DreamBox Learning® Promotes Dianna Winegarden to Chief Customer Officer


Third female C-suite appointment in the last year as company scales for growth

BELLEVUE, Wash. — March 24, 2022 —  DreamBox Learning (“DreamBox”), the leading education technology provider and pioneer of intelligent adaptive learning, announced today that Dianna Winegarden has been promoted to Chief Customer Officer. With this new role, DreamBox will strengthen its commitment to fostering thriving, engaged, and successful customers across its personalized, research-proven dual-discipline learning solutions.  

As Chief Customer Officer, Winegarden is responsible for leading DreamBox’s customer strategy and cultivating a company-wide devotion to nurturing an enthusiastic and growing customer base, including broad responsibility for all customer initiatives such as: customer support, customer success, customer operations, and professional services. A key strategic role at DreamBox, the new position will drive cross-functional programs to design, innovate, and continuously improve the customer experience across an expanding range of products and services. 

“We are delighted to elevate Dianna to Chief Customer Officer where she will continue to lead our Customer Organization to further strengthen our district partnerships and ensure their students and educators are equipped with the support, services, and engagement they need to grow and thrive,” said Jessie Woolley-Wilson, President and CEO of DreamBox Learning. “Dianna embodies what it means to be a values-driven leader at DreamBox. She is a proven innovator, creative thought leader, and passionate customer advocate who continues to demonstrate her strong commitment to unlocking learning potential for all learners, regardless of who they are or where they live. I am thrilled to recognize Dianna’s consequential contributions to DreamBox growth and success with this promotion.” 

Winegarden brings nearly two decades of experience leading global client services for high-growth technology startups and global enterprise companies. Prior to this new role, Winegarden served three years as DreamBox’s Senior Vice President of Client Success, where she was instrumental in driving customer retention to an alltime high  and tripled the professional development business revenue beyond company targets. As part of a high-growth services strategy, Winegarden also launched a new online learning platform called DreamBox University, which provides a wide range of professional development courses to help educators accelerate their learning on their own schedules. 

“I’m honored to take on this new leadership role as DreamBox continues to raise the bar on delivering a world-class customer journey for school district leaders, educators, students, and families,” said Winegarden. “Jessie has been a mentor to me since I joined DreamBox three years ago, and I continue to be inspired by her, our strong executive team, and DreamBox’s mission to transform the way the world learns. I am excited to continue to build programs that keep the customer at the center of everything we do as we navigate this new era in education together.” 

Winegarden joins a growing executive team at DreamBox. Most recently, DreamBox appointed two other female leaders to C-suite positions, including Lakshmi Nidamarthi as Chief Product Officer and Ronit Peled as Chief People Officer. 

Today, DreamBox supports approximately 6 million students and 400,000 educators across North America, Mexico, and the United Kingdom. To learn more about DreamBox, visit  https://www.dreambox.com/

About DreamBox Learning  
DreamBox Learning®, the leading K-12 education technology provider, is radically transforming the way the world learns. As the only dual-discipline solution rated “Strong” by Johns Hopkins’ EvidenceforESSA.org in both mathematics and reading, DreamBox uniquely provides schools high-quality adaptive learning solutions independently proven to accelerate student growth. Built by teachers and for teachers, DreamBox empowers educators with robust data analytics and content-specific professional development solutions to complement instruction. DreamBox supports 400,000 educators and approximately 6 million students in all 50 states, the District of Columbia, Puerto Rico, and throughout the United Kingdom, Australia, Canada, and Mexico. For more information, visit  www.dreambox.com.    

eSchool News Staff

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