Ryan McCann: But generating software, it is not the same thing as running a business. And in many ways, I think AI is really shifting value away from software creation toward software operation. You know, once you build a prototype, once you, you know, you need a real operational system, organizations absolutely still need governance, security, permissions, deployment options, backups, reliability. They need a system that they can trust. And at least in the near term, that part of the equation, I don't think disappears simply because software is is a lot easier to create.

And I think that's where FileMaker is strong and that's where I think FileMaker is gonna continue to be strong.

Ernest Koe: Welcome back to another episode of The Context Podcast. AI is changing what it means to build software, which in turn has profound implications for companies that make software that make software, like FileMaker. So today, I am sitting down with Ryan McCann, CEO of Claris, an Apple company. Ryan stepped into the top job about a year and a half ago TSS AI started to tear up the whole software world. So this isn't a story about a normal handoff.

It's a story about steering a ship while the water itself is changing. In this conversation, Ryan walks through the choices he had to make early on. What to build, what not to chase, and who to listen to when everyone has an opinion. We get into why he thinks AI is not hype, but also why most businesses are nowhere close to using it the way the headline suggests. We talk about what this all means for FileMaker developers and Claris partners.

If software gets easier to generate, does that make people who build it less valuable or more? Ryan makes the case that knowing the business behind the software is the part that doesn't get automated away. And finally, we close with the FileMaker 2026 release. What it signals about where Claris is headed and what Ryan sees coming over the next two years? Hey, everybody.

Welcome back to another episode of the Context Podcast. And today, I have the real pleasure of sitting down with Ryan McCann, CEO of Claris, an Apple company. And welcome, Ryan. It's good to have you.

Ryan McCann: I'm really happy to be here.

Ernest Koe: Yeah. So, Ryan, let me let me start up with this. You have been CEO of Claris now almost less than two years, right? Did I get that wrong? Yeah,

Ryan McCann: about a year and year and few months.

Ernest Koe: So I'm really curious, how's it been going? I mean, this was obviously a fairly big transition. Yeah. What what did you have any regrets? How how do you feel about this this change?

What have you learned? Yeah. I'm just kinda curious what what's going on in your head.

Ryan McCann: Yeah. I mean, it's it's it has been a ride for sure. I think, you know, under normal circumstances, stepping into that kind of role is you know, it's it's a it's a big responsibility. And so, you know, I feel like there's parts of it that are you know, that just feel very natural for me in the operational aspects of, you know, understanding a business, running a business, you know, running a p and l, managing revenue operations. You know, I've got a pretty good handle on marketing, you know, product development efforts, those kind of things.

Building and and running teams. You know, I've I felt pretty comfortable with with all of that stuff. I think that what has been probably the most challenging, but also the most rewarding part of this experience is just given, you know, the change in our industry over the last year and a half and and how fast things are moving and how much is shifting. Really trying to get a a very clear, you know, path forward for our business, for our employees, for for our ecosystem, and navigating that. Like I said, I mean, under under just, you know, the normal environment circumstances, it's it it it it feels like it would have been a reasonably straightforward transition, but that's a that that the you know, how AI is reshaping the whole software industry is added a level of complexity that has got my full attention.

That's for sure. But I'll tell you, man, I've got an advantage. First of all, I've been I've been here for a long time, so I'm pretty close to our employees. I'm I'm I'm pretty close to a broad set of folks in the Apple ecosystem. I'm I'm pretty close to our existing developer community.

So there's just literally no shortage of resources that I trust that I can leverage, tap into, partner with to help guide me through a lot of these harder parts of this job. So I feel very, very well supported through this transition. It's it's it's been the hardest but most rewarding thing that I've ever gone through, and I I honestly there's nowhere else I'd rather be.

Ernest Koe: Yeah. The did you did you have a thesis about what you wanted to do with Claris when you took over about a year ago? And how how has that changed for you given AI and everything else that's happened?

Ryan McCann: Yeah. I had a very strong point of view. And so, you know, the the kind of transition happened fairly quickly. But from day one, I had a a strong sense and understanding for where this market was going, and I had some pretty strong conviction around what was going to be necessary for us to succeed. You know, I think it it just the nature of the technology advancements over the last couple years represents, I think, either a generational opportunity or or an existential threat to any software company, really.

And, you know, being able to kind of understand the the assets and advantages and and the risks, it it just it gave me a sense of urgency and clarity and and focus in terms of, like, what what has to be true in order for me to believe that we can succeed, and that means change. And so I was I I think it that that that understanding gave me a level of clarity. That urgency gave me a level of clarity that allowed me to to to advocate really strongly for, hey. If I'm the person that's gonna do this for the long run, here's what here's how I'm gonna do it, and here are the things that I believe are necessary, and here's where I'm backing it up with. And I think that that conviction oh, it it has served me well.

Right? What I believed to be true is true. You know, it's it's playing out to be true. And I feel like the risks that I perceived are are, in fact, that they are real risks, but the opportunities, I absolutely believe, are real as well. So

Ernest Koe: What are those risks and opportunities?

Ryan McCann: Well, the the the risks are, you know, associated with, you know, kinda what what AI is doing to software development and and not not not understanding where your durable advantage is and and not understanding where you shouldn't compete. Like, those that that could have set us down a path in some weird places that know, I think that the stuff that we're seeing with the development is it's becoming so commoditized so quickly that, you know, if had we gone all in down a path that was different and trying to compete in that space, you know, it would've I felt like it would've been a race to the bottom. So making the wrong product decisions, I I think, would've been a a really big risk. You know, we would've we would've lost a lot of time trying to compete in a space that it's not necessary to compete in. I think the opportunities are are really revolve around what I believe is durable in terms of our our product advantage that, you know, I don't believe is going away anytime soon.

And and understanding how to establish a road map that, you know, really is is focused on, you know, investing in and strengthening in in that kind of the operational control of of of what we have to offer today while, you know, opening up our platform to, you know, a wide variety of of agentic capabilities. I feel like that's going to serve us well, and it's going to better enable and differentiate our developer community, and it's going to, you help us to get into mark new markets. But I think making the wrong the wrong calls there would have would have been, you know, not good for us. And we had some choices to make, you know, a year ago that I I like the choices that that we've made. Yeah.

And I and I'm not taking credit for these choices. Ernest, you know as well as anybody there. You know, I've brought, you know, in a combination of, you know, really good people from the outside into our organization, elevated really good people that have been here into positions to help influence and control those decisions. And I've tapped into some of the best and brightest from within our community to help inform, you know, that path forward. So my strategy has been get a a a diverse set of of perspectives from people that I that are credible, that I trust, to help me to to forge a path forward for our business.

And like I said, I I think we've made some good choices, and I'm really excited about kinda how we're positioned and set up for, you know, the the the coming years. Yeah. Yeah.

Ernest Koe: I know I know it's only been, you know, a little more than a year, but I I do feel like the the the channels of commune communication have been healthier, if you will, you know, between partners and and players. I'm I'm speaking from my perspective. You know, I'm not sure this is universally felt, but I certainly feel like there's been a lot of attention paid to to devs and to the partner community. But I wonder though, you know, how do you how do decide, a, who to listen to, and b, what to say no to. Right?

Because I can imagine that there's a lot of noise, and some good, some bad, some speculative, you know, some aspirational things. I mean, I'm sure you're getting phone calls from everybody all the time sometimes saying, you did a great job. Or Ryan, how could you how could you have done that? That's a completely bonkers thing to do. You yada yada yada.

Right? Yeah. So when I when I imagine myself in your shoes, a, I don't want the job, but b, I I can just imagine your day just filled with emails and phone calls and text messages. You know, you you open up the shop. Right?

But you're getting this this torrent of of information coming in. And I think I'm just really curious as as a leader, like, how do you how do you discriminate between what's signal and what's noise?

Ryan McCann: That's a really good question. I think there's again, I because I've been around I've been in this company for a long time, and I've been around this community for a long time. I've had the opportunity to to to observe, you know, a a wide range of people and their abilities. And I I I I the people that I listen to are the people that have the strongest grasp on the customer and on the developer demonstrated. Right?

So I tend to air towards the side of you know, like, at the end of the day Mhmm. We're building a product for a specific set of personas. And it doesn't matter what we think is a good idea. What matters is what our customers think are are a good idea. Right?

Because at the end of the day, just what matters is adoption. And so I have been very, very intentional about surrounding myself with people that are closest to the problems, closest to the the the real value that they're experiencing, closest to the pains and the gains. Some of those people absolutely come from within our organization, and and some of those people come from within our community. But I'm I'm I I I really have a bias toward people that represent the voice of the customer and the developer in decision making. And I also am very results oriented, and I make decisions based on, you know, where we have demonstrated traction and adoption.

I mean, it's to me, it's very basic and straightforward and probably will sound stupid to a lot of people that might be listening to this that, you know, if if you if you're making the right decisions, people are going to more and more people are gonna adopt the the feature, the capability, whatever it is. If you're not making the right decision decisions, then adoption is gonna be low. And so one of the very first things that I did in moving into this role was establish a a mechanism across our our our product development efforts that, you know, really stat you know, created some standards around how we validate the decisions that we're making and kinda control the releases of things that we're doing. And you kinda have to earn the right to keep going, and that's all based on rapid feedback of of from customers and and and adoption. And so as I see you know, I I know for any area of investment, like, I'm establishing is what I consider product market fit.

Right? And until we get to that point, you've kinda gotta earn your your wave through those different milestones. And then I know what that final gate is that if we get through that gate, this thing is we hit it right, and and now let's pour, you know, more engineering effort into it. Let's start to bring in go to market efforts around this and messaging efforts around it. So I think those two things, it's it's the people that are that are actually the the the persona that that, you know, uses our products, surrounding myself with those people and listening to them constantly and and and bringing them into decision making about what our roadmaps are gonna look like and being really intentional and deliberate about pacing, you know, our product development efforts in alignment with progress.

And if we get down a path and we're just not seeing it, we just stop. It's just not happening.

Ernest Koe: Yeah. You know, always seems to me that one of the core challenges that Claris has or maybe FileMaker has as a product is that, you you you talk about about the customer and the developer, and and, I mean, they're not really the same personas. Right? I mean, the economic buyer, the person paying the bills, licensing, is not the developer who uses the product on a day to day basis to deliver value in the organization or is a partner or consultant or whatever. So I think one of the things that I've been sort of wondering how you think about is it seems to me that the feedback loops, because of that duality, tend to be lagging or tend to be muted attenuated for Clarius.

Right? Because you're not seeing the revenue hit directly when you ship a feature for developers necessarily. There's got to be uptake. There's got to be lift. There's got to be adoption.

I remember a year ago, 2025, when some of these AI things dropped, and it's like kind of crickets from buying perspective, partly because adoption was slow with AI, and there was a lot of noise and all that. So I guess my question, Ryan, is, like, you know, how do you manage that at Claris? Like like, do you do you kill something too early because, you know, you're not you know, signals on revenue aren't aren't mature enough, but but maybe you've killed it too early because we haven't actually enabled and and allowed enough runway to happen for something to to take root?

Ryan McCann: I mean, there's always that risk, I guess. I I I I don't believe that I over index on near term revenue because I mean, if you look at our you know, we have, you know, our our mission for the year, our three core strategies for the year, one of them is based around kinda new product development, and the other two were very much tied to, you know, retention of our existing customers. Mhmm. So a lot of our product road maps are in service of meeting developer requirements that don't necessarily immediately translate into into revenue growth. But the first of all, our our our renewals business is a is a huge part of our business.

Right? So I have to protect that at all costs. And I wanna make sure that we have the right balance of investments that are gonna keep developers building in our platform. That to me right now is is probably the most important thing. And that doesn't that doesn't necessarily translate into immediate revenue.

At the same time, there are things that, you know, in in the areas of of new innovations that I think are gonna expand, you know, our our our footprint out into new markets and into potentially new personas, including, you know, business user more targeting of of business user personas. But that's not my my highest priority for this year and for revenue is really about around retaining what we what we already have. And and, again, because I am surrounded by people that are helping to inform me relative to the things that are most important for developers to continue building in our platform, it gives me the confidence. Our retention rates are actually as high as they've

Ernest Koe: I was gonna ask you about that. Yeah. Have you is that are you feeling solid with current business and retention?

Ryan McCann: Yeah. I mean, yes. No, definitely the numbers are what they are. Right? And so quarter over quarter for the last five quarters, you know, we've we've seen very strong retention.

I you know, it's

Ernest Koe: But this is this is important. Right? Because, I mean I mean, last quarter, there was, I think, almost universal panic about SaaS companies and software companies going upside down because of AI and whatnot. I mean, did that show up? Any there was any softening at all from your perspective from a from a from Claris' business model or Claris' business itself?

Did you see that happen?

Ryan McCann: No. And I went through that feeling of panic. It did that it's almost perfectly coincided with my moving into this role. Yeah. My my observations of where this market was going at that time, you know, when I talk about potentially an existential threat, you know, there's this this this this I don't I don't wanna call it hype necessarily, but it's if that's true, then this is gonna be true, and this is gonna be true, and this is gonna be true, and this is gonna be true.

So you see what is possible, and you start to envision how that could impact your entire business model, your product, and all those things. What I have come to understand is that there are very real barriers to adoption, and there is a major gap between energy, enthusiasm, and excitement and practical application. I think one of the most telling experiences that I had was last year during our international conferences. I was out in Japan. There was a team that was out in Europe.

There was a team that was in Australia. And during that conference, our goal was to really get a level set for adoption within our existing community because you're just hearing this, you know, this this all of this noise about AI is gonna eat the world. And you know, through, you know, forty, fifty different interviews, conversations, polls of of people at these conferences, a 100% of them are excited, energized, looking forward to, you know, experimenting and exploring AI. And and at the time, less than 5% had actually done anything meaningfully with with it. And so I'm not suggesting I mean, I I'm I'm we're seeing the ramp.

Right? But I think that there is this is a journey. It's a journey for everybody. And the barriers that exist today that are preventing, you know, AI from running the entire world are are significant. Some of the barriers that that I'm seeing, you know, pretty consistently, I think there there's really three things that I see show up over and over again amongst a myriad of other barriers.

But the first is, you know, related to kind of a a lack of imagination, I guess, for the for for the lack of a better term. You know, a lot of organizations today are thinking about AI through the lens of productivity, writing better emails, better summaries, faster content creation. I think a lot of people are doing that. But I think the the bigger opportunity is really reimagining or rethinking how work gets done, how decisions get made, how people interact with systems that run their business. And for a lot of organizations, that challenge isn't necessarily access to AI.

It's it's really having to to understand and and and conceptualize working in a totally different way. So that that to me is one of the big gaps. There is also still definitely a a skill gap, And I and that's not going away overnight. You know, I think we see a lot of examples of a lot of people can build, like, create software today, like, end software. But the reality is that there's a lot more to deploying real systems that run your business.

Large companies can afford, you know, to bring in AI specialists, engineers to kinda figure all this out, but most our segment, and mid sized business segment, they just don't have those resources on their bench. You know? They're they're busy running their business, and they're trying to serve their customers and ship products. They know AI is important. A lot of them are worried they're getting left behind, but a lot of them are still trying to figure out, you know, where to start and how to start.

And and again, I mean, I'm I'm not this isn't like a one or one or two off type conversation. I might hear this over and over and over again across our existing base. And I think the the the third barrier that comes up a lot is trust. You know, in a business environment, trust is not optional. And I don't think organizations are debating whether or not AI technology is impressive.

I think they're asking whether or they can depend on it. Can they trust the information? Can they trust the recommendations? Can they trust it to serve as part of a critical business process? There's a lot that goes into accuracy, relevance, privacy, security, reliability.

You know, those barriers are not trivial.

Ernest Koe: Yeah.

Ryan McCann: And so I think where we see our role and why my my my confidence is is, you know, continues to grow. I I I continue to feel a little bullish about the opportunity for all of us, for our entire development, for Claris as a company, is that we have the we we have a a proven track record over decades of meeting customers where they are on that journey and attacking those barriers, you know, delivering technology that that people are actually able to use, you know, that's approachable, helping them understand what's possible, you know, through examples of use cases and business outcomes, maintaining trust, you know, with strong governance, security, operational controls, understanding where those barriers are, and and and establishing a road map that's designed to, as we always have, go and break down those barriers. Those barriers aren't going away overnight. I am not dismissing or minimizing artificial intelligence. It is in in in certain areas, it is unbelievable, the transformation that it's driving.

But in in a lot of the areas that we're we're in, there's still a lot of barriers, and I think that's that's our opportunity. So,

Ernest Koe: I mean, it sounds like you don't think it's hype per se, but the benefits are not evenly distributed yet. It's almost like we're in a j curve moment of this innovation. Right? I mean, like, there's there's a lot of investments getting getting sunk into trying to adopt AI. And it feels like larger organizations, enterprises have more capacity.

Obviously, they can divert existing r and d, existing opex into AI investments. They can they can burn some tokens and burn some cash. You know, I I remember six months ago, people people are universally saying, well, you gotta just burn, like, all the tokens. Right? And the engineers gotta burn as much tokens in in salary as as as as they have in in in their salary.

And I I've always thought that was kinda crazy. I mean, it's doesn't doesn't doesn't to the reality of how businesses run. Like, sure, if you're managing a business, you're managing costs, you're managing top line. If your costs don't generate top line automatically, then there's only a limited amount of runway you have with that strategy. Yep.

But coming back to trust, you know, I, yeah, I think it's a weird time because it's, there's so much about AI that's being led by people who have really deep convictions about it. And I count myself as being one of them. Like, I think that this is a profoundly important technology, and it will change and transform the way we do things. And I think it it it has the potential of doing a lot of good. It has the potential of doing a lot of harm as well.

And there's obviously that's a whole separate topic. But it's one thing to have a personal conviction where you can only risk your own personal brand. And it's another thing to risk the company's brand. Right? I mean, that that's like the gap that's really hard to to to close.

You know? And and I I feel that way about my little company all the time. Right? Yeah. It's one thing is I'm just messing around and building all kinds of stuff.

Deciding whether or not to turn that into a product, that's a much bigger problem. Yep. Right? It's like just because we can build, that's not the same thing as making a product or making something that has durable values, you say, over time. So, you know, I'm I'm just really curious how how this plays out.

But I wanna come back to something. AI is not hype per se. You feel like there's something there. Is that is that been challenging at Claris in terms of taking your organization to this change from a I'm I'm asking like a change management question. Right?

Yeah. Because you you you are obviously, aside from being a company, an an organization that makes products, you have an engineering and technical team. You have a product team. You have marketing teams. How is AI being absorbed, and how how is that moving through the organization?

What have you seen that's valuable or or tricky or or or challenging to implement?

Ryan McCann: That's a really good question. And I actually think I I probably would expand the the management of change out to beyond just internal use of AI technologies. I think in a bigger way, it's how how am I how are we managing the the the change that's happening in our market the way everybody else is? Starting with the the technology side, you know, in a lot of ways, am speaking from experience. I mean, I I we work at Apple.

We're a technology company. We have the benefit of massive, you know, resources to help us to to build and deploy AI solutions internally, whether it's through our own resources or through shared Apple resources. We have a a a wide kind of variety of AI tools that enable us to, you know, uplevel productivity within our organization much more quickly. So there is definitely an adoption curve that happens. I think we're in a lot of ways, especially in the areas of product development.

I'm starting to see it on go to market teams quite a bit more. You know, we're we're kind of on the other side of the trough of that, and we're we're we're starting to kind of see significant gains in in productivity across a lot of different teams. I personally am not experiencing, like, elimination of, you know, massive parts of our business because AI is doing everybody's work. I think the reality is what people say the reality well, what half the people say the reality is going to be is that you're getting, you know, two, three x productivity out of people than you were a year and a half ago. And so that is allowing us to do things at a much higher rate of speed, at a much higher level of quality than we ever have before with the same number of people.

We're able to take on more projects. We're able to to to sign up for more. And I and and and I think that that is only going to continue to increase as more and more tools are available to us and and people are onboarding into those tools. I think we we monitor usage of AI, especially across our product development organizations. I've got some really good engineering leaders that are doing a great job of making sure that, you know, that that that our engineering organization is is, you know, kind of pioneering in that direction and and getting the full benefits of productivity through, you know, what AI can do in terms of software development.

So, yeah, it's pretty awesome to see. And I think there's a lot of, you know, the learnings that are happening across teams are impressive. Right? And so you're seeing the the organization up level pretty quickly. I think probably the the challenge that's been bigger is just how do we, you know, navigate our employees through what's happening in our industry and what's, you know, what's going on in our market and what's that gonna mean for us.

I I think that, you know, that first of all, I think our employees are really, really excited about how the industry is evolving and the opportunities that it is creating for us. There is certainly uncertainty, if that makes sense. You know, I think the the disruption is a gift in a lot of ways, though. It sparked a life in this organization that's tangible. I don't I don't prescribe or subscribe to, you know, putting posters on the wall that, you know, tell people to inspire.

I've always believed that, you know, the the internal motivation comes from purpose, and we derive purpose through confronting challenges and opportunities that carry depth and weight. So I think my job job of the leaders at Claris is to set a very clear path forward, state with intention where we must win, be very decisive about what we're not going to do, and get all wood behind as few arrows as possible so that everybody's focused on progress against the things that matter the most. And when you have a path forward in an evolving market that, you know, where you have a differentiated position, a durable position, and the opportunity to capitalize on some new innovations, and you couple that with traction, people become inspired. Urgency increases. They have purpose.

And I think over the last year and a half, you know, I've I've watched that momentum grow within this business, and it's becoming contagious. You know, as teams internally start to break away, whether because of their utilization of AI technologies or because of their clarity of purpose, they start making progress towards specific business initiatives. It kind of raises the bar for everybody around them. And I shine a light on that. You know, I I'm big on reference models like look at how this team is functioning.

Look at how this team's operating. And you find that teams within the organization are now constantly being challenged to raise their level of performance and that energy just compounds. And at the end of the day, I think the proof is in the results. You know, when you see you start to see adoption of of features that you're bringing to market, new capabilities you're bringing to market, when you start to see sentiment improving within our community and with our customers about the increasing quality and clarity of our messaging, you start to see an increase in engagement from developers based on meaningful programs and events that breeds confidence. It's it's it's kind of it's it's to me, it's about harnessing the disruption, you know.

Obviously, we have to be out in front of and and I want us to be pioneering like I I I we we and and I'm telling you in a lot of areas of the business, we absolutely are. I mean, I the up leveling that I'm seeing across this engineering team is insane.

Ernest Koe: Yeah.

Ryan McCann: We are pioneering.

Ernest Koe: I I love it. I mean, I think I mean, I I'm always encouraging you and and, you know, product and engineering at Claris to to do more in public and to take more risks in in a way. Because I think I think we're we are in a different moment. Right? I mean, I think that I think your instinct about not getting too far over the horizon on on promises and whatnot, I think, is absolutely sound.

But is there a way that we can experiment and be clear that we're experimenting? Is there a way that we can say, hey, we don't know this is gonna work, but we should try it. And and I say this because one thing that strikes me is that yeah. Let's let's let's imagine that AI is creating 10 x productivity in some areas. Right?

But it's but that doesn't translate to 10 x speed. Right? Because if you look at an organization, you are as slow or you are as fast as your slowest, quote, department or team or or whatever. Right? So if engineering can ship 100 features, but if marketing can't keep up with that velocity, then you don't have a go to market strategy.

Yeah. So I guess I'm I'm wondering how you think about execution models pre AI and post AI or in in the agentic area, era. Like, do do you think that that you see a need for, you know, reassessment or we gotta do things differently? How how do you how do you think about that?

Ryan McCann: I think that I I really like our the foundation that the way that our our teams are structured. I mean, we are we are an agile business. I think that for a period of time, I think we over indexed a bit on process. And I and and to me, a lot of, you know, execution comes down to to being able to thread that that perfect, you know, line between people and process. I I like our framework that that we use internally to run our business.

You know, we've got, you know, teams across the organization that roll up to bigger teams across the organization. We have a a consistent cadence of sprints and events. We're able to see tangible evidence of progress in short increments of time. Those things all cascade up toward a very few number of business strategies. I'm I'm I'm over the last year and a half, I think we've done a lot better job of integrating, you know, the the product, the engineering, and the go to market functions together.

So, actually, I like our operating model. As I was saying earlier, you you hit a really good point. And I'm not gonna call out any specific part of the business, but it is becoming very clear when you start to see one part of the business that's breaking away, that's got a dependency on the other part of the business that hasn't quite gotten there yet. It it does shine a pretty big light on that. And you are you have better clarity in in terms of where you need to put you invest and and put your focus on up leveling teams, up leveling people.

Sometimes you have skill gaps. Sometimes you just don't have people that you need that you've gotta bring in from the outside. So I, you know yeah. I I I like the way that we're structured. I like the way that the teams are integrated.

I've got a I I I really like our our leadership team. I like the talent that we've brought in from the outside, and they brought new life. I think for me, it's about really quickly understanding where we have critical gaps, Closing those gaps, whether we're bringing them from within our existing community, whether we're bringing them from other technology companies, whether we're bringing them from inside, closing those gaps as quickly as we possibly can, and and just making sure that that every, you know, leader in the organization is managing their teams in a way that is keeping pace with the rest of the business. But I don't I don't I don't think there's there there wasn't necessarily an overhaul to our operating structure, and and I think that the the framework or the scaffolding for we run scrum at scale. I think it's actually a perfect framework for this era.

Actually fits really, really well.

Ernest Koe: Yeah. I I I bring that up because I think that, you know, from my perspective, the and I think some of the insights I I think I'm getting really come from my own experience with how AI is adopted internally at Proof and how it's how we are both leveraging each other to use that jargon word in in the in the AI era and how we're we're trying to keep pace with each other in terms of productivity. Right? And I think a lot about my customers and our customers for that matter, my clients, our customers. And I can imagine that this is a profoundly weird moment where you see some real highlights where AI is kicking butt in some areas.

But then, you know, you've got a lot of productivity, but it doesn't translate because you're still bottlenecked by processes or business systems or certain departments that can't be automated or they don't have the technical skills to implement AI. One concrete thing that jumps out to me is I run into this quite a lot these days, which is we try to do something. We we deploy a amazing solution into testing, into UAT very quickly for a client, And then it has to go to legal for review. Right? Yeah.

And so it doesn't matter if I shipped a 100 features in a week. I I can't roll that out until legal has gotten through the backlog in in in saying that this this passes compliance or this passes muster and whatnot. And I wonder if a lot of the change management issues that we're seeing in terms of, hey, is this really hitting bottom line? Is this really affecting top line? Has partly to do with that disconnect, right?

The disconnect between like the gearing is not similar across the organization. And I'm not saying this is happening internally, but I'm wondering how, you know, are you seeing this too from your customers?

Ryan McCann: I think we were very careful in it's just the nature of of, you know, being app Apple is is is very safe, very secure, you know, very focused on privacy as everybody knows. Right? And so there's there's whether it's the products that we build and ship have to meet a certain standard. The things that we use internally have to meet a certain standard. There was a period a year and a half ago as this really started to take off where I feel like we were hamstrung.

You know, we were being held back because of the amount of restrictions and regulations of of what we could use, what we couldn't use. We've gotten past that. And and, again, that's one of the benefits of being a part of a company that's this size is that there are massive armies of people across the organization, across all of Apple that are standing up and building AI tools that are that are approved, that are safe to use, those kind of things. So today, I I there's nothing holding us back. We have access to all of the, you know, all of the cutting edge capabilities that that we need to have as a business.

What's now holding us back is just the the speed at which people are able to adopt them.

Ernest Koe: But mapping that to the customers of Claris, my clients. Right? I mean, I can imagine that they're going through a very similar journey organizationally as well, maybe with fewer resources and more challenges. Until their legal gets unlocked or until their marketing gets unlocked, it doesn't matter how fast their product teams are shipping with AI and not shipping with AI. They're still just still like hobbling along with with with the inability to really prove that AI is is is getting traction.

Ryan McCann: Right? Yeah. I think that's what we were we're hitting on that a little earlier, and I it kinda goes back to, you know, this we're an example of an organization that has those resources.

Ernest Koe: That has that. Exactly. That

Ryan McCann: has that ability. Right. And when I was mentioning, like, kinda call out three barriers to adoption, those are three of a very long list. Those are the three big ones. But I I mean, every single business is gonna have a different point of view.

There are people that are very risk averse. There are industries that are very risk averse, especially regulated industries. There are, you know, small, mid sized businesses. Like, I don't care. Let's YOLO this thing, and we'll figure it out.

I think it it but within any organization and, I mean, I honestly, we could spend three hours on this subject.

Ernest Koe: Oh, yeah. Yeah.

Ryan McCann: There are personal motivations to either go fast or not go fast. There are organizational motivations to go fast or not go fast. It it does require where you have interdependencies internally that everybody's kind of gotta be on this on the same page. And that's why I called out trust as probably the biggest barrier to adoption because I see that as being over and over again That is not gone. That is not removed.

It it is a real thing within a lot of you mentioned legal as an example. You know, you get financial data, patient data, Social Security numbers, student information. Like, you know, people aren't gonna they're not gonna risk their jobs in for the sake of gains that they're gonna get for AI. So it is going to take time for the world to to responsibly grow into these types of technologies. We we're seeing a lot of areas where there's much more appetite for adoption than in other areas where it's very, very slow and and it's methodical.

So I think what you're experiencing with your clients is is is consistent with what we're seeing across the entire market.

Ernest Koe: Speaking of of trust, by the way, congrats on 2026 release FileMaker. I was just spending quite a bit of time this morning and yesterday looking at the release notes and trying to do our own go to market on that, and it's it's a beefy release. I think I think it's almost like it's it was it was understated in terms of how important this this release is. I mean, no no blame or anything like that. Just think, you know, digging into the details, I mean, there are I I I think that this this is a a more important release than it looks just on the surface just because, you know, the the features are quite technical in some in some places.

So, anyway, congrats on that. And and that was a think this this is a big deal. But also, you wrote a blog post, which I need to call out about a month ago now about the future filmmaker 2026 and how this fits into the agentic era. Right? And I think where it relates to trust for me is that it seems to me that we have an opportunity here to really frame the value proposition of FileMaker and the product line in this question of trust.

Because the stakes for security are much higher. The stakes for getting things right are much higher. And if I were to try to optimize my business to take advantage of AI, I think what I would try not to do is to do all the undifferentiated heavy lifting that I need just to stand up a thing to get to the first base. I mean, building with AI means that you have to reinvent your stack, reinvent security, reinvent all the things, and then figure out who's gonna manage and and take care of that, then it seems like we've we've kinda gone backwards. Right?

Yeah. Do you do you does that resonate to you? What's how how you how you're thinking about this?

Ryan McCann: Yeah. I mean, I I that's why I say my my confidence just continues to grow about the these these ingredients that we we have to work with right now that I I think are are major advantages for us. You know? I think, you know, in in the area that that that we live in, the category that we live in is, you know, in the custom app development world. You know, I think AI is is is, in a lot of ways, just changing what's valuable.

Right? Historically, writing code was a bottleneck. Building interfaces was a bottle bottleneck. And, you know, I think AI is is dramatically reducing those barriers. I think today, you know, speaking from experience and speaking from what I see all over the place, anybody can describe what they want in natural language and have the software generated for them.

So front end development is becoming a lot easier. Code generation is becoming a lot easier. Prototyping is becoming dramatically faster. But generating software, it is not the same thing as running a business. And in many ways, I think AI is really shifting value away from software creation toward software operation.

You know, once you build a prototype, once you, you know, you need a real operational system, organizations absolutely still need governance, security, permissions, deployment options, backups, reliability. They need a system that they can trust. And at least in the near term, that part of the equation, I don't think disappears disappears simply because software is is a lot easier to create. And I think that's where FileMaker is strong and that's where I think FileMaker is gonna continue to be strong. I think there's another shift though that's happening and I mentioned it in a blog post, but I don't know that people really necessary I mean, I think our developer community appreciates it, but I I I I I don't know that it's it's not talked about as much.

It's it's AI doesn't just amplify software development. It amplifies domain expertise. So we're gonna see a proliferation of software like nothing we've ever seen before. Everybody can just type in what they want the system to do. And so you're gonna have software rising up in organizations all over the place, but far fewer people actually understand what software should be built and how a business actually operates and what constraints exist and what risks need to be managed.

And that's where I think our developers, you know, have have always excelled and are gonna continue to excel. They've always been problem solvers. Right? So they our developer community has been inside of businesses, working alongside of businesses, understanding problems, workflows, operational processes, data relationships, how organizations actually function, and they understand the context behind the software. So a developer that really understands business domain domain, today, they're they're gonna be able to explore more solutions.

They're gonna be able to build prototypes faster. They're gonna be able to automate more stuff. But because, you know, they they understand business problems and they understand contact context, they're gonna be able to leverage AI in ways that, you know, people like me or business users that are just spinning up AI solutions ever could. So I think it's the combination of operational control matters, you know, through the Clerix platform. The investments that we're making in agentic development flexibility, AI assistance for schema and workflows, and the deep business expertise that exists within our entire developer community.

We got, you know, a lot of partners, and we have a lot of developers with an organization. That positions, I think, all of us really well for this next era of of software development. Yeah.

Ernest Koe: I think I think that definitely resonates with me, Ryan. I mean, I think that Famiga developers, Claris developers have been closer to the problem solving domain than to the I'm gonna get in trouble by saying this, but than than to the engineering and and coding programming domain, generally speaking. I mean, certainly, there are lots of people in our community who are experts in in all the ways. Right? Both they can they can sling TypeScript and FileMaker and talk to the client and and figure out how businesses work and all of that.

But in general, I think that where our strong suit has always been, it's about really grokking what businesses need and and how they function and to solve a problem that's like a problem for them and then for the for the team, for the department, for the company at large. I think this is the exciting part about AI for me in a way. It's like it's it's just another level of abstraction, and FileMaker has always been a level of abstraction so that we can do less of the programming side and more of the, you know, problem solving side of the equation. You know, I I two two thoughts about that. So, yeah, I'm I'm I'm excited about the agentic future of FileMaker.

I think I think that's that's going to be an interesting thing as as things roll out and and and evolve. I I wonder, though, if you worry a little bit about how our community is feeling about this moment. Right? I mean, do you think that that yeah. I mean, so so much of FileMaker development specifically over the past years has been about carving a a role in this way of using a product that that can translate business ideas to to solutions very quickly.

But if agents can do that, then if your business is grounded in being a technical expert, how do you make that transition? If do you need to make a transition? You know? Do you how do you if if if I if I'm if I'm a senior file maker developer, for example, at a company, I don't know what call it Volvo or Macy's. I don't know.

I'm just making something up. Right? And do you think that that's a net threat to to your to your job now that people can just vibe code anything? You know?

Ryan McCann: I I I I I I don't think so. I I think what gives me confidence goes back to what we talked about earlier, which is I'm not we're not making decisions in isolation. We're making decisions that are based on strong involvement and feedback from our existing community based on what the path forward is. I think that there's there there are innovations that are happening that are making a lot of what goes into building, you know, applications easier and faster, but there are things that are always going to be necessary that, you know, are gonna require a certain level of skill. You mentioned earlier that there's these, you know, these these high end developers that have insane skills and, you know, engineering capability, development capability, but also can talk to business.

I think that everybody is somewhere on that that kind of spectrum. Right? And, you know, our our our goal is to to find the best path forward to bring expose these powerful technologies and bring them to our developer community so that they can use them, you know, in a way that's achievable for as many people as possible. I don't you don't you you the need to understand business context doesn't go away overnight. Domain experience doesn't go away overnight.

We're just trying to give people the tools that match the moment so that they can build at the speed of the moment. That's our goal. Right? But do I I I I don't know that necessarily I'm qualified to to to assess whether or not, you know, our developers value erodes because I'm not a developer that has a business model that's based on delivering solutions. I I don't believe that the value in our community erodes in any way.

That's my opinion. I think you are way more qualified than I am to assess that. You know what I'm saying? And and and so I guess the question goes back to you. Do you think your role, you know, diminishes based on where you see this innovation going?

Ernest Koe: It's it's a tough question, Ryan. You know, I think that I think it would be disingenuous to say that our roles are not changing. And I think if I saw myself principally as a programmer and and I were stuck in a way of programming that, you know, is artisanal, so to speak. Right? This this typing things out by hand.

I'm manually clicking through things and not using agents. Then I think, yes, my my job is at risk for sure. Right? I think that is that is probably there's no sugarcoating it. I I think that the the way AI has hit the world where we see the the most impactful, real, transformative change today is encoding.

And a 100%, if you are not using agents today, then you've got a problem. And I think this in a way, what's happening with FileMaker 20 you know, the future of FileMaker with agent development, I think, hopefully coming to the platform, that gives me a lot of hope. It doesn't it doesn't leave people orphan and gives us a way of transitioning into a more agentic place and to and to then step into a more abstracted way of solving problems, you know, more business focus and coming back to our core roots of being problem solvers. Right? So I think I think that part is worth calling out and not sweeping under the rug.

Right?

Ryan McCann: I agree. I I think, Ernest, here's my realistic take.

Ernest Koe: Yep.

Ryan McCann: Coming from the business, the side of the business, right, and talking to a broad, a vast, you know, group of business leaders across many, many sectors. The role of a of a of a a partner for sure. Right? A a Claris partner for sure. As we've talked about, expands what you just described.

Like, for people that are just just you know, they're they're manual coders. Yeah. That you're gonna have to evolve out of that, I think. But our our developers, even in house developers and certainly our partners, they are thought partners. They are strategic advisers.

You're not gonna find a small business owner, you know, a thirty, forty employee company that's gonna go and try and run down this path on his own. I mean, more than ever, that person's gonna bring somebody into the equation that knows what they're doing, that is going to be a strategic adviser through this through this shift. And I that's always been my experience based, you know, with our with our developer ecosystem, in particular, Aclaris partners, is that they actually understand how to work with businesses to lead them through

Ernest Koe: Sure.

Ryan McCann: You know, innovation changes. Yeah. And it's a very valuable skill set. So when you asked me the question earlier, it's like, is that need gonna go away? I would say that it's actually I I and I'm speaking from experience.

I'm speaking from firsthand knowledge and talking to business leaders. People are afraid. They don't want to be left behind. They don't know how to get started. They they there's so much fear uncertainty and doubt.

The the demands for people that are trusted advisers and thought partners, they can navigate them through this this market shift. I only see going way up. I mean, it's not gonna get less.

Ernest Koe: Right. Yeah. I I think that rings true to me. You know, the way I think about this, Ryan, is is like, I think there's going to be some near term disruption for sure that if you I'm speaking from as as a as a you know, putting my developer hat on for a minute, that the transitioning out of the old ways of delivering value, making software or or systems is a thing that that needs to happen. But if we get through that on the other side, then I think that the the demand for our services and the demand for more software is actually, you know, unbounded.

Right? And in a way so I I I go through this thought experiment from time to time. I sort of think, what happens when AI allows you to create all the software you want? Well, what we know today that any piece of software that exists requires attention and maintenance and update and upkeep and change. Right?

And so, yes, you can say that, hey, you know what? We have AI to help with that too. So AI can do all the maintenance and all the updates and all the upkeep. So so turtles all the way down. Right?

But really when you net it out, all that just means is that we are creating a lot more problems for ourselves as we keep using AI. I mean, good but problems nonetheless. It has to be somebody's job to take care of all these things that we're building and bringing to the world. Know? I've built so many things in the last six months that I couldn't do before because the economics of it just didn't make sense for me personally.

And I was I was in such a high thinking, well, I can do all that. I'm gonna deploy all this and I'm gonna use all that. It turns out that guess what? Then it became my job to take care of all those things. Yeah.

And I I didn't have the bandwidth to take care of because my job is to run the company and not to build software. You know? Yeah. Now I'm thinking, well, I gotta hire three more people to take over and do all these things that I I I I've been building. So, anyway, I mean, it's yeah.

If you

Ryan McCann: think relative to the world. Right? Like, you Yeah. Are the the small business segment, the mid market. Right?

You're on the far end of the spectrum of people with knowledge, understanding, know how know how vision, what's possible, what's not there yet. The the rest of the world, like, if you feel that way, imagine what the, you know, the the CEO

Ernest Koe: of a of a of a

Ryan McCann: packing company feels or the VP of operations for a restoration company. Like, they want and and they they'll sit down and vibe code a solution that is gonna help them more effect effectively track their, you know, their inventory and their employees. But the second that they're like, okay. Wanna share this with my team now, but hold on. I don't want Sue to see what Bob sees, and I don't want Alan to be able to get access to the okay.

Okay. AI told me that it's not gonna let that happen, but I no. No. No. I need to bring an adult in the room.

I need to bring a professional in the room that actually can provide me with that assurance, that that governance, the security, the permissions. And then how am I gonna deploy this? Now I just built 20 different systems.

Ernest Koe: Right.

Ryan McCann: But how am I gonna manage this? So so you're describing, I think, what is the problem? I think there's good when I mentioned earlier a proliferation of software, I think that is actually creating a much bigger problem that you're hitting on right now where the the the needs for people like our Claris partners are only gonna grow go up because at some point, nobody's gonna wanna take on the responsibility of making all you gotta do is make one mistake. Once you make that mistake, you're like, okay. Hold on a second.

I I don't I don't trust that this is this is the way for me to run my business. So there's always gonna be a need for help with governance control, operational reliability. I just I don't see that going away. You can use AI to tell you the the way to do all of those things, sure, today. But that's that's I don't believe that matches the reality of what real business people, especially in the small and mid sized business segment are gonna do.

I haven't seen the experience. I haven't seen it. I just haven't seen evidence of that. I've seen evidence of of what I'm describing right now.

Ernest Koe: Yeah. This is a I I feel like we are going through probably waves of transition in the next however many months and years. Right? I mean, the economics of how you deliver software is changing, how we restructure our business to be able to capture the value of AI and to price things correctly. And those time and material may be on its way out for one one example.

Right? If you can ship code at 10x velocity, then what is time anymore? We used to have this proxy for value with time. It's like, that doesn't make sense anymore. So I think all those things are really interesting things that we can spend hours on.

But maybe let me try to kind of bring this to a close here by asking you this question. Is your vision for the next two or three years for Claris and for FileMaker and the other initiatives or ideas that have been cooking in the back. What what do you see your customers how do you see them experiencing Claris, the brand, and the products?

Ryan McCann: I I wanna just I I my vision is to to stay true to our purpose. In doing that, we are going to be pretty successful at meeting this market where it is on its journey, being having a realistic understanding of where the barriers to adoption are, and being the company that as we always have meeting organizations where they are and helping to facilitate them through this journey. Right now, I think what we gotta get right is what we've been clear about working on. That's the next step in this journey for us. There are steps behind this in in the journey that I think create that I'm I'm confident create a lot of opportunities for us.

I I believe that we're gonna be able to do a lot. Be thoughtful about how I say this. I think that being a in an environment where trust is a major barrier, being a part of a company that has got some real advantages in the area of of trust. Having, you know, a a, you know, a kind of a unique position on understanding business problems and and delivering AI approaches towards solving business problems, I think, makes us kinda special as part of Apple today in a way that we maybe haven't been in the past. And so my vision is that we're playing a much bigger role as part of, you know, the broader Apple ecosystem.

My vision is that we're able to play a really big role in helping navigate our entire community. I'm not talking just about, you know, partners and developers, all of our customers to start incrementally walking them down a path toward transforming their business because it's true to what we've it's our purpose. That's always been who we are. And I think for us right now, that is an advantage. So without going out too far in terms of the product road map, I I'm I wanna deliver really, really well on what's right in front of us and what we're communicating to the community.

I do believe the '26 release was an important release. Maybe I'm over indexing a little bit on let's not, you know, you know, let's not hype ourselves up too much. We have a lot of work to go a lot of work to do, and we got a ways to go here. I think that if we execute really well on the on the road map that we have over the next six months that that we're being pretty communicative about, that that's setting us up for, you know, what I believe is is behind that. A lot of it's gonna change for sure, but I am excited about our position as an Apple company.

I'm excited about our, decades long purpose, especially in a moment like this. And I'm excited about the assets that we have through our developer community and our ecosystem that are hard for other people to replicate. And there's gonna be more that I will reveal over the next two, three months in terms of longer range product strategies once I get to that, you know, that level of assurance based on, you know, product market fit and and traction in areas that we're exploring that will will pave a little bit clearer path for what I think the next two years will look like beyond that.

Ernest Koe: Well, I hope you come back on the show to talk about that because that that would be very interesting and exciting for us to to go over. But, yeah, Ryan, thanks so much for being on here today with me, and we'll talk to you next time.

Ryan McCann: Been awesome, man. Thank you for having me.

Ernest Koe: Just as a reminder, this is available on YouTube as a podcast. Make sure you check out the show notes for links to things we've mentioned in the show. And if you can take a minute to pause and subscribe, we would really appreciate it. Better yet, if you can share it with a friend, that would be pretty awesome. No matter what your role is in this community, you are proof of how awesome this community is.

The work you do with FileMaker and the Claris platform is amazing. Email us at the ContextPodcast@Proof.sh, and let's share your story.