 Hey everyone, this is Carlos. I am the founder and CEO of Product School and today I'm here with Piero Sierra Who's the CPO Chief Product Officer at Sky Scanner. Hey, Piero Hey Carlos, great to meet you. Pleasure to meet you. I'm so excited to have you. You know one of my favorite things to do is to Literally get to meet people who are building some of the products that I use every day I've been using your product for a very long time to book flights and hotels So, you know happy to put that to the name What's Sky Scanner? Well, let's talk about the the beginning because Chief Product Officer is a big title for a big company as well But how did you break into product? Well, I mean I guess going going way back I'm sort of American but I grew up in Italy in Brazil and as a kid just I love computers And so I taught myself to you know, write programs and games for fun just for fun But then and then after that I became a self-taught engineer and I did that for a few years professionally, but then I realized kind of needed a more solid computer science foundation So from there I went to a US university and where I got a degree in computer science and then in 1995 I applied for Job at Microsoft in Seattle and that was a great experience But during the interviews they you know, they do a coding interview They looked at my code and they said, you know, you should be a product manager which I assume is a compliment and if my code must have been so tiny and wonderful that they decided I should be a product manager to be honest. I had no idea what that was I just thought I'm gonna code for a living and they said actually, you know You probably better at PM and so they pushed me into that career track didn't know what it was And I also thought I'm gonna do Microsoft for a couple years And then I'm gonna do other things because I just figure I get some good foundations from that and Instead I fell in love with products and I told Microsoft to Microsoft is a great place to be and so I thought I would be there two years And I blinked my eyes a couple of times and 20 years have gone by I literally spent 20 years at Microsoft I made incredible friends there. I was married in Seattle had kids all that I worked on great products and things I You know into the Explorer. I guess that's fun now, but that used to be a product You might have heard of it and then I worked on windows and MSN messenger and a product called skydry Online pod storage all that was really fun. And then when Microsoft bought Skype You recall and then I must have been like 12 years ago or something But I moved to London because Skype was headquartered in London So I moved to London to run the Skype products team here And that was a ton of fun and a great education because Skype was a true start-up in the sense that Microsoft Obviously was not so I kind of got a taste taste for that and I really fell in love with kind of that start-up Mid-sized company approach to things After Skype I found a leader sky scanner and obviously the product a great product But I fell in love with with the company and the culture here sky scanner is just this kind of vibrant US style start-up And travel like it has an Asia and the different ways of doing things and it has a very it's a very ethical company it's got very good kind of European if you like ethics and Always putting the traveler first and our partners first ahead of even a revenue and things like that It's been very interesting, especially in industry the travel industry as you know, it's not entirely 100% trustworthy So it's nice to be the good price and it feels really great. So that's kind of what brought here Yeah So I have to ask this question. You said you spent 20 years of Microsoft in different roles and different products Now when is that that moment where it's like, okay now you're going to switch gears We're going to join a way smaller company like what was the status of the company a sky scanner when you join and what was your first title there? I so scanner was Well-established so it was already Startup that had I don't know maybe 20 30 million users at the time on a monthly basis It was a popular product that people used especially in Europe at the time. It was mostly European based The core functionality of sky scanner was very good, but the product was not the experience was not connected at all It was very disjointed. It was just it was just like a good back piece of code with a lot of a testing You buy on top of it and no brand no story no connection No consistency and a quite a limited feature set So I saw but I saw the team and I saw the team is so much better than the product Maybe help the product a little bit as and I when I joined I joined a sky scanner as a CEO director and then came with And then eventually chief product officer. So that was the path there I must say at Microsoft my you know and maybe as career advice or for other people that are doing this I look back on the 20 years of Microsoft. It was it was amazing time. I don't regret it But it was too long and I feel like I probably should have moved on sooner I saw it, you know your city for example You've had so many different experiences and I've really only had I consider them three And I don't feel like it's quite enough and there are definitely several years of Microsoft that felt the same Like I'm doing the same thing. I'm doing it Well, I'm not learning as much and so and it's always hard to jump into the deep end of the pool And try something new. I'm a conservative guy. So but by nature, I don't jump as much as other people do I'm very jealous of people who are just like every two years. There's like, let me invent myself Let me try something completely different. That's not been my path. But but I would recommend that path to people instead of mine Which obviously you mentioned that when you broke into product it was almost by chance because your code was you know I think let's put it this way that the employer had a different expectation. I'm also a frustrated engineer and How does someone go from being a good individual contributor? In product to eventually lead product teams as a chief product officer Interesting how do you scale up in that sense? Well, the the great so the the key definition of Product is a leadership function within, you know Engineering which is about building things and so and leadership is is a thing that you sort of There's a core that you probably have to have and that's probably what Microsoft signed me I you know, I joke about my code not as good as other engineer I'm sure that's true But I also think that they did see something in me that they said actually This is somebody that probably could be a reasonable leader and the thing about a Microsoft another company I think is common in the product journey is that we take Very junior people that are actually just coming out of college But we put them in leadership positions almost from day one like most for example most entry-level product managers will work with Seven or eight engineers from day one and those engineers can be like, you know 15-year veterans with tons of experience that know how to do things and somehow that product person is still supposed to Lead them not on everything. It's a it's a partnership But they are saying this is the problem space and this is how we're approaching and these are the priorities, etc so it's it's Officer core in in the army or something like that. You're looking for leadership And obviously there are people that naturally demonstrate some of that and other people have to develop it And there's so many different leadership styles and probably there's some selecting bias that happens there as well but and then so that's the entry level and then in terms of of You know moving on and getting promoted and then getting to eventually bigger and bigger things Well, there's so many different aspects of that obviously it's about being good at the job and doing it well and being successful it's also I think about maybe finding that balance between Being a good leader, but also finding ways to subsume your ego If you understand what I mean by that because you you want to be able to Set direct and guide people But you don't want to all be about you and I actually think that the people that are able to get results and Lead, you know groups of engineers to deliver great things that have no market fit, etc But that aren't it's not about them, but it's always about the team I find that they get promoted more often and at microsoft and You know the one thing I used to say of microsoft Thinking about it because I spent 20 years there seeing multiple people go from intern to, you know VP basically seeing people really getting people promoted across that path and one of the things I kept saying was It The justice will prevail in time Right, like the good people will rise to the top and you know, there might be one promotion cycle Where something unfair happens somebody doesn't realize that you were actually the key contributor for x and y Or and somebody else gets promoted that you think well that person's a coconut and how better than they are Whatever it is and passing over that it just is actually a negative spiral that will slow you in your career as opposed to if you're able to just Push that down not worry about that focus on results and focus on making the people around you great You know, that's funny, but I actually think at least in the companies I've worked on that actually works And I like that perspective especially in a world where it's a lot of turn around and as you mentioned some people are Switching jobs very often and I really admire people who are here for the long game who are focusing on like Really a 10 years from now type of outcome who are optimizing for a big win not just for themselves But for their team and I agree with you. I think product Requires to put the ego aside because in a way we're on the sidelines right like these days We have engineers designers marketers. They're supposed to get credit when things go well And in a way, I think we should also take responsibility when things don't go so well Absolutely So what does your day today look like? um Well, so in my case, uh, I need a product and our design team is actually grand and design Team so it's very large team. It's about 150 people At this scale and my job is mostly Organization right sitting broad direction organization structure staying aligned with boards staying aligned with my executive peers Setting targets, but actually I try to think of my job as much as possible as setting things up and getting out of the way You know getting out of the way of the product Leaders and the design leaders who should be making the real decisions of what we go do And I know that that can sound a little corny But getting out of the way and actually more importantly keeping the rest of the company out of the way Uh can be quite a hard balancing act, you know, we'll have some Revenue target, you know revenue was soft this quarter So we want to hit that and word wants you to hit that and company wants to hit that commercial team wants you to Hit that it makes sense. You want to do that. But actually Product or design team that is saying we need to go slower to go faster here We need to invest this can take three quarters for this thing to fly But once it does it's going to be great. Here's why it's going to be great. We have the hypothesis is valid We've tested it. It's real But you just need to give us nine months to get this done And so creating space for that to happen Ends up being a lot of my job. I also sometimes joke that my job is saying no, right like 90% of the time it's it's it's no and then 10% of time I can see yes stuff So that's that's a lot of it And then of course, you know Think about your priorities and the okr planning and execution process is a big part of my day But you you mentioned 150 people team and not just engineers but many different functions and and we've seen that There's not just one playbook. There's so many different ways a product team can be organized So how do you think about different work models and what have you found successful for you? No, that's a great question. I I'd love to hear your perspective on that question because you probably have been exposed to even more organizational models Me I can tell you at sky scanner. We we thought long and hard about different models We actually evolved our story a year over multiple years But the the core thing that we've done is first of all We've organized our engineers into squads and then our you know squads and the tribes pretty standard stuff But the the challenge in is how do you match that to the business? Right and because there's many ways to organize the bdc business You can organize it by channel So you should have somebody an app somebody looking at web site You can organize it by software and later cake right back end middleware and then you are layers on top You know, you can organize it by business in our case We have flights of towels and cars and I guess advertising are the four big businesses So you can imagine an organization that looks like that And so you have all of these possible dimensions for how you organize a business And you need to figure out the right ones. I've actually in our world We've taken out channels because you can't think in four dimensions So that the main thing to do is to pick two of those And say like, you know, in our case, for example, we organize ourselves by Channels by journeys So top of funnel middle funnel funnel and then by platform And if you can fatten the dimensions You can create an work structure that can resist strategy changes because the problem is your strategy will change every six months And things will come up and you want to come up with an organization that can kind of resist uh Support any strategy like without having to be completely redone all the time because the reworks are Help at our scale, you know, we have you know, 1600 engineers. It becomes really really hard to reorganize folks. We really try not to do that So that's that's That's the most explicitly chose to go away from a gm model. You've probably been exposed to this I'm allergic to that from microsoft Microsoft has uh, you know, the thing is work chart diagram We have in an apples case. It's Steve jobs in the middle and everybody Microsoft is like all these different islands with guns pointed at each other. This is the old microsoft By the way things that change a lot that when I was there that's very much the model And so I I tend to think that uh Works create walls And you want to try to think they don't solve problems. They create problems, right? Like I the best work is no work Just we're all sitting around the table coding together But at a scale you can't do that so how do you design that we've been very allergic to thief them and Individual leaders we try to do everything discipline based And everything so everything's have all the pms regardless of what Team they work on or what kind of they're part of report up into, you know, keep product officer all the engineers are up into the chief technology officer, etc We try to keep all the disciplines separate That model's worked pretty well for us. I was actually quite excited about that model at scale. Um, but there's other models that can work as well, of course It's good. Can I ask a question to you? What are you seeing and what do you think is person? I started to see some patterns because I I love asking this question I'm a nerd when it comes to a behavioral organization and And I've seen first of all, there are certain classics that still stick like the amazon two Pizza team approach like really breaking down things into small squads that you can fit with just two pizzas Um, but I agree with you. I've seen more and more companies using the approach of the customer journey Rather than the channel because in this world where everything's kind of only channel. It's Really hard to assign a huge channel Yeah We try to do the channel thing So for example, we tried to have a team that was like the app is a channel And we're just going to have a team that owns the app end to end But the problem is First of all, like you said the customers are on the channel. They search on the web and then they come into the app They do a booking nick while they're traveling. They use the differences. They maybe they're on a friend's computer They're still trying to sign in see the same data and then for the teams that are thinking about the journey How do I get a customer to move further down my journey engage more with the things that we have to offer? Those Those people found it very very hard to then say well now I have to go to the I don't have any app engineer So I have to go to the app team and ask them to do something for me. So we don't do that. We've organized ourselves Really by my journey of course the platform team. So there's a data team for everything There's a supply team for everything, etc But that seems to work quite well for us actually And I think at some point nothing wrong with um You know if you're a company the size of a microsoft or an amazon It's just that probably becomes impractical. I hear amazon. Actually, sorry apple really does this at scale I haven't worked at apple, but I hear that they have disciplined leadership all the way through the company I don't know how real that can possibly be given the breadth of the company the number of people the number of projects But uh, I don't know because so they don't share much So it's really hard to get but one challenge that I've noticed with this approach Which is more focused on the on the customer journey rather than the channel So there has to be a strong partnership with marketing teams Like it's really hard to define a line in between what is marketing versus what is product? What is product marketing? So how do you think about that? Yes, so, uh, I think if you find an answer to that I would I would be so happy because that is absolutely Fundamental problem that everybody struggles with and you know, he I I'll start by saying what I believe is true, but I have not achieved personally I know that some companies are a lot closer than we have. We're still struggling on this journey But I believe that that uh product and marketing are actually not different In now there's different specialism. So you're gonna market people that are quite good at marketing product people that are good at product and designers good at designers But the product is the thing that should be marketable So, uh, what is the difference between answering a question for the trial in our case travelers, right? Because we're a travel company on google for sco and answering it on our product If you ask, uh, you know, who flies from from london to miami if you type it into google Skyster has an acl page for you that will say here's who here's the answer to that question But if you go to the product itself you ask that question you get a different answer in a different format And so for example, why why are sco pages not our core product pages simply, you know Put onto a dedicated url like google could read, right? And so can those things come closer together or think about merchandising like the merchandising activities, which is like In a given market, you want to talk about certain things Maybe in one market we want to talk about insurance in another market We want to talk about hey that's some domestic sale option or another market we want to talk about tells So, you know the merchandising for how we talk to customers has to be deeply embedded in the product We think about the The good market activity So you're typically a lot of what used to happen at skyscraper a lot actually was that the product team Would come up with a great product and we do a bunch of experiments problem space Uh, experimentation double diamond, then they would chip nvp Then we would get they would a test it's working this thing it looks really good And then when it was done it would put the marketing team said look what we did Please market it And the marketing team would go like are you nuts? This is not like if not designed to be marketed for stars. You missed yet. I don't have a unique url I don't have a way to you know, there's all these missing tools that I have Then it doesn't fit into the narrative But we're trying to talk about from a marketing perspective And so trying to bring that together is the ultimate challenge Well, we're what we've done at skyscraper to get closer to nirvana, but we're not on nirvana But we're doing to get closer to that is one to make sure that there's only one Engineering team. There's not a separate engineering team for product from marketing Because I think that can get you in deep trouble. We actually used to be that way I mean that I'm building a lot of marketing technology that had to be thrown away and product that couldn't be marketed So we we have only one engineering team. That's number one And then we actually have a pm a product marketing manager function Whose job it is to connect these two worlds and to stitch them together So for example, they they manage like how do you do a good market properly? So there'd be a pm thinking about some problem and a pm Will go to that pm and say well, have you thought about this? Have you thought about that that's connected to this marketing person Let's figure out what's happening in brazil right now and try to stitch that together Into something more coherent when we actually launch it and pm is a new funding for skyscanner We've only had it for a year, but it's working well and we want to work that whole down So I used to abuse the PMs and Microsoft. It's a it's a powerful function. It's not right It's a very special company in via pm. That's a whole other conversation I agree. It's so powerful. I I wish I hadn't learned about this earlier I come from an as you as well from an engineering background I was under this impression of like well Good pms into great code And now we're seeing this transformation around a good pms Really have to write copy and really understand the business side of things and the user more than Or not just the technical aspect Yes, I I would say there's there's many kinds of good There's so many different paths into product and so for example, there are obviously like you said engineers that become product managers There's marketing people that become product managers Sometimes there's like the entrepreneurs that become most CEOs are effectively product leaders or not all that in tech They tend to be And then there's even now you're seeing a lot more like data scientists and people with a strong data background become product managers and so Sort of naturally They will all bring with them the prior knowledge and that's the lens that they will apply and so If you come from a computer science background and engineering background and your product manager You probably need to do a lot of learning and marketing. So that's what okay, son Don't you know that that's probably the thing you come from marketing You probably want to learn more about the software development life cycle and how to work with engineers to get things done and try to close those apps Because no, there's you know, I don't think there's any unicorns that just show up with all of that knowledge And company it's good diversity too. Like so just to be clear, you know, we have several for example technical product managers that oversee an api that That's totally fine. They're very good at that And you know, you don't need them to go designing UI and work with design or figure out how something Should be marketed and work with the marketing team. So the special is in can be useful Yeah, and it's great that there are options these days Because like that was before we were like, okay the product manager is like one was the only member of the product team and now we're seeing how Diverse this is and first of all, yes, there are a lot of different types of pms But there are also a lot of people who are part of the product team who who are not just Pre pms and I think that's great example would be pmm. But you know, we can talk about Program managers business and this data. I also consider honestly design and engineering and even marketing part of the product team because as you said This is a team sport It is a team sport and that this connects back to your point or your question around organizational design and how to do it because if you're going to say That you have a discipline based model, which means that you know under the ceo There's going to be a number of Chiefs for disciplines and the reporting lines go vertically down from those people That means that the only place it actually all comes together is at the ceo Right, whereas if you have gems each each gem is like a little mini ceo effective, right? If you're going to say you do a discipline based And you're going to say to make anything happen You need to have You know a product person a marketing person a pmm a designer obviously an engineer leader or whatever it is and it's the same sport Then you really need to search for people that are great at collaborating and working together and turning off their egos Because if not, it all falls apart because if you have two of those people Let's say a marketing person and a product person that can't Can't figure out a way to solve a problem or resolve it Their natural instinct is to go up a level and escalate it But in a discipline model That just escalates all the way up to the ceo because there's no it doesn't come together in some smaller So and that that's why the gem thing is so tempting so many companies are tempted to say it's too complicated I just want one person who will decide everything and like you know, so In our case, I just want one person who will own flights and you know, so I don't have to worry about hotels I don't have to worry about the app I just want but it doesn't actually help and So instead what we do Is we really really focus in our hiring process and in our development process on finding ways to collaborate together on the team sport piece on turning off our egos and And we're very allergic to that like one of our key cultural And we're not the only company of course to have this but we have a very high degree of allergy Towards uh self-centeredness, you know, we are our core value at sky scanner is is travelers first Then partners the sky scanner then team and then me in that order and if you can't get With that value then, you know, it's probably not the right company for it And there are other ways to be that can be perfectly successful. But that's how we do it And piero, what are you excited about learning these days? Oh, well it's interesting because The problems I'm most passionate about aligned well with our mission But given that I get this more or less set the mission with my exact peers that maybe is not a coincidence Our mission is is to lead the world in modern and sustainable travel and that those there's two days modern and sustainable And what we mean by that those are the two problems that I'm most interested in these days. So the modern one what I think of this is kind of first of all how primitive travel shopping is Compared to almost any other form of shopping, you know, if I asked you to pull out your phone right now and order 46 inch TV While you are talking to me, you could probably get a TV figure out the reviews You know, just in the background with one hand you could probably figure everything out You need click buy and it would show up on your doorstep tomorrow And if you don't like it, you could return it right like buy one click and all of that through the obvious The amazon's but other merchants as well. It's just so easy to do all that in commerce But if I said to you, you know, book a flight to london You know right now with your phone just pull out your phone and book a flight to london There's no way that you could do that and the truth is that technology has Turned us all into travel agents. We all have you know, it's been great Like we all you know, we all have those tools whether it's a You know, speedy archylax guys can or whatever google you can just find all of this inventory and all that But how do you it's huge darkside because now you spend eight or nine hours planning stuff You can't book everything into the same place. You don't get consistent service when you do it So in some senses I mentally want to turn back the clock a little bit to Hold enough to use the travel agent, you know go to the travel agent say what you want Get great answers get a couple of choices and take care of the rest So heading more in that direction is interesting and doing that in a way that is Able and still part of our business model that's far the other big problem that I'm interested in sustainability I mean, you know travel travel is is a force for good in the world It brings people together it moves barriers. It brings more as it's commerce. It's all those things and we love it It's just it's a human thing But it comes with a huge Downside I mean that's obvious and even I have to tell you when I was interviewing for sky scanner I love the product But I was hesitant to join a company whose role was to you know success for sky scan is put more more people on More airplanes for less and less money, right? That's success and that's good for business But for the planet that's that's not so good. Luckily. I found A very like minded team at sky scanner That was deeply aware of the impact of travel and trying to do what they could to improve things And so we've now we've now said sustainability isn't isn't just a CSR corporate social responsibility for us, but that's our mission What can we do with with software in our position in the marketplace? You know, we're basically a search engine for all of these travel things to really encourage More sustainable travel can we teach people what is better? What which choice is better than another choice? You know this flight actually because it flies You know, it's a short haul that flies shorter than this other flight or it's a specific airplane a model of aircraft Or it's this percent full all those things affect how much You know co2 it's going to emit so can I teach people To care about this and choose those things because if I can Then what I can do is I can go to the suppliers in the airlines and I can get them to create more supply it's like a little bit like You know we all love organic food now But we have to be taught that organic food is better and we have to be taught to prefer organic food We cost a little bit more But if you buy organic food and then the suppliers like whoa these people are paying more and actually you know I can save on So the suppliers stepped up and made more organic food and that's a cycle So what we're trying to do in sky scanners to learn about that cycle and see how much we can contribute to the industry And kind of push that forward and that's a very very Space and a very hard space to actually do anything with but it's fascinating. So spending a lot of time on that I enjoy it our conversation and and I love your leadership style and how you you also lead with with your heart and with purpose Um, I think it's important for the long term and also for the next generation We all care a lot about how things are made where they come from and I kind of was a long term vision behind um, is there anything else you would like to say to Spinding an entry-level PM who are looking up to you thinking. Oh my god, you know, he's done a lot of cool things I would love to be cpo one day. How can they kind of accelerate their career? Well, um, yes, I think I'll go back to the point I made at the beginning of this Which I think is still true which is look, you know join a company And don't worry about getting promoted if you spend your time thinking about getting promoted That's almost certainly and managers hate that but you know what they hate They hate the PM that comes in and instead of talking about all the problems that they've solved They talk about like, you know, how am I going to get promoted making the checklist? What is the tick tick thoughts so I can get to the next level like It actually hurts you it slows you down in your career So if you can ignore titles ignore rank ignore layers Especially in a bigger company and just just if you find something that you believe needs to Get done go and make it happen after permission not for forgiveness You know, just push it through and and try to let go of your ego a little bit and not take yourself this seriously I honestly think that's good for your advice. I it's only work for me But thank you so much. Um, yeah, let's keep building cool products and um, thank you so much for your time. Thank you Wonderful Carlos. It was great to meet you. Cheers I mean