Introduction
Ceci [00:00]
Hi and welcome to Top of the Ops, the podcast where we have real conversations about what happens behind the scenes of startups. I'm Cecilia, ex-VC at Talis Capital and now FD at PortalOne.
Bea [00:13]
And I'm Bea, ex-VC at Lakestar and now Chief of Staff at Praktika. Today we're joined by Olivia Elf. Olivia has been on Sana's executive team for the last five years, joining as Chief of Staff and rising through Director of Operations to her current role as VP Operations. She was there through Sana's Series A, all the way to its 1.1 billion acquisition by Workday, one of the largest AI exits Europe has produced. We're going to dig into all of it. Olivia, welcome to Top of the Ops.
Olivia [00:45]
Thank you so much for inviting me and having me on the podcast.
Five Years, Four Roles, One Company
Bea [00:48]
McKinsey, to Chief of Staff, to Director of Operations, to VP Ops, all at the same company except McKinsey. You stayed, and you kept moving through the company as the company itself was scaling around you. When you joined Sana in 2021, did you think you would still be there five years later?
Olivia [01:06]
I'm definitely one of those people where if I'm in, I'm in. And I knew pretty early that if the company itself was going to be around, I would also be there. But as both of you have experienced in the early stage, you really never know what's going to happen. I was very committed to be there and make it as good as possible. I really didn't have a grand plan or anything, but I've always admired people who stay through things, especially when things are really tough. One of my biggest role models there is Hillary McAdams, who used to be on our Sana board. From graduating out of college she joined Oracle, which was quite a small company back then, a few thousand employees, and she stayed for the first 18 years of her career. That's the kind of career I'm extremely impressed and obsessed with. So having that in the back of my mind, it wasn't that I knew Hillary back then, but those kinds of stories, I knew them and I just wanted to live it.
Is Loyalty Dead in Startups?
Ceci [02:11]
That is very fascinating and refreshing. I'm going to go completely off track already and just ask you a question. When I look back and think about my parents' generation and their relationship with employment, I see a lot of loyalty, a lot of growing throughout one company. And when I look at my generation, or the younger generation, it kind of feels that sense of loyalty is decreasing quite a bit. Maybe as somebody who's been a bit more loyal, who hasn't done the two-year skip from company to company that we sometimes see in the startup scene, how can companies try to build again that sense of loyalty? What's there to do, or is it just a personal vibe?
Olivia [02:55]
It's a very good observation. The cycles are definitely shorter in everything now, so that plays into it. There are much shorter hype cycles than in previous generations. And I think that's a fault of the younger generations, this "the grass is greener" jumping towards the next hype all the time, instead of thinking you actually have the agency to build something in the company you're in. I'm always looking for that. I've run thousands of interviews since I joined Sana five years ago, and I'm always looking for the people who also stayed when things were tough, or boring, or any of the more negative things, and who felt they had the agency to change things. Because the people who jump ship instead of trusting that agency are very hard, or not as fun, to work with.
Why She Joined Sana
Bea [03:56]
Was there something that pulled you to Sana specifically in 2021, and maybe something about that culture that made you stay? Give us a bit of a look inside Sana's culture, because it seems a pretty good place to be if you stayed there five years.
Olivia [04:13]
The reason I joined in the beginning, this is 2021, was that I started to have a genuine feeling that AI as a technology would have an impact like nothing else. That was one thing. The second thing, which was stronger, was that the first time I met Joel, our founder and CEO, we had a coffee and he talked me through the thesis and what he believed about the world. I really liked it, but I wasn't fully awake yet, or obsessed. And he noticed, of course, because he's a smart guy. Then he said, we're going to build a company based on all of the principles we believe in, which is a place where people can do their life's work, no compromises, extreme principles, all of those things. And I really woke up from that. I couldn't think of anything else for the coming weeks, and that made me excited enough to drop what I was doing and join Sana and take the bet. There are many things that made me stay. We talked about the loyalty piece and wanting to see things through, but one is that we really have built a company based on all of these crazy principles that everyone told us we would have to give up eventually, and we've just continued going, and it's been very, very hard, which is fun.
Doing Today What You Did Six Months Ago
Ceci [05:42]
I love how you've highlighted, on one side, the resilience of looking for people who've gone through the hard bits of a startup, the ones you want to keep on your ship, but also being quite ruthless about the principles you're going to build the company on. And talking about principles, you said something to us before the podcast that I'm going to repeat here: if you're doing today what you were doing six months ago, you're failing. I love that. Spell it out for us. Maybe give us some examples of what you've stopped doing at Sana in the last six months, and some advice on how people can reinvent themselves in their day-to-day work.
Giving Away Your Legos
Olivia [06:31]
This is so deeply engraved in how we think at Sana, so I'm very happy you picked it up. There's this concept of giving away your Legos, the idea that ownership is temporary by design. I'm not sure if I'm hijacking the concept of giving away your Legos, but that's how I see it. It basically means we've designed Sana so that you pick something up, you improve it, you make it yours, you package it, and then you automate it, or outsource it, or hand it over to somebody else, and you go and find the next hard thing. That's how the DRI areas work at Sana. You own something until you've solved it, then you find a way to forward it and not own it forever. This way of operating has very interesting side effects. Basically nobody is protective or territorial. Normally that doesn't exist in a startup, because there's no turf to be protective about. There are just more problems to solve all the time, or opportunities, if you want to call them that. Another interesting side effect is that every time something changes owner, it gets rebuilt from scratch a little bit. If you've built something the way you thought, and you hand it over, the next person will automatically reinvent it, so nothing becomes a static "we do it this way because we've always done it that way". And the last thing is that nobody is worried to pick up difficult things, because they're not worried they'll have to maintain them forever. It's a very fun and cool way to run a company. The reason it works as well as it does is because we've always been growing. A growing company is so much easier to run than a static or stagnated one. In practice, everything I've done in the past five years has worked that way: building a team, setting up a North Star, defining the first principles, then letting that team run by themselves.
Bea [08:43]
Could you give us the latest example of something that changed hands from you to somebody else?
Olivia [08:51]
The clearest ones are probably almost full teams. This actually happened a lot during the acquisition, where a lot of us had to step out for a long time, which was very uncomfortable, because we also couldn't communicate why we were so absent. A big part of it was during the summer, so that helped. But it was the mega crash course in giving away your Legos. I wasn't entirely sure a particular small team or leader would be ready to grow or own something fully, but I didn't really have a choice in letting go.
Ceci [09:35]
One hundred percent. And I think the acquisition was one thing, but growing a company in general is such a good lesson in, it's a boring word, delegating, or letting go, or giving away your Legos. It's interesting, because it tends to be in contrast with the profile of people you hire in a startup. The greatest leaders are also the greatest delegators, but that tends to coincide with very high achievers, very ambitious, who can be quite jealous or controlling of their processes. The way you've instilled it at Sana is intentional, you have to let go, which is a great exercise that makes people progress in their leadership faster. If I'd joined a company at the start of my career with this principle, I'd have saved myself a lot of back and forth with delegating, which I think I've overcome now, but I'm 34, so it's been a while. How do you instil it in people? Is it a combination of leading by example, having it spelled out, seeing everybody do it?
Olivia [10:51]
It really is all of the above, all the ones you mentioned. And once again, this luxury of growing a company means letting go doesn't feel like a loss when there's always a harder problem next. That's my point about running a growing company versus a stagnated one. As you've both seen up close, in a company there are millions of problems to solve. The least likely problem is that there won't be interesting problems. The most important thing is for each individual to be able to surface them and understand that anybody can jump on them.
Sanyans Have No Toes
Olivia [11:27]
There are principles we run that lead to that. One is, we say Sanyans have no toes, which means you can jump on any problem you see and pick it up, no matter whose it is. And because Sanyans have no toes, you can also never say "well, that's what I'm doing". It doesn't mean those feelings don't exist, it means we're deliberate that that's not the company we want to build. The other way to tactically build such a culture is to have uncapped or undefined roles. I am not head of finance, I am not senior manager of whatever, you just are. A lot of people have picked this up. We've always had extremely generalist roles where you just jump on any problem. That's another way of not building a protective or territorial org, so every person sees any problem as their own to solve.
Ceci [12:25]
I'm really fascinated by those principles, because they resonate a lot with my own idea of how a startup should run. I've always been quite against really structured job descriptions and really structured roles, because you tend to attach yourself to that function and that description. Whereas in a startup that changes really quickly, you shouldn't attach yourself to the problem you're solving right now, but to the bigger problem, which is the entire company. That creates a sense of fluidity, and it's a lot easier to let go of one problem when you're replacing it with something more fun, more engaging, harder to solve. Sometimes it's easy to install this fluidity early on, but as the company scales, people say you have to create boundaries and ways to move from one place to another.
Chief of Staff to VP Ops in Four Years
Bea [13:20]
Talking about going from one role to another, you yourself went from Chief of Staff to VP of Operations in four years. A lot of people don't get the chance to do that ladder. How did you make it work? What had to be true for that arc of growth to work? And a lot of people get confused about what a Chief of Staff is, what a VP of Operations is, what a Director of Operations is, and those roles can be really different across companies. So your two seconds on what each of them meant for you.
Olivia [13:52]
I'm super confused too. For me it was never a clear cut. It wasn't like one day to the next I was one thing and then the other. When I came into the company I could almost operate as an ops leader from the beginning. That's the reality, there was no clear cut. I've come to believe that the single most important thing you can do as you grow your career and join a company is to find a leader who believes more in you than you believe in yourself. I really did, with the people around me, not only Joel but everybody I worked closely with. They push you into things you wouldn't have taken on, that you'd have hesitated to do. You borrow their certainty that you can do it before you have your own, and build your own meanwhile. I say this to the folks who join Sana straight out of uni, that's really the biggest unlock, and they have to find that person. We also train our leaders to do this. I try to give it to everybody I work closely with, because it's the biggest unlock. I've seen it over and over: you put the harder problem on someone's table and they very likely move the boundaries of what they thought was possible. I speak to people all the time who are joining companies, and I ask, who's going to be your leader? What do you like about them? And they don't know. I didn't know that much before signing my Sana offer either, but if I had to do my diligence on one single thing when joining a company, it would be who is my leader and what are their traits.
The "Fully Uncapped" Operating Principle
Ceci [15:40]
I think I now fully understand the other principle of Sana you told us about before, which is that everybody's fully uncapped, as an operating principle. I didn't fully understand it before. Do you mind explaining it to us? And I'll tell you my two cents after, and ask you if it's true.
Olivia [16:00]
I like that. There are a lot of ingredients to this fully uncapped thing. The main thing that creates it, as I alluded to earlier, is having very undefined roles. Strictly defined roles really create a ceiling, and they cap people. What we've tried to do is hire generalists for most roles, even very specialised ones. We've been very extreme about this. Then when our strategy changes, or in the beginning when we did a few pivots, we actually have a team that can do that, and we're not stuck in a strategy because we have very specialised people. That's one of my strongest operating principles, to not create too-defined roles. The other way to achieve this uncapped potential is to give context, not control. If you shape a new team or a new DRI area, you say what we're trying to achieve, maybe the North Star, the milestone, the problem as you thought it was, and then you let them run on it. First of all it gives really cool results, because it gives full ownership, you don't hand them an idea of a solution. But it also creates really uncapped people, because they take from all the different domains, they go around and talk to people, they understand things nobody had understood before. So those two, along with coupling somebody with a leader who believes in them more than they believe in themselves, are the most important things.
Ceci [17:40]
Before, I was a bit skeptical when you told me last time. I was like, wait, how is that possible, if somebody's fully uncapped but the company itself is somehow capped? Let's say you're a technical recruiter only doing recruiting. At some point you might want to be head of people, or chief people officer. But if that role is taken, how is it possible for you to be uncapped? But if you're hiring a generalist, they could go and solve another problem in another team, or something else on the operations side. So now I fully understand it when you match it with the principle of having no toes.
Olivia [18:14]
You're pointing to something very important, and we've seen this over and over at Sana. People change completely what they're doing. They want a new challenge, we find them one, or they find themselves one most of the time. I think that's quite a characteristic of a really excellent Chief of Staff, moving yourself and finding new problems over and over. But when does this go wrong? How does the principle fail, and what can you do to avoid that? I jokingly used to say about this generalist profile that they're extremely good people, and especially of that profile they're extremely annoying and very hard to manage. It's a bit of a joke, but it's really true. It's much easier to run an organisation with clearly defined roles, clear hierarchy, all of that. I truly believe it's easier. This way of running things is much more interesting, much harder in many ways, but because of those things you go in directions you never knew were there, and that's the only way of coming up with something novel. My CEO at some point told me, I know you're doing your job well because I'm starting to hate you a little bit. And I took it as a compliment.
Everything Must Be Fractionally Beautiful
Ceci [19:36]
My CEO also told me he'd pay me so much money to go away sometimes. There's another principle of Sana, which is that everything needs to be fractionally beautiful. Explain to us what that means, and maybe give us an example.
Olivia [19:49]
I have a favourite saying I keep repeating, and I think Sanyans are somewhat tired of me at this point. It's, how you spend your days is how you spend your life. Because of that, I've come to believe that building and running a company is one of the most meaningful things you can do in your life. Some people are very motivated by spreading the product, or whatever it is they're making. I'm more motivated by the point that people go to their job every day, and if you make something cool and beautiful and meaningful, you've actually created a change or made a mark in people's lives. That's very cool to me. Beauty and joy are two things that have meaning in themselves. We're not trying to create a beautiful or joyful company because it leads to another end, they're meaningful in themselves, and that's a very important distinction. Sanyans are extreme dreamers in that sense. We used to talk about being pragmatic dreamers, because dreamers are also very difficult to work with, but with the pragmatic side it works. To be more specific, we designed our office, we have a Sana stamp under every ceramic, we create mission patches for each of the teams, every ritual has a name and is beautiful if you zoom in. If you take the whole company and zoom into the smallest component, that component in itself has to be beautiful.
Ceci [21:19]
One of my life's mottos is finding beauty in everything that I do, so this really resonates with me. I think it's really important to install this sense that everything you do, also in the detail, needs to be joyful and beautiful, because it creates new meaning for the smaller things people tend not to want to do.
The Finance Pushback: Lean vs Beautiful
Ceci [21:38]
I'm going to be the devil's advocate as the financial person in a company now. How do you manage being lean and fast and focused with spending time on the smaller things, or spending resources on creating that specific environment? How important is it, and how do you quantify that, if at all?
Olivia [22:01]
Generally, I don't see any tension between building a fractionally beautiful company and a well-functioning one. For an ops person, a neatly designed company or process that works perfectly with scale and automation, and is super clear to everyone, is one of the most beautiful things there is. Beauty is about smoothness, first principles, removing friction. And many times in ops, beauty is being invisible, which is a little bit of the difficult part. I always say to the ops team at Sana, we've done the best work if nobody notices us.
Bea [22:44]
What is one of the most beautiful processes you built in your time at Sana, something that made you proudest because it really falls into this principle?
Olivia [22:53]
A few come to mind, but I'd have to mention the promo crash that we do. It's beautiful because it's very scrappy and it means a lot to people. When somebody gets promoted, we, the senior leadership, jump into a surprise call where the person thinks they're going to have a one-on-one with their manager. We do a round of congratulations and talk about what the person should focus on next. Going back to meaning, to me, if it's meaningful it's beautiful. There are more complex ones I'm also very proud of, but the promo crashes have a special place in my heart.
Ceci [23:32]
From our end, maybe it's just basic common sense, but if somebody's ill, or has an occasion, or gets married, or has a kid, we always send a very nice present. I think that's amazing, because people go through their lives while working their asses off, and it's just the basic principle of thank you for what you're doing. We appreciate that you also have your own personal life and you're somehow making it work with this crazy startup that we have.
Inside the $1.1B Workday Acquisition
Bea [24:05]
I would like to move on to the acquisition, because it's very rare for a startup to be acquired, and very rare for an operator to go through one. A lot of our audience is either thinking about going into a Chief of Staff role, or any ops role, or has been in an ops role for a year or two and still has to progress to the next level, let alone go through an acquisition. So Sana was acquired by Workday for 1.1 billion. Great result. From an ops seat, walk us through what happened, whatever you can share, and how did the role change for you? What did you have to go through? We're all blind here, we have no idea what happens.
Olivia [24:53]
There are a bunch of eras in this acquisition. First, there was the due diligence era, which lasted about two months. That was a very hectic, very intense era. Then there was this limbo era, when DD was over but before the announcement, and when I say announcement I mean both to the world and to the rest of the Sanians. That was a very strange period, because we couldn't run business as usual, and we had this big thing we knew we were going to announce. I'm a person who normally works with a lot of transparency, it sounds like I'm patting myself on the shoulder, but I cannot keep two stories in my head, so I normally just say whatever's on my mind. There was announcement to close, then close to employee transfer, so all of this happened over a few months.
The Hardest Day: Announcing the Deal
Olivia [25:49]
The clearest before-and-after was the day of the announcement, when we could make it public to the rest of the Sanians. That's probably one of the hardest days of my career so far, because we knew everybody was going to have a very strong reaction, and most of them very mixed, with a lot of pride and joy and celebration, and then worry or mourning. We knew the reactions were going to be very strong, so that was a tough one. After that there hasn't been a very clear before-and-after moment or week. Ever since, we've just worked on integrating Sana into Workday. We still operate quite independently under Joel, and he's recently taken on the Chief AI Officer role at Workday, which is very cool, and he's very right for that role. It's going to be very fun to see what he does. It's been about finding what we do uniquely that Sana should keep running as-is, or keep growing, and what we can integrate with Workday and potentially hand over. It's been an operator's dream, really cool to go through. I really wish for most operators out there to be able to go through this one day, because it's a crash course in everything you've thought about. As an operator you're always thinking, oh, when we IPO, when we're 2,000 people, when we're 4,000, it's just scale, scale, scale. And then all of a sudden it's not incremental anymore. It's not, oh, we grew by 10 people last week, it's, all of a sudden we're 22,000 people. It's a very fun and crazy period to get to go through.
Ceci [27:44]
It's fascinating, and we're really lucky to have you here to tell the story. My gut reaction: one of the reasons I love working in startups is that you're still small, still nimble, still in control. When you're faced with this imperial ship of a large company that you have to integrate with, is there any tension between what you're bringing and how you operate, versus how the company has operated so far? And how do you work around the lack of nimbleness a larger company may have?
Olivia [28:22]
Yes, for sure, there are very different operating models. What's cool now is we get to have one foot in a startup and one foot in a public company, and the years we're going through are probably going to be the craziest of all, maybe not of all time, there were dinosaurs at some point, but crazy years for tech. It's going to be a very cool seat to have in 2026, 2027, 2028. When you're used to being cowboys, basically running everything, having an idea one day and doing it the next, it's a very different environment. But I used to think that as we matured we'd have had to make a lot of those changes anyway. So it's a bit of a crash course in growing up and becoming a public company, but it's nothing we could have ignored anyway.
Why She Didn't Take the Exit
Ceci [29:26]
Connecting to how we started, about your arc and being loyal to the company. A lot of people think, I'm going to exit and just retire, get out, live my life, I got my stock options compensated, bye-bye. What kept you there?
Olivia [29:46]
I don't feel ready for retirement. For me, personally, I can't think of a more fun thing to do than integrating a company that you know every single corner of. It truly is a once-in-a-lifetime opportunity to integrate something you know so well into a whole new world. I'm drawn, as I mentioned at the beginning, to seeing things through and sticking around when things are very tough. Just like I've been amazed by people who've gone through long arcs, the Hillary McAdams example of 18 years at Oracle, I've always been amazed by people who've been through an acquisition like this. For me it's the challenge that persists that's interesting, and the curiosity of, I just want to learn this now and see how it plays out, and I really want to make the absolute best of it. I want the Sana acquisition to be the most successful acquisition of all time.
Bea [30:46]
You've kind of unlocked the next level of problems and challenges for yourself. You're like, okay, I've done all of this, fast forward to level ten, there I am.
Olivia [30:58]
One hundred percent, it's all a video game. I genuinely think, maybe it's my bias, that if you look at your work and career as a game, and you try to have fun and go through the next levels and challenges, it's really rewarding. Maybe I'm a dopamine addict, I always need to have fun. I have a life principle: if you stand between two paths in life, you should choose the one that gives a better story. To me that's a good compass. In this very specific moment, it's about seeing it through and continuing to learn with it.
Building Before the AI Wave, From Europe
Bea [31:36]
Maybe moving to our last section before the rapid fire. Sana was actually born before the AI wave hit consumer consciousness, but it's now talked about as one of the AI exits that defined the moment. Looking back to the early days, what was different about how Sana was built that let it ride that wave? Was it luck? Was it deliberate?
Olivia [32:08]
The foundation of the company was extremely intentional and deliberate from day one. I don't know how much is luck, it's very hard to say. When I came into Sana there were 20 people, and I had a one-on-one with everyone the first week. I'd ask them what we're building, what they're doing, all of that. On the question of what we're building, you had as many different answers as people, it was complete chaos. But when you asked why they were there, what they appreciated about the company, their favourite rituals, everybody gave the same answer. It was almost like it was rehearsed. So we barely had a product, we didn't have any of that, but we had a company, we had an idea of what the company wanted to be. That makes me believe it was a very strong foundation to build on. Because of that, and because of the principles themselves, it was built for a chaotic world. We built for pivots, for insane technological development, for not having product-market fit, which meant we built a company that would thrive in the harshest environments rather than one that would just be okay if things were stable. With that, we were well set out for what was to come.
Bea [33:47]
I'd like to ask you one question on Europe versus US, as Sana has been built between Stockholm and London. We hear it all the time that US founders are just better, that the US is a better market, that you basically have to be a psychopathic person to make a business succeed. Whereas I'm hearing a lot of opposite principles from you. Is it possible to scale a business to this size in Europe, and in Stockholm specifically? Tell us why it's been possible for you to achieve a massive result while being in Europe.
Olivia [34:24]
People say that companies growing up in a smaller market have to think global from the beginning, because they have a smaller TAM and can't ignore that. I think that's one part of it. Building in Europe is extremely special, many people say that, but it's very hard to pinpoint exactly why, and many have tried. We have the basics that are needed, the crazy talent, the network, and then we have a few other things that mean a lot, like nature, equality, and trust, which is apparently a huge one. If I had the answer, many people would be interested in it, but I would never build a company in a different place than Sweden. I'm happy people have opened their eyes to Europe, and northern Europe too.
Bea [35:14]
My same question to Cecilia. She works for a Norwegian startup, and some of the principles are similar. What do you think?
Ceci [35:23]
Generally speaking, in the US you have pure grit, hustle culture, no matter what's in front of me I'm going to go straight through it. In Europe in general, and maybe in the Nordics it's slightly more obvious, there's more elegance in how you solve problems. I don't know whether it's because you don't have the idea that you have to work 150 hours a week. You mentioned the principle of fractionally beautiful. I think it's inherently a bit more in our culture, how to elegantly build a company, how to balance things a bit more. I don't have the answer, but that's where I lean. And I think all of that is built on values in the end, which is always a bit of a non-answer. If you're building a company for different reasons than just chasing the next round or an exit, I think you'd build something better.
Olivia [36:27]
I agree. You could probably also talk about the grit of European founders. If the immigrant theory is true, that if you're an immigrant you have more grit, you want to prove everybody wrong, you have a chip on your shoulder, then that must be true even more for European people, because it's way easier to be an immigrant in Europe than in the US. Maybe it's easier, hence it comes with less grit, because you have to prove fewer people wrong.
Ceci [36:57]
I did move to the UK when I was 21, and I did have a bit of a chip on my shoulder to just make it.
Olivia [37:04]
Did you both come from a small place, because you said you're from the same place? Is it a small city? My hometown is five thousand people, and the nearest city has two hundred and fifty thousand. But there was always this sense of, I have to get to the next bigger city. As for now, it's, I have to get to the next biggest problem. So there's a bit of a parallel there.
The Montessori Kid Theory
Ceci [37:28]
Maybe a personal question to you. I saw you post about being a Montessori kid on LinkedIn, and I was wondering whether you think there's any link between being a Montessori kid and the spirit you have, being quite a generalist and trying to solve problems in a creative way, maybe less structured than others would be in their approach.
Olivia [37:50]
I'd like to think that. It's hard to attribute where it comes from, of course, but I was at least schooled that way. I was schooled in the way of, I'm not even going to tell you the problem, I'm not going to tell you the solution, and I won't tell you the format, you have to come up with all of that yourself. The problem part is huge when you run a company, because there isn't going to be a list of problems. Once you find the problem it's hard to find a solution, but even harder is to define the problem and then prioritise what you're going to do. So it definitely comes from that. I also grew up in a smaller town in the north of Sweden, and I went to Montessori. We were out in nature all the time, and you build this appreciation for nature and beauty that's so deeply rooted.
Ceci [38:44]
I do think there might be a correlation. For the Italian way, for example, you're channelled into a path and given praise at each point of the path if you do things in a certain way. That's the complete opposite of Montessori. I had to remove myself from this principle actively, over and over again, and it took a long time to then think creatively.
Olivia [39:05]
In a way, I'm a little jealous. I wish I'd had a little Montessori education, it sounds great. It is Italian, right?
Ceci [39:12]
I know, but somehow traditional Italian school is the opposite of that. I had to be the really rebel teenager kid, like, I don't care about any of this, I'm just going to go my own path, and that really enabled me to see my own path.
Bea [39:28]
Me and Cecilia were opposites. She was the rebel one, I was the very diligent one.
Olivia [39:33]
I love that. This was a hard thing, trying to be a rebel in Montessori was impossible, because everyone was like, yeah, that's totally fine. And it was like, no, I'm a rebel. They never gave us the opportunity to be one.
Ceci [39:44]
There's a lot to say on education, and there's a whole different episode to make. Montessori, I believe, is going to be much better suited for incorporating AI in school, because the traditional school system is not ready for what's to come.
Olivia [40:01]
Absolutely, because you're given an empty chat and it's up to you to find the next problem to solve. There are so many parallels there. In the AI era it's way more important to stimulate creativity rather than give skills.
Rapid Fire and Goodbye
Bea [40:18]
Now we'll move on to the rapid fire round. What does operator craft look like when the ground under you keeps moving?
Olivia [40:25]
Leaning into chaos is the first thing I try to teach, and not controlling it. Find people who really thrive in it, not only people who tolerate it.
Bea [40:42]
Second question. AI, favourite tool for your day to day? Sana is not allowed as an option.
Olivia [40:44]
I have to say, just the Claude chat window.
Bea [40:47]
One thing every Chief of Staff or Head of Operations should stop doing in 2026.
Olivia [40:53]
Impossible question, I refuse to answer. It's like, how long is a rope?
Ceci [40:58]
Well, Olivia, thank you so much. This has been brilliant. I've personally learned a lot about values, operating, and working in an ever-changing and scaling startup. Thank you for being so generous with your wisdom before you retire, as we said.
Bea [41:19]
And thank you to everyone listening. If you enjoyed this one, subscribe, leave a review, hit a like, and thank you so much for tuning in. And thank you, Olivia, this has been amazing.
Olivia [41:30]
Thank you so much. I had so much fun talking to you both today.