Cara Allamano and Shelley Osborne

Cara Allamano and Shelley Osborne

Take Professional Development VERY Personally with Udemy’s VP of Learning and SVP of People, Places and Learning

On the first episode of Season Two, Rituals Edition, Erica sits down with Udemy’s SVP of People, Places and Learning, Cara Allamano, and VP of Learning, Shelley Osborne, to talk about how crucial it is to keep learning, both personally and professionally, especially as we’re seeing an incredible shift in the global workforce due to the pandemic. Indeed, they’ve seen enormous growth since the pandemic began, with courses around resilience and working from home well soaring in popularity. Listen to find out how their entire philosophy around the importance of learning set up Udemy perfectly to meet this global moment of change—that is to say, no matter what’s going on in the world, continuously learning is always a great bet.



3:03 – “I’ve had some wonderful mentors over the years that have really taught me about the intersection between business and people and how they don’t have to be mutually exclusive. That actually there’s true power in helping people achieve success individually, and that ultimately feeds into the success as a business in the broader context. And really focusing on learning as the lever that helps us get there.”

15:54 – “As tenures at companies have gotten shorter and there’s more of a shift toward an individual really owning and managing their career—they see learning as the currency. They see so much change in the world, that the only way to continue to really be successful is to be able to continuously upskill, continuously grow in their role. And how do you do that? It’s through learning.”


17:11 –  “So D.E.A.L. stands for Drop Everything And Learn…And what we’re really trying to do is give people permission. We want to give people the automatic ability to stop and learn and recognize that it’s part of their workday to set aside time for learning.” 

31:27 – On showing her team how the pandemic was impacting her: “I had a team member ask me directly, how could I be so positive with everything that’s going on? And I had this awakening moment where I realized, oh I need to let them know I’m struggling too. And took that time to be more real and authentic than I’d ever been before about how I felt about the pandemic, the challenges, everything that we were facing. And I just saw the dynamic within my team change.”



Shelley’s courses

Shelley’s book, The Upskilling Imperative

Connect with Cara
Connect with Shelley
Connect with Udemy
Connect with Erica