How I Built Resilience: Jessie Woolley-Wilson of DreamBox

Courageous Talks

Jessie Woolley-Wilson, CEO of DreamBox, emphasizes the importance of 'benevolent friction' in leadership. This concept encourages open dialogue by being tough on ideas but gentle on people, fostering innovation and growth. Jessie explains, "We want to be hard on ideas but soft on people," highlighting the need for courageous conversations to democratize learning opportunities and accelerate impact 1.

   

Remote Management

Managing a remote team during the pandemic, Jessie Woolley-Wilson prioritized employee safety and customer care. DreamBox's strategy focused on supporting staff first, ensuring they could effectively serve school customers and ultimately protect the company's revenue. Jessie notes, "The default was not what do we do to take care of revenue? The default was what do we do to take care of our talent so that we can take care of our customers?" 2.

   

Transparent Leadership

In the face of uncertainty, Jessie Woolley-Wilson's authentic leadership style involved transparency and adaptability. She openly communicated what she knew and didn't know, fostering trust among her team. Jessie recalls, "A lot of people said, you can't lead like that. You can't tell people what you don't know. But people already know what we don't know. They need to know that you're going to be authentic about that." 3.