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  • Enterprise AI

Plainsight Appoints Jonathan Simkins as President and CFO


Plainsight Appoints Jonathan Simkins as President and CFO
  • by: Source Logo
  • |
  • October 1, 2025

Plainsight, a leader in operationalizing computer vision through modern infrastructure, has appointed Jonathan Simkins as President and Chief Financial Officer. Simkins, with extensive expertise in machine learning, infrastructure software, open source, cybersecurity, and investment banking, will drive business operations and support Plainsight's mission to deliver scalable, enterprise-ready computer vision solutions.

Quick Intel

  • Jonathan Simkins joins Plainsight as President and CFO.

  • Expertise from Kosai (acquired by Root.io in August 2025), Canonical, and Appgate.

  • Focuses on scaling operations for computer vision AI infrastructure.

  • Addresses $30B market opportunity in scalable vision AI deployment.

  • Emphasizes team empowerment for rapid growth and accountability.

  • Targets logistics, manufacturing, and QSR industries.

Scaling Computer Vision Infrastructure

Simkins' appointment comes as Plainsight advances its VizOps platform, providing a standardized infrastructure layer for enterprise-grade computer vision. "We’re excited to have Jonathan join Plainsight," said Kit Merker, CEO of Plainsight. "He has a unique ability to build strong teams and guide organizations through transformation and scale." Simkins' leadership will enhance Plainsight's ability to operationalize AI at hyperscaler volumes, reducing compute costs through innovations like OpenFilter.

Simkins' Proven Track Record

Most recently, Simkins founded and led Kosai, an open-source supply chain security innovator acquired by Root.io in August 2025. Previously, he served as CFO at Canonical, Appgate, and CyberGRX, where he built high-performing teams during periods of hyper-growth. His philosophy of empowering calculated risks and fostering accountability aligns with Plainsight's goal of democratizing computer vision for general software engineers.

Market Opportunity in Vision AI

The $30 billion computer vision market is ripe for infrastructure solutions that enable repeatable, scalable deployments. Plainsight's modular, use-case-agnostic design accelerates impact across industries like logistics, manufacturing, and quick-service restaurants (QSRs). "Computer vision has been around for years, but recent AI advancements are making it far more scalable and enterprise-ready," said Simkins. "Plainsight is building the platform that takes computer vision beyond pilots."

Driving Enterprise Transformation

Plainsight's solutions transform images and video into structured data, enabling quick deployment and high accuracy. By equipping engineers with expert-level capabilities, the platform reduces operational costs and supports real-world AI applications, positioning Plainsight for sustained growth in the evolving AI landscape.

Jonathan Simkins' expertise will be pivotal in Plainsight's expansion, ensuring the company delivers greater value to customers deploying computer vision at scale. This appointment reinforces Plainsight's commitment to innovation and operational excellence in the AI infrastructure space.

About Plainsight

Plainsight’s computer vision AI software rapidly transforms images and video into structured, intelligible data. 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.

  • Computer VisionAI IfrastructurePlainsightExecutive AppointmentMachine Learning
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