Founder’s Corner: Jessie Woolley-Wilson on reimagining learning and startup strength through purpose

July 24, 2017

DreamBox Learning’s CEO and president Jessie Woolley-Wilson joins host and Omidyar Network partner Shripriya Mahesh for episode three of the Founder’s Corner podcast. During their conversation, Jessie discusses the advice she received from Reed Hastings about a better way to set mission and vision, why bridging passion and purpose in her work has helped build great teams, and her family’s immigrant story, which still inspires her to this day.

Listen Now 

Jessie explains why unlocking the learning potential of every child may be the key to unlocking human potential. She also shares:

  • Advice for young professionals on asking for what they deserve in pay and in work;

  • The importance of ditching hubris and staying open to feedback as a startup leader;

  • How to hire in a competitive market by attracting talent through mission;

  • Why giving employees room to choose their own experiments is highly beneficial. 

Jessie is a two-time recipient of EdTech Digest’s EdTech Leadership Award. Seattle Business Magazine awarded Jessie with the 2015 Executive Excellence Award in the CEO of the Year category, and Forbes placed her on its “Impact 15” list for being a disruptor in education. Prior to DreamBox, Jessie held leadership positions at top EdTech companies, including Kaplan, LeapFrog SchoolHouse, and Blackboard, where she worked in the K–12 group.

Jessie’s insights into leadership and learning serve as true guideposts for what it takes to steer a successful startup venture.

Subscribe to Founder’s Corner on iTunes, SoundCloud, or Overcast, and learn more about DreamBox Learning here. Join the conversation with Shripriya Mahesh and Jessie Woolley-Wilson on Twitter at @OmidyarNetwork #ONFoundersCorner.

Omidyar Network's Emerging Tech team invests in early-stage startups that aim to build great for-profit businesses that can change the world and achieve positive societal benefits at scale.

It looks like there's some information missing
By clicking, you agree to the Terms and Conditions


Swarna Pragati raises INR 500 million in debt funding from State Bank of India

Today, an estimated 450 million people lack safe and secure homes in rural India—with two key causes being a widespread lack of formal property rights documentation and exclusion from the formal financial economy.



Newslaundry and Teamwork Arts join forces to host The Media Rumble

The Media Rumble, an annual event hosted by Omidyar Network’s investee Newslaundry and Teamwork Arts, attracted senior Indian journalists and renowned global media influencers for discussions on traditional and new media in India.  



Tinkergarten raises $5.4 Million Series A to deepen its presence in 48 US states and increase the number of children learning outside

Tinkergarten today announced that it has raised a $5.4 million Series A round of financing led by Owl Ventures, with additional investment from existing investors Omidyar Network and Reach Capital.