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DreamBox Learning® CEO Named Entrepreneur Of The Year® 2019 Award Finalist in the Pacific Northwest

April 3, 2019

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After milestone year and strong year-over-year company growth, CEO and President Jessie Woolley-Wilson is honored for her leadership

SAN DIEGO, Calif. — April 3, 2019 — DreamBox Learning®, the company that pioneered Intelligent Adaptive Learning™ technology, announced today that CEO and President Jessie Woolley-Wilson is a finalist for the Entrepreneur Of The Year® 2019 Award in the Pacific Northwest region. Widely considered one of the most prestigious business awards programs in the U.S., the program recognizes entrepreneurs and leaders of high-growth companies who are excelling in areas such as innovation, financial performance and personal commitment to their businesses and communities, while also transforming our world. Jessie was selected for driving DreamBox’s company growth, leading a major market transaction and her unique approach to leadership of “benevolent friction”— to be hard on ideas but soft on people.

“It’s an honor to be recognized amongst so many other impressive leaders and innovative companies in our region,” said Woolley-Wilson. “Awards like these are really a testament to a great team and an important mission. Every day I am inspired by some of the most brilliant and hardworking individuals in the industry, who are each driven by a passion to provide high-quality education to every child regardless of where they live, where they come from or what they look like – this is every leader’s dream.”

This recognition comes as the K-8 digital math platform is experiencing the strongest growth in its 12-year history. This year DreamBox has expanded to support over 3 million students and 130,000 educators in every state in the U.S., Mexico and throughout Canada. Buoyed by a $130 million investment in 2018 from The Rise Fund, the world’s largest social impact investment fund, DreamBox is positioned to continue expanding into new school districts, most recently securing a 5-year agreement with the Austin Independent School District.

“We created The Rise Fund to support leaders who have a bold vision to change the status quo in their industries and drive social impact at scale, and Jessie perfectly embodies this mission,” added John Rogers, Partner and Education Sector Lead for The Rise Fund. “We’re excited Jessie is being honored, and we look forward to continuing to support DreamBox in bringing adaptive learning to more school districts, educators and students.”

The winners of the Entrepreneur Of The Year® 2019 Award in the Pacific Northwest region will be announced at a gala on Friday, June 14.  The regional award winners are eligible for consideration for the Entrepreneur Of The Year National competition. Award winners in several national categories, as well as the Entrepreneur Of The Year National Overall Award winner, will be announced at the Entrepreneur Of The Year National Awards gala in November, 2019.

This year Jessie also received ASU GSV’s #PowerOfWomen award, which recognizes female CEOs and founders who have announced market-leading transactions or activities in the last year. Jessie is also nominated for “Big Tech CEO of the Year” by GeekWire. 

To learn more about the Pacific Northwest Entrepreneur Of The Year® program, visit www.ey.com/us/eoy/pnw.


About DreamBox Learning 

DreamBox Learning, founded in 2006 in Bellevue, Washington, is the only K-8 digital math program powered by students, built by and for educators, and independently proven to positively impact student achievement. DreamBox dynamically adapts and differentiates in real time based not only on students’ answers, but also on how they solve problems. Along with actionable reporting and tools that empower differentiation for all learners, DreamBox gives teachers content-specific professional development and provides administrators with insights about how all students are progressing. The company’s pioneering platform has won more than 40 top education and technology industry awards and is in use in all 50 states and throughout Canada. DreamBox is available for PC and iPad. For more information, visit https://www.dreambox.com


Holly Nolland, 

RH Strategic for DreamBox Learning



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