CEO School and the Future of Work with Stephane Kasriel - a podcast by Barry OReilly

CEO School and The Future of Work with Stephane Kasriel
In this episode of the Unlearn Podcast, Barry O'Reilly speaks with Stephane Kasriel, the CEO of Upwork—the world’s largest freelancing platform where businesses and independent professionals connect and collaborate remotely. Upwork is driving the future of work conversation, and discovering what it really means along the way.
Creating Capability To Continuously Change Stephane feels one of the most exciting aspects of the tech industry is how quickly it changes— a key competency he believes people must develop is adapting to that change, learning continuously, and unlearning what is no longer useful.
He talks through two specific changes Upwork has experienced: the switch from traditional waterfall development to remote agile teams, and sourcing and clarifying Upwork’s values from within.
Secrets To Distributed Agility Several years ago, no one believed that agile could work in teams that weren’t co-located, but Upwork—along with other companies like GitHub and Automatic—has demonstrated it can. It takes an open mind, strong culture of feedback and honest personal evaluation to understand if working remotely is a fit for you.
Making this clear during hiring is crucial. Not everyone will be passionate about or motivated to work in a distributed manner—and that’s okay. It’s better to discover it as quickly as possible because it means the people who join your organization are aligned with the opportunities and affordances of distributed work. They’re happier, more productive and stay longer.
Challenges Transiting To The Top Transitioning from one role to another can be challenging, but the transition to CEO is unique. There’s no CEO school. Stephane shares how he found his way by applying many of the strategies that made him successful as a product and engineering leader. Actively learning from the people around him—wherever they are in the hierarchy—helped guide this approach to lead the company forward.
In the tech industry, where so many founders are CEOs, knowing where to step up and step back is key in creating a healthy culture within leadership teams. Stephane shows how he’s tried to let the smart people bring their skills to bear.
Unlearning At The Global Level There are a handful of things reshaping the economy: automation technologies, the acceleration of the rate of technological change and innovation, and the geographic mismatch between where jobs are being lost and where they’re being created. Stephane talks about how these forces are causing changes in the labor market and how you need to approach learning to stay current.
It’s the people who can be in the habit of doing new things, and consistently adding new small skills who are ultimately going to be successful. Stephane adds that if we can’t embrace change, we’re doomed. We’re part of the future that’s coming; we can be a part of making it happen, or let it happen to us.
The Power of Remote Work Upwork is focused on making remote work possible, and that’s not just about profitability. When the cost of living becomes unbearable in the big tech centers, but other towns are dying for a lack of good jobs—the best solution can’t be for everyone to move to expensive cities. Responsible tech leaders need to abandon the idea of having their entire workforce in a single building in a big city. Many jobs do not need to be on-site, and they shouldn’t be. Society as a whole will be better when we start making growth and success inclusive of more people.
It’s not a good outcome for the world to have a huge part of the population unemployed or underemployed. One of our most precious resources is the human mind, and we shouldn’t be wasting it.

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