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DreamBox Learning’s CEO Jessie Woolley-Wilson on startup strength through purpose


For the third installment of this season’s Founder’s Corner podcast, I sat down with Jessie Woolley-Wilson, the inspiring edtech leader who is transforming the way students learn with DreamBox Learning. On this episode, you’ll hear Jessie share the lessons she’s discovered about setting mission and vision, the mentoring she gives young professionals about asking for what they deserve and her perspective on bridging passion and purpose to build great companies.

Jessie is the CEO and president of DreamBox Learning, a Seattle-based startup aimed at reimagining learning for kindergarten-8th grade students in mathematics. Previously, she held leadership positions at top edtech companies, including Kaplan, LeapFrog SchoolHouse and Blackboard, where she worked in the K-12 group.  A two-time recipient of EdTech Digest’s EdTech Leadership Award and a recipient of Seattle Business Magazine’s 2015 Executive Excellence Award in the CEO of the Year category, Jessie has been lauded for being a disruptor in education.

All that’s to say that Jessie’s insights into both leadership and learning serve as true guideposts for what it takes to helm a successful startup venture.

Listen to this episode to hear more about Jessie’s journey, including her family’s immigrant story, which still inspires her to this day.

Founder’s Corner brings you bite-size lessons and relatable tales from today’s premier founders and CEOs so you can get ahead of tomorrow’s roadblocks and build a great company faster than ever before. Listen above and subscribe on iTunes, SoundCloud and Overcast for new episodes.

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