Overview
Drake Pruitt serves as Chief Executive Officer and Board Member at SundaySky [1][3]. Pruitt is a private equity CEO and operating partner experienced in driving business transformation and growth, serving in portfolio company CEO roles to drive growth initiatives and value creation through modern approaches to execution, operations and culture, and advising portfolio companies on product strategy, product operations, and company efficiency through strategic application of AI [2]. In addition to the SundaySky role, Pruitt holds a position as Operating Partner for Product and AI Innovation at Clearhaven Partners [4]. Pruitt's prior experience includes serving as President, Chief Executive Officer and Board member at OPENFORCE [6], Chief Executive Officer and Board member at Lionsolver Inc. [8], and Founder of Genius:Group [9]. Pruitt holds a Bachelor of Arts, Cum Laude from the University of Pennsylvania [11], a Certificate in Management and Technology in Emerging Blockchain Technologies from Saïd Business School, University of Oxford [12], and a Certificate in Organizational Design and Strategy in Digital Transformation from MIT Sloan School of Management [13].
Profile introduction
PE CEO, and operating partner, experienced in driving business transformation and growth. I serve in portfolio company CEO roles, driving growth initiatives and value creation through modern approaches to execution, operations and culture. As an operating partner, I advise portfolio companies on product strategy, product operations, and company efficiency through strategic application of AI.
Career history
- Chief Executive Officer and Board MemberMar 2026 to presentSundaySky
- Operating Partner, Product and AI InnovationMay 2025 to presentClearhaven Partners
- Vice PresidentNov 2018 to Jan 2020Anaconda, Inc.
- President, Chief Executive Officer and Board memberJan 2016 to Sep 2018OPENFORCE
- CIRJan 2015 to Jan 2016Private Equity Target Search
- Chief Executive Officer and Board memberAug 2012 to Dec 2014Lionsolver Inc.
- FounderJan 2011 to Dec 2012Genius:Group
- Senior Vice President of Global Business DevelopmentJul 2009 to Jan 2011Deluxe Entertainment Services Group
Education
Bachelor of Arts, Cum LaudeUniversity of Pennsylvania
Certificate in Management and Technology, Emerging Blockchain Technologies2018 - 2018Saïd Business School, University of Oxford
- MSCertificate in Organizational Design and Strategy, Digital TransformationOct 2021 - Jan 2022MIT Sloan School of Management
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