Diana joined the Ventures Board in 2023.
Dianna Winegarden was most recently Chief Customer Officer at DreamBox Learning, a company with the mission to transform the way the world learns. She has built a reputation as a leader who drives business results while also delivering clear value for customers. Her career spans start-ups and large technology companies across a wide variety of industries.
Prior to DreamBox Learning, Dianna held various executive roles including COO for Level, CEO for HeyThrivy, and Global Director for Client Services & Solutions at Investis while based in London.
Dianna joined Ventures to support entrepreneurs who want to build better economic opportunities and thriving businesses with training, coaching and access to capital. Her own experience in starting companies has given her a deep appreciation for anyone that can move an idea to a sustainable business. She has served as a coach and a judge for Innoventures in past years and was also a member of the Ventures Board of Directors from 2019 – 2021, re-joining the board in 2023.
Dianna loves spending time traveling overseas with family and friends, as well as trying new hobbies that she will likely abandon.
She holds a BA in International Relations from Drake University, and an MBA from the University of Washington.
