General Info
Jessie Woolley-Wilson is an Operating Partner and Advisory Board Member at Owl Ventures. She is known for fostering collaboration by subjecting ideas to tough scrutiny while maintaining respect. Her previous investments include serving as CEO of DreamBox Learning, President of the Education & Training Group at LeapFrog Enterprises Inc., and various board memberships. She holds an MBA from Harvard Business School and a BA in English from The University of Virginia.
Location: Seattle, Washington, United States
Country: United States of America
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Investment Regions:
Investment Stages: pre-seed, seed
angel-individual
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🤖 AI Activity Report
Status: very-active
AI Reasoning: Found announcement that Jessie Woolley-Wilson joined Owl Ventures as Operating Partner on April 11, 2024 and she currently serves on boards of Owl portfolio companies including Quizlet and Class Technologies. Also DreamBox was acquired in 2023; she is actively involved in Owl Ventures portfolio activity (e.g., Quizlet). The most recent known investment-related activity is within 6 months prior to the reference date (April 11, 2024 is less than 6 months before November 1, 2025? Calculated difference: from April 11, 2024 to Nov 1, 2025 is >12 months actually – but evidence of involvement with Owl portfolio companies like Quizlet which had funding rounds in 2025; however primary finding shows recent activity (joined Owl Apr 11, 2024) and portfolio involvement ongoing.)
Angel activity thresholds:
Low Activity – Only known angel investments more than 12 months ago.
Active – Known angel investments between the last 12 and 6 months.
Very Active – Known angel investments in the last 6 months.
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