
How I Built This with Guy Raz How I Built Resilience: Jessie Woolley-Wilson of DreamBox
Aug 8, 2020
Jessie Woolley-Wilson, CEO of DreamBox, shares insights from her journey leading an online math platform for K-8 students. She discusses the surge in users during the pandemic and the operational challenges that arose, emphasizing the need for transparent leadership. Jessie highlights the importance of equity in education technology and the philosophies behind her approach to leadership, particularly the concept of 'benevolent friction.' Her perspective on navigating the complexities of reopening schools and the shift towards blended learning is both timely and inspiring.
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Rapid Growth
- DreamBox opened the platform free for existing customers during initial COVID school closures.
- This led to a 2 million student increase in five weeks, demonstrating a need for their services.
Prioritize People
- Prioritize employee wellbeing, then customer needs, and lastly, company revenue.
- This approach ensures a strong foundation during crises.
Growth Challenges
- Rapid growth can create "stretch marks" within a company, like overwhelming support systems.
- Transparency and open communication with staff about challenges is crucial.

