Jessie Woolley-Wilson, former CEO of DreamBox Learning, has joined Silicon Valley venture capital firm Owl Ventures as an operating partner. She led DreamBox for more than 13 years, with the company specializing in selling education technology software to K-12 schools. DreamBox was acquired by Discovery Education in 2023, and Woolley-Wilson stepped down from day-to-day duties at the company in October. Owl Ventures is known for its focus on education technology and has over $2 billion in assets under management, having invested in DreamBox in 2015. Woolley-Wilson has held leadership roles at various education-related organizations and is on the board 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 local community bank based in Washington. Level, which graduated from Techstars Seattle in 2018, developed a credit service targeted at independent contractors. Edelstein mentioned on LinkedIn that the business recently exited after closing three transactions, including with Found and Giggle Finance. He did not provide further details about the acquisitions. Edelstein previously worked at the Grameen Technology Center, Caribou Digital, Microsoft, and McKinsey.
Kurt Shintaffer, co-founder of Apptio, has joined the board of Precanto, a Washington D.C.-based startup that is developing headcount forecasting software. In another move, Kyle Munson, who was a marketing leader at Zillow Group and Flyhomes, has become the vice president of demand generation at Maryland-based cybersecurity startup Huntress. Meanwhile, Smarsh, a communications compliance company based in Portland, Ore., has added two new board members: Sagnik Nandy from Okta and Tim Scheve, a former exec at Janney Montgomery Scott.
These latest transitions and appointments in the technology and startup industry showcase the movement of experienced professionals into new roles and companies across various sectors. Jessie Woolley-Wilson’s move to Owl Ventures highlights her continued interest and involvement in the education technology sphere, while David Edelstein’s shift to First Fed represents a pivot into the financial industry from the fintech sector. Kurt Shintaffer’s addition to the board of Precanto and Kyle Munson’s role at Huntress demonstrate a trend of industry experts bringing their expertise to startups in various regions.
As the technology industry continues to evolve and adapt, experienced professionals are bringing their knowledge and skills to new companies and sectors. The addition of Jessie Woolley-Wilson at Owl Ventures and David Edelstein at First Fed showcases the importance of leadership and innovation in the education technology and financial sectors. Similarly, the appointments of Kurt Shintaffer at Precanto, Kyle Munson at Huntress, Sagnik Nandy, and Tim Scheve at Smarsh reflect a trend of industry veterans joining startups to drive growth and development in emerging technologies and markets.
Overall, the movements in the technology and startup industry indicate a dynamic landscape where experienced professionals are seeking new challenges and opportunities to make a significant impact. Jessie Woolley-Wilson, David Edelstein, Kurt Shintaffer, Kyle Munson, Sagnik Nandy, and Tim Scheve’s transitions to different roles and companies underscore the importance of leadership and expertise in driving innovation and growth in various sectors. With these changes, the technology industry continues to be a hotbed of activity, with professionals moving between companies and sectors to drive progress and creativity in the ever-changing landscape of technology and entrepreneurship.
