← BACK TO PROFILES

Dileepan Narayanan

Chief Product & Technology Officer·Afiniti·San Francisco, CA·

When coding is commoditized, judgment wins

Dileepan Narayanan

The single quality that becomes the most critical is judgment. The AI is sometimes too eager to please, and it tells you it's complying with your request when there are parts it's actually not.

Dileepan Narayanan is Chief Product and Technology Officer at Afiniti, a company that builds predictive and agentic AI for enterprise contact centers. Afiniti's edge is what Dileepan calls the canonical through-line: connecting customer engagement data with outcomes data, both on the call and long after it ends, so its models can pair every caller with the agent best suited to handle them and predict which decisions actually lead to resolution, retention, or a sale. The company has been building world-class machine learning models for twenty years, long before the current agentic wave. At Afiniti, Dileepan holds a dual product and technology mandate, leading an organization of roughly 300 across product, engineering, applied AI, technical program management, and customer success.

Before Afiniti, Dileepan spent nearly seven years at Amazon, where he led the launch of generative AI applications for Amazon's global selling community and product teams across the Alexa AI and AGI organizations, shipping innovations like Teachable AI, Alexa's personalized conversational AI, and multimodal learning for Astro, Amazon's home robot. Earlier, he held senior product and engineering leadership roles at Ruckus Networks, Broadcom, and Cypress Semiconductor, building IoT platforms and market-first wireless and touchscreen technologies. He joined Afiniti in 2025.

Dileepan believes coding has been commoditized, and that this reveals where the real work now lives. When a prototype takes a week and production takes four to six, the bottleneck is no longer the software development lifecycle; it is the coordination around it, the meetings, reviews, and alignment. His answer is small cross-functional pods of eight to ten, where a product manager, UX designer, architect, AI modeling architect, and evals expert build together and roles collapse into builders without functional expertise going away. The quality he screens for above all is judgment: AI works like a junior engineer that is too eager to please, telling you it complied with your request when parts of it quietly did not, so someone has to know where to go look.

What drives him now is staying hands-on. In today's world, he argues, CTOs cannot afford to be a step removed; everybody needs to build, because that is how you learn what looks good on paper but does not work. His focus is on writing the principles and charters that guardrail AI, teaching it his first principles so it thinks simply, and designing products for the least cognitive load rather than the most impressive spec. And he is optimistic about the pipeline behind him: college graduates are native to these tools, their learning curves are infinitely accelerated, and he thinks we are selling people short if we bet they will not adapt.

Read full transcript of interview
Dileepan Narayanan

So I'm the chief product and technology officer of a company called Afiniti. Afiniti is a company that builds state-of-the-art predictive and agentic AI, enabling enterprise contact centers to amplify their internal investments through additional sales and retention opportunities.

Josh Rubin

So the contact centers. What do you mean by that?

Dileepan Narayanan

So contact call centers. So you call customer support. Somebody, an agent, picks a call at the other end of the line. Today, it's a human agent. It's increasingly transitioning to an AI picking up your call at the other end of the line and escalating to a human as the need may be. So that's where we've linked overall.

Josh Rubin

The new phone tree is now actually, in many ways, being an agentic AI answering questions. A lot of swearing, I imagine, that's happening occasionally with those agentic systems. That ever so slight latency is what drives people crazy, I imagine.

Dileepan Narayanan

That's right. And it's very interesting because there are workarounds for those latencies. So when an agent is looking up information, you could say something like, give me a moment. There are ways to mitigate the latency through the customer experience. We're getting to a point where the underlying technology is largely robust right now. Where customer support organizations are falling short is in the CX. It's ensuring the right customer experience, where an agent can actually earn trust with the customer. It's the agent being able to think like a human. It's the agent being able to have the context to figure out which of its decisions will actually lead to the resolution of the issue or a successful confirmation.

Josh Rubin

Is that a data issue? A call tree is deterministic, but this is probabilistic, because you're talking about how many different ways a person could react to the system. So how are you starting to fix that problem?

Dileepan Narayanan

It's a data, context, and decisioning issue. Ultimately, when you talk to a human, a human knows where to go look up the data that's needed across all of these different siloed data elements. A human also has the context on what you are, what your persona is, what your demographics are, what you're likely to say, what your frame of mind is likely to be when you call about an issue. And most importantly, a human knows what to do to close a conversation, to retain you as a customer, to upsell you. These are the things that an AI is not yet good at. And it's not because the agentic capabilities are lacking. The underlying technology is actually getting to a point where it's becoming increasingly robust. It's just the fact that the underlying data systems are so siloed that the data systems don't talk to each other. And it puts a lot of burden on implementing the AI right. So the application layer and the user experience layer becomes of parallel importance.

Josh Rubin

Because the data layer isn't there. Do the call centers simply need to move all of the data on prem to attach to the thing? Will that fix some of these problems?

Dileepan Narayanan

That's a big part of the problem. So some of the data is on prem. Some of the data are spread across CRM databases to contact center platforms to interactive voice response and voice agent systems. So there are multiple systems that don't talk to each other. And it's these silos that break the cameras apart.

Josh Rubin

And how are you breaking down some of those silos? I think about if you're all getting into, what is it, ElevenLabs, and using that for voice training? Well, that's one system. But you should be able to pull some of that stuff in locally so you don't need to access a third party for something like that. Is that the goal? You just bring more and more directly in-house to connect via direct connection as opposed to API over the cloud?

Dileepan Narayanan

So a big part of what Afiniti does and does really well is it's able to connect the customer engagement work streams, the customer engagement data, with the outcomes data. So we have state-of-the-art predictive AI models, which are able to connect customer engagement patterns to outcomes, both short-term, like on-the-call outcomes, to longer-term outcomes, in terms of what customers do after they hang up. Do they survive as a customer, or do they go find somebody else? So Afiniti has the through-line that is able to connect across this journey. And it's this canonical through-line that helps us build a very robust predictive model, where a model is able to make decisions and predict the outcomes of those decisions very robustly.

Josh Rubin

That's interesting. You have enough data to take what you think is probabilistic, but it's actually increasingly deterministic. If you react this way to this situation, there is an 80% chance of this resolution, because you have enough data to back that up.

Dileepan Narayanan

That's right, for customer implementation. But the data conversation is so nuanced. You look at large enterprises, they do not want data to leave their premises. They want total control over their data. So what we've gotten really good at is building models and model workflows that can quickly learn the setup within a customer, within a client setup, on the fly. And while safeguarding a client's data, we're able to very quickly train these models to predict very accurately in terms of what engagements would lead to what outcomes.

Josh Rubin

In real time?

Dileepan Narayanan

In real time.

Josh Rubin

That's fascinating. I think about that. Basically, you hash out, to a certain extent, the proprietary data, but you're able to then get the model to train up real time. This person's acting this way. This is what it needs to connect to. You don't need to know exactly what's happening here, but it's close enough. That's really interesting. As a CPTO, you're thinking very deeply about product all of the time, which means you're thinking about your customer. Is your customer the call center, or is your customer also that person on the end of the line that's their customer, ultimately? How are you thinking your way through that?

Dileepan Narayanan

That's a great question. So our primary customer, the people that derive the most economic benefit from our solutions, are the call center business owners. They pay the bills, basically. But it's so hard to decouple the client from the end customer, because the client succeeds when they offer a bar-raising customer experience. So the conversations all, they're two pieces apart, as far as we're concerned. So we look to amplify a client's ROI while ensuring a bar-raising CX, which enables them to go approach their customers better, improve the quality of their interactions, improve sales, retention. It all starts with the experience being trust-earning and bar-raising.

Josh Rubin

It's interesting, as I think about this, because yes, the agentic engine of your talking to an AI voice chat is fine, but it's secondary. It's actually not the interesting tech here. The interesting tech is actually using those real people as data points with real conversations that you can then feed into the thing to come to the conclusion, this is how people behave. This is how actions behave. Now, once people are using their agents to talk to other agents, that will change the game again. I imagine you guys have been deep in machine learning and deep learning since before all of these agentic systems, yes?

Dileepan Narayanan

Way before. So we've been building world-class machine learning models for the last 20 years. And the way Afiniti built its market leadership is by building what we're calling agent-to-customer pairing, whereby we optimize for the agent that we have fronting a customer call or a customer contact. So we ensure that the best agent is put on to handle every customer, to improve the outcomes for the greatest number of customers calling in. And that's how we improve the ROA of the business overall.

Josh Rubin

And because you've been doing this for so long, unlike a lot of newcomers in this space, you have guardrails already implemented. Not because you're regulated, but simply because all of your different customers are so protective of their data sets. How have some of these new tools, the Claude Codes, entered into your current workflows? I imagine this increased productivity, the ability to ship more product, but in general, how are you incorporating them?

Dileepan Narayanan

That's a great question. So Infosec and legal priorities are at the top of the technology. The reason we've been so successful in building this end-to-end view of the data is that we've figured out a way to address Infosec from the ground up, information security from the ground up. So as we think about bringing in AI tools like Claude Code, we're very deliberate in instituting organization-wide policies where any of the data that we use to improve productivity cannot be sent out of Afiniti service. They cannot be used for model training, for example. And so anything we develop is primarily data but Afiniti-deed-dense. It's just like an engineer developing code, and nothing leaves our code repositories, for example. And the other part of it is just the productivity, and all the code that's built ships in the same manner as human-built code. So there's nothing different about AI-generated code that we ship out today.

Josh Rubin

So you're still, I mean, it does mean the bottleneck moves. You're still having to QA all of the code. You have a human in the loop going line by line and validating this stuff, or are we entering into kind of the compiler era where we say, "It's probably fine"?

Dileepan Narayanan

So that leads us into the whole discussion about how we're implementing AI. So a couple of points. One, when coding gets commoditized, when the operationalization of coding and even the thought process of building products has gotten commoditized, all of the conversations are around, how do you build the right product? How do you have the right checks and balances? And how do you ship with velocity yet preserving the CX in a trust-earning model? So we have a bunch of guardrails right from ideation through shipment to ensure that what we're building and shipping is far from the AI slop. And so we're very intentional about the process. So right now our organizational structures are a lot more multifunctional and a lot flatter as well. So just the process from ideating from a customer feature request or an idea to getting through to a prototype happens in a cross-functional pod which has a product manager, a UX designer, an architect, an AI modeling architect, and QA and an evals expert as such. So the whole thought process is multifunctional.

And there's also been a horizontal collapse across the roles where everybody's a builder now. The differentiation between who's a product manager versus who's a UX designer versus who's an architect is kind of collapsing down the horizontal. But at the same time, it's a fallacy to assume that the functional expertise is going away. And these are realizations that people come to as they build, right? Where right now the role of the UX designer, for example, has changed from actually doing the design, implementing the design, to actually telling the tool what a good design looks like. And the same with a product manager.

You have machine-readable specs that are getting put out by these AI tools. You have machine-readable business requirement documents. You have machine-readable design documents, design artifacts. But the real differentiations are going to be around, where's the intentionality in the product? What product are you building and why? And how intentional are you about the process? And how do you ensure that the process itself is good enough where you ask for a product and you get exactly that, to the specifications you asked for, without a drift in scope, without a drift in specifications or a drift in the customer experience. So it's that end-to-end process and the checks and balances around them that would differentiate a good product from a bad product. And a simple example is today, when organizations write documents and they communicate, you're now moving to a world where you ask the AI a question and it spits out a 60-page requirements document. And the way people end up reading it is they are unable to deal with the cognitive overload. So they end up sticking it back in AI and getting it summarized. So there are two AIs talking and the humans in the middle, right? So when this happens, the conversation's not about how complex a product you can build. It's about what product will actually serve its purpose in the simplest manner with the least cognitive load to humans with the right pace. So the conversation's very quickly evolved from what looks great on paper to what's actually useful.

Josh Rubin

This is the first time in any of these conversations I've done that somebody's brought up the cognitive load of the end user. And that's an incredibly important bit of the thought process here. And that has not occurred to me before. But yeah, I think about my own usage in it and what it spits out and everybody dealing with this fact. Cognitive load, we have a limited amount of RAM in our own heads and AI is constantly overloading it. How are you attacking things? Has that always been part of your process for product development, or is that just an increasingly important part because of these new AI tools?

Dileepan Narayanan

So our processes are heavily guarded. So I've quickly come to the realization, I think in today's world, CTOs cannot afford to be hands-off at all. Everybody needs to be a builder. And I can clearly see a difference in the industry. You're clearly seeing a demarcation between people that actually use the tool, get their hands dirty and build, versus people who are a step removed. And to me, that is gonna make all the difference tomorrow. As I'm building, I'm coming to very profound realizations on what looks good on paper but doesn't work. For example, something as simple as what a business requirements document is or what a product requirement document is, it's just changing immensely.

If you tell AI to build a thing, unless you're very specific and intentional in the definition, and until the definition is shared across the product spec, the UX spec, the architectural spec and the AI spec, AI is gonna build whatever it thinks is right. And it sometimes takes the agency to simplify things and make decisions on its own. And some of these decisions are honestly latent and transparent to the user of the tool. And so the BRD as a contract just changes. The requirements document, the contract, needs to have the right through lines between what a product manager thinks, what a UX designer thinks, what an architect thinks, what an AI modeling architect thinks, what a QA person thinks. And what defines good or bad, like the QA around it, the unit tests, the evals, the acceptance criteria. So as you define multiple aspects of a product, this granularity needs to come through, this through line needs to come through with every aspect of the product. If it doesn't, AI is going to end up making its own assumptions and simplifications. And then you end up spending a lot more time undoing what you've done.

Josh Rubin

We're in this era currently because we're so early into it that we are not optimizing AI answers for actually how humans consume information. My background is in news. Now, I've also thought about the different ways news is delivered to people. Print, radio, and television. And for information density, print has the most, in just pure, raw information. But you have to think about it all the time. Then there's radio, which is theater of the mind. You're listening to something, and that's a very different experience that you're having with it and how you process that information. Versus television, which is a very passive experience. AI spitting out an incredibly long answer to an incredibly short question is absurd. And of course it's causing everyone anxiety. So if you're thinking about your end product user and you're developing product, I was trying to think how we solve for this cognitive load issue, and are enough people thinking about that from the end user perspective?

Dileepan Narayanan

So the amazing thing about today is the agency to build anything is there. And so what would make a product really bother me is the ability to go simplify, where the AI is going to build just a whole lot, which is too much cognitive load for humans. So a lot of my focus these days is in building the right principles, it's in building the right reviews or charters that guardrail the AI, that tell the AI what is a simple UX, what's a bar-raising, easy-to-use UX versus what's complicated. And the amazing thing about AI today is not everybody's version of the AI tool is going to be the same. I'm finding as I'm building that these tools are adapting to how you want to build. So every time you go ask it questions, every time you tell it to fix something, it's adapting, it's prophylactically applying those fixes the second time it does it. So I see a world where the real A-team builders are also going to build versions of these tools that are going to increasingly think like that.

So as people build more and more, as their habits, as their best practices get codified into how the agent actually functions, how the agent actually makes a very logistical decision as it's building products, as it's building code, then the emphasis is all about how do you teach it the right practices? How do you keep it from straying? How do you impart your first principles whereby it's thinking simply, like you? That's where a lot of emphasis needs to go in terms of the building.

Josh Rubin

And how you think impacts how it thinks. I think out loud, and I've often found the conversations I have with Claude in my car are far more interesting and illuminating than any text conversation I can possibly have. It's super interesting. We're going to pivot here, we're going to stay here forever. How big is your org? You're handling product people, engineers, all of that. How many people do you have working for you right now?

Dileepan Narayanan

Yeah. So I have a dual role in terms of being the CPO and the CTO of the company. So I manage product engineering, applied AI, technical program management, and then I have a customer success, product success org as well. So that org is close to 300 people right now overall.

Josh Rubin

And you're podding, it sounds like you podded out, which means you're optimizing for thoughtful conversation amidst those people. We're obviously hearing things about 8,000 at Facebook, and 14% out of Intuit, and all of this down. It sounds like increasingly, yes, the enterprise people are doing what enterprise orgs do, but at a layer below that, it's not that they're firing, it's not that they're hiring either, it's that they don't necessarily know what to hire for yet. And so they're just kind of waiting to see where things net out. If you had kind of infinite money right now, and you could hire exactly the kind of people you need, who would you be hiring for right now?

Dileepan Narayanan

That is a great question. So through my own journey, I found that at this point, more people does not directly translate to scale in terms of what you build, what you ship. And in fact, when coding's become commoditized, if you're able to elucidate your idea very clearly, and you're able to build products, and you're able to turn out prototypes in, say, a week, and you're able to take products to production in, say, four to six weeks, at that point the code generation, the building, the operationalization of the software development lifecycle is no longer the bottleneck. The bottleneck occurs amidst all the coordination that happens, all of the reviews that happen, when people need to pick up the phone and call each other, or set up meetings, set up review boards. It is all the coordination that's actually taking more time.

And if you have larger than ideal engineering teams, you're in a situation where engineers are aligning with engineers on architecture and the sessions, trade-offs, and that's potentially going to take a lot more time, versus the time they would actually take to iterate and build the final product. So I think the size of the pod becomes the most deterministic quantum at this point. And ideally, it's going to be a right-sized pod where you have functional experts who are able to view every part of what the tools are providing. If you have a product pod with product managers, engineers, architects, AI architects, and a UX designer, once you have the functional expertise, the ideal size of the pod, that's going to be, to my mind, if you're looking at a portfolio with some legacy products as well as new products that you're building from scratch with AI, I think a pod of eight to 10 should be able to build the product ground up with optimal coordination, where people coordinate when it's necessary, but they're not wasting time aligning on decisions. And there's this healthy balance between moving fast and moving with clarity. So when that happens, and when companies can build products in a matter of weeks and months, then ultimately, a lot of the investment is about how do you build a channel with your customer base.

Josh Rubin

Well, it's also, they can build a product within hours and days at this point, so it almost feels like the sprint is shifting to the conversation, the validation. We built the thing, does it do the thing that we need the thing to do? That's the time that's being spent, that argument. And are you then optimizing for particular personality traits within the pod? And what are those traits? Is it ability to deal with increased cognitive load, resilience, for example, or curiosity, or ability to manage chaos and pivot and iterate? I think about what an engineering org was in yesteryear, with a long-suffering product person that was all about taste, and then a slightly autistic engineer who was logic-driven and could go into the thing. That's not the org of the future, it feels like.

Dileepan Narayanan

No, it's not. I mean, you can think of these AI tools. These AI tools are pretty smart and doing really well out of their tasks. And so it's almost like everybody has a junior engineer at their disposal right now. If you tell a junior engineer exactly what to do, that person will do a great job of it. And today you have AI doing the same thing. So the single quality that becomes the most critical is judgment. You need to be able to look at what the AI is doing. Sometimes the AI is too eager to please. And when you tell it something, it automatically assumes your point of view and it tells you that it's complying with your request. But there are parts of your request that it's actually not complying with. It's simplifying, it's building initial prototypes when it's telling you it's done a full audit. So the conversation sometimes falls through the cracks. And so it's critical for somebody to show the judgment at every point of the conversation to make sure that nothing gets lost in translation. So it's almost exactly like working with a junior engineer with whom the jury's still out for you. You're still forming an opinion of whether they're a trusted person, how often do I need to inspect the work? And so you need somebody with high judgment. And to your point, you need somebody who can absorb the cognitive load. Because there's so much code that's being generated right now, to an earlier point, no human's gonna be able to view thousands and tens of thousands and hundreds of thousands of lines of code. So you need somebody with the judgment, increasingly, to figure out where to go look, where the AI might most likely be right, and where do you need to go inspect.

Josh Rubin

Are you worried about, I mean, when we're using AI for junior engineers, that means you don't need junior engineers anymore. Judgment is a learned trait, it's the acquisition of wisdom. The only way you get wisdom is by, by and large, screwing up a bunch of times, which is that junior to senior pathway. Do we still have a pipeline of those people coming through in this environment?

Dileepan Narayanan

I think to say that we won't need junior engineers is not the right framing. As we've hit the agentic AI age, already information access is at your doorstep. And right now, with these AI systems, you have curated information that's been delivered right as you type a prompt for it. And so learning cycles are also getting immensely accelerated, even as the tooling to go produce artifacts or to produce information is available. So the way I think the world will evolve is that college graduates who come out, their learning curves will be infinitely accelerated. I think we'll see a lot more high-judgment people coming through the ranks a lot quicker. People will start using these AI tools earlier, which means there'll also be the familiarity with using these tools. These college graduates now understand the way to use these tools much better than anybody who started using the tools later in the game. So I think the availability of expertise is gonna shift, the profile is gonna shift, I think we're going through the shift right now. I see college graduates around me, and they're just so much more proficient and so much less resistant to using these tools versus people who've been in the industry for a while. So the skill of acquiring judgment is still a skill that's up for grabs. And your own equity as a person is being evaluated every day.

Josh Rubin

It happens anyway, so that makes a lot of sense to me. So the fear about juniors going away is actually born out of a senior or an executive transporting themselves back in time and asking themselves, if I popped up tomorrow as the 20-year-old I was, in this environment, no one would hire me. Well, of course no one would hire me. You're a time traveler, you're crazy, but you're not native to the space. These guys, they are. You need to give them more credit than you're giving yourself at this point.

Dileepan Narayanan

I mean, the world's been through multiple cycles like these. At some point we did not have physical help. And then machines were invented. And people became smarter in terms of learning how to use these machines and how to become an order of magnitude more productive. And the same thing's happening where mental work is getting outsourced, right? And at some level, people are going to adapt and figure out how to use these tools to turbocharge their capabilities. I think we're selling people short if we think people will not adapt and find new pathways to get on top of what they need to do.

GET INVOLVED

Be part of the
conversation.

Whether you're a CTO who wants to be featured, a company looking to sponsor, or an engineering leader wanting a seat in the room — there's a place for you here.