Ray Ploski is a GTM advisor and seasoned executive with 13 years of experience at the intersection of AI, enterprise software, and product-led growth, currently shaping AI-driven software modernization and category strategy. He has led Field CTO and strategy functions at HashiCorp and Red Hat, guiding Fortune 500s through cloud adoption, platform modernization, and partner ecosystems while earning recognition like HashiCorp’s Field MVP. At CoreStory he’s building the “context layer” for AI-driven engineering—turning codebases into living specifications to eliminate hallucinations and enable intent-driven development. Ray blends technical depth with GTM craft, advising startups and enterprise execs on product positioning, partner programs, and sales enablement. He thrives in ambiguity and is especially focused on vertical AI agents, code intelligence, and reducing the gap between business needs and software delivery. Based in Bend, Oregon, he pairs a rare mix of developer-facing credibility and executive storytelling to help teams ship, learn, and scale.
13 years of coding experience
20 years of employment as a software developer
Masters Studies, Distributed Computing, Masters Studies, Distributed Computing at DePaul University
History, Biochemistry, History, Biochemistry at University of Illinois Urbana-Champaign
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