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October 3, 2025
Seattle-based Plainsight named Jonathan Simkins as its president and CFO. In this role, Simkins will help scale Plainsight's business operations and advance its mission to provide highly scaleable, enterprise-ready infrastructure software for computer vision. Simkins brings expertise across machine learning, infrastructure software, open source, cybersecurity and investment banking. He was most recently the founder and CEO of Kosai, an open-source supply chain security company acquired by Root.io in August 2025. Prior to Kosai, he held mostly CFO positions at Canonical, Appgate, CyberGRX and a number of other technology companies. Plainsight's computer vision AI software transforms images and video into structured, intelligible data.