Former DreamBox CEO Joins Owl Ventures; First Fed Appoints Seattle’s Level Co-founder as CIO


Key Takeaways:

– Jessie Woolley-Wilson, former CEO of DreamBox Learning, has joined educational technology-focused venture capital firm Owl Ventures.
– David Edelstein, co-founder of Level, has been appointed as the chief innovation officer at First Fed.
– Woolley-Wilson remains on the board for Quizlet and Class Technologies.
– Edelstein transitioned after selling Level in multiple transactions.
– Kurt Shintaffer and Kyle Munson have made new career moves.

Woolley-Wilson’s Journey with Owl Ventures

Woolley-Wilson has a distinguished tenure in the ed-tech sector, having spearheaded DreamBox Learning for over thirteen years. DreamBox, an ed-tech software provider for K-12 institutions, was established in 2006 and later acquired by Discovery Education in 2023. Woolley-Wilson transitioned from her day-to-day responsibilities in October.

Owl Ventures is a top player in the ed-tech investment landscape, boasting over $2 billion in managed assets. The firm had invested in DreamBox back in 2015. Adding to Woolley-Wilson’s substantial credentials, she has held leadership positions at Blackboard’s K-12 group, LeapFrog Schoolhouse, College Board, and test-prep company Kaplan. She retains her board seats at Owl Ventures portfolio companies Quizlet and Class Technologies.

Edelstein’s Shift to First Fed

Meanwhile, Level’s co-founder David Edelstein has embarked on a new chapter in his career at First Fed, a community bank based in Washington. Edelstein announced the transition on LinkedIn, revealing that Level had recently exited the business after finalizing three transactions over several months, including with Found and Giggle Finance.

Established in 2018, Level emerged as a Techstars Seattle graduate company, pioneering a credit service aimed at independent contractors. Prior to this, Edelstein helmed the Grameen Technology Center as director and has also gained experience at Caribou Digital, Microsoft, and McKinsey.

Key Professional Shifts

In other corporate movement news, Kurt Shintaffer, co-founder of Apptio, has decided to join the board of Precanto, a startup based in Washington D.C., developing headcount forecasting software.

Kyle Munson made his move from his previous marketing leader roles at Zillow Group and Flyhomes to join Maryland-based cybersecurity startup Huntress, now serving as vice president of demand generation.

Moreover, Portland-based communications compliance firm Smarsh has announced the addition of two new board members – Okta executive Sagnik Nandy and former Janney Montgomery Scott executive Tim Scheve.

These dynamic shifts in the technology and educational sectors indicate the constant change and growth inherent in these industries. With experienced leaders like Woolley-Wilson and Edelstein embarking on new opportunities, it suggests a promising future for their respective ventures.

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