Jessie Woolley-Wilson, President + CEO of DreamBox — Glambition® Radio Episode 196 with Ali Brown
 - Ali Brown

Jessie Woolley-Wilson, President + CEO of DreamBox — Glambition® Radio Episode 196 with Ali Brown

She’s been driven by a singular belief that all children need and deserve high-quality learning opportunities, regardless of who they are or where they live. And the LEADERSHIP lessons gained from our guest today are worth listening to this episode over and over again.

Today on #GlambitionRadio, Jessie Woolley-Wilson, CEO of DreamBox® Learning, shares her truly inspiring story of combining tech + education to create a unique career path that’s now changing the future of learning for students everywhere… and inspiring leaders to welcome challenges that enhance their own professional growth.

On, you’ll hear how Jessie’s not replacing teachers, but supplementing education with new technology that adapts to children’s individual learning capabilities. DreamBox currently serves over 4 million K-8 students and approximately 150,000 teachers. The company provided more than 350 million math lessons across the U.S. and Canada in 2017, and Jessie recently secured an impressive $130 million investment from The Rise Fund.

On this episode of Glambition Radio, you’ll hear:

  • How Jessie was mistaken for an office assistant during her initial pitch for $10M+ of funding — and how she responded in that moment
  • How luck doesn’t happen by accident, but by preparation — and how to ramp up your good fortune by being humble, acknowledging weaknesses, and improving them
  • Why recognizing and shining light on women of impact is essential (because when one shines, all others are illuminated)
  • Why encouraging ‘benevolent friction’ at work (and at home) is the key to unlocking more attuned and productive relationships in all areas of your life
  • How to reframe what should have happened into what could have happened — to produce your most desired outcomes (this one’s a tough pill to swallow, but so worth it!)

So head to Apple Podcasts now to listen to this episode of Glambition Radio (or download it for later).

And come join in the conversation on Instagram or Facebook.



P.S. I would love your review! If you enjoyed this episode, please leave a review and comment on Apple Podcasts. Select ‘Listen in Apple Podcasts,’ then choose the ‘Ratings and Reviews’ tab to share what you think. I would really appreciate it. Thanks!

Show Notes:

Site Design & Development Alchemy + Aim