Drake Pruitt

Chief Executive Officer

Drake Pruitt is Chief Executive Officer of SundaySky. He is a seasoned executive with more than 30 years of experience in enterprise software.

Drake also serves as an Operating Partner with Clearhaven Partners, the controlling investor in SundaySky. He joined Clearhaven in 2025 from Amazon Web Services where he served as Senior Innovation Advisor in the private equity business unit. At AWS, he engaged operating partner and portfolio company executive teams from the world’s leading global private equity investors to assist with digital transformation, scaling innovation, and driving adoption of AI.

Prior to Amazon, Drake served as Vice President for Anaconda, Inc., the leader in the open-source data science platforms. Before Anaconda, Drake served as President and CEO of PE-backed Openforce, where he led the company through a full-scale digital transformation and modernization. Earlier in his career, Drake served in senior executive roles for several public companies, including as SVP of Business and Strategy for Ascent Media (exited to Deluxe Entertainment), as CRO of Aquantive (sold to Microsoft), and as General Manager for Nextel (exited to Sprint).

Drake is a graduate of the University of Pennsylvania with a Bachelor’s degree cum laude in economics and operations analysis. He has also completed post-graduate programs at MIT and Oxford.

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