Gerardo Dada
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Gerardo Dada

Field CTO·Catchpoint Systems·Austin·

Watching the infrastructure everyone else ignores.

Gerardo Dada is Field CTO at Catchpoint, the internet performance monitoring and observability platform that helps companies understand the health and reliability of the digital infrastructure their applications depend on. He's spent his career at the intersection of deep technical knowledge and the ability to translate it to business buyers — a combination rare enough that he's essentially invented his own career path around it.

Gerardo moved from Mexico to Austin in 1998 and has worked through some of the most consequential moments in enterprise tech. He helped launch the Rackspace Cloud in 2008 during the early days of cloud computing, ran developer marketing globally at Microsoft, and managed the database performance monitoring portfolio at SolarWinds. And as a teenager back in Mexico, he became the first authorized Commodore computer dealer in his home state — selling computers before most people in the region had ever used one.

At Catchpoint, Gerardo thinks about the invisible infrastructure underneath all the software everyone is racing to build. Modern applications depend on a sprawling web of third-party services, CDNs, DNS providers, and internet backbone connections — and when any of those dependencies fail, the application fails with it. Catchpoint's platform monitors these connections from hundreds of global vantage points, giving engineering teams visibility into problems that traditional APM tools can't see.

He's also been watching the AI acceleration with a specific take that sets him apart from most of his peers: as code generation becomes cheap and abundant, the technical moat around software companies will erode. The value will increasingly come down to marketing — understanding customers, defining problems, and getting someone to choose your product. On CTO Studio, he brought that perspective along with 25 years of experience bridging the gap between engineering and go-to-market.

Read full transcript of interview
Gerardo DaDa

I am a technology marketer. I've been in marketing since I was a little kid.

Gerardo DaDa

I started my first business when I was in middle school working on technology and moved to the States in 1998 here to Austin, Texas, and I've been working for technology companies since that.

Josh Rubin

Now, field CTO, which is kind of that intersection between marketing and tech, you have to have

Josh Rubin

to be able to communicate technology and how did you find yourself in that role.

Gerardo DaDa

The question is why field CTO? I started before ... While I was starting in marketing, I started working with computers. This is with the original HP150, time in Sinclair, we had the one kilobit of memory. Then Commodore, I became the first dealer of Commodore computers in the state where I lived in, in Mexico.

Gerardo DaDa

I became very technical. I deployed Nobel network networks back in the 90s, built computers on my own, et cetera, et cetera. I've always been very curious and learned about technology. As a marketer, I think it's fundamental that you understand your customers, understand their problems, and understand how they think about problems.

Gerardo DaDa

For me, being able to understand the technology at a deep level has been always a strength that helped me become a better marketer. As a consequence, I've been engaging with a lot of these buyers, CIOs, CTOs, for a long time. I was part of the Microsoft Executive Briefing Center for years, being in front of them twice a week, large teams of CIO CTOs. They usually don't want to talk to a marketer. Marketing I think is just above used car salesman in terms of credibility.

Gerardo DaDa

I adopted the title of field CTO just to have a little bit more credibility at the beginning. Obviously you then need to deliver when you actually talk to people and prove that you know the stuff and you can add value to the conversation.

Josh Rubin

They'll show on marketing until they want to know when nobody's buying their product.

Josh Rubin

That's just me bitching about engineers and technology people as a marketer.

Gerardo DaDa

It is interesting that now that everybody's freaking out about Claude and being able, Antropic being able to generate code, then say, "Okay, if everybody can generate any application at any moment, then what is the value of software?" They realize the value of software companies is going to be in the marketing. Really understanding customers, understanding what problems you need to solve, how to solve those problems, and then marketing the software to other people.

Josh Rubin

The narrative and getting into the buyer's head.

Gerardo DaDa

Exactly.

Josh Rubin

What are you currently in the market? What are you putting out there?

Gerardo DaDa

I work for a company called Catchpoint Systems based out of the entire world. We're a very global company, completely distributed. After COVID, our founders moved out.

Gerardo DaDa

What we do is we actually are the company that monitors the core internet for large companies.

Gerardo DaDa

You remember maybe when Meta went down three and a half years ago, nobody had Facebook or WhatsApp or Instagram for most of the day? There's something on the internet called BGP, Border Gateway Protocol, that went down and they were not paying attention to that. We are the only company in the world that has the visibility into the inner workings of the internet down to the actual experience of the end user. What's happening inside companies in terms of their internal systems, internal networks, to identify those kind of problems and solve them.

Josh Rubin

That product becomes increasingly more important with the advent of AI. I was watching my own website get attacked yesterday from overseas. Are you seeing an increase in adoption of your technology because of AI?

Gerardo DaDa

The reason why AI is more interesting for us as a technology adoption, as you pointed out, is because most companies are building a dependency on those AI systems. If you're a bank and you have a chat agent that is based on chat GPT to provide customer service, if chat GPT stops working for you, you don't have customer service. You need to monitor chat GPT, understand how is chat GPT behaving for your bank, have a resilience plan where if chat GPT is down, then you can switch over to something else and being able to act on that very quickly. That's kind of the systems we're doing. We're also helping companies that have very large, complex clusters of servers to deliver on that AI, monitor that technology as well.

Josh Rubin

What are you monitoring specifically?

Gerardo DaDa

You can monitor the response times. You can monitor that they're actually giving you the right answers. You can monitor the connectivity between AI systems. There's something called the MCP servers that is kind of the integration point between AI systems and other systems. You can monitor that your MCP servers are working. You can monitor inner workings of an AI system, like those clusters of servers and databases and systems. End to end, because everything's based on the internet and what the company does is internet performance monitoring, we monitor all that connectivity and that all those systems are working as expected.

Josh Rubin

Are you simply monitoring ... There are expectations that they have. This is what normal operations looks like. You're monitoring, this is outside of the mean, it'll hurt somebody.

Josh Rubin

Is it looking or is it able to detect malicious attacks, things of that nature? Is it operating as a cybersecurity like?

Gerardo DaDa

It's not a cybersecurity system. We only play in security in terms of detecting hijack attempts when somebody's trying to steal your DNS or your BGP or some of the basic foundational things on the internet. What we do is basically first alert you what is the user experience and then determine the root cause. A great example happened with Walmart. I don't know if you remember back in December of last year,

Gerardo DaDa

Azure went down, AWS went down, then then Cloudflare went down. When Cloudflare went down, it impacted a lot of businesses because they put Cloudflare in front of most of their IT, other technology.

Gerardo DaDa

The difference was in some cases, if you're not paying attention to how Cloudflare is behaving, companies will have downtime because things will stop working. Everybody's in IT, they get their beepers going off, they go into a war room, they're trying to figure out what's wrong, take them two or three hours to figure out what's the problem and solve it. In the case of Walmart, one of our customers, they get an alert, "Hey, your systems are down because Cloudflare is down, reroute them." One command, reroute traffic to another origin server, and the downtime they expected was 30 seconds. They even thank this publicly for doing that. We see that all the time with our customers. Amazon, Azure, cloud providers, hosting providers, banks, et cetera.

Josh Rubin

Shook and gears a little bit.

Josh Rubin

You've obviously, you came up from a young age and been playing with technology, you've seen technological shifts before.

Josh Rubin

With the shift into AI tech, same difference, how are you feeling about it?

Gerardo DaDa

There's three aspects of it. Part of me, I'm a bit skeptical in the sense that, "Hey, AI is going to replace everything we do, everything's going to be automated and magical." Well, I see all market is still very busy. If this was true, we'd all be hanging out, taking time off because our AI agents are doing all the work we needed to do and we should be worrying about next generations. There's a real concern about apprenticeship. For example, surgeons,

Gerardo DaDa

you go from ... You go to school and then you're operating with a robot.

Gerardo DaDa

There's no apprenticeship of standing next to the surgeon as part of a team and learning by doing.

Gerardo DaDa

That's going to be something as a side we need to figure out. That's the first part is maybe skeptical. The second part is,

Gerardo DaDa

I think it's going to be fundamentally transformative for everything. I don't think anybody knows what the future is going to look like. I think if three years ago you'd have asked people, "Hey,

Gerardo DaDa

AI is going to be able to write a white paper for you," you'd be thinking that's crazy. Obviously, there are some roles like content writing that are more at risk than others. I don't think anybody can see five years into the future. I'm a big U2 fan. It's almost like they have a song where it says, "You're thinking about a place. You're packing your suits to go to a place you've never seen, a place you have to believe, you have to have faith to believe in that even exists." That's where we are as a society. The last part, which is in the middle of the two, I was listening to Neil deGrasse interview. They said, "Well, if you think about computers back in the computer revolution that you and I were part of, a lot of people were concerned like computers are going to do all the work, then what are people going to do?" Now computers are everywhere in everything. You have sensors and computers in your phone and your car. My car has probably 150 computers inside, and we still are busy and there's still more problems to solve and there's still more interesting things to do. It just enabled us to bring our thinking one level higher.

Josh Rubin

Last question.

Josh Rubin

Obviously, talking about AI and talking about busy, replace everybody? No. No. We'll find something else to do. It may solve a problem, but there's an infinite amount of problems potentially to solve. For your company, for you, has it changed how you hire, how you build a team, what you're looking for?

Gerardo DaDa

The first thing that's changed for me is that it makes it easy to distinguish the people who are comfortable in their job and the people who are curious and they want to get better and they are experimenters. That's the people I like to hire my team. You ask people how you play with AI, what are you doing with it, what are you found that is interesting? That makes it very easy to find people who are different. I've seen people who are like VP level people who they need to bring a marketing plan and they send me something straight out of chat GPT where you can see all the emojis and the lines and the formatting. It's like, "Come on, you're a VP, really? Just didn't even read it?" I see this from a lot of teams are just being lazy and just taking the output of chat GPT versus the people who think chat GPT is going to be making me better. It's a sparring partner. You bounce ideas. You hit, "What about this? What do you think about this?" When I do that myself, I find that maybe 60% of what AI recommends is bad, but the other 30% is really good and makes me a better marketer.

Josh Rubin

Good.

Josh Rubin

Actually, the marketing, no, the history, yes. I say that because it's about opportunity in this space. You came up from a state of Mexico. You end up moving here. Do you see this technological shift providing more opportunities for other people in any particular place, time, coming up like you did? Our company obviously, we hire in 10 different Latin American countries. That's where we see the growth happening. Where are you seeing the opportunities in this economy?

Gerardo DaDa

If you think about AI, AI consumes everything that is out there.

Gerardo DaDa

The problems that people have solved, AI is really good at solving and commenting on that. Write me an email. There's so many emails out there they can learn. In fact, AI will send you an email, produce an email that looks like every other email out there. It's like repeating, it's like a reflection on the conscience of the world. Whereas the value we bring is being specialist and bringing unique knowledge to the world. The more specialized, the more focused, the more deeper knowledge that you bring, the more opportunities you're going to have. The world is getting flatter with AI. With COVID and technology, it really doesn't matter where you're located anymore, for the most part. I think people who embrace that idea that you need to be an expert and in the case of marketers, bring the knowledge of how customers think and being expert in your customers, I think that's going to be a secret sauce that's going to make people more successful.

Josh Rubin

The skills that have had a win for friends and influenced people has always been a mark of success. Does AI make it easier for people to do that or less likely? Maybe it's a matter of, you can't be mediocre anymore.

Gerardo DaDa

Mediocrity means that you're just, look at your inbox. We're going to get a lot more semi-personalized emails and spam calls and text messages that are all AI generated, which means they're in-personal. They're not really that personalized and they're not human. People who say, "Okay, I'm going to leverage AI, but I'm going to make this human really personalized and really connect with people at the human level," I think those are going to be the people who win. As a marketer, it's so easy to produce large amounts of content that is meaningless and doesn't really have a point of view that the more that you have interesting and valuable content that really explains a point of view in the way that AI is not going to be able to do that, I think that's going to win from a company perspective as well.

Josh Rubin

Can you generate uniqueness at scale and marketing messages at scale in that way?

Gerardo DaDa

No. You can generate uniqueness on your own build. What we did at our companies, we listed what are our point of views that we think are unique and are valuable for the market. For example, we have this concept called value-based observability. I was just talking to somebody this morning and I listened, so I love this idea. Once you have that concept, AI can help you explain that same concept in different channels, in different formats, great explainers, great videos, right blog posts, derived content, but the original ideas need to be original and need to be human.

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