In this episode of Revenue Career Ladder, Jesse Woodbury joins Jamie Pagan to unpack a career that’s evolved through curiosity, adaptability, and a lot of hands-on learning.

Now leading RevOps at Language I/O, Jesse shares how his unconventional path—from recruiting and IT to automation and revenue operations—gave him a unique lens on solving complex problems. He talks openly about navigating ambiguity, the pressure to specialise, and how developing technical range became one of his biggest career advantages.

This episode is full of practical takeaways for anyone working in (or with) RevOps, as well as those figuring out how to turn curiosity into a career.

Expect to learn:

• Why RevOps isn’t just a function—it’s a mindset
• How to find clarity in messy, undefined roles
• What Jesse learned from working in recruiting, IT, and marketing before landing in ops
• The value of technical range in modern RevOps roles
• Why identifying and solving invisible problems can make you indispensable
• How to assess whether to specialise or stay generalist over time

Watch on Stream by Dealfront: https://www.dealfront.com/resources/stream/series/revenue-career-ladder/

Follow Jesse Woodbury: 

LinkedIn: https://www.linkedin.com/in/jessewoodbury/

Follow Jamie Pagan: 

LinkedIn: https://www.linkedin.com/in/jamiepagan/

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