> I want to just call this out for the leaders on the team that are or the leaders in the audience that are listening. This is the first thing I tell them to do is I say define the golden path to using AI and it takes three pieces. It takes finance and procurement. It takes legal and it takes security. And what I tell them is it's really not going to benefit the acceleration of your team to say we'll go heads down and figure out how you can get chat GBT and cursor and you'll get your three little little tools and we'll let you know what they are. You actually need what you called out which is a very fast path to experimenting with reasonable tools to identify which ones are going to work for your team. And that rapid experimentation is really really important. You can't go do a big like multi-month evaluation of one code editing tool because as you said they're changing so rapidly. And so I love this documented place of like here's the tool, here's the status, here's the data you can put in and the data you can't put in. Here's how you get a license. Here's how you get help. Um is just very very very useful. and and if you can get this done, then it all starts to snowball from there because people have a place and a path to go down. So, I this is probably like not the most exciting screen share we've seen. Like, it's a it's a table and a confluence talk, but like I just want everybody to pause, screenshot this if you do not have this in your org. Like, you need it. Need it today because this is going to be the thing that changes how you work. I love this. >> Yeah, 100%. Um, and like once you kind of get that ball rolling, like you know, there there's a separate channel too, like I think it's called like the AI knowledge center. It's meant to be sort of like the product AI channel but more like broad-based. And every once in a while, someone be like, "Hey, can I use granola for this?" And someone outside of it, you know, someone who's just familiar with this with this process would just like, "Hey, yeah, go check out the thing. You know, yeah, you can use it, but you have to get approval, yada yada yada." And so like once you sort of get the ball rolling, you have really good documentation, you just sort of reemphasize this is where you go, this is the process. And on the on the flip side, I mean, I'm not in legal, security, IT, that sort of thing. But like when that those groups um that that group those groups are responsive to an organization that wants to experiment and try this stuff, then that the the flywheel just just keeps going. And um you know like I said in the beginning of the year there was a lot of like confusion about what I can do and whatever and now I wouldn't say it's all gone but like it is nowhere near the top list the top of our list of things that like we are concerned about when it comes to AI transformation. Well, I love this. You know, just to recap, you've shown us how you become a change agent. You know, sort of incept your organization into taking this seriously as an initiative, how you use synchronous meetings and asynchronous Slack channels to drive this as a consistent practice over time. And then you use OKRs to actually measure does any of this matter? And you're showing that like if you put these simple things in place, you can actually inlect those measures which you know just in the looking at the sentiment. Um, I like that last question that you had on the sentiment survey which is like I think this is going to have a positive impact on our employees and that went up and that is a huge win for for a company because a lot of people are feeling fear about their careers, uncertainty, doubt and so the fact that you can show you can do these very simple things and inflect that sentiment very positively in your employee population is also fabulous. So, uh, Brian, this was great. Thank you for showing us again like I could not write a better playbook for getting AI adoption in a team. This is what I've done. I you it works. Let's do this. Let's repeat this and stamp it out in our our own teams. So let's get to some lightning round questions and then we'll get you back to all your fun AI projects. The first question I have is okay. You showed us like you're incepting people and you're you know managing your stakeholders and all that kind of stuff. What is your favorite thing you've built with AI over the last year for for work? I've built a lot of really cool things. Um, the one that I'm most proud of, but it's it's kind of geeky is that I built my own MCP server for Pento. Um, so, uh, back maybe back in the spring whenever when MCP was becoming really hot, uh, folks have been talking about MCP and like how it could be applied to to Pendo. And um what I clearly saw was after using tools like deep research that is essentially like an agent that can you know basically run a bunch of web queries over and over and over again to sort of build up sort of a a research document. I had spent you know I've been in in tech for a while. I I'm a designer now but I've also spent time as a PM and I've done a lot of growth work. And one of the things that is common within growth is you're you're constantly moni monitoring like dashboards of conversion rates and retention and blah blah blah. And every once in a while a number will like dip or will dive, right? And then you're you're off and you're spending like the entire week trying to understand like what is it like? Do we have like an issue? Do we have a bug? Like is there something going on, you know, in one of our regions? uh you know like if you're doing a year-over-year comparison like maybe a holiday fell you know last year and not this year and so like that's why these and usually it's it's like some common sense thing but like if someone above you sort of sees this and they're just like wait a minute like fire drill like we got to go figure it all out and that like just eats up your whole week doing like a lot of like iterative research right looking at the data from different angles and I'm like this could be like like a deep research like query but having access to like our data right um or usage data could be uh like a killer and like NCP is a technology that can leverage that if I can give the AI tools to run these queries and then like use its intelligence to like look at the data and be like oh what about looking at it by region let's look at it a year let's look at it blah blah blah um and so that was sort of like the idea that I had of connecting like okay how this is how MCP could be useful um for our customers right because we also we're a product analytics um provider and so I had this conversation with my colleague colleagues and they're just like I don't know if you know because we have like a a bespoke quering language. It's not SQL, so it it takes, you know, the AI doesn't know how to write those queries, but I I thought I had a way of doing it that that could sort of overcome that. And so over a couple of nights, um I basically just leveraged the MCP documentation giving it to cursor. I have no idea how my I built an MTP server. I have no idea actually how it works, but I understand like right. It's like a lot of >> I'm laughing. I'm laughing. Everybody close your ears. I legitimately approached MCP servers as true sorcery sorcery before I built one. I was so I don't there's there's some branding issue that that the MCP platform and framework has because it seems like sorcery. So I was with you until I actually built one and like you know wrote the code and then I was like oh okay I get it a little bit. There's a lot of elements that make it like really hard to gra like model context protocol. Like what the hell do those words mean? Yeah. >> Like it doesn't actually speak. >> Even the naming it's just okay. So MC framework uh caretakers you might as well call it magic context protocol for for all we know. >> Yeah. Yeah. What one of my most uh popular sessions like so you know it's not just me doing the sessions during product day. other people will do them, but like one of my most popular one one was called WTF is MCP and I just spent like a whole hour telling people what MCP was and afterwards they're like, "Oh, I get it now. It's kind of like web search but like more tools." I'm like, "Yeah." But anyway, >> so I I I built this thing and like I have like so you know my wife also so works in technology but she's in marketing and I'm sitting like next to her and you know how it is like you have a baby and like you know your your nights are a little bit slower and so you have some slack time just kind of like hang out and she's watching TV and I'm sitting there on the laptop like working on this MCT server and I got it to do a thing right I got it to like you know I wrote a query uh a prompt within claude and it talked to my MCP server and it ran a thing and it returned data back and I was just like, "You have no idea how how credible this is." And she's like, "I don't know what an MCU is." Like, "What is an MCU?" And I'm like, "It's not MCU, it's MCP. God damn it." Um, so I recorded so I recorded a demo of me using it. And um, this isn't the exact one, but this is something very similar, which was um, I so I have a the my own MCP server that I hooked up and I was I was just using the public APIs, right? So like I have test accounts for Pendo. I didn't have any special access. I don't have a dev platform. I was just able to like do this on top of the APIs. Actually, any customer could do this. Um, and so I had this MTP server that can do things like just grab really basic stuff like how many pages uh which pages are the top pages, how often they accessed, you know, what are things, you know, what what does this this visitor do and that visitor do? Um, so I was like, can you create a beautiful dashboard that shows me which pages, features, and guides were the most used over the last 30 days? And I think the key thing was that I'm combining accessing the data and uh having it create a dashboard. Uh so I won't kind of go through all the things I did made a bunch of tool calls. That's not really important. But the important thing was at the end I had it put the data into this uh artifact. I'm I'm sitting here in clawude and it's not I mean I wouldn't ship this but just visualizing the connection between taking Pendo data which now you know only exists within Pendo or you can also export it and there's other ways of getting access to it but making it accessible on the level where someone could just type in a thing like tell me who what the top pages are and then show me a dashboard really like changed people's minds and with over the next like couple months like I'm now chatting with the CTO. The CTO is creating another versions MCP um and you know he's so he's create like we're we're iterating creating uh starting to like productional productionize um some of these elements. I mean what I've done here like they just they kind of moved on the it wasn't the code that I wrote or vibe coded was not important. What was what was important was like I was able to demonstrate the value of this somewhat you know hard opaque technology um to folks that like didn't maybe didn't see it in the same way and that has now actually that has like significantly impacted our road map. So like we're working on a lot of agents within Pendo um that are leveraging sort of the MCP but you know behind the scenes and um there's other things that we're planning to do with MCP and we might have gotten there anyway. Um but that uh that uh definitely sort of accelerated our timeline for that. Well, congratulations uh for for cracking through that. And I think what you said is exactly right, which is like the code that you wrote is not important. Like people get so wrapped around the axle on the quality of like quote unquote vibecoded stuff. Not the issue. The issue is until you can internally display value, it is really hard to get anything done in a product organization. And sometimes you can internally display value by saying a customer wants this. Like very easy sales comes. I got like a top quarter making deal. Customer wants that. Okay. Like we love it. But something that's a little bit more nebulous, something that has a little bit more of an intangible value. Like I think we could use this new technology or this new framework MCPS to give our customers a better experience of our product. Like it just doesn't click until you can touch it. And so the more you can use these tools to let your peers sort of like touch your ideas, I think the more as you said you can like impact the road map which is what I hear all the time from designers, engineers, product managers like I'm tired of the road map being given to me. How do I like impact it? And this tool these these tools are definitely a way way of doing that. >> Yeah. And I would say one just one tip around this which I think is really important to emphasize is that you know you might sit sort of like you know you might be designer or PM um I think it's really important for everyone to understand how this technology works like I think you got to get a little more technical you got to understand how LLMs are working you have to understand what like what an agent is you don't have to be able to code these things you don't have to be an ML engineer but um if you are a creative person or someone who is sort of in the solution space and uh is trying to think about like what like what are the different ways that I can apply AI to this this problem. You won't arrive at anything really interesting unless you understand the underlying technology. It's like an architect. Like architects, yeah, they they design like pretty buildings, but they also understand how plumbing works and electric and the electronics work, right? Like they're they're not like the electricians and the plumbers, right? But like in order to build a functional building that stands up and and is functional, right? like you got to have power sockets, you got to have room for the pipes, like all that stuff is important. I think the same thing applies to PMs and designers. And I think if you're an engineer, I think it's also useful to understand like the business side, the customer side, the you know, like to really empathize with the the issue, the the problems that your customers have so that it, you know, like what we're all looking for is basically how do you sort of connect the dots between the technologies that we have available to us to solve customer problems. H I couldn't hype you up more because I have been screaming from the rooftops. This is the era of the hard skill. Like you need the hard skills to take advantage of this stuff. I I didn't call it out earlier, but I saw one of your sessions was like intro to HTML and CSS. Like that is actually going to be the unlock for your designers because if you can read CSS, a whole world has opened up to you with these vibe coding tools. And so yes, you need to know how the stuff actually actually works. Okay, so Brian, last question. This has been so great, but got to have your your strategy here. When AI is not listening, when that NCP is not being vibe coded correctly by cursor, what is your go-to tactic? How do you get it unblocked? Do you yell? >> Uh, you know, I I I don't want to say that I don't yell, but I do yell sometimes. >> >> The the other thing that I do too, which I think is also really helpful, is I say, "Okay, you're not you're not quite getting it." Like think think about a different way of approaching this, right? Like I I'm trying to nudge it to like it maybe it's sort of like locked into a certain sort of >> uh groove and I'm trying to to make it think a little more broadly. I I don't know if that actually helps, but I've found that like sometimes that's useful. So like >> if I'm not yelling, it's just like, "Okay, you tried this a million times. Think about five other different ways that you can solve this problem." and and and go for it. >> Yeah, I think that's probably more effective than my no that I do when it's not working. Well, Ryan, this has been awesome. Where can we find you and how can we be helpful? >> Yeah, so you can find me on on LinkedIn. Um I try to post when I can and um yeah, I mean, if you're if you're a product builder or um you know, you're interested in working for a a company that is sort of embracing AI, you should check out Pendo. >> Awesome. And thanks so much. Thanks so much for watching. If you enjoyed this show, please like and subscribe here on YouTube or even better, leave us a comment with your thoughts. You can also find this podcast on Apple Podcasts, Spotify, or your favorite podcast app. Please consider leaving us a rating and review, which will help others find the show. You can see all our episodes and learn more about the show at howiaipod.com. See you next time.

Summary

Brian Greenbaum shares how he initiated an AI transformation at Pendo by leveraging his personal experience with AI tools, creating a structured approach to team adoption through synchronous sessions and asynchronous sharing, and measuring success through OKRs and sentiment surveys.

Key Points

  • Brian Greenbaum, a product designer at Pendo, initiated an AI adoption movement while on paternity leave after experiencing the power of AI tools like Cursor.
  • He proposed a cross-functional initiative to uplevel the entire product organization's AI skills, focusing on designers, PMs, and engineers.
  • The approach included two key components: synchronous sessions (bi-weekly) for hands-on learning and interactive exercises, and an asynchronous Slack channel for continuous sharing.
  • To measure impact, he used a sentiment survey to track changes in employee attitudes toward AI and created an AI Knowledge Center to document approved tools and usage policies.
  • He built a custom MCP server to demonstrate AI's value in solving real product analytics problems, which influenced Pendo's roadmap and product development.
  • The initiative created a culture of radical peer-to-peer sharing, reducing information hoarding and enabling faster experimentation with AI tools.
  • Leadership support was crucial, with the CPO and other executives actively engaging and promoting the initiative.
  • The success of the program led to Brian being recognized as a thought leader and opening new career opportunities within the organization.

Key Takeaways

  • Start an AI initiative by leveraging your personal experience and passion to inspire others, even if you're not in a leadership role.
  • Create a structured approach with both synchronous (sessions) and asynchronous (channels) components to drive consistent adoption.
  • Measure the impact of your AI initiative through sentiment surveys and OKRs to demonstrate value and justify continued investment.
  • Build a centralized resource like an AI Knowledge Center to document approved tools, usage policies, and data restrictions.
  • Demonstrate tangible value by building prototypes or tools that solve real problems within your organization to gain buy-in.

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AI Business & Strategy

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Topics

AI adoption product team transformation AI learning approach synchronous and asynchronous learning AI sentiment survey golden path for AI tools MCP server AI in product design leadership opportunity AI tool usage

Entities

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Brian Greenbaum Ryan Claravo Shishta
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Pendo Google DeepMind
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Pendo Cursor Bolt.new Lovable Google Gemini MCP server
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AI LLMs AI agents MCP prompt engineering AI tools

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0.85 (Positive)

Content Type

interview

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intermediate

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educational inspiring professional promotional