Plainsight enters next phase of growth and innovation with new leadership.
SEATTLE — December, 18, 2025 — Plainsight, the leader in operationalizing computer vision at enterprise scale, today announced that Jonathan Simkins has been appointed Chief Executive Officer (CEO). Simkins was formerly President & CFO of Plainsight. He succeeds Kit Merker, who will be continuing on in an advisory role to ensure a smooth transition and sustained strategic momentum.
Under Kit Merker’s leadership, Plainsight completed a multi-year mandate to sharpen the company’s strategy, strengthen its computer vision platform, and prepare for enterprise scale.
“Kit accomplished what the company needed during a pivotal time for Plainsight,” said Spencer Powers, Chairman of the Board at Plainsight and Head of Special Investments at DRW Holdings. “His ability to clarify strategy, build teams, and deliver meaningful customer value has positioned Plainsight for long-term success. We are deeply grateful for his leadership, and we’re excited for the next chapter under Jonathan.”
In his role, Simkins will lead Plainsight’s strategy and execution with a specific focus on strengthening and scaling the company’s computer vision platform as it embarks on an ambitious phase of expansion. He will ensure that Plainsight’s technology infrastructure, product roadmap, and delivery capabilities are tightly aligned with customer needs and emerging market opportunities.
Simkins steps into the CEO role with a proven track record and deep alignment with Plainsight’s enterprise infrastructure software vision. As President & CFO, he played a central role in guiding operational and go-to-market strategy, and enabling the company to scale. He previously founded and led Kosai through its acquisition by Root.io, and held CFO and COO roles at Canonical, Appgate, and CyberGRX. His background, spanning machine learning, infrastructure software, open source, cybersecurity, and investment banking, uniquely positions him to lead Plainsight through its next phase of expansion.
“It’s an honor to follow Kit and build on the solid foundation he put in place,” said Jonathan Simkins, incoming CEO of Plainsight. “Plainsight has the technology, the team, and the vision to redefine how organizations deploy computer vision. The demand for scalable, secure Vision AI infrastructure is accelerating, and we’re uniquely positioned to lead the market forward with new technology not being built anywhere else.”
About Plainsight
Plainsight’s AI infrastructure software rapidly transforms images and video into structured, intelligible data at enterprise scale. Its modular, reusable, and use case–agnostic design enables solutions to be deployed quickly, scaled effortlessly, and applied with exceptional accuracy across industries. By equipping general software engineers with the capabilities of computer vision experts, Plainsight is democratizing computer vision and accelerating real-world impact.
For more information, visit www.plainsight.ai.
Media Contact
Lexi Lutz
Director of Marketing
pr@plainsight.ai
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