Product Leadership at AppFolio with Kyle Triplett

Probably my favorite thing is to-do lists, tasks. Like, you know, where is AI going to change the game for people? To me, it is about ad hoc and particularly recurring tasks that people have to do where they're locked into a screen. You're going to be able to have AI solutions handle many of those tasks and free up time for you and your people to go do the more important things. So to me, if I take a step back and I'm like, okay, why does AI excite me? What gets me out of bed in the morning? It's the idea of building products that create a digital experience that changes the way that people can interact in the physical world.

Thank you. Thank you for having me. Definitely excited to be here.

Alright. I don't know who's familiar with me, but you have to bear this story again. You probably have some fans out there.

I don't know. We'll see. So I'm Kyle Triplett. Thank you for everybody who's listening. I'll start with just background on me. I actually began my career in real estate private equity. I worked for a number of years in the space, and at the time, we were a Blackstone fund that ultimately became Invitation Homes. So I was the Director of Investment Management for the Los Angeles and Southern California region. I had a really awesome opportunity there to see the rapidly changing single-family space and be part of that growth.

Yeah, so it would have been beginning of like 2013 time frame all the way through to 2017.

Um, so I did acquisition, disposition, asset management, all those fun functions, and got to meet some amazing people and really developed an absolute love for the real estate space. So I am, without a question, I'll be in the real estate vertical in the property management area for my career. Just a huge passion for the physical nature of it. Love the fact that it's a sticks and bricks business, the human connections, all those pieces. So for me, super compelled with the opportunity to be a part of that. And so in 2017, I met who ultimately became my business partner, and I joined as part of the founding team for a company called Dynasty. We were focused on building digital employees for the real estate sector. We had a really amazing team of machine learning engineers, traditional engineers, folks who brought a pretty amazing level of talent to the space. I was the lucky person to get to join them and be a part of things. It was a really special opportunity to be kind of first to market as far as this digital employee, AI agent concept.

So this would have been 2017.

Yeah, I mean, we were even the way we were pricing and monetizing these things was very early days. So obviously didn't have the large language models of today to be able to do that, but we used machine learning, deep learning techniques to build our products. We were fortunate to grow really quickly. Our flagship product, Lisa, we actually have the patent for the artificial intelligence-based digital leasing assistant. So we were the first to market there. Pretty exciting. We grew that business, got a number of enterprise customers, large public groups, folks who did full deployments. During that process, I got introduced to AppFolio and originally talked to the founders and leadership team and developed a relationship there. We ultimately decided that that's the home that we wanted, just so ahead of the game on believing in this next technology wave of artificial intelligence. And early 2019, which is crazy, it's coming up on six years for me, we joined AppFolio. During my time, I've done all different kinds of stuff here. Initially integrating the product, really focused on how we bring it to the hands of the AppFolio customer base, but then ultimately led into the broader product development organization at AppFolio. I led a number of different zero-to-one products and projects for the company: Stack launch, the Max tier that we released, RealmX, and our AI products, in addition to tons of different areas of the product in accounting, leasing, maintenance. I got to run all the different aspects of the product suite. I just recently took over as head of product, which I'm super excited about. For me, it's like I came from a background where I knew I could steer a jet ski, a small team moving fast, doing all the stuff. Now it's like you got to get in the cruise ship and figure out how to operate at scale and maintain that startup energy, that startup speed, that conviction, but also ensure that we operate well as a large business. That balance has been super intriguing for me. It's been a lot of fun, and I'm super grateful to be a part of things.

Yeah, so you're totally right by the way. My other business partners, as much as I love them, have gone on to do different things. For me, it was the love of the real estate space and my belief that even during the process of betting, if we were going to exit, who would we want to exit to? I felt like AppFolio had an incredibly special opportunity to change the landscape of the industry. I'm a genuine believer in that. We had some folks enter the business like Shane Trigg, who's now the CEO of the company, who I deeply believed in and really like instilling this vision, this idea that we could power the real estate industry, that we really could change the way that folks do things, change the experience for our customers, change the lives of our customers. I felt like it's unique to have an opportunity to make that big of an impact at scale, and I wanted to be a part of that. So that was the big motivator for me: just loving the space and actually believing that AppFolio was the right company to be able to truly change things and change the landscape.

It's a totally real stereotype to think that. I think that it's easy to fall in that trap. AppFolio is a growth company, and at the end of the day, if we're going to be a generational business, we're going to be a growth company. I don't think there's any other way to operate. But at rapid pace, you know, willing to really embrace innovation and change the way you do things. I'll try not to rabbit hole too hard here because it's something I'm actually really passionate about, but I believe that speed is a superpower, and specifically speed of execution. So to me, it's the best strategy and it's incredibly powerful. I don't personally have any interest in going slow, just to be totally honest with you. I get bored. We're speeding this up. Get bored, real talk. So yeah, we're here to change the industry, we're here to change our customers' businesses. Our customers don't want to wait. They don't want to wait for the next wave, the next big thing that's going to happen. So driving a culture of momentum, driving a willingness to disrupt ourselves, to me that's totally crucial to being that long-term growth company, being that generational business. So something that's super important to me is that AppFolio doesn't rest on its laurels. We don't just say, oh, we're big, we have a lot of scale, great job, high five everybody. That's not what gets it. Which would be tempting. It's tempting, no doubt, and you know, fall in that trap. We've maybe even had instances of falling in that trap. One of my favorite comments I heard pretty recently from one of our R&D team members was, 'AppFolio feels like a startup again.' It's beyond exciting to me to drive that culture forward, to make our people understand that they're part of something bigger and have an opportunity to make a real impact. This is an awesome industry to actually make real impact in. Yeah, love speed. I could talk about it all day, but it's not enough to just be fast. That actually, you know, it can't only be speed. There's principles in how you execute and how you execute well while still moving quickly. Some examples I'd throw out there: extreme focus. You have to have extreme focus on what you're doing, very clear mission, very clear vision. You have to be customer obsessed. Know the problems you're actually solving. If you're not customer obsessed, it doesn't matter if you're going to move fast. Another one I'd throw out there is a refusal to accept constraints. Don't just assume that because something is working the way that it's working today that that's the way it's going to be forever. Don't accept constraints. Have a willingness to disrupt, operate under that lens. At the end of the day, the thing I care the most about on this speed of execution concept is the say-do ratio. What we tell our customers we're going to do, we deliver on. That's very important to me. So anyway, TL;DR, super important part of our strategy to be agile, to drive innovation. Launches like Stack, launches like RealmX, those wouldn't have been possible without this mentality. I'll give you one example on why I think if companies don't do this, they're at risk. Let's use the AI example. I don't think anyone predicted the speed at which generative AI would be changing the technology landscape. If they tell you that they did and they're not Sam Altman, I don't believe them. So honestly, yeah, it's just I think understanding that there's a technology wave that you create a vision for, that you understand how it can impact your customers. We were able to leverage our culture of agility, this culture of focus, and be first to market among the large PMS providers with a suite of GenAI products. That's incredibly exciting to be a part of. I think that's the competitive advantage that AppFolio will have, and I love that you're calling it out.

100%. Yeah, thank you for calling it out. So to be super clear, we absolutely continue to invest heavily in SMB and single-family. If you want to pair property types to it as well, but SMB space for us, we love our SMB customers, no doubt about it. The product began with an SMB focus. We have successfully scaled our business. We have brought larger and larger operators. We have enterprise-level firms using the product now very successfully. But we still have a massive install base of SMB customers that we want to serve, and we still sell a very high count of SMB customers every single year to switch to our software. So this is not going to change. SMB will continue to be a core part of our product strategy. I can say that with extreme confidence. Actually, we're thinking deeply about how do we better serve our SMB customer base. What are their product needs? How do we think about packaging the product in a way that is going to really align a cost-to-value concept, make sure that people are actually getting the value out of the software? And then what tools can we enable to even share value together? I think that's another important part of the relationship, especially with SMB companies. So look, I believe AppFolio is the right solution to power SMB businesses. I'm biased in saying that, but I genuinely believe it. We hear from customers who switch from other providers about the amount of efficiency that we deliver. We hear about mobile capabilities that help them when they're in the field doing tasks outside of the office. We get big marks on usability, on ease of use, on being able to actually use our interface. It's very intuitive. That's typically one of the big things that we sell on. The fact that we try to create experiences that are in one place, so even when you're using outside point solutions, you're using Stack partners, which we absolutely encourage, we still think having experiences driven through a single place, having that system of record, it's a game changer. It creates truly meaningful value for people. So our aim is really to be a long-term partner for SMB customers' businesses. We want them to have access to the same level of innovation, the same type of insights, the same type of support that a larger customer would get. So that's again an important part of our product strategy and an important part of our business strategy.

Yeah, that's awesome. When there's a big success story of growth and they can legitimately say, 'Oh, I've been using AppFolio since we were 50 doors or 100 doors,' and now the coolest story is people come, they're a small business, they start with 100 units or whatever, and then they've scaled up and they're a couple thousand. That is incredible. It's got to make you feel good. I mean, honestly, hopefully you can kind of tell, authentic passion for it. It's incredible to watch and talk to those people, see their faces as they do it. The concept that we can help them scale without them having to linearly grow their headcount or grow their... they are able to do things efficiently to really scale their business to new levels, new heights, achieve their goals. It's very cool.

Yeah, like literally every day. Yes. We have investments across the whole platform. The extreme focus piece is critical. You don't want to bite off too many major initiatives at any given time, but at the same point, we are doubling down on our investment in R&D. We are not in a position of pullback. We're innovating across all different parts of the platform. So I think about areas like maintenance, accounting, leasing, screening. Honestly, successful customers, when I think about who is getting a lot of value out of our product, they are staying up to date with the changes, the new features, the agile development, and they're trying and adopting things. They're actually focusing on getting the most value they can out of the system and utilizing that wide range of tools. So you could be in accounting. We released a bank feed, which is a new reconciliation process to pull transactions directly in. That's the kind of thing that's really exciting to see customers utilizing. Could be using maintenance requests and using our owner portal to be able to make sure that their owners can actually approve maintenance requests. There's just so many examples across the platform of things that folks can utilize that I want to see more and more of. You have Stack, you have RealmX, you have the big ones, and I'm very proud obviously of those releases, but they are already getting tons and tons of adoption. So to your point, it's what are all the smaller features, the things that people can use and should be using? I'd also pinpoint not just the major workflows of leasing, accounting, maintenance, but also just delivering experiences to owners and to renters. I think using AppFolio, you can actually create experiences that rival what a bigger national company is able to do or put out to their stakeholders. So I'd highlight things like owner portal enhancements, customized performance reporting for owners. I'd say big investments, which you just saw from Future conference, in AppFolio Space and the end-to-end resident experience. All these things that allow us to make the experiences for renters or owners better, all through the property manager, so that we are empowering our customers to be able to empower their customers with the best possible solutions. So there's tons of examples. Every day we see different products, different levels of adoption. One thing I will say just on differences between market segments, we do see a lot of times lower adoption of the actual product features with some of the SMB customers than we do with our larger customers. You tend to see more power usage particularly in a lot of the leasing, maintenance, accounting workflows. So I would just press people to really think deeply there about what are you not using today, why are you doing it outside the system? There's so many things that people can get access to that are literally included in their subscription that they're able to just go in and make their business better.

Exactly. We want people to feel like the cost they're paying is having real value delivered for that, right? Yeah, so we call it 'What's New.' It's like what's new in the product. So if you're an AppFolio customer and you're listening, go click the 'What's New,' read about it, actually use it, training, all those pieces. The other thing I'll throw out there too, as we think about AI tools, there's opportunities to make it easier for people to utilize features through things like natural language without having to learn different UI patterns. So there's new opportunities to think about how we make it easier for folks to interact with software too. So just know that we're thinking about that too. We know that it can be a lot to learn. People are extremely busy. There's change management even on your own platform to go out and adjust to new features.

Yeah, so overall, yes, we do see it ultimately replacing our resident portal. We think of AppFolio Space as this end-to-end resident experience. We want to create a best-in-class experience for the property manager to be able to offer to their residents. So I would add in, we had our acquisition of Livly, which was super exciting. That's really bringing in resident concierge, the ability for folks to get access to internet, to utilities, to moving services. So we're thinking really a lot about the journey through the AppFolio Space app. Yes, it will ultimately be a replacement, but there's tons of value that we want property managers to be able to allow their residents to get access to, and ultimately even share in the economics of that as well. That's another really important point for us. So if you think the whole resident journey, you kind of go from listings and showings into the application and screening phase, then you get into resident onboarding, the concierge, all the different services that folks need to actually get into the unit. Then you have things like benefits, what are some of the benefits that they get during the lease phase? And then ultimately where we may even go with a lot of larger multifamily buildings is like community IoT, different features that folks need when they're living at the building. So thinking of it really as this all-encompassing resident experience, resident app, that's consumer grade, that gives property managers the ability to give their residents amazing experiences, and then ultimately again share with AppFolio in the economics.

Yeah, but I don't pretend to say that I know where AI will head for the broader technology landscape. So I can focus on property management though.

Um, so I'll actually reverse course a little just to think about how we got here. You mentioned we had our AI initiatives and AI Factory. We've had a lot of these things running for a number of years. Here's where I can definitely pinpoint. I'll give a ton of credit to AppFolio's founders who showed us the vision that they had for AI within the property management industry many, many years before the hype of what you see with AI today. I love that. Yeah, I mean, they were... so just to go back to what made AppFolio successful and some of the big moments that were critical underpinnings, the founders had successfully jumped on and really thought about cloud and mobile, both as two major technology waves that occurred that sort of propelled AppFolio's product forward. They had this, we're close to Santa Barbara, so it's like a technology waves exercise, think about the next wave, the next thing that's going to happen. This is 2018 time frame we're all talking, and it's basically like AI is going to be the next wave. It's going to hit, it's going to happen, and we were particularly early. It actually took longer, I think, even than they were anticipating for this kind of bigger technology shift to occur. But I just give them a ton of credit because that was one of the most important reasons for the acquisition of our company: just the acknowledgement, their conviction, the investment in AI, our belief that we were going to join a larger company that actually believed this was going to change the industry. It was just super exciting. AI is again, I don't want to rabbit hole too hard on the AI topic, I can talk about it for too long, but AI is a broad term. It's an umbrella, it's a discipline. There's a lot of subcategories beneath that. If you fast forward four or five years, the reason that we're talking about this right now is the emergence of generative AI, the ability to create content, to have large language models and foundation models, to have the titans of technology pivoting into what is becoming the underpinnings of the next wave of tech. AppFolio found itself super well positioned to take advantage of this. We've been bringing talent in for years. We'd had initiatives up for years thinking about how we would build and embed AI products. We had centralized data, so it's a benefit of not being super acquisitive. Our data wasn't spread across all these different solutions, which is not something to take for granted in the property management world. Totally. I think I was super grateful as this wave hit that we were actually competitively positioned to move super quickly on it. Having data in the right place and with the right structure and format is a critical part of being able to interact with LLMs. Love that. That's like a reaping the harvest metaphor coming up for me, where you invest all this time and effort of properly formatting the tables and keeping it up to date, and you finally get to sow some of those... I don't know, I'm mixing up my metaphors. But if I'm being totally honest, there was a time period where it's like, okay, is AI actually going to hit and have the impact and the outcomes that people are kind of thinking that it would? Well, that's obviously out the window now as far as belief in our business on it. But I was just very grateful that we were able to, whether through good vision or fortune, just be able to step into this next wave. So to the original question just on how it's going to change the property management industry, I can go through a lot of the releases that we just did, but at a high level, it really is about driving true efficiency within our customers' businesses. What I mean by that is there's a number of different areas that you can pinpoint that have real value and we can create real outcomes in. So you could think about things like reporting, the ability to query your data in natural language super easily, get answers back, be able to filter that information without having to navigate join tables or do any of those pieces. Very exciting. You have communications. That's one of the biggest things that we see generally with generative AI. People using ChatGPT to run communications. We're embedding all of that with context, and that's a really important word. We have context over what you're trying to do. You're able to actually curate responses, do a lot of repetitive communication, surface that up to people, and have them be able to just say, 'Yeah, that's great. I want to change it, make it more professional, make it more friendly,' whatever it is. Saves a ton of time. Probably my favorite thing is to-do lists, tasks. Where is AI going to change the game for people? To me, it is about ad hoc and particularly recurring tasks that people have to do where they're locked into a screen. You're going to be able to have AI solutions handle many of those tasks and free up time for you and your people to go do the more important things. So to me, if I take a step back and I'm like, okay, why does AI excite me? What gets me out of bed in the morning? It's the idea of building products that create a digital experience that changes the way that people can interact in the physical world. So you're now able to go spend more time on human connections, spend more time at the physical asset, which is, as I said before, one of the things I love about real estate. Everyone has a real estate story. No matter what, you went into a building today, you did something that touches real estate. It's very cool to me that these advancements in technology can create experiences that give more time back for people to do more of that. So that piece to me is incredibly exciting. It changes the user's life. It gives them time back, meaningful time back, in reporting, communications, to-dos, training, whatever it is. The last thing I'll hit on is just around outcomes. When I think about the next wave of AI, and we'll talk about it in terms of our vertical, but this is really true across the board, AI needs to deliver actual outcomes to be valuable. This is not just for the sake of marketing or saying we're different. We'll build traditional UI where it makes sense. I'm not injecting AI for the sake of just marketing something. The outcomes that can be created, we want to fundamentally change the margin profile of the property management business. We want people to be able to scale their business with far less headcount than they would otherwise have to, not have to linearly grow headcount in order to be able to scale. A lot of people have staffing challenges, a lot of people have issues in hiring. They love their staff, but they want to be able to have people have more fulfillment in their job, to actually feel better about the things they're doing. These are real things that can be accomplished. We can use any number of the new experiences that we just released as examples of this. But again, change the margin profile, give people more fulfillment in their jobs, free them up to be in the physical space.

So a couple areas actually. I love that example. So you have the reporting side, that's what you just touched on. We have this concept internally we call 'text to data.' Basically in natural language, in text, you can ask a question, get data back. So yes, query the database, be able to get that information back. Number two would be actually creating communication tools so that you don't necessarily have to be the one doing all those follow-ups. How do we automate some of the communication proactively? You get into predictive analytics and some of the capabilities there. If it is a work order that's going to set off the owner or whatever it is, predicting and then communicating proactively is the type of optimization that we're thinking super deeply about. So there's a lot of ways to drive forward on solving these problems through AI. I would love to have an opportunity to be able to have people not have to feel like they're dealing with that difficult resident, difficult owner. They're able to actually proactively take care of some of these problems.

Totally. It's a very real thing in R&D. Such a good question. So look, the agile mindset is to put products in customers' hands and iterate. Back to that mantra of speed as a... I will say as a larger company, we have to do that safely. We don't want to put things in customers' hands that are going to get them or ourselves in trouble. But I am a big believer in phased development. I think you can start with alpha or beta customers. You can get that feedback early without doing the broader release. You can curate who you're going to work with, so you kind of lower that level of risk. I think those are important parts of that process. But we do talk about internally the concept of an MVP, a minimum viable product. I think what's important is if you're going to go the route of agile development, you're going to put products in customers' hands and you're going to iterate, which honestly I think most of the time is a better way to go than doing some kind of long waterfall project where at the end maybe the market's changed and you don't even have the right product anymore. So I'm a big fan of innovating through iterative development. That said, what you don't want to do is to have an MVP where you walk away after you release it. I think there's a tendency to get things out, but oh, it's out, so let's move on to the next thing. That would be the no-no. Make sure that you continue to durably invest in the thing. If you're going to release to customers, you're going to put it in their hands, and this is something that we've had to do a lot of learning on and look in the mirror at too, just to say, okay, how do we create that durable ownership? If we're going to put products in customers' hands and we're going to go from beta to what we call a live release to all customers, how do we make sure that we're getting that feedback, that we make the adjustments to the product, and then we have durable maintenance over making sure that the iterations are captured and ultimately it's meeting the full need? So does that make sense?

Yeah, we call them check-the-box features. I don't want to be in a situation where it's just to check the box feature and then you kind of walk away. It doesn't mean that you're always going to get it completely right, that every single thing will be done. But I think this is part of that extreme focus concept. When you're going to prioritize something, you're going to go out and make it happen. Make sure that you actually can run the cycles on doing it the correct way and durably maintain it, which is kind of a question of resource allocation.

Well, beyond just we want our customers to have choice, there are areas that we don't want to have to build every single thing. It's great for us to be able to have point solutions who are wonderful partners to us, who are going to be able to prop up these things. We can't pretend that we can continue to grow at just this exponential rate, biting off every single thing. That's not feasible for a business. So that's literally one of the reasons why you create the platform, create an ecosystem, allow people to build on top of it, and you have this virtuous cycle through all parties. What we care about is unifying the experience for customers, having a single place where they can really go and get all the things that they need done, but have the openness that allows them to do what they need to do and not have to have us sort of half-ass check each of the boxes.

Yeah, so I mean, and it has, I mean, still only been about two and a half years, right? So it's still newer, but it has scaled incredibly quickly. It's been awesome. There was certainly some dogma, if you will, in AppFolio history around being more of a closed ecosystem, wanting to build a lot of the experiences ourselves. I think the theme of why still remains the theme of why. We believe that we can really curate the best possible experiences for customers, make it easy for them to do things in a single system. But there are ways that you can do that without having to also be more of a closed ecosystem. So we made the push to actually open up, to make AppFolio an open ecosystem for partners. And actually, I'll talk about this in a minute, but even giving now read-write tools for customers directly as well. So a pretty big shift in strategy. I think that came certainly from the backgrounds of some of the leaders coming into the business. It came from listening to our customers. This goes back to that if you're customer obsessed and you actually listen to the problems they're having, folks were wanting to use outside solutions for many different reasons. Blocking them on doing that is not a winning strategy. We wanted to actually give them choice, give them the opportunity to work with outside partners. So I'm super excited about Stack, and honestly, the results that we've seen have been pretty jaw-dropping. In that time period, we have close to four million units now that are connected to Stack. That's a pretty astonishing number. That's incredible given the time frame that we're talking about. But the adoption and the relationships have been amazing. So I love our Stack partners. I've literally even become friends with some of our folks or founders that we get to interact with. So when we think about customers needing more breadth, more depth, not wanting to be locked into just our solutions, those were a lot of the big motivators for us. I can say we're not pulling back. We are certainly pushing more towards being even more open, surpassing even a lot of the people in the space with how open we are at this point. We released a read-write API that's available to customers. So if folks have developers on staff, if they want more access to their data, if they have the capability to do a lot of that, we're providing those tools directly to them as well. So anyways, it's been a fantastic endeavor for us. I think a big success for AppFolio.

You use the word 'principles.' There's principles and conviction around things that you genuinely believe. Those should be very hard to change. I think there's basically different degrees on your willingness to adjust your business. A lot of that comes down to the values, the principles that you have, sort of the roots of what make your company different or unique. I think, not to keep beating this horse, but the concept of being customer obsessed and listening and being very close to the market will actually allow you to challenge your principles when necessary. I would just say having dogma or beliefs for the sake of those beliefs is not the right way to go. It's much more about there are core values on who you are that you don't ever want to lose, but remain nimble, open to learn, and be willing to adjust if you see and hear things in the market. That same intelligence, that same creativity that made you create those early predictions, don't assume that you're going to bat a thousand on this. I think there has to be that willingness to disrupt, that willingness to learn, that willingness to be wrong. I think those are things that are super healthy when you get enough data, enough information to know that the market's changed. And again, this speed concept, if we think about one-way door and two-way door decisions, this idea of if you go down a certain path, is it a one-way door you can't ever go back? Be really hesitant on those decisions. Have a lot of data, have a lot of conviction, understand. But when it's two-way doors and you can move and you can pivot, be quick, be decisive, make decisions, be wrong, and adjust. As long as you continue to pivot, to iterate, I truly believe that those are the companies that end up being the most successful.

Absolutely, blessed. Thank you for having me. I love being on the show. Thank you.