Jessie Woolley-Wilson, former CEO of DreamBox Learning, has transitioned to a new role as an operating partner at Silicon Valley venture capital firm Owl Ventures. Woolley-Wilson led DreamBox for over 13 years, where she oversaw the sale of education technology software to K-12 schools before its acquisition by Discovery Education in 2023. With Owl Ventures managing more than $2 billion in assets and being a key player in the education technology sector, Woolley-Wilson’s experience will be valuable in her new role. She has also held leadership positions at various organizations including Blackboard’s K-12 Group, LeapFrog SchoolHouse, and the College Board, and currently serves on the boards of Owl Ventures portfolio companies Quizlet and Class Technologies.
David Edelstein, co-founder of Seattle fintech startup Level, has taken on the role of chief innovation officer at First Fed, a community bank based in Washington. Edelstein announced on LinkedIn that Level recently exited the business after finalizing three transactions, but did not provide further details about the acquisitions. Level, a graduate of Techstars Seattle, specialized in providing credit services for independent contractors. Edelstein’s extensive background includes working at the Grameen Technology Center, Caribou Digital, Microsoft, and McKinsey.
Kurt Shintaffer, co-founder of Apptio, has joined the board of Precanto, a startup in Washington D.C. that is developing headcount forecasting software. With his experience in building successful tech companies, Shintaffer will bring valuable insights to Precanto’s growth and development strategies. Meanwhile, Kyle Munson, who previously held marketing leadership roles at Zillow Group and Flyhomes, has taken on the role of vice president of demand generation at Maryland-based cybersecurity startup Huntress. These new appointments reflect the ongoing trend of tech industry professionals moving into leadership positions within innovative startups.
In addition, Portland-based communications compliance company Smarsh has added two new board members: Sagnik Nandy, an executive at Okta, and Tim Scheve, a former executive at Janney Montgomery Scott. With the expansion of its board, Smarsh is likely looking to tap into the expertise of these industry veterans to drive its growth and product development strategies. The addition of seasoned executives like Nandy and Scheve is indicative of Smarsh’s commitment to staying at the forefront of the rapidly evolving communications compliance landscape.
These recent moves in the technology and finance sectors highlight the ongoing evolution and innovation within the industry. With experienced leaders like Jessie Woolley-Wilson, David Edelstein, Kurt Shintaffer, Kyle Munson, Sagnik Nandy, and Tim Scheve taking on new roles and joining boards of innovative startups, the future looks promising for companies looking to drive growth and stay competitive in the ever-changing business landscape. As the industry continues to adapt and evolve, the expertise and insights brought by these seasoned professionals will play a crucial role in shaping the future of technology and finance.
