From Puzzles to Pento with Sabrina Castiglione

00:00:01:23 - 00:00:26:05

Daniëlle Keeven

Welcome to another episode of Beyond the Budget, where we explore the human side of finance through the eyes of CFOs. Today, our guest is Sabrina Castellani, the chief operating officer at Pento. Sabrina has left her mark in the finance industry, but her unique approach and impressive accomplishments, notably as the CFO Atlassian Sabrina's journey is one of remarkable contrast.

00:00:26:13 - 00:00:48:01

Daniëlle Keeven

She has navigated the analytical worlds of chemistry and finance, while also holding a deep passion for the fantastical evident in her love for the Wheel of Time series and her unique collection of the Lord of the Rings Swords. Growing up, Sabrina embraced her individuality as an equal kid, a personal style that she carries with her to this day.

00:00:48:22 - 00:01:14:17

Daniëlle Keeven

This sense of uniqueness spills over into her professional journey as well, from developing and monetizing an original puzzle game to being the seventh employee. Atlassian. Sabrina isn't one to shy away from uncharted territories. Her leadership style centers around the concept of healthy, productive conflict. Having experienced the rapid growth of a team of 7 to 95 in just two years.

00:01:15:01 - 00:01:56:07

Daniëlle Keeven

Sabrina understands the importance of embracing the changes that come with scaling and the necessity of evolving from a generalist to a specialist. Beyond her professional accolades, Sabrina is a dedicated advocate for diversity and equality. She is actively involved with the YS campaign, promoting careers in STEM for women. Alongside her analytical acumen, she also values empathy and connection. After recommending fiction reading as a way to understand different perspectives, join us today as we dive into the vibrant and multi-domain world of Sabrina Castellani From her early days as an emo kid to her current role as the CEO at Pento.

00:01:56:15 - 00:02:23:21

Daniëlle Keeven

Sabrina has seamlessly blended her love for the fantastical with her career in finance, proving that CFOs are as diverse and unique as the companies they steer. My name is Angela Keegan. Let's uncover the hidden stories of finance professionals as they navigate money, investment and growth. Let's look into the person behind the CFO title. Let's go beyond the budget.

00:02:25:09 - 00:02:51:00

Daniëlle Keeven

Before we get into the episode, if you enjoy the show, please leave a five star review of the podcast wherever you listen. It helps the panel studio's team tremendously and lets us continue to uncover the hidden stories of CFOs. So why don't you tell us your name, your company, and in just a few sentences, what your company does?

00:02:51:00 - 00:03:18:07

Sabrina Castiglione

My name is Sabrina Kass, the audit. I am the CEO at Penn and we make payroll painless goal for UK businesses by automating the payroll process and then as a finance and people person, this is something particularly close to my heart. Yeah. So I grew up just north of London face called Hertfordshire, but if you think of it as like Greater London, it kind of is technically I was born and for so that makes me in North London go by.

00:03:18:18 - 00:03:39:17

Sabrina Castiglione

That's quite some time ago now. So yeah it's you know, commute about that weird mix of like not quite urban and not quite like rural. So you get these kind of fields interspersed with, you know, industrial parks and things like that. But I was there until I went to uni and then, yeah, I came down to London and never left.

00:03:39:17 - 00:03:55:19

Daniëlle Keeven

And let's take it way back. Can you describe your childhood bedroom for us? Like was it shepherds or did you have to have your own, do you have any posters on the wall that you grew up with? Cats or did you only get a cat when you got older? Like tell us what the situation was?

00:03:55:19 - 00:04:17:19

Sabrina Castiglione

So I have an only child, so I, you know, I did that whole maximization of resources thing nice and early. So I got that bedroom all to myself, no one else stealing baths. And actually there was a spare bedroom that was next to mine where I actually spent most of my time. And it was papered wall to wall where Lord of the Rings at one point, even all four walls ceiling the door.

00:04:17:19 - 00:04:38:03

Sabrina Castiglione

He could barely see the final attack. And actually, in the end, I have right now there are five swords on the wall because like, it's just like my little Lord of the Rings armory. So, yeah, massive fancy CG from way back when. So my actual bedroom was like quite play in the final, like neutral and sparse. And then there would be theater spare bedroom where I would spend all my time.

00:04:38:03 - 00:04:40:03

Sabrina Castiglione

That was just fancy chaos.

00:04:40:03 - 00:04:41:22

Daniëlle Keeven

And what did you want to be when you grew up?

00:04:41:23 - 00:04:57:01

Sabrina Castiglione

Yeah, I never really knew, but I am. But I asked my mother once what she thought I would be when I grew up, and she said she wasn't sure either. But my grandmother was dead certain that I would be a lawyer because, like she told back to you this one, that was that was her thinking.

00:04:57:02 - 00:05:10:23

Daniëlle Keeven

And you said you were an emo kid, like pink hair, fringe over the eyes, black, skinny jeans. It seems like you kept some of that style with you up to this day. Yeah, Well, what was the origin of your interest in all of these, this goth and emo style.

00:05:10:23 - 00:05:35:23

Sabrina Castiglione

By the I was just like your classic dissatisfied rebel child would just say it was, I think, a way to the act now. I mean, I love the music was into like post-hardcore then, still into post-hardcore now. But yeah, it was just kind of the scene that I was in at the time, you know, Not really. I wasn't really engaged with all the people I was at school with, had a group of friends outside of school, and that friendship was very focused around music, the kind of fell into that.

00:05:35:23 - 00:06:02:21

Sabrina Castiglione

So yeah, these days it's more than the my people describe my sense of business funeral is that the funeral is a board meeting. They all kind of blend into each wall to wall, smile, black dresses, nothing else whatsoever but young just Amy child growing up in a Italian family, you know, strong Italian family weight. And I was, you know, very, very kind of different to the whole go and do like the childhood thing.

00:06:02:21 - 00:06:07:21

Sabrina Castiglione

And then get married and have kids. And I think I was rebelling against that from quite a young age.

00:06:07:21 - 00:06:13:03

Daniëlle Keeven

And were you into math or finance as a kid or did that come up later in life?

00:06:13:12 - 00:06:37:11

Sabrina Castiglione

Definitely not. Finance, Like, I was always quite good at maths, always quite like, quite enjoyed, like I did maths and advanced maths but like cheesy and then massive five or maths A-level. But I was never like time. I get into it for its own sake if that made sense. And but at the same time it just I did, I just always kind of made sense to me, like I never had that kind of dread of maths that some kids have.

00:06:37:11 - 00:06:55:18

Sabrina Castiglione

I do remember once my mum who works a barrack she brought home like the Lego maths test, so they would give like the people that they would hire to buy this little bank. And by I'm probably am like year six or seven might happen a an end. So I'm doing quite well and see I don't carry a lot of people for this path.

00:06:55:18 - 00:07:15:09

Sabrina Castiglione

So I was always something I have sort of like a natural affinity for would be unfair to say that I have like any kind of particular love of it, to be honest, but I like the logical element of that. I think in almost all roles that kind of logical analytical ability is underrated. The ability to just kind of fast principles figure things out.

00:07:15:09 - 00:07:42:15

Sabrina Castiglione

But I think the pace at which the world moves now wildly, like my mum's went to the same place my whole like over 30 years she's been there and it's like, that's amazing and just does not happen now. Like jobs, just companies even just change too much. And I think just the ability to like reason things through, figure things out is just so underrated and people who write experience a lot, but an experience is invaluable.

00:07:42:15 - 00:08:04:10

Sabrina Castiglione

It helps build up those pattern matching abilities that you know sure you to write on to sometimes. But I think whilst people appreciate that like just that ability to be someone who can figure things out is really important. I think if I took one thing from all the years of maths, it's just that I did it as something to it that helps you start thinking about how to get from A to B and to just kind of figure out a way.

00:08:04:11 - 00:08:26:17

Sabrina Castiglione

I think that's like a lot of like creativity in maths that's kind of overlooked. But at university I ended up doing chemistry, but I actually specialize in physical chemistry, which is I like the physics and the chemistry and although I remember any of it now back, there's something just really beautiful about the application to the real world. I think if I went back in time, I probably would have them physics and like, so I'm even kind of closer to that.

00:08:26:21 - 00:08:42:17

Sabrina Castiglione

But I think subjects like that, like math and physics, are things that you already really get to the really, really exciting stuff by the time you get to uni and it's like a lot of like laying the groundwork with all of that and I kind of wish I'd realized that earlier. She seduced by like fires and flames and bumps and batters which I take away from you.

00:08:42:17 - 00:08:45:02

Sabrina Castiglione

Then I really get to university. Now I proclaims.

00:08:45:06 - 00:09:03:17

Ben Hillman

My favorite part about getting to know you through what you've mentioned to us and through what you've shared online is that you're several interest in the fantasy genre, including your favorite series being like Wheel of Time and all of your association with Geekery. But I'm very curious when you're because this is something that I imagined for myself. But when you're reading, which scenario do you imagine more?

00:09:03:20 - 00:09:10:20

Ben Hillman

Do you imagine yourself as one of the characters that you would read about, or do you imagine yourself in the same world as the characters you would read about?

00:09:10:23 - 00:09:29:13

Sabrina Castiglione

And I think it depends on if I am reading it or if I'm thinking about the books. And I mean, I probably spend like a disproportionate amount of like especially like just about the Bay to sleep time thinking about whatever is I'd most recently read. I think when I'm reading it, I do sort of really absorb myself into like the character's shoes.

00:09:29:13 - 00:09:48:21

Sabrina Castiglione

But I think afterwards, after the fact, I think I very much saw where the story goes outside of I do really love fiction, though. I think it's one of the few ways that you kind of like, actively go and build empathy because it's one of the true ways that you can actually put yourself in someone else's shoes and live free that shoes for for a while.

00:09:48:21 - 00:10:10:13

Sabrina Castiglione

And you don't really get that with anything that takes that experience and puts its own color on. I like watching a TV show or even like audiobooks I don't find are as good for this as just like being able to paint like the whole picture in like your own head. But you know, I have a role that sets kind of, you know, I knock off the final scenes, but I also the call of the people, teams and talents and hire.

00:10:10:13 - 00:10:38:12

Sabrina Castiglione

I mean, you get to a certain point in your career and you have two kinds of problems that you're ever solving, like you're solving like logic problems. And some of those are math. Some of that is a sequence and some of those are first principles or your solving like people problems, which is like group psychiatry and like trying to like get an organized groups of people to do something and to the degree that I have any skill in the latter, I put it down to like spending a lot of time reading fiction on borderline refuse to read nonfiction.

00:10:38:12 - 00:11:00:20

Sabrina Castiglione

Like I'll read a blog or read a summary, but I find it really hard to read like business books. Batch B, some of the things that you know have worked really well have come from things that like seeing some of these other interactions play out in practice and like getting a view behind other people's eyes that are sometimes like very different to you and very different motivations and incentive structures and things like that.

00:11:01:04 - 00:11:16:08

Ben Hillman

The biggest thing I want to pick up on there for me personally is I struggle with like reading, with focus, and there's probably a little bit of dyslexia in there as well. Audiobooks are kind of my default if I need to read something because you know, I can I feel like I can get through it a little bit easier.

00:11:16:08 - 00:11:32:04

Ben Hillman

But I'm very much with you where it's like, I don't love audiobooks where there's a lot of personality from the actual from the narrator, because it feels like, you know, I'm already getting this. Like, you know, when you're reading, you're getting, you're reading it like second hand in a way. It's like you're, you're putting your own personality into it.

00:11:32:04 - 00:11:48:12

Ben Hillman

You're putting your own inflection on the voice and everything like that. And when you hear it, when you hear it being read by someone, especially if they like, kind of read like in a way that you maybe weren't picturing the character, it's like you're that what you're saying there is that empathy is like one level removed. So I'm very much aligned with you on that point.

00:11:48:16 - 00:12:17:17

Sabrina Castiglione

And I love rereading books like, you know, my favorite books I probably reread every year. And then I don't think you'd get by and people often say, Why is that still like exciting? And it's like, Yeah, because she'd been just a really different picture over it every single time when like you interpret something in different ways and maybe that is just like in book snobbishness part of me, but I just kind of hate anything that tries to like curve like one concrete interpretation on like the picture of what I'm looking.

00:12:17:17 - 00:12:35:08

Ben Hillman

At the last little thing and then I'll toss it back over to Danielle. Is So you've mentioned it, and I know you mentioned in your SEO Secrets video that is out there about building Your Lord of the Rings sword collection. I'm wondering I want to know more about that. Like, do you have Sting? Do you have Andrew Like, like when did that whole when did that start for you?

00:12:35:16 - 00:13:03:19

Sabrina Castiglione

Yeah, I mean, I can give you like a level to say that has had a five, which is a alwen sword. I have a there we have Strider sword and like of fighting knights over here we have Andrew Mill which is out and so yeah, them and then this this isn't the Lord of the Rings sword and this is a sword that my last company, when I was leaving as a leaving prison, they went and got me a sword and they engraved with a company like that.

00:13:03:19 - 00:13:20:19

Sabrina Castiglione

So yeah, that's my, my little Lord's tattooed via email. Cyber security. Yeah. Yeah. So it's got the little Parthian hexagonal logo on it, both on the sword and on it has got the scabbard, but if I put the scabbard up on the wall, it keeps falling off. So. Yeah. So it's a real they are real but they really had.

00:13:20:20 - 00:13:29:02

Daniëlle Keeven

You said you initially focus on chemistry well at uni including early focus on STEM with your time abs. I want to say this right exit tech excited.

00:13:29:02 - 00:13:29:18

Sabrina Castiglione

Excited.

00:13:29:21 - 00:13:33:07

Daniëlle Keeven

Yeah. It's high tech. Thank you. What drove you to that place?

00:13:33:07 - 00:13:51:17

Sabrina Castiglione

Initially, I was always like a so a quite small kid and like, you know, did well at school. I know kind of doing chemistry just because as I said, I think like if I went back in time, I would probably have done the physics, but I wanted something that was both like logical but applicable to the real world.

00:13:51:17 - 00:14:12:01

Sabrina Castiglione

And I really, really loved the subject of school. Like have like a really natural affinity to apply. I probably would have like in the years going up to university, maybe even the first couple of years, actually the best, if I had to guess, would have said I'd become an academic, just end up learning, right? And like that's really cool and that academics get to go and do learning every day, right?

00:14:12:01 - 00:14:35:04

Sabrina Castiglione

But as part of my degree, it was like a four year degree and you come out with a master's, but that fourth year was a year kind of doing research. I do not have the patience it takes to do research, especially not in chemistry, where you go into a lab every day and you do something and you do it again, another again, and then you spend an inordinate an amount of time like applying for funding and things like that.

00:14:35:05 - 00:14:51:02

Sabrina Castiglione

It stops feeling like learning. And I know this isn't true for those of my friends from university who went on to do chemistry and love it. But to me it felt like I'd gone into like a factory job to just kind of do things over and over again. So that didn't work out for me. So then I was like, Well, I've got to go disappear.

00:14:51:02 - 00:15:16:01

Sabrina Castiglione

Exciting. I guess I'll go do actuarial joking like the most boring thing in the world. But I mentioned that my my parents are Italian. They look like, well, I can be a doctor or an accountant or like, you know, some kind of like something professional actuarial felt like, oh, so they probably be quite good at plus gave. It turns out that when I'm bored with something like I am terrible just terrible to be around full stop.

00:15:16:01 - 00:15:39:04

Sabrina Castiglione

Like if I am not excited by what I do. But I somehow stuck it out for about five years doing pensions, actuarial which just kind of fell into is like, well, I guess, you know, my dream of being an academic is dead. Why not dedicate my soul to like, doing this instead? And then sometimes towards the end of that, someone who just knew me much, much better than I knew myself, said Giovanni.

00:15:39:04 - 00:15:58:17

Sabrina Castiglione

Well, because I come home and started complaining of I and it probably it most stays over the last five years. Now I Why don't you try speaking to start? I think you'd actually really appreciate be in the order in the chaos of my upbringing, my response was just kind of like, well, baby shape. But that's not a thing that adults guarantee.

00:15:58:17 - 00:16:14:19

Sabrina Castiglione

Like, right, I've got responsibilities. I've got to get have a proper job doing some planning. But this person convinced me, go speak to some companies, see what it's like. And in the end, I think one of the things that got me over to blind, they were like, And maybe they'll go bust in three months. So it's not like they'll blame you, right?

00:16:14:19 - 00:16:34:20

Sabrina Castiglione

This was kind of before I was entering the final three. I was in startups where if you go bust in three months, they will absolutely. Blainey And yeah, I came across Cassian and they were hiring for a chief of staff, which is like the most wonderful, vague title that everyone just shops, whatever, whatever gaps there are that need filling like under that row.

00:16:35:08 - 00:16:54:03

Sabrina Castiglione

But they had a commercial co-founder and two salespeople that two technical co-founders and a data scientist, and I just really wanted someone else to make all of the other stuff just go away. And I was like, Well, that sounds like ridiculous babble, so quite often. So I let's get that day. And then, yeah, fast forward six years.

00:16:54:03 - 00:17:06:19

Ben Hillman

Because I know that you've mentioned I think it was in that same sea of video secrets video where you came around a technology by I assume you mean tech like a fairly fortuitous route. Is that is that what you're basically what you're just talking about? Okay.

00:17:06:21 - 00:17:29:08

Sabrina Castiglione

I look back on that and you know, when sometimes you're just like, how much does just build up and being in the right frame of mind at the right time, looking for the right thing when the right opportunity is there? It was just the pace that someone had convinced me to go and start speaking to companies. And this one company with these amazing, amazing co-founders happened to be hiring for the perfect role term.

00:17:29:08 - 00:17:51:09

Sabrina Castiglione

I put me and know I knew at the time a perfect stage of company to like, go in there with just the best attitude towards, you know what, like she'll figure out how, which you know is it isn't leeway that everyone would give or get in these companies. And then we went on this grave journey together that allowed me to then learn all of this stuff.

00:17:51:11 - 00:18:13:13

Sabrina Castiglione

Yes, actuarial has links to up to finance. But so really what I was doing before and you just kind of pick everything up as you go, I mean, I was CFO for a while actually when I became CFO of TASHIAN and I started doing CMA for like the accountancy qualifications. So I actually qualified as an accountant off that becoming a CFA.

00:18:13:14 - 00:18:32:08

Sabrina Castiglione

You know, this wasn't something that I really felt that I had any like God given right to be on this path for. There's a lot of luck in that by always thinking I just because like, it's luck doesn't mean you do. Absolutely. Take it and run with that and make the most of that what you can. So it was like very, very fortuitous.

00:18:32:09 - 00:18:45:18

Sabrina Castiglione

I like to think I would have found my way somewhere here eventually, but I was very lucky that I was actually exactly that moment, that particular role was that with those amazing, amazing people, some of the best years of my life about company.

00:18:45:21 - 00:19:04:06

Daniëlle Keeven

I have a question. Why that? Because I was looking at you being CEO now. You've been a CFO usually typically in a C-suite when a CFO is very respected and a little bit of reverence there to some degree, but you've been in the role like, so how does your interaction now differ having done that as well before becoming a CEO?

00:19:04:07 - 00:19:29:04

Sabrina Castiglione

I guess maybe it's better to like come back to like how I approach it. Like I'm an early stage company person, the 2000 person company that has like very distinctly siloed, well-defined roles and like some degree of stability. That's probably not me, partly because I love to meddle and get involved in things like outside of my we met and, you know, really kind of understand the business.

00:19:29:04 - 00:19:52:04

Sabrina Castiglione

But I also just fundamentally believe that especially in early stage businesses, like there is no job that is too small, like there is no responsibility that is too low, that you don't do zero tolerance for like not being in the details. Like if you need to, like, go and sell something. I don't have like 12 layers of people to like push this down to like, you go and you figure out you solve it yourself.

00:19:52:06 - 00:20:08:13

Sabrina Castiglione

So I do know I am One says like there's this kind of like no reference in it because it's just kind of like, it's cool, it's just another job, but it's just that instead of just being responsible for your one job, we are responsible for all of the jobs below you. And like if for whatever reason, they can't be done, but you go and you do it.

00:20:08:15 - 00:20:18:14

Daniëlle Keeven

So tell us about your time implementing and monetizing an original puzzle from your s because you're in limited LinkedIn experience. That was towards.

00:20:18:14 - 00:20:46:09

Sabrina Castiglione

The end of like my very last actuary, which actually was probably partly why the person who told me go and speak to TAC was like very strongly of the opinion that I should criteria is it was like a potato lab at the time and I like to think that I always had like a project going. It just so happens that for like the last six years, like the project has been my company and it turns out that the best thing in the world, because I am never more energized than like when working on my project, I'm like, I get to draw every day and get paid for it.

00:20:46:10 - 00:21:04:14

Sabrina Castiglione

Like, amazing, amazing. Like the best life hack that there ever was. But my project at the time was I had just decided because I, my partner at the time, he did some like part time development for like the golf club website or something. I forgot when I was like, Oh, that looks cool. Can you show me what you're doing?

00:21:04:14 - 00:21:21:14

Sabrina Castiglione

Is I, you showed me like a little bit of, a little bit of JavaScript, a little bit of HTML. I started like trying to build this, like, little puzzle game. I think I still have it on my site and I'm going to go and see it. It probably doesn't work anymore because it's just been bad for so long and there it is still there.

00:21:21:14 - 00:21:38:12

Sabrina Castiglione

And it was like one little thing where I would like go and I just wanted to learn like a little bit of coding. So I went from I built this game and like when I say monetize, like I put out saw that that makes it possible for the monetization, but it was like a little project that I was trying for for a while.

00:21:38:12 - 00:21:58:01

Sabrina Castiglione

Just this was, this is kind of even before Tech was like really cool. This was like 2015, 2016, you know, the rise of like 2020 and 2021 had already happened. It was just like a little self tool project. Yeah, it was pretty fun and was probably what prompted someone to sort of say, Why don't you go and look into that?

00:21:58:07 - 00:22:05:20

Daniëlle Keeven

You got to do tech as an employee. Number seven as senior staff. Atlassian, tell me about your interview for that role. Did you feel like you nailed it?

00:22:06:00 - 00:22:29:17

Sabrina Castiglione

I right thing actually funny story they told me afterwards that and at the time I basically the whole company would go and interview someone. Right. So I have like all three founders and like one of their alpha employees as well. We had like the interview and Tim, the CEO, like, Walk me Out. This was back when we used to do interviews in person, like how long the day was like, walk me out to the front door.

00:22:29:17 - 00:22:46:20

Sabrina Castiglione

And they told me afterwards that they'd got to Gaffer were like, okay, we're going to him when he comes back. Him as a temporary, he comes back here. There's like, I think she's our one and they all were part of the like excited. And I think she's right. They're out of our league just like can't let it run for like a few for like 10 minutes or so.

00:22:46:22 - 00:23:08:03

Sabrina Castiglione

I just knew with that team that they were just excellent people. The kinds of people that I would happily spend a lot more hours and I would have a spend doing anything actuarial in, I think given day with I'd still have energy at the end of it. It turns out that we were all at the same university, at the same time, but we were like one friend away from being friends.

00:23:08:03 - 00:23:25:01

Sabrina Castiglione

We eventually found that who like the one friend, was that like we all knew. But I never, never thought that to introduce us. But yeah, I do know sometimes as an interviewer, I hate it when people say these things about you just click with someone or you just know or you just get a feeling. Sometimes you just do.

00:23:25:02 - 00:23:45:15

Sabrina Castiglione

Like I walked out of that and I thought, You know what? These are the people I'm going to be spending the next few years of my life with. And and it was that. It was absolutely amazing. And I got a thought out of it, which not many people can say that. And it goes to show you how well they knew me, because I think, you know, most people, we got them insisted on leaving if they'd a bit like, well, are you sure what you're trying to say here, here It was like, show love it, show love it.

00:23:45:15 - 00:23:46:05

Sabrina Castiglione

It's like.

00:23:46:06 - 00:23:55:21

Daniëlle Keeven

Okay. And you mentioned that you only started a process of qualifying as an accountant during your early startup years. What did it look like while still having the responsibility of a full time job?

00:23:55:22 - 00:24:24:18

Sabrina Castiglione

It was intense. It also became a little bit of a close down awful, but like a little bit of a game as in, like just, you know, what is the fastest they can possibly, like run through this particular exam. And I'm like, by this point, you know, had been doing the books and all the rest for years and picking up a lot of like the basics just, I mean, Googling, asking people, the community of finance people in London is really wonderful and generous and happy to take the time to, like, sit with you over a spreadsheet and figure things out.

00:24:24:21 - 00:24:45:10

Sabrina Castiglione

But it came down to like a really careful calibration of like, how quickly can I die from having to open the textbook to sit the exam? And I think in the end we got it to like on the four days, but each of those and so I it was like a pretty like managed thing, depressingly, like Christmas was like my Bonanza period where you take two weeks off with like complete three exams all year.

00:24:45:11 - 00:25:16:19

Sabrina Castiglione

But it's time. But it was, it was like a pretty intense 18 months. And, you know, startups are like the easiest places to chill and like, carve out some time. But I was fortunate by that point to just have an amazing team around me. You know, people who are Ivy Cilic has been doing great things such as Emma, who is head of finances still there and doing absolutely incredible Page, who was the head of people and she's now VP, one of the multiverse, Iva who is like head of legal and she's now head of legal incident Bio PI, just an amazing team around you.

00:25:16:19 - 00:25:30:15

Sabrina Castiglione

And actually just like a lot of really kick out Scrum women, which was great. And we all just kind of met into it and we just kind of coordinate around like we know that some of us are going to be out or busy at this time, but it's just the magic of working with great people. You can make things happen.

00:25:32:16 - 00:25:47:18

Daniëlle Keeven

Changing culture of a company as it grows, including our experience going from 7 to 95 employees in two years. Tashian I'm particularly curious about your thoughts going from a generalist. When a company is small to a specialist when a company is much larger.

00:25:47:20 - 00:26:08:07

Sabrina Castiglione

I guess the whole thing for me is that I don't think I ever really became a specialist. I think probably that's why I wanted to come out of, you know, Cassian, which I think was, you know, nearing 300 people say when I left to kind of go back to an early stage thing is that like there is just something in my soul that rebels look at a specialism and during the same or even similar things every day.

00:26:08:07 - 00:26:35:10

Sabrina Castiglione

And I don't actually think that that's necessarily true of any job that is truly the same every day. I am not someone who is going to ever love going deep. I'm like just fine or just people or just legal and, you know, and that's hard. And I think it was one of the the hardest realizations to come to Cassian and like this company that like I loved so much love the people I was around, loved the business steering while growing.

00:26:35:10 - 00:26:53:10

Sabrina Castiglione

And it was just a case of, you know, what's going to be great to me is like not the same thing. It's going to be great. The company. Like that's a hard, really hard realization to to go through. But I think in some ways it's one of the beauties of start ups is that they do change so much.

00:26:53:10 - 00:27:13:21

Sabrina Castiglione

But, you know, but the hard part about it is, is probably going to change past the point that it's like perfect for you because like what you hit that point, you can only kind of go down, go down from there. So I loved it, but just realized that being like a total specialist, this is probably never what I want to do, or at least not for like a good long while.

00:27:13:21 - 00:27:36:14

Sabrina Castiglione

And I think, you know, it's a transition that is painful, like the first time. And I know a few people who've done this transition a couple of times, and it doesn't sound like it necessarily gets easier because, you know, you form this bond and you have this knowledge and rapport and you have great people around you. But I think if there's one thing I really prioritize, like in addition to like fast principles, thinking is like self-awareness.

00:27:36:14 - 00:27:52:12

Sabrina Castiglione

And I think you've just got to be aware of what the world is that you're interacting with and like. Understand when it's like you that changes to meet the world. Perhaps it's like when the world changes to meet you and it was like, Am I the wilder of this company that is doing great? He's not going to change the thing around me.

00:27:52:12 - 00:28:10:09

Sabrina Castiglione

I like I have to either choose to accept that or change my proximity to like the situation and very, very difficult decisions to make. But ultimately, Right. And I love panto as much as I love Tesla and but it's always just hard to to kind of do the right thing sometimes.

00:28:10:09 - 00:28:32:12

Daniëlle Keeven

What would your advice be for people in that situation? Because I hear what you're saying. I think being in a start up so early makes it very personal and the ownership is very close to your heart and you kind of see it as your baby, whether you're the founder of or not. And what would your advice be for people that are kind of unsure whether, like you're saying, it's ever changing?

00:28:32:12 - 00:28:47:09

Daniëlle Keeven

It will go through so many phases. When do you say, okay, it's time like you're talking about self awareness? I agree. But what would like some of the telltale signs of, Hey, we're going down the wrong road or actually, hey, I need to steer this for myself. It's time to move to a different I think.

00:28:47:09 - 00:29:05:15

Sabrina Castiglione

The first thing, if you've got to be willing to like to be the thing that is wrong in the situation, you know, it's very natural, especially like when you're going through in your career for some of those realizations to like to make it about the company. You know, things that I often hear when I see other people going through this transition is like, Oh, it's changed.

00:29:05:15 - 00:29:31:03

Sabrina Castiglione

Everybody out of touch now. Leadership doesn't know what it's doing anymore. The companies making the wrong decisions, all of the great people have life. I think probably from having been in like a shop perspective and kind of watched other people go past the point where it's healthy, like kind of was able to kind of see whatever. A lot of the stories that make total sense is like the sense mechanisms that people tell themselves when they hit that stage.

00:29:31:03 - 00:29:50:17

Sabrina Castiglione

And so I was really conscious that like I did not want to go into that stage, like at all. I wanted to see it coming. I'd like to recognize where the point would be and not end up being, you know, the person looking to blame. The thing that I really loved and help build the outpouring like the stage was perfect for me.

00:29:50:17 - 00:30:17:17

Sabrina Castiglione

But I think some of those like the common the common thing and it's not so much about, you know, are you reminiscing about the good old days? Everyone reminisces about the good old days, you know, even if the good old days were like six months ago, it's more a case of does that come with like a feeling of bitterness, like, you know, do you resent some of the great from the company for, you know, go into a point where that thing that made it so special to you because you could sit across all different things like is is no longer an option.

00:30:17:17 - 00:30:37:13

Sabrina Castiglione

I think it's particularly hard for generalists because, you know, if you really don't want to specialize, like the business will outgrow you at some point. And that is really, really hard for all of the reasons that we said. Like it's possible it's your baby, but like, you know, even people who actually have babies like the kids grow up and move out sometimes.

00:30:37:13 - 00:31:04:01

Sabrina Castiglione

But I would say like go into it with like honesty. I think if you've got great people around you, great managers, great founders, that they're not going to see that as like a negative. Like they will probably see as like a really mature conversation and just make sure that you're always leading on the way out. So many people I see, you know, even like the last ten years who have just burned every bridge on their way out of a company or just like checked out so early.

00:31:04:01 - 00:31:21:10

Sabrina Castiglione

I like that is like a last impression, like the last taste that you leave in people's mouths. And it is such a shame because it really covers a lot of what the experience that people have that I think what ever situation you're in, like when you're back to the last day, like be there, be there and care as much as you can.

00:31:21:10 - 00:31:41:06

Sabrina Castiglione

I think when I look at a lot of the people who, you know, left either, you know, Pentair or Tesla and at various points in time and those who I'm still in contact with and think really the ideal a lot of them really like they left us they started on a really, really good now realizing that like it is a job, it is not a family.

00:31:41:06 - 00:31:49:01

Sabrina Castiglione

You know, you can take those relationships with BE, but they put care into making sure that they left in a way that was really positive.

00:31:49:04 - 00:32:03:18

Daniëlle Keeven

And what did it feel like when you first became CFO? It looks like you had to assume some other responsibility at first before shifting the focus solely to that role by being the head of people, head of talent at different times. What what was it like for you?

00:32:03:21 - 00:32:29:04

Sabrina Castiglione

I mean, lovely obviously to be recognized, but honestly, like a little bit anticlimactic. I mean, by that point I had kind of been doing the finance all of the finance of the fundraising, the board, investor relations and things for quite some time by that point. And the reason I use the word anticlimactic is because I was I'm an investor conclave recently with another former person who's recently signed his own company, and that was how he described it to other people.

00:32:29:04 - 00:32:59:00

Sabrina Castiglione

I was like, wow, I think it's a really simple like, well, she already. And so I kind of felt a bit like that. But but also just amazing to be recognized. You know, I think it is hard for companies of a certain stage to really like homegrown talent, like when they're not quite big enough to have like big formal programs, but not so small that it's just like, you know, that real rocketship, the founders really kind of leant into supporting me and I it's not something you can take for granted.

00:32:59:00 - 00:33:23:14

Sabrina Castiglione

It's had amazing people around me in terms of what the day to day of the job like it did. I'll change like a hair between like day before and day after. And, you know, it was probably an unusual CFO role compared to some. Certainly it wouldn't look anything like a much later stage CFO role because it was still so split across, you know, all G and areas plus whatever thing was on fire, like a given point in time.

00:33:23:14 - 00:33:39:17

Sabrina Castiglione

And a lot of people asked me about how it was CFO before and Crowe, he like, what's the difference? It's like, it's not really, it is the thinking and resource of last resort where there is something that needs to be picked up or a fire that needs to be put out, like that's where you guys are.

00:33:39:17 - 00:33:56:16

Daniëlle Keeven

You previously say that when you get to 40 or 50 people, a company can feel a lot more corporate. We said the most important thing is to embrace is figure out how to make it healthy, productive conflict as a part of your culture in order for your business succeed. Can you talk to us a little bit more about that?

00:33:56:21 - 00:34:02:03

Daniëlle Keeven

What does that productive conflict look like from a CFO capacity?

00:34:02:13 - 00:34:25:14

Sabrina Castiglione

So the way I think about it, when you're like a 20 people group, you can probably find ways to keep 20 people happy, like with a decision. You know, you can you can probably do something and get 20 people like fully, genuinely on board, but it's time you hit 50. Like it's getting really, really hard. And like suddenly you have to shift an objective away from making everyone happy like you were going to have by that point.

00:34:25:14 - 00:34:59:18

Sabrina Castiglione

Are you going to have more specialists? Not everyone's going to be a specialist, but like you may have a marketing class and a sales person and an engineer and they all have slightly different focuses. And Lens is about the North Star that is like really, really critical to them and actually you don't want to take that away. The way I often think about it is if you draw up like on like a piece of paper, all of the things that different areas of the business care about, sales care about winning new business, marketing cares about leads, brand customer success, cares about retention and adoption.

00:34:59:18 - 00:35:17:04

Sabrina Castiglione

Engineering cares about scale, ability. And you look at any of those things and you think, Well, nobody's too bad, right? Like ideal world, I'd have all of those and they'd all be perfect. But then you have like a set amount of product and engineering resource and you have to pick one over the upper right. Like you can't. Well, I'm certainly not anymore.

00:35:17:04 - 00:35:37:13

Sabrina Castiglione

You call go and hire like a hundred different teams. You just do everything. There are going to be some trade offs. You're going to have to one day say, you know what, we're going to build something and it's for new customers and like it is focused on new customers. And we're going to have to prioritize existing customers. It's really important we expand our ICP and that is obviously going to sound better to a salesperson.

00:35:37:13 - 00:35:54:19

Sabrina Castiglione

And then it goes to see us passive and like that is that is conflict and like trying to take all of that conflict out of a system is just impossible. Once you reach any kind of scale and stage, once you actually have specialisms, you know, these people are specialists because you want them to care about how to be really good at the thing that they care about.

00:35:54:19 - 00:36:13:23

Sabrina Castiglione

But that is going to come into conflict with my career as a business. And the other reason it's important is because everything sounds like a good idea and isolated if you want to see I'm a sales person says you should really build this thing, because then I could go and I could sell it for money. And the salesperson says, You should really go and build this thing, because then I can keep these customers and we won't lose money.

00:36:13:23 - 00:36:29:11

Sabrina Castiglione

And marketing say we should really build this thing because we can market off the back of it and we can get all of these leads. And the engineer says, Oh, would we do this? Like we'll be able to scale more. All of those things make perfect sense in isolation, and if you try and do all of them at the same time, you go bust in like three months.

00:36:29:11 - 00:36:54:00

Sabrina Castiglione

Like, you know, you split your focus, you split your energy, spread money in every possible direction. You need to be able to have the conversation. It's all of those pieces together and comes out. Come out with an answer that is the best focused thing to do, which is not going to be a compromise. Like often the compromise between two things that make sense in isolation is something that makes no sense at all.

00:36:54:00 - 00:37:14:12

Sabrina Castiglione

And if you're not willing to, whoever is as a finance person or a CEO to say today, we are going to focus existing customer retention or where the focus is going to be on new sales and say no to some of those other things, especially if you're doing that because you want to keep people happy, you will make bad decisions or you will make halfway house decisions.

00:37:14:12 - 00:37:40:21

Sabrina Castiglione

It's like a compromise. It doesn't really meet either objective. So I do think like creating an environment, once you get to that size where that conflict is not seen as a bad thing, what challenge is not seen as a bad thing where like people understand that it's about getting to the best angle together, not just the best answer from within is really important, both from like a company building perspective, but also from a finance perspective, because otherwise you're going to be in that classic example.

00:37:41:09 - 00:37:58:15

Sabrina Castiglione

The finance person mum says no, they go ask the CEO. Dad. See, I thinks in isolation. Sounds like a good idea, gives it the green light and suddenly it's like, Well, what do I do now? I've yet to meet a finance person who doesn't go, God, I know exactly what that feels like. Why do you say that?

00:37:58:18 - 00:38:11:10

Daniëlle Keeven

And can you talk to us about your involvement with the Wise campaign? It seems like you had a consistent attachment to encourage careers in STEM, as well as promising diversity and equality as promoting. Sorry, the first inequality.

00:38:11:12 - 00:38:30:20

Sabrina Castiglione

Yeah. So I was involved in the Wise campaign for a number of years, particularly in the early testing days, and it came out of, you know, this was the first job I'd ever been responsible for talent teams or recruiting. I thought that the careers that I had come from in like actuarial and finance were bad. And then I got involved in tech recruiting.

00:38:30:20 - 00:38:47:12

Sabrina Castiglione

I like, okay, yeah, there is no diversity or there is like very, very little diversity. And this was back in that everyone's in an office. Stay within commuting distance in London and just you might see 200 applications and not a single woman. And it was just.

00:38:47:12 - 00:38:48:12

Daniëlle Keeven

Really.

00:38:48:13 - 00:39:06:12

Sabrina Castiglione

Startling. You know, you hear about it, but just until you really see it is is quite hard to believe just how few women there are in disciplines like computer science. And I was talking about this with my sister. He was like, well, why don't you go and see if there is, you know, who else is out there trying to solve this?

00:39:06:14 - 00:39:26:22

Sabrina Castiglione

And came across the Wise campaign, which is a campaign for gender equality in STEM more or better put like better gender parity in STEM as well, trying to encourage more women and girls into STEM industry. So science technology, engineering and maths. And what that turned into is they had like a board called the Young Professionals Board for people under 30.

00:39:26:22 - 00:39:53:03

Sabrina Castiglione

That's actually why I stopped doing it, because I went past there, went over the hill over the age 30 and was no longer young enough to be that on the Young Professionals board. And we really had a commission to try and take the fight earlier because what we realized it was all very well saying there aren't enough women in tech jobs best because there aren't enough women doing tech at university because there aren't enough women doing tech A-level, because there aren't enough girls picking tech at GCSE.

00:39:53:03 - 00:40:17:19

Sabrina Castiglione

And it's one of the really hard things that like the British education system, makes you choose those subjects so early, and especially for women, you pick it at exactly the point that all of your hormones are like piling on all of the peer pressure and telling you to conform. It is. And basically that age. And if your friends are going and doing drama English and Spanish, you're going to end up going and doing drama English and Spanish.

00:40:17:19 - 00:40:36:22

Sabrina Castiglione

So I do have like this big belief that gender parity in especially in computer science and I speak about that just because it's the one that I'm close to closest to being in tech. It really is a generational challenge and it is something that we have to address way, way earlier, because the impressions that we have around what subjects are and all to girls just sets in.

00:40:36:22 - 00:40:58:05

Sabrina Castiglione

So young. Yeah, and it's partly why I'm quite a five of the international baccalaureate system, partly because it makes people do a science, do it humanities, do maths, and keep some of those doors open for later. Whereas a lot of people really don't realize the doors that they're closing when, you know, they they turn away from some of these subjects at a young age.

00:40:58:09 - 00:41:19:00

Ben Hillman

So you mentioned earlier on in our interview that the best perspective that you can get from reading a work of fiction is that empathetic connection that you get with that with the author. How do you feel that perspective helps you engage with folks that are reporting to you? Obviously, we're looking from like sort of a CFO capacity. I know you're currently and then is there a book that you recommend your direct reports read to get to know you.

00:41:19:02 - 00:41:44:11

Sabrina Castiglione

In terms of how it helps? I think it's just a case of it's very easy to project and to interpret someone's like response as like the response. What would you be doing to kind of through that response? But I think, you know, it's always key to try to understand the giving person's motivation. And so what makes them tick and even just simple things like how they how they respond, how they like to receive feedback.

00:41:44:12 - 00:41:59:00

Sabrina Castiglione

Yeah, there are there are some people that I know I can just buy something off over on Slack and it will be totally fine in our office where it's like, I'm going to call because I know like if I'm not having like a face to face pseudo face to face interaction, that this is like not going to land well.

00:41:59:00 - 00:42:20:06

Sabrina Castiglione

So I think that the main thing is just by being able to pick yourself in the shoes of people very, very different to you, it just help build up a repertoire rather than kind of like a one fits all management style because everyone's different. And a lot of the things that go with, you know, with working with people is just kind of on the standing and embracing those differences rather than trying to make everyone a clone of you.

00:42:20:06 - 00:42:44:12

Sabrina Castiglione

But also, you know, just to take time to like, understand people's interests and to care to make sure for you the level things, the small questions that you demonstrate and you actually care about them as a person rather than as a human resource. So you are like trying to like, run forward in a particular direction. And I think good management is just, you know, table stakes in like any industries, like cars, particularly tech, because these are knowledge industries.

00:42:44:12 - 00:43:05:20

Sabrina Castiglione

There is no mine or factory or something producing a physical output. Very few have any kind of like hardware, real world physical to everything is just a product of great minds. And the more that you can build trust with those great minds, the more you can have conversations that have like productive conflict and challenge. Get to the right answer fast.

00:43:06:04 - 00:43:25:02

Sabrina Castiglione

Then like all of like the lovely finance buzzwords like productivity and things like that come in. But, you know, but that's like an output to just treating people well and having a good relationship and I mean treating people well. I think it means looking out for their best interest, which is not the same as being like perfectly nice all the time.

00:43:25:02 - 00:43:45:19

Sabrina Castiglione

Sometimes what you need to do is you need to push someone through like something that very day one like Ted or like that is hard to help them get to. The thing you can see is really going to unlock their potential. I liken it to kind of like going to the gym. When you go to the gym, you know, if you come out and you're not like sweating or tired, probably you've not done anything to actually grow your muscles.

00:43:45:19 - 00:44:02:10

Sabrina Castiglione

Like there's a degree of like discomfort that you have to kind of go through in order to grow. And I think work is the same, but it's very hard to help people through that period of discomfort if you don't have trust, because otherwise you just seem like a horrible person, just always trying to make them do a thing that they don't want to do.

00:44:02:10 - 00:44:32:13

Sabrina Castiglione

And in terms of a book to get people to Naomi, I don't think there's any one book or the one book I always do recommend to people is Jonathan by Neil Stevenson. And the one thing I always say about it is don't read anything about it. Just go and read the book. I think probably if people are the very few people who do make it all the way through and often probably get why I really like, it's a book that very much celebrates logic and celebrates past principles, thinking it's a very deep, quite, quite philosophical.

00:44:32:13 - 00:44:47:16

Sabrina Castiglione

I don't think anyone who read it would be surprised that I really like it. I'm not quite sure it necessarily would get someone to know me. So I just like confuse them even more. But it is a great and I would recommend it to anyone who is willing to like get through a pretty long read.

00:44:47:16 - 00:45:03:08

Ben Hillman

And is there someone maybe it's from that book or from Wheel of Time or any other fantasy novel that you're a fan of? Is there someone fictional you'd completely trust to be your CFO? For one, to be a CFO for one day, I feel like it's Aragorn because he would know how to use your sword, but like, that's just me.

00:45:03:12 - 00:45:28:09

Sabrina Castiglione

There are a lot of great characters. There is one in the Wheel of Time, which is like going to mean nothing to anyone who doesn't know the Wheel of Time. Buyer. Her name's Swan Sanjay, and she is like the Amazon, see? And she is like, you know, she was born as like the daughter of a farmer and like what her way up to like a top up like that most powerful organizational and they are all kick ass women like kick ass women in the world.

00:45:28:09 - 00:45:34:11

Sabrina Castiglione

Just no peer like, you know small as how get to the point like safe pair of.

00:45:34:11 - 00:45:39:14

Daniëlle Keeven

Hands And what advice do you have first of all, looking to become a CFO themselves?

00:45:39:16 - 00:46:05:18

Sabrina Castiglione

I think especially if you're in finance, every temptation to go down the route of perfection and to make everything very neat and tidy from a finance perspective. And I'm like, I get it. Like, that makes life easier for you as a finance people. And we have really nice strict policies that like, make everything nice and neat and, you know, you're not going to have to figure things out too much because you process everything to within like an inch of its life.

00:46:05:18 - 00:46:27:02

Sabrina Castiglione

But the joy of like a really senior finance role and particularly as the CFO is not so much in having like the most perfect set of accounting that, my God, like it needs to be good. Like you need to like get through your audits and things like that. I will say like completely forget the accounting side of things, but the value is understanding the drivers in your business and the investments in your business.

00:46:27:02 - 00:46:45:09

Sabrina Castiglione

And that is not just money investments. That is time. Time like the time that is spent, especially in knowledge industries, that is like a conscious choice and an investment. And you need to understand all of the levers in your business and be that person that when someone goes to the CEO and says, Wouldn't it be lovely, we had another three engineers, we could build this thing.

00:46:45:09 - 00:47:15:23

Sabrina Castiglione

And you say, okay, there's that, and that pulls these levers that has this this impact. But wouldn't you rather pull those levels that are going to have that impact? Because actually, if we did y Z in marketing, that would deliver this better. You need to understand the levers within your business better than anyone else. And what I would say to that is that especially if, you know, it's a new company or a new role, I go down to whatever level of detail you need to get that information and to feel that you understand those levers.

00:47:15:23 - 00:47:40:00

Sabrina Castiglione

I spend a disproportionate amount of time bugging engineers to explain something to me about how part of our system works or how something affects something else, or where the data structure in our payroll engine works. Because I just know that, like when I'm sort of sitting there and working with my CEO on the roadmap, like I need to understand like how much work it's going to be to to get to an outcome.

00:47:40:00 - 00:48:16:08

Sabrina Castiglione

And you know what? The drivers are there for quick wins that might then do things for retention or take down the amount of people on who are necessary to support 100 new customers or any of those things. And a lot of those are not financial, but they are drivers and they are levies that you can pull. So that would be my advice, which is that yes, please get the accounting right, but also make sure that you are the person who is just laser focused on like driving the best possible outcomes from the business and using back the amazing seat that finance has to just see every bit of spend that investment in the company and

00:48:16:08 - 00:48:24:18

Sabrina Castiglione

just only own it more than people are comfortable with. You are like, go metal, ask questions and yeah, know your business better than anyone else.

00:48:26:20 - 00:48:44:00

Daniëlle Keeven

Special thanks to Sabrina for being on the show. You can find her on LinkedIn if you'd like to see Thanks yourself. Remember to leave a five star review if you enjoy the podcast. We'll see you next time on Beyond the Budget, a podcast from Padma Studios dedicated to helping you build Butter SaaS.