In this episode of What’s Up at Work?, host Sam Clyde Schroeder sits down with Jessica Jung, President of Oswald Companies, to talk about her path to leading one of the country’s top insurance firms.
Jessica shares how rolling up your sleeves can model the kind of leadership people want to follow, how to find anyone’s “superpower,” and how leaders can create safe environments where people feel comfortable challenging the process.
And don’t miss how she realized that outworking everyone isn’t sustainable (sound familiar?). This episode is part leadership masterclass, part reality check, and all about building a workplace people are drawn to.
Timestamps & Topics
- 00:54 Jessica’s nontraditional career path to business
- 03:00 Managing people right out of college
- 05:45 The moment that changed her career trajectory (and her confidence)
- 10:58 Why “rolling up your sleeves” still matters in leadership
- 13:25 Advice for those stuck between wanting to grow and needing to keep learning
- 14:40 The importance of inviting doers and diverse voices into decision-making
- 16:40 How Oswald helps employees discover and apply their “superpowers”
- 19:10 What it takes to create a culture where people feel safe speaking up
- 22:00 Behind Oswald’s big move to a new HQ
- 25:00 What it means to be an employee-owner
- 27:30 How to make a less-than-glamorous industry feel magnetic
- 32:00 Supporting women and underrepresented voices
- 33:10 HR Hot Seat: Mel Robbins, staying grounded, and how to stop working your life away
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🔗 Visit Oswald Companies: https://www.oswaldcompanies.com
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