CEO, WeTransfer (pre-Bending Spoons integration; current status unconfirmed), WeTransfer (a Bending Spoons company)
"From Keyboard To Boardroom – Path From Engineer To CEO" Alexandar Vassilev | PMF 2024
Alexandar Vassilev, CEO @ WeTransfer In this fireside chat with Oliver Heckmann, Alexandar Vassilev shares insights from his ...
Transcript (29 segments)
O
Oliver0:04
I'm going to invite first um Oliver here on stage for this special setup what we have um Oliver so maybe a big warm of Applause to Oliver so Oliver you are uh actually a board member of the tech Leadership Summit we met last year as you were keynoting here at the conference and you spent 14 years at Google yeah and now you moved on to Koda maybe just tell me why why did you do that why I moved on to ca yeah I think we'll touch on it in this discussion as well but um like I mean 14 years is a frankly it's too long for to do anything yeah um I I'd say basically 14 years is four years too long but you you started here in surc at Google first so that come back and please keep take it from here thank you yeah thanks it's good to be here and now I have the honor of basically asking Alex who is standing over there and who is this CEO of V transfer was the CEO of the German Media Company join before and before that uh he was at Google actually given that we talked about leaving Google Alex is one of the few people who left Google twice yeah um so we can talk about that in a second as well um and um and now he's here uh disclaimer we worked together uh too long time ago why I have Google of course while we were both at Google here in in surk um and yeah so the way we're going to do this you have seen the barcode um oh there was a barcode would be good to get that up again because if you're basically scanning the bar if you're basically following the instructions with the barcode uh you can basically um add questions which will then show up on this iPad that's why I'm holding it here um and I'll try to weave your questions into the discussion so if you if something comes up I'll try to do my best job of um trying to read the questions uh ask questions myself I've prepared a whole bunch of questions but of course it's going to be more interesting from you if you get your own questions answered so with that setup um let's get um going so Alex why don't we actually start in chronological order then we get uh don't get confused so um I think we'll talk about the us later but let's we're in Europe let's start in Europe if I'm not mistaken you were born in Bulgaria and that's also where you had your first Enterprise yeah so um How was your Life as a teenager and uh your relationship to technology growing up in Bulgaria
A
Alexandar Vassilev2:35
yeah uh so yeah I'm Bulgarian uh grown up uh and raised basically uh in Bulgaria it's interesting because I didn't even know a lot about technology uh I grew up as part of the you know Communist Regime and the transition afterwards which was let's say not very technologically focused uh but at some point there was a bank that went bankrupt and my dad somehow managed to bring a computer at home I don't know how he wound that one up uh but that was literally the only thing that kept my attention for more than 5 to 10 minutes so uh I found that world entirely fascinating um started getting really good at recognizing when the dial-up modem was actually going to connect to the internet and start spending a lot of time on it and basically uh got fascinated by the technology and taught myself to code uh found out that not many people can do that and not many people knew what that was so ended up seeing opportunities here and there to help people get on the internet whether that's companies or people that led to one thing led to another and I uh started my first company uh that was a Service Company helping companies build their web platforms uh and it was all self-taught so no mentors no knowledge uh just a lot of grit and uh a lot of mistakes uh along the way
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Oliver3:53
great and before we uh do the transition to um Google and the first parts of your career if you think back of like your worldview of Technology as you just shared growing up in communist Bulgaria and compared to your view now what's changed what's the same
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Alexandar Vassilev4:11
yeah I would say a lot has changed uh you know people say don't work your passion uh because it's going to become a job and that's what happened technology used to be This Magnificent thing that I couldn't wait to wake up to read about and now it's just means to an end uh to help solve a problem to build something interesting so that kind of novelty wore off quite quickly uh but what left is this fascination with the magical element of Technology seeing something for the first time that's new seeing how it works um seeing what problem it solves and that Ingenuity constantly keeps you on your toes and that kind of kid-like fascination with technology is still there but yeah now it's just a job in many ways and it's a means to an end
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Oliver4:57
so now I just got a whole lot of questions added here um I'll actually tee you up with a longer question and then I'll scan and try to weave in the questions here so um if we move on from Bulgaria uh you joined Google um tell us how that felt when that was I think it was very early on how that felt yeah
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Alexandar Vassilev5:51
yeah yeah well imagine this kid from Bulgaria Landing in a place uh um that I will say it's a middle of nowhere in Missouri and there's a person in the audience who knows that place very well because I met 21 years ago there um I went to a college in a small town in the midwest uh and then when I finally had to pick a job I applied to Google on a whim and somehow they said yes so I found myself as a very young excited naive person Landing in New York City starting to work for the number one company back then uh in 2007 it felt magical I remember walking through that office and just feeling like I'm on the top of the world I'm in the place where things are happening both the City and the company I was the stupidest person in the room uh which was an amazing feeling uh working with some incredibly brilliant people and the best part was it was unstructured I walked in they point me to my desk and said go there find your laptop go there talk to your team and do something productive and as a young person who is an entrepreneur at heart that was just the best setup it's a risk-free opportunity to build something amazing and I'll always be thankful to Google for that opportunity yeah
O
Oliver6:33
umm the wow there's a lot of questions getting added um I will try to switch to the audience question I will weave them in there many um on the co topic so we'll let's go through a few more prepared ones and then I promise I'll weave them in um the now Google has changed a lot since since you joined I think it's especially a lot of that unstructured figure everything out yourself will feel differently today um but maybe tell us concretely like what did you work on yeah
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Alexandar Vassilev7:02
yeah I started my career at Google in a very interesting position which had an engineer in the title which meant that I wrote code for tools back then if you remember Oliver it was the time where we thought nobody else can build better software so we'll build all the software in the world that we need so I spent a lot of time building internal tools and also handing out keyboards which was also a very fun job but at the end of the day I focused on building internal products then when DoubleClick acquisition closed I focused on working with engineering teams as a TPM to build advertising products for which I was for the first time not the user yeah which was also very interesting experience and then I got a call from someone I want to mention his name who convinced me in a 30 minute call to pack my bags from New York and move to Zurich which I was even surprised about and that person sits on my right here so I moved to Switzerland and we did have a lot of fun trying to help people with talent build businesses on YouTube which at the day was not really an easy job but that was one of the most amazing parts of working on YouTube and you know shipping things and going home and seeing people using them on the tram was this amazing reward that you get so you know short things and then I left Google I came back again with the huge help of Oliver and I worked on Google search so I got to see very different aspects of the company in terms of size complexity but also in terms of product selection and execution yeah oh yeah that's a given yeah maybe explain to the audience on how much faster yeah when I joined Google we were about 10,000 people when I finally left Google for the second time I think we were 200,000 something like that at YouTube you sat in a room you talked about it you went back and within two days you build it when I went back to California with Google search it was more about completely the reverse you know speak for three weeks and then try to build it before somebody stops you so it's a very different business very different type of setup a lot more bureaucratic as you will with complexity it's a very different company so yeah I'm sure you had the same experience at some point exactly
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Oliver9:22
yeah yeah the um actually let me now switch to some of the audience questions a bit out of order there um thank you there's a voting mechanism in the tool as some of you have discovered that helps sorting the increasingly long list um so as we're kind of getting to the end of the Google thing and actually no let's do one more thing and then I'm going to ask the top question here that will flow more nicely so the um as I mentioned earlier you have left Google twice and not just once there's a lot of ex-Googlers at the conference probably in this room right now and maybe a lot of people who are kind of at Google right now what was the what good advice can you give someone and doesn't have to be Google specific and if you're basically doing the same thing in the same company for a longer time how do you actually figure out that it's time to leave and do something else
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Alexandar Vassilev10:15
um it's a great question I think the benefit of Google at least when we were there I think you were in the same boat is that I think I had about 10 jobs in three different locations in different type of job categories within the company so I felt that there was always a progression that I was learning I was stretching myself I was doing interesting things but I remember the final time leaving we had a small team that had an idea of how to keep Google search competitive and end up becoming a pillar of Google search strategy and I remember sitting in Charlie watching this OKR session and just realizing that I had become too complacent I was not learning I was just cruising I felt that it was a lot about talking rather than building and I felt that I was missing that part of what made me happy in my professional career so I literally walked out of that OKR session and said okay that's it I need to change and I need to change soon because I feel like I have a lot more to go and learn and a lot more to go and build and I felt that I was not doing that at Google by the way it was quite similar for me I noticed that one you know we always hate when you're sitting in a meeting or you have a great idea you're excited and someone says oh we tried this before we tried this three times before and it doesn't work and at one point I realized that I had become that person I caught myself saying that oh wow and that was literally for me the wakeup moment of okay I have been doing this for too long time to do something else
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Oliver11:43
um so let's tackle some of the audience questions let's start with the top voted one thank you Adam is it even possible for a young engineer or product manager uh to climb right to the top in this saturated environment
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Alexandar Vassilev12:04
yes it is possible um I will only talk out of my experience the biggest progression I saw in my career I would say in the first five years was when I was taking risks and trying new things and I don't know if you can argue that it's very competitive now so that's a bit difficult but on the other hand every day I talk to very ambitious companies doing crazy things and sometimes it's difficult to say I'm going to leave a company X where I feel very secure where I have good opportunities where I'm progressing and take a leap somewhere outside so the answer is yes but you have to go and find a path that perhaps has a bigger risk reward ratio but ultimately it's something that you feel uncomfortable with the moments where you stretch yourselves are the moments where you will grow the most and I find myself jumping disproportionately upwards after leaving Google and taking a risk on a company that's perhaps too young that I can bring things to the table and distinguish myself so yes you can you have to be sure you want it that's the other aspect because it's all glamorous to have these big jobs but they take a toll so you have to find out what motivates you and what your risk appetite is and if you can combine those two things I think it's still possible there's a lot of new we are also on a technological precipice of change and that is always a time for great opportunity if you seize it but I'll argue that it probably won't come from a massive company where the political aspects will be more difficult to navigate in the short term
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Oliver13:49
yeah it's a perfect segue way to join because when you left Google the second time you basically became a product manager you left Google behind and moved continents and went back to Europe to join a company that at least I hadn't heard of at that point in time tell us about that while I'm sorting through the next question
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Alexandar Vassilev14:09
well we came up with the name so I'll be surprised if you did but this is exactly what I mean when I decided to leave Google and wanted to come back to Europe I did what every smart Google person would do when searching for a new job I called Meta and Amazon and then applied luckily enough I got offers for both and really realized at some point that I'll be just doing the same job with a different color badge and at some point I was very lucky that I had a conversation with Eon Zender who basically said there is this crazy opportunity to come and be employee number one in a business that was just formed that has some ambition but they don't know how to structure a product driven business and you can try to make it work and it spoke to me it spoke to me back to the times when I was an entrepreneur it spoke to me about being more horizontal I saw opportunities to learn things to build teams to shape it the way I want it and that just made the decision very easy and I will not lie to you it was incredibly difficult the biggest learnings and the biggest stress in the first two years of Join but once you see the ball starting to roll and the results coming in you cannot beat that feeling it's just fascinating
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Oliver15:29
yeah I can imagine um going back to the leaving a new job and then we'll go to the second part of that the COO part but let's first leave with the leaving there's an audience question what are the things you think are needed to prepare yourself to leave a job and to start a company a business plan or conviction about the idea or the team and to what extent yeah
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Alexandar Vassilev15:49
if you're starting a company it has to be something that you're deeply deeply passionate about and I say that with full realization of how cheesy it sounds but ultimately it's so difficult to grow a business that if you don't have that passion and you're not waking up every day with the desire to solve that problem you're going to probably burn out somewhere along the way you have to surround yourself quickly with a few people who share that passion with you and you can lean on and just quickly realize that it takes a village to build anything so I don't think you need to be particularly ready nobody feels ready to start a business nobody feels ready to have kids nobody feels ready to get into a partnership the reality is you make yourself ready once you do it and I've noticed that for many folks taking the first step is always the most difficult and once you start walking it doesn't matter how treacherous the path is you just keep pushing forward so I wouldn't overthink it of course caveat to that is depends what your situation is you may have a family financially etc it has to work but suspend your fear for a second and take the first step because most likely what will happen and I have to thank Oliver for that you realize that there's always a way to go back I remember when I first told him I was leaving and I was a bit nervous he's like oh yeah if you don't like it just come back six months from now it's fine just come back check out how it is and then come back and that just gave me such an amazing thing to fall back to so I actually don't think I ever thanked him but you'll find that there's always a way to get back getting forward is where the benefit is
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Oliver17:39
this is actually a pretty general piece of advice if you're doing a good job at a company and you're not fired and you're leaving a good job behind you the risk is smaller than you intuitively think because there's growing demand in our profession it's not a shrinking industry yeah there's always that job or a very similar job probably in the very same location possibly at a better salary available so the risk that often people worry about if you're analytical about it and consider the type of industry we're in it's often way smaller than people think and you'll be surprised how many people will help you even without asking yeah
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Alexandar Vassilev18:21
so yeah try to take that first step now
O
Oliver18:23
um there's another audience question now going to the CEO part more if you think back your time back then or if someone wants to follow a similar path what skills are most valuable for becoming a CEO technical skills people management business finance leadership other stuff and where would you recommend to our audience as product managers and engineers so where should they invest first and most
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Alexandar Vassilev18:56
so in terms of a skill set I don't think there's a prescription for you to follow I think one of the biggest learnings for me as I climbed that ladder was around the need to be adaptive basically adaptability is the key thing so if you're coming from a particular area and that's your strong suit that's great bank on that but ultimately constantly challenge yourself to be adaptable because everything changes and the things around you change when I first took the reins of Join I didn't know I mean I had a little bit of knowledge about accounting and finance and things like that but you'll be surprised how quickly you can fill those gaps with the right people but ultimately do you have a view of where you want to go and can you convince other folks to come and follow you on that journey in terms of actual skill set what I'll say is that the biggest ability that you can develop that I think you can scale because being a CEO of a company of 10 people is very different than being a CEO of a company of a thousand people and depends on the scale if you have the ability to go deep into a problem and get your hands dirty but then always find a way to go back and see the forest for the trees I think you'll be successful the biggest challenge is when people get stuck in one or the other if you get stuck in just big vision and never care about the details you find yourself losing the ability to steer the ship and vice versa if you find yourself to be the hero every single time because you're deep in the trenches solving that problem well that means that you cannot scale so that ability to go up and down is how I see a lot of folks get stuck when they climb ladders at places like Google is when you cannot switch between being the hero and being the person who enables the heroes so that's a skill set I would try to practice if I was in any of those shoes or starting it again a lot earlier because we all think we love technology I'll just go build it and it's going to work and if it's not working I'm going to go in and fix it that gets you to here and if you want to go here that doesn't scale
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Oliver21:01
yeah that's really good advice let's go to the opposite because the top voted audience question right now is what's the worst advice that you ever gave or have received
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Alexandar Vassilev21:17
that's a tough one I don't know if it was advice that I received but it was a pit trap a huge trap that I think I was very close to falling into and I see a lot of folks falling especially as they get into these executive roles which is I'm the executive now I have to be making decisions I have to look strong I have to know what is happening I tell people what to do the reality is that that's not really the case and if you're doing that you're probably making a lot of mistakes being a CEO doesn't mean you are powerful and in control and barking orders it's about realizing what's missing in a puzzle and trying to fill that puzzle whether that's people technology niche comparative advantage positioning etc so don't fall into that trap if you look at books or movies it's the big shot with a big office makes all the calls everybody's afraid of them and that literally is the worst thing you could imagine because I can bet a lot of money that none of you wants to work for a person like this so don't become that kind of person that's a mistake that I see a lot of folks other than that I wouldn't say that anybody gave me terrible advice maybe because I didn't really ask in the beginning and that's probably my fault I would have loved to get some good advice and some bad advice but at least some advice early on but yeah I would say that
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Oliver22:47
yeah well there's one more question I want to ask you and then I think it's time to switch to the WeTransfer time but this is more about the planning horizon for career how much did you think of your career path and I interpret the question as longer term planning and where you end up in 10 years versus focused on the best possible work at the moment so how much did you plan ahead how much did you just try in each moment to make the best possible decision
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Alexandar Vassilev23:19
I think I did subconsciously exactly what Google does in many ways with these moonshots ever since I was a founder at the age of 17 I always knew I wanted to run a company I don't know why don't ask me why I didn't have a lot of people to look up to why that's good but I wanted to run a business that was as much planning as I did everything else for me was about how do I acquire the most diverse experience and how do I acquire the most diverse battle scars from doing difficult things I find that if I make a plan that's more than a year or two in advance I probably will change it 100% of the time if you asked me six years ago if I'd be the CEO of a file sharing company I probably would have told you no why would I do that but it turned out to be one of the most rewarding experiences ever so I've always chased the difficult choices and the experience and the risk rather than the safety always with the mind of I want to be there I just don't know the path I've seen some other people's paths but I don't know what mine is I'll just try to navigate and take risks and acquire more knowledge and shape it later in my career so I wouldn't spend a lot of time thinking about planning but rather doing
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Oliver24:38
yeah I think that's also really good advice so now let's um if I just to finish on that question I think there was a second part of this how much do you focus on being doing now I would say that any step of the way and I got that advice actually from somebody at Google early on is people always want to be at the next thing already but you have to become undeniable in the thing you are right now so I would focus I would take this risk if I were in my shoes again but I always try to be the best I could in that particular aspect and if you can do that I think you'll generally have a successful career even if you don't get to that particular North star you aimed for you'll also have much better job satisfaction if you aim for that
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Alexandar Vassilev25:17
um so let's talk about the why you left Join how the transition to WeTransfer worked why did you do that you started WeTransfer you went back a bit more to the roots you started as CTPO yeah it was a really interesting transition Join had done incredibly well we had massive expansion plans to go across Europe things were going well and then COVID hit and my funding basically dried up and for those of you who play in the content game especially in production and things like that you know how much you depend on fresh capital to continue to build great content to purchase great content so we were just ahead of the curve on burning and we did very well 10% market share in Germany after about a year and a half in the market against Netflix Amazon Prime Disney Plus but at some point COVID shook the ability of our shareholders to fund it and they wanted to scale it back to become just a German entity which we were already so it required a very different setup of business it required to be probably acquired by one of the shareholders so we built all these plans but at that point they didn't need a growth product CEO to integrate something into a broadcaster so we shook hands I left I found my successor and then my non-executive chair of the board of Join was actually on the board of WeTransfer and he said why don't you come and explore this amazing business and the more I got to know it the more I got excited decided and I had a very candid conversation with the CEO whom I give a lot of credit who basically said listen I've been around here for four or five years the next phase of growth of this business is product-led growth and that's not my strong suit so I'm looking for someone to be my successor and in that discussion what became apparent to me is that the company was structured not as a tech company but more as a media company and I joined as CTPO to give myself the opportunity to focus on restructuring the organization on engineering and product and make that a good machine before I take the reins of the business and we did just that about a year later I restructured the business I scaled the tech and product and I eventually took the reins
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Oliver27:48
yeah now I know we have a minute or so left so try to get to that I want to weave in the last top voted audience question as well but if you try in a minute tell us like what I know WeTransfer as a story that some people might know others not an IPO and then recently an acquisition so what's next for WeTransfer what can users in the audience expect
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Alexandar Vassilev28:15
yeah so a little caveat to that thing that you're reading up there perhaps with my name on it is that I am the CEO of WeTransfer for another couple months we ran a process this year and sold the business to a company called Bending Spoons I firmly believe the commitment from Bending Spoons is to keep the product and what makes WeTransfer special as the community of creative professionals alive so I don't think the product is going anywhere I presume that there will be a lot of interesting developments but yeah the business is in the hands of others now and they I'm sure will drive it to new heights and it was a process over the last few years where we tried to go public which yeah I don't recommend for people to scale and try to go public at the same time it's nice if you can segment those things and unfortunately we won the worst timing award because we tried to go public three days before the first rate hike back in 2022 which for those of you who have experience with that meant we were trying to convince investors to invest in a time where NASDAQ was going minus 10 minus 10 minus 10 which is not the most beautiful moment to do so but the company didn't depend on that we were profitable we were growing so we just put our heads down continued to pedal forward and continue to grow and luckily three years later we had an opportunity to execute a transaction and sell the business
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Oliver29:46
awesome now we are at the end of time we didn't get through all the audience questions there were simply too many but I hope you got good advice I'm also you'll be around so we'll be hanging out here or at the coffee machine or knowing Alex at the bar so you'll have the opportunity to ask more questions thank you everyone