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A guy with a scarf · Aug 5, 2026

Ep. 59: Gabriella Vacca - International Executive in Telco and Streaming - Movement Is Life

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A guy with a scarf · A guy with a scarf

Gabriella Vacca and I studied computer engineering together in Turin, where she was the more solid student, and she went on to build the more solid executive career: Olivetti, Omnitel, Bouygues Telecom in Paris, Cingular and then AT&T in California, ESPN Mobile, Gogo, ten years at Comcast, and five years as CTO of Sky Italia until last July. She left for the United States with two suitcases and a plan to be home inside twelve months, and thirty years later she is in Philadelphia with a very clear view of how leadership behaves at different sizes.

That view is the spine of the episode. Leading 200 people and leading 2,000 are two separate jobs, and the second one only works if you engineer it on purpose, which is where almost everything else we discussed comes from.

She puts the threshold somewhere between 100 and 300 people. Under it you know everyone by name and the “WHY” travels through you in person, which she summed up as “it is easier to inspire your team with the “why”, and not only with what and how.” Over it, in her case thousands of people across Italy, the UK, Germany and India, the why has to be built into the machine.

Her method starts from the standard Gartner pyramid of operations, project delivery and transformation, with a foundational layer added underneath that asks which values the organization actually holds and how those principles connect to everyone touching the work, business stakeholders included. Internal KPIs hang off one side and external KPIs off the other, so the technology numbers and the business expectations have somewhere to meet.

The first value she named was transparency, and she called out how boring that may sound before making it concrete. Giving the business access to all your internal reports is too specific (or technical?) to be readable outside the function. Her analogy is a visit to the doctor. You don’t need a doctor simply to read each value in your lab report, you can do that yourself. You need interpretation, empathy, and a clear explanation of what the results mean: Am I okay? What can I do to improve? Should I be worried? The same is true of the relationship between a business and its technology organization and this calls for “meaningful transparency”.

She earned that value in a room in the States with lawyers present, on a project whose KPIs didn’t hold up under scrutiny. When she challenged the KPIs, her team admitted they had chosen not to share the full picture. She ended the meeting on the spot and explained to the business stakeholders that: “We need to address the missing data, and then we will come back to you. I apologize that we didn’t uphold our commitment to transparency”. Values become real when upholding them carries a cost. In this case, transparency meant admitting a failure publicly and showing the commitment to the value itself. A value that matters only when it is convenient is not really a value.

Gabriella separates the change that happens to you from the change you choose to lead. She compares the second kind to crossing an unfamiliar forest that you never crossed before, without survival training.

To make it through, you must keep the destination in sight, prepare for what you may encounter (including bug spray if you happen to be allergic to mosquitoes!) and surround yourself with people who have skills you do not. That, she frames as an act of humility. You must then communicate clearly enough for the team to follow:this is where we are going, this is how long we believe it will take, these are the values that will guide us, this is what I know and what I do not, and this is my commitment to getting all of us safely to the other side.

The self-knowledge becomes very practical. She knows she needs seven hours of sleep to function well. During COVID at Comcast, a company of 100,000+ people, she had to move call centers and thousands of people to remote work. It was crisis management in hard circumstances. One of her first decisions was to establish shifts for everyone, including herself, and to designate someone who could take over if she became too tired or had to take care of personal family situations or, worst case, fell ill.

One of her first decisions was to establish shifts for everyone, including herself, and to ensure that every team member had a designated backup who could take over if they became too tired, needed to deal with a family situation or, in the worst case, fell ill. The operation had to continue 24/7.

Our two careers rhymed here. In telecom, you fix the issue when it happens, the sooner the better. In media, as she put it, “the damage is already done. It’s real time. You are on screen.” At Sky, her team tracked near-miss KPIs, counting how often they came close to failure and how often they had to switch to contingency. Once a failure has been broadcast, it cannot be undone; the near-misses are what help you prevent the next one.

My own version of that lesson came early in my career, at a World Cup event in Austria, when I mistakenly broadcast an outdated ranking live on television. The woman leading Olivetti’s sponsorship side, a genuinely fair but tough leader, told me “You are good. You made a mistake. Tomorrow is another day”. I have carried those words with me for the past thirty years.

We both grew up near Turin, in a culture where education was measured against the higher score and anything less was seen as falling short. Gabriella described it as a perfect storm: being constantly measured against the best of the best is difficult enough, and it also comes with the belief that taking a risk, and therefore failing, is deeply personal. That combination held her back when she was younger.

Moving to the States forced her to rewrite that mndset, which she distilled into four words. “Movement is life. Movement is learning.”. She learned to accept calculated risks, the kind that would not bring her to her knees financially, and to be satisfied with 90% or 92%. Pouring 100% of your energy into a single destination, she realized, leaves too many opportunities unexplored.

She now describes herself as “a swimmer, not a diver.” She can dive deep when necessary, but doing so comes at the cost of seeing the broader landscape. As she sees it, the role of a senior leader is to make sense of complexity so that others can make sound decisions—including recognizing when the right technology decision may be the wrong decision for the company.

Gabriella hosts a nine-episode series, “The Reality of Women at Work”, the first podcast of the EveCareers.com Network. It began when someone she barely knew asked her to help create a message for women, and she said yes! on the spot. She connects that moment to her definition of luck: readiness plus opportunity, combined with the ability to seize that opportunity by actually saying yes.

I asked her how she sees the position of women at work today. She reads the current situation as a function of two main variables, the culture of the company and what the individual is willing to do inside it. On the second she is direct. People often come to mentoring sessions with a complaint about something that is not working. Her response is to ask what they are doing to change it. Raising an issue in a way that others can hear turns a complaint into a constructive proposal, and creates the energy for change. This is what turns you from an observer to an agent of change that makes things better for everyone.

Overthinking came up too, and she recognises the tendency in herself. The mentors who told her to “shake it off” identified something she has since turned into a discipline: reflect on it once or twice, accept it for what it is, and then refuse to that negative space. Her daily reflection follows a fixed ratio: three good things for every bad one, because the brain latches onto the negative and must be trained to do otherwise.

The line I keep coming back to capture the purpose of leadership itself: I want to be a chip in your brain, not a line on your to-do list.

That is the test. A team that needs you in the room to function has simply be given a to-do list. The harder thing, the thing Gabriella spent thirty years learning to build, is a shared understanding of “why” that people carry into rooms where you will never be present.

She now divides her time among her strategic advisory work, a give-back portfolio of mentoring and advising start-ups that cannot yet afford to pay her, and her personal life. In her free time, she continues to learn, sometimes casually, sometimes with real intent, about subjects ranging from gene editing and synthetic biology to quantum technology and post-quantum cryptography readiness, while making time for friends and family, exploring, talking and simply living everyday life.

Movement is life—and she means it literally.

Sources

Read the original on aguywithascarf.substack.com

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