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Product pioneer, navigating innovation and impact

Fail Faster

Episode 446


30 minutes

Elio Damaggio is a product leader with over 15 years of experience in cloud computing, IoT, and AI.

Currently serving as the Head of Product for AWS in the Next Generation Developer Experience organization, he is building new ways to empower software developer teams with AI. Elio began his tech journey as a product manager at Microsoft, where he worked on Azure Mobile, IoT, and big data services. At Microsoft, he amassed an impressive portfolio of 11 patents, all related to cloud technologies and IoT. Elio’s passions extend to gaming, where he enjoys RPGs, strategy games, and adventures. He’s also an amateur musician, wasting time writing songs with his acoustic and electric guitars.

Podcast transcript

Khushboo: Hi, Elio. Welcome to the Fail Faster podcast and happy Friday. 

Elio: Hello. Hi, Khushi. Happy Friday. How are you? 

Khushboo: Pretty good. Thank you. Awesome. I’m super excited to be talking to you today. And thank you for coming on the show to talk about the cool stuff that you are doing and your experience. Also pretty much around product management and AI. You know, that’s the talk of the town. And we have a very interesting topic here. So I’m super excited for the conversation. But before we get into that, why don’t we start with a quick background. So let’s kick it off. Like, you know, where were you born and raised? What was childhood like? And what are your family dynamics? 

Elio: Absolutely. So I was born in Rome in Italy. That’s where I grew up. I had all school and I got my master’s degree in computer engineering in Rome. I worked for a couple of years there as a software developer. And I was really attracted to more technical endeavors and like really getting deeper from like Italy, we’re very far from where big tech and where technology is being created. So I definitely had an interest in that. My route for that was flying for a PhD. And that’s how I got in the US. I got into University of California in San Diego, where I got my PhD in computer science. And I also met my future wife. So that’s how I got to the US. It was my path into technology. 

From my PhD, I interviewed with all your big tech companies, your Google, your Microsoft, your Amazon, Yahoo at the time. I’m really dating myself there. But you know. And one of the things that I did there is that instead of taking a software engineering role, which was what was expected, I went for program management at Microsoft, which is this kind of role that’s in between product management and program and technical program management was kind of a in between role, but was more was definitely closer to the customer. The idea was that how are the users going to use your software, how you should build it, I was really attracted to that part of the of the business. 

So I went up and I did this kind of strange transition from like super deep technical PhD in computer science stuff to product management kind of role. In Microsoft, I spent a long time in nearly 11 years, all of them working in cloud computing. I was in Azure mobile. In 2011, I had like a Mac issued by Microsoft at the time was a really strange thing. My team was the one that went to did the news because we were we did a big presentation with a Mac on stage at a Microsoft conference that was really strange at the time. Maybe some people right now wouldn’t think of that at the time, it was really strange. And I went on to to do some IoT data services. And that’s where things started becoming related to AI. 

And in the last couple of years, I moved to AWS focusing on AI cloud products. That was an intentional transition. I was playing with AI for some years, then this whole like, chat GPT and DALI and all of mid journey and all of these things came out and things kind of really blew up. I was I was, I was really surprised by that. Although I remember playing with GPT 3, kind of the predecessor of chat GPT, and going to my walk, and I basically said, look, this is ready. It’s coming. And my daughter was chatting with like before chat GPT was chatting with Legolas. She’s a Lord of the Rings fan. 

Khushboo: Oh, wow. That’s interesting. So, you know, I know like how you know the story, like how you got into technology, you know, after you’re like, after growing up in Italy, but what exactly fascinated you to be in technology? So what was the inspiration when you were growing up? Like, how did you decide that you want to be in technology at first place? 

Elio: Yeah, I mean, that’s, that’s strange. I mean, both parents are electronics engineers. So I kind of grew up in a household where it was very much about technology. And I think that it was kind of, it wasn’t as popular as it is right now, especially in Italy. Italy is much more as a country oriented towards humanities, literature and history, philosophy and doing things such as physics and computer science are kind of not really very popular. They definitely were not popular when I was a kid. The whole, you know, like, nerd kind of thing. 

It was something I definitely grew up with that. I really liked video games growing up, not too much, but enough. And then I saw like, slowly, all the various things that could, that could be enabled by that, like being able to write a book with a word processor. I mean, I was a kid in the 80s, couldn’t do that. I mean, you had to write things with a pen and paper, being able to have a word processor and print something was really cool. You can write a story and it looks like a book. And then there was image editing. And it’s like, oh, you can take a picture and change this thing, and then you can print it out. 

And, and then things became possible with music. And I have like a big interest in music. And then you could do things with music. I remember the first time that I heard that MP3, I was like blown away. It’s like, what do you mean? Now you can have music that comes from the computer and then you could make music with the computer. Everything was like really coming together. 

And that basically made me want to study engineering and you know, computer engineering, and and kind of go deeper from like that perspective. I had other interests growing up. I consider doing things such as philosophy as a major in college. I didn’t end up doing that. I kind of thought, hey, if I want to read about philosophy, I can do it on my time, which I’m doing. But I ended up going with technology. In Italy, that wasn’t a great career choice, basically. That’s how I fundamentally got out after working for a few years. I said, look, this is not working. So I basically said, look, I either I had this kind of Hail Mary. And I said, hey, I’m gonna try to do this PhD in the US, which seemed like it’s far I mean, from Italy is a far place. And I said, Okay, let’s try to do that. And on the other side, I said, Well, you know, if that doesn’t go, maybe I’m gonna get, you know, business masters and do something more traditional in Italy. That’s that was thinking at the time. 

Khushboo: Awesome. So talking about your career, and you know, like the journey that you took, if I have to ask you, from where you started to where you are today as head of product at Amazon, what are like one or two stories that are your biggest wins? Something that you’re really proud of, something that gives you pride that okay, you were able to achieve that in your life. 

Elio: I would say that the first one has to be applying to the PhD program in the US. That’s definitely one of the things that really, really changed my life. I, I would, I would have moved to a different country, I would have never lived here. And I was closer to where technology is being developed. So there was deeply consequential. And one of the things that I consider it a win is that while it did take a lot of effort between like, taking all the tests and getting all the recommendation letters and making sure that that stuff happened and was in line, there’s a lot of luck that’s involved in those things. 

One of the things that I realized in my 20 years is that while there is this expectation or understanding is that, hey, if you work hard, and you do things, then you’re going to get the results. And while that is true, it is also a little bit of a numbers game, especially for things such as PhD program, you may have a specific concentration that year in a specific department that doesn’t have funding, so they do not have a spot for you. And that has nothing to do with what you did. So I consider these things a win. 

I can think that I’m partly responsible for being able to succeed there. But in the end, I also am grateful that I had the opportunity and that stars lined up. So that’s definitely one situation where like, you know, that’s a win. I’m proud to have done all the work and to have succeeded there. But I always am grateful because I understand that many things do not depend only on how much effort you put in and kind of realizing that. That’s definitely one part that I always think about. 

The second instance that I really consider a win was during my career in Microsoft, I had the opportunity to join this team that would then go on to become Azure IoT. And that was working on Internet of Things technologies. But at the time, it wasn’t sure that we would have had that opportunity. In big companies, sometimes project gets assigned to different teams and things may go your way or couldn’t. And at my level at the time, I had absolutely no say in what would happen. So I took like a big bet there that ended up being successful. And I ended up spending like six years of my career in Azure IoT. The team grew 100 fold in like, six years. So it was really, really great. Lots of experience, lots of career growth, working with amazing people. And my win there is really about taking a chance. And knowing that you’re taking a chance and not being afraid of it. Well, I mean, not being afraid, you probably are going to be afraid, that’s okay. But opportunities come about all the time. And sometimes you don’t have a lot of time to decide. And it’s really like important to take advantage of them when they arise. 

Khushboo: Yeah, yeah, absolutely. And I love that. I love those stories. And also, the last part where you said you take a chance, and in fact, our show is very much aligned to what you said, like take a chance and fail faster. I know you learn in that journey where it’s like, okay, you fail fast, you know, you know, you can bounce back stronger. So on that point, quick failure question, like if you have to tell me one epic failure that has also taught you what not to do. So you know, failures are part and parcel of our career growth and whatnot. But tell me one epic failure that you’d like to talk about. 

Elio: Well, one that first comes to mind is basically what we were talking about. I had an opportunity of some time where my manager says, Hey, do you want to lead this product? And I said, Oh, I actually like what I’m doing. Let me think about it. And then I basically lost the opportunity that went to somebody else. So it’s really about sometimes you don’t know when it’s going to happen. And that kind of, I don’t want to say that it haunted me. But I thought about it for a long time. And it’s like, now I’m dealing with it now. But as you know, it’s a few years ago. So it’s not like relevant that much anymore. But not taking a chance. It has to be something that has to be very intentional. 

You really had, you don’t want to be just caught off guard and just not making a decision. And then ends up being your decision. Yeah. So that’s definitely one fader. The other one that’s really big. It’s about people. Building software and applications and technology products, or honestly, products in general, it’s a deeply people-influenced and people-oriented activity. Even, you know, when you’re building software, when you’re building things that look very much like super technical and in the weeds, there’s a lot that goes into how people perceive things. And as a product management, you’re definitely required to think about users. But you’re also building the product with your team. 

And the effects that people aspects have on the work and on the final product are enormous. I have like this story when I was working in a large team, and it happens that there are reorganizations and teams are moved. And I was thinking about the product. This is obviously the best decision for the product, the best technical decision, the best decision for the users. And a big project that I have and a big kind of failure, I mean, I was able to salvage part of it. But I spent, I would say like more than six months trying to have something happen. And in the end, it didn’t happen because internally, the team wasn’t aligned. There were some people that did not agree with the vision, had a different vision, had different interests. And some of those things, it’s very hard to say what’s right and what’s wrong. You’re also like, you can be in very tense conversation. I remember this conversation where, you know, for privacy reasons, I don’t want to give too many details. But I ended up being in a room with this person that was very senior, and he was like borderline crying. 

And at the time, I was like, maybe like 35 or something like that. And there’s like this 50 plus old man that’s like really emotional, like talking about his team and what was happening and what in his mind I was doing to his team. And there are those aspects are really, really important. And it’s important to consider them in like trying to affect change, trying to build a good product, trying to achieve large results, you’re not going to achieve a lot by yourself. It’s all like part of a team and multiple teams, and multiple collaborations. So the people aspects are super important. 

Khushboo: Right, absolutely. I agree 1000%. And thank you for sharing, you know, that’s inspiring. Now, talking about like, let’s get into the world of product management. So first of all, what do you think how to become a PM? Like not the Prime Minister, but the product manager? 

Elio: Of course, of course, I was a PM in two big tech companies. And I have a lot of colleagues and I mean, ex colleagues that also work in other companies, but I have a view of a product management that is specific, mostly to big tech. So I want to put that out there so that people know how to interpret the things that I’m saying. There are multiple ways to get to product management. And every company has a slightly different approach to what product management is. First, you know, what is a product? In some companies is like, it’s a piece of software that gets sold. In other companies, it’s more of an experience. In other companies, maybe, you know, a service or a financial service or like things like that. 

So that’s, that’s very important. The kind of background that that you need can also change. Like in tech, you can find people that are coming from a, from a business perspective, and then they focus on aspects of product management and products for which the main value proposition revolves around business. And that is like very common. There could also be products that pertain towards people experiences and, and how they interact with, with a service. Think about like product management in a, in a company like Meta working on Facebook or, or Instagram. And then it’s really about how users are going to use it. And it’s very much about engagement and measuring engagement and, and having that feel of how people would use it and having like the analytical skills to, to be able to do it at scale. Very different is also B2B. So product management is really a very complex role because it’s not really well defined what you’re supposed to be doing. And I noticed sometimes you say, oh, you know, you’re the mini CEO of the product. 

That is really a strange definition because usually as a product management, nobody does what you want. And while it’s true that you’re like a CEO in the sense that you have a feel for the end to end, and you do not know the details of all the specific, all the specific areas of the products, you know, the technical engineering, the finance part, the selling part, and all of those things, you do not have authority. So the things that I would say, how to become a PM, a product manager has to be a leader. And being a leader is not something that people make you, but it’s something that you do. And I have many product managers that report to me, and I try to teach them that sometimes they have to be leaders. 

It’s like, I cannot go and tell other people, it’s like, oh, follow this person, because he’s the leader. It’s like, that’s, that’s not how it works. You have to have a vision, you have to be able to communicate it, you have to want to do what it takes, even if it’s, it’s not really clear. And those are like things that keep popping up. And you can get to that point from a technical and engineering, from like a sales or customer support position, think about customer success. Sometimes you have a good feel of what a customer needs. And you can grow into a PM from there, you can grow into PMs from the marketing side, get into product. So you can really get at it from like many, many places, but you really have to be a leader, which honestly is the opposite of telling people what to do, is that you do things so that people want to contribute as well. And just being able to deal with ambiguities and do what it takes. 

Khushboo: Yeah, yeah. And like, how crucial it is for product managers to develop a profound understanding of user behavior and also psychology, you know, when, especially when conceptualizing and developing products, and also how can this understanding be effectively integrated into the product management process? 

Elio: That is, that is a very good point. That’s why I was talking about like, understanding the people aspects of product management, because that’s true for users, that’s true for your colleagues. I believe it really comes from a place of empathy. You have to understand and really try to put yourself in the shoes of somebody that is trying to use your product. What are they trying to achieve? What is their real problem? And there are many techniques for it and people following this podcast, I’m sure they’re familiar with the, your jobs to be done and design thinking and all of those techniques. 

But it’s really, you have to be a person that is really interested in understanding what is the person trying to achieve and, and when something doesn’t happen, really try to understand why. And let me talk about a specific example. This is regarding AI, like I’ve been trying to integrate AI and products for a few years now. And one of the things that, that I keep noticing is that one little, maybe psychology, but kind of user behavior that is important to understand, is that, well, let’s talk about two, but the first one, let’s assume that you have some kind of product that uses AI and tries to solve one of the problems that you have. 

Now, if the product is pinging you, is saying, hey, what about this? And it’s kind of distracting the user or being a notification or like something like that. The product has to be, the precision has to be really high, because if you interrupt me and then you’re telling me something that’s useless or false, then I’m not having a good experience. So the bar for precision, if you’re pushing, think about notification or interruptions or whatever your user interface is, it’s really high. Instead, if you have a situation where you’re saying, hey, I’m a product that gives you insights on something that tells you things that may be, then the bar is a lot lower because fundamentally people look at it and say, hey, maybe I’m finding something that’s really cool. So you go, you open your box and sometimes you find something that is a really good insight that’s helping you. 

And the bar can be a lot less. If you want to talk numbers, because you’re a product manager, you have to think about that. You have to be like in the 80s percent precision if you’re bothering people. And you just have to be around, you know, maybe 20, 30 percent if it’s an insight. Because if I open a box and one in three times I get something really good that’s helpful, I’m going to keep opening that box when maybe I have a downtime or like, and I don’t feel bad if, oh, this insight wasn’t particularly great this time. But if I bother people, that has to be really, really, the precision has to be really, really high. 

Khushboo: Absolutely. So now, you know, like product management and AI, you know, AI is the talk of the town. And, you know, I want to know, like, how can product managers leverage AI driven technologies to gain deeper insights into customer behavior and preferences? And also, how does this data influence the development of more personalized and user centric products? 

Elio: Yeah, so there’s actually two aspects of this, like, like you were saying, on one hand is how do I infuse my product with AI? And on the other hand is how do I use AI to create a better product, even if my product has no AI in it. And lately, also, we tend to think of AI only, not everybody, but there’s a very much of a focus on generative AI or like chat GPT kind of creation. And there’s a lot of AI that is really not that and is more similar to very advanced statistics and classifiers and like an insights that are not generative AI, if you will. So if you think about how you can use AI in your product development lifecycle, or like when, when you’re like understanding things, there’s a lot of it is what AI can do for any kind of processes. 

And of course, everything starts with data. What kind of data do you have? Do you trust the data and that can be quantitative data, like, you know, I have my how many users and churn and adoptions and, and all the traditional product management metrics, they can be used with like understanding and doing segmentations and like things like that. But one of the things that maybe people may be interested in knowing is like, okay, there’s this old chat GPT thing and generative AI, how can I use to do that? Well, all of a sudden, you have an AI that understands natural language. And that’s huge. Because we used to have like sentiment analysis was very crude. 

People are happy, people are not happy. You can really start like summarizing user feedback, if you have a lot of user feedback in English words, you can start asking the AI to roleplay a user and saying, okay, I think that these kind of users have those problems. And this large models know a lot about what specific roles issues are, they read all of the internet. So if you’re targeting car salesmen, and what their problems are, when you know, they have a lot of inventories in their car lots, those AIs read all the Reddits that those guys put on the internet. So you can literally ask chat GPT and say, as a car salesman in this positions, what are your problems? And what about and you can have a lot of ideas. 

Now, it’s really, really good to use those technologies to help your creativity. They really are amazing at like, coming up with ideas that you wouldn’t come up with just in a very short, short amount of time. So I would I would definitely use for research, for customer research. Now that doesn’t end to understand like, natural language data that you may have lying around. The other thing, big thing is that you should start small. Yeah, it’s really easy to say, oh, big data, look at all this data that I have here, all of these things. And then you basically run in this big, big process to try to get amazing insights. And you just can your organization cannot absorb that there’s a matter of skills and understanding, and start small. 

And that’s usually where it’s really hard, especially if it’s a, if it’s a project that’s mandated, like top down is like, oh, we should do this big data AI thing. And I see a lot of customers of my products that are in that position. And all of a sudden, they have to create this infrastructure from nothing. And that’s really hard. So pilots, proof of concepts, starting small, and try to do something that at the beginning you understand, and it doesn’t matter if you’re not using the latest, you know, machine learning techniques, or the latest technologies. In the end, everything starts with data analysis, what can I know? How can I influence my, my process? And how can I go from there? 

Khushboo: Yeah, absolutely. Thank you for sharing that. It really was very, like, I think these are golden nuggets, I would say, like, you know, this is really great information. And you know, I wish we could talk more, but we should definitely do another episode because there was so much I wanted to talk to you about. But for today, before I let you go, if people want to reach out to you and know more about the work you are doing, where can they find you online? 

Elio: Yes, online, the best place to reach me is on LinkedIn. So Elio Damaggio, I usually I use that platform for like messaging, and I publish articles about AI recently, and mostly like AI trends for the future right now and related to product management. So they’re not too technical. This is really about how, how expected to affect what we’re doing. 

Khushboo: Awesome, cool stuff. Thank you for sharing. And thank you once again for coming on the show and sharing these amazing insights. 

Elio: Absolutely. Thank you so much. It was great. And thank you for the opportunity. 

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