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Dec 19, 2022

Not everyone follows a linear career path, and pursuing a non-traditional route can often equip you with useful skills you wouldn’t otherwise have acquired. Our guest today, Wesley Gilbert, Global Head of Talent Acquisition at On, has had a varied and eventful career journey. After becoming disillusioned with the acting industry while running an events company, Wesley Gilbert discovered his enthusiasm for recruitment through pure chance. In our conversation, Wesley shares how a fortuitous encounter facilitated his first recruitment job at Google, what he learned during his time there, and how he realized the inflexibility of a larger organization wasn’t for him. We spend some time discussing his time at Uber, how he landed a job there, and why he finds the early-stage startup environment so stimulating. He goes on to expand on his passion for problem-solving and how working in an entrepreneurial environment has helped him become a well-informed leader. We also discuss the pressure many of us experience to become more specialized (and the benefits of being a generalist) before Wesley shares his advice on how to become a well-informed leader. There’s no correct way to approach your career, and Wesley is living proof of that. Tune in for a refreshing perspective that will inspire you to follow your curiosity and find environments that allow you to thrive!


Key Points From This Episode:


  • Introducing today’s guest, Wesley Gilbert, Head of Talent Acquisition at On.
  • Learn why Wesley describes himself as being on a never-ending search for talented people.
  • Why agreeing on the perfect candidate is easier than agreeing on the perfect pizza.
  • Wesley’s early career as an actor and his experience running an events company.
  • The surprising story of how Wesley entered the industry as a recruitment coordinator at Google.
  • What Wesley learned from working at Google and why it wasn’t a perfect fit for him.
  • Wesley’s time at Uber and how being at a rising startup allowed him to grow.
  • What Wesley has learned about the work environments that motivate him.
  • Wesley’s appreciation for the high rate of problem-solving that you need to do at an earlier stage startup.
  • How Wesley became Head of Talent Acquisition at On.
  • The mix of leaders Wesley has worked with and what he has learned from them.
  • The pressure generalists often experience from managers to become more specialized.
  • The strengths and benefits of being a generalist leader.
  • Wesley shares his enthusiasm for sourcing.
  • Why sourcing is often oversimplified and how to attract high caliber talent to the role.
  • Wesley’s advice on how to build a career that allows you to become a well-informed leader.




“I realized really quickly that this was a great place to learn about recruitment. They have a lot of best-in-class processes. And they have a really great team.” — Wesley Gilbert [0:07:20]


“I started to realize that, ‘Hey, this is actually a really interesting career where you get to have a ton of impact on people and really help to make their dreams come true.’” — Wesley Gilbert [0:07:36]


“I realized that very quickly, I didn't fit in an environment that was quite as big as Google and gave me so much inflexibility.” — Wesley Gilbert [0:08:10]


“I think the sign of a good leader is that they surround themselves with people that are better than them, that are smarter than them.” — Wesley Gilbert [0:20:18]


“It doesn't matter how senior you are when you come into a company. We're going to give you some autonomy, we're going to give you some scope. And we're going to give you the trust to go and do that. And that means that you just attract a completely different caliber of people.” — Wesley Gilbert [0:27:47]


“Don't be afraid to take a sideways move. Don't always feel like you're chasing that next promotion, or you're chasing that next stage in your career. There's absolutely no race to the end.” — Wesley Gilbert [0:30:15]


Links Mentioned in Today’s Episode:


Wesley Gilbert on LinkedIn


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