CEO School and The Future of Work with Stephane Kasriel

Listen and subscribe to the Unlearn Podcast at
Apple Podcasts | Stitcher | Google Play | Google Podcasts | Spotify | iHeartRadio

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 Upwork specific changes the company has experienced, the switch from traditional waterfall development to remote agile teams, which has made developing new projects faster, easier, and more in line with what customers are actually looking for. And how by sourcing and clarifying Upwork’s values from within the company has enabled them to scale their remote-first culture and successfully secure remote-first fit talent. Listen from 5:30

CEO School and The Future of Work with Stephane Kasriel

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 Automattic—has demonstrated it can. Stephane highlights how it takes an open mind, strong culture of feedback and honest personal evaluation to understand if working remoting is a fit for you. 

Making this clear for anyone wishing to join the company is crucial. Not everyone will be passionate about or motivated to work in a distributed manner—and if that’s the case, that’s okay. In fact, it’s better to discover it as quickly as possible, because it means the people who join your organization are aligned to the opportunities and affordances of distributed work. They’re happier, more productive and stay longer. Listen from 10:45

Challenges Transiting To The Top

Transitioning from one role to another can be challenging but 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. By actively learning from and soliciting feedback 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 health culture within leadership teams. Stephane shows how he’s tried to let the smart people supporting you bring their skills to bare. Listen from 18:00


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 particularly how you learn, and how you need to approach learning to stay current. 

He highlights 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 have to remember that we’re part of the future that’s coming one way or another, and we can be a part of making it happen, or let it happen to us. Listen from 25:25

The Power of Remote Work

Upwork is focused on making remote work possible, and that’s not just a matter of 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. Stephane points out that following this path doesn’t end well for anyone. 

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 taking a larger view of where the world is going and 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. Listen from 30:25

Listen and subscribe to the Unlearn Podcast at
Apple Podcasts | Stitcher | Google Play | Google Podcasts | Spotify | iHeartRadio




More About the CEO

Start Your Unlearning Journey

Unlearn: Let Go of Past Success to Achieve Extraordinary Results by Barry O’Reilly

Get notified of new podcasts and be the first to get access to Barry’s latest case studies, tools and techniques by joining his award-winning newsletter

Recent Podcasts

Daniel Elizalde is the VP and head of IoT for North America at Ericsson. He’s spent more than 20 years working in industries, from manufacturing to aerospace and energy.  Today, Daniel also teaches courses on the decision framework that he’s created. Barry O’Reilly welcomes Daniel to this week’s show to discuss how much the concepts…

Diana Stepner is the VP for Product Management of Innovative Learning Solutions at Pearson. She enjoys building product experiences that customers love as well as weaving innovation, experimentation, and technology into actionable product visions and roadmaps that accelerate growth. Barry O’Reilly welcomes Diana to this week’s show as they discuss finding her voice and why…

Barry O’Reilly is delighted to welcome Alexander Osterwalder, famed author of The Business Model Canvas, The Value Proposition Canvas and most recently The Invincible Company. Alex is also an entrepreneur and speaker, and one of the world’s leading experts on innovation and entrepreneurship. In this exciting episode, they discuss some of the aspects that help…

Subscribe to our newsletter and we’ll send you news you can use. No spam, ever.

Barry O'Reilly 2020. All Rights Reserved ©