Ray Ploski is a GTM advisor and seasoned executive focused on AI, enterprise software, and product-led growth, bringing 12 years of recent experience across startups and large vendors. He currently leads AI-driven software modernization and code intelligence go-to-market at Crowdbotics while advising stealth AI startups on pitch decks and VC introductions. Ray built Field CTO functions, drove HashiCorp’s AI GTM and the transition to BSL licensing, and earlier founded Red Hat’s Developer Program and DevNation—demonstrating a rare mix of technical depth and market storytelling. He specializes in vertical AI agents, DevOps and platform engineering, and turning COBOL/Java/C# legacy estates into maintainable, intelligence-driven architectures. Based in Bend, Oregon, he’s known for thriving in ambiguity and translating executive vision into repeatable product and GTM plays.
12 years of coding experience
20 years of employment as a software developer
Masters Studies Distributed Computing, Masters Studies Distributed Computing at DePaul University
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