Women who build what’s next — The pathbreaker

As Chief Product Officer at Vend, Francesca Cortesi’s journey has been anything but linear. From fashion in Milan to helping scale some of Europe’s fastest-growing technology companies. Her story is one of bold pivots, continuous learning, and trusting the pattern that every setback can lead to something greater.

This International Women’s Day, we begin our Women Who Build What’s Next series with a pathbreaker who proves that the future isn’t built by following a straight line; it’s built by daring to create your own.

How did your journey into tech begin?

Completely by accident. I normally say that I fell into tech and product management.

I started my career in fashion in Milan — about as far from tech as you can get, and that was a really conscious choice. Then life, not work, brought me to Sweden. When I tried to get back into fashion, it just wasn't working. That's when I started to question what my direction should really be.                                      

I was already working in project management, and that felt close to home, as I was used to organising things on time and budget from my Milan days. But somehow that role felt too limited. I found myself asking questions — about the product, the users, and why we were building what we were building. Turns out that curiosity led me straight into product management. 

Tech wasn't my dream when I grew up. I didn't even know what product management was back then (and there wasn't even the title product manager — can you imagine?!). Nobody handed me a roadmap or told me "this is how you get into tech." I just followed what interested me and kept learning.                                       

If I look back at it, nearly two decades later, I've gone from fashion to tech, from PM to CPO, helped scale some of Europe's fastest-growing companies, and I'm still asking questions 😉 The path wasn't straight, but that's exactly what made it mine.

Was there a pivotal moment that shaped your career direction?

Honestly, the first pivotal moment wasn't an open door; it was many closed ones. 

When I moved to Sweden and tried to get back into fashion, it just didn't work. It was rejection, after rejection, after rejection, not the happiest moment in my life. But it was those rejections that forced me to question everything and look in a different direction. Leaving that path behind to start a new one — with fresh eyes, naivety, and people who believed in me.

Looking back, the moments that really shaped my career were the ones when I dared to take big steps. Saying yes to leading 15 people despite having zero staff experience. Accepting my first CPO role and suddenly becoming the boss of my former colleagues. Leaving my “perfect job” to start my own company.

At the beginning, it was someone who believed in me more than I did and opened a huge door I was naive enough to walk through without overthinking. Sometimes I couldn't do it and had to learn the hard way. But I did learn. 

Then, over time, I realised there was a pattern: every low has been followed by a high. 

When I mapped out my life and career journey (yes, I used the user story mapping framework), it became so clear. The closed doors, the failures, the hard times, the scary leaps — they all led me somewhere better.    

The pivotal moment wasn't one moment for me. It was learning to trust the pattern: prepare, jump, learn, grow. And trust that the people who open doors for you often see something you can't see YET.

What helped you grow or gain confidence along the way?

Doing the work, I quite honestly believe there's no shortcut. I learned by being in the room, making decisions, getting things wrong, and figuring out how to do it better next time.     

Confidence didn't come before the experience; it came from it.                      

With one important caveat: I didn’t do it alone. I learned along the way that asking for help and having a support system that gives honest feedback and helps you become the better version of yourself is the best growth hack you have.                 

Curiosity helped too. One important insight is that when you grow, you put yourself in new contexts, situations, and rooms, and the worst thing you can do is to assume that what worked for you before will work again. I've made unlearning (and asking questions to get context) part of how I operate. Letting go of what made you successful before is harder than learning something completely new, but I find it essential, especially in tech, where things move so fast.                                         

And last but definitely not least, self-reflection. Taking time to look back at what went well, what didn't, and why. Understanding my own patterns — what energises me, what drains me, where I add value and where I get in the way. That self-awareness became the foundation for everything else.                                                      

Confidence to me isn't a fixed goal. It's something you build, lose, rebuild, and carry forward, one new experience at a time. And yes, imposter feelings come with the package, they tap on my shoulder every time I take the next big leap, and I have learned to go through them together with my cheer squad, and a rephrasing in my head “I do not know how to do this…yet”.

What barriers — visible or invisible — do women in tech still face?

The visible ones are obvious: fewer women in leadership, fewer women in the room, fewer role models to look up to. I’m still often the only woman at the table, it's hard to ignore, and quite honestly, quite frustrating. 

I have not seen the changes that I would have liked to see in the past 15 years. When everything moves so quickly, this is one matter that seems to go really slowly. We need to show girls how fun it is to work in tech, have male allies who can open doors, and share the stories of the amazing women in tech who are paving the way.                 

And then there are the invisible barriers that are harder to navigate, because they are so rooted in culture and expectations.

The subtle things, like comments on your clothes, or the invisible expectations, like being seen as "too assertive" when a man would be called "decisive." And if you think it doesn’t happen, I encourage you to look at the amazing talk Caroline Farberger gave some years ago at the Women in Tech, Sweden, conference. She is one of the few who can speak about how the exact same person gets different treatment and expectations based on her gender.                        

More companies are recognising that diverse perspectives aren't a nice-to-have; they're a competitive advantage, and I am really glad Vend is one of them.

But we're not there yet. The barriers are real, and pretending they don't exist doesn't help anyone.

What would you tell someone considering a career in technology today?

Do it. Seriously, just do it.                                                        

You don't need a computer science degree. You don't need to have been coding since you were a kid. You don't need to fit some stereotype of what a "tech person" looks like. I came from fashion, I like nice clothes and high heels, I moved to a new country with no network — if I can find my way, so can you.

What you do need is curiosity. The willingness to ask questions, even when you feel like everyone else already knows the answers, the humility to learn, unlearn, and learn again. Because, especially in tech, what works today might not work tomorrow.             

Find people who believe in you, especially when you don't fully believe in yourself yet. Dare to walk through the door, and when imposter feelings show up (and they will) remind yourself: "I don't know how to do this... yet."                               

Tech is one of the few industries where you can reinvent yourself, where your  background is an asset, not a limitation. The problems we're solving need diverse perspectives, we need people who think differently, who've lived differently, who bring something other than the same playbook everyone else has.                      

So if you're considering it: prepare yourself, and then jump. 

It won't always be easy, but you'll learn, you'll grow, and you'll carry that experience into whatever comes next. The path doesn't need to be straight. It just needs to be yours. I’ll see you at the top!