Ray Ploski
Building the Context Layer for AI Software Development at CoreStory
- Role
- Gtm Advisor at Stealth AI Startup
- Location
- Bend, OR, US
- LinkedIn followers
- 500 followers
About Ray Ploski
I help companies bridge the gap between vision, strategy, and real-world execution.As a seasoned executive at the intersection of AI, enterprise software, and product-led growth, I specialize in building and scaling category-defining platforms. My current work at Crowdbotics focuses on AI-driven software modernization—turning legacy systems into intelligence-driven, maintainable architectures. Whether it’s through code intelligence, vertical AI agents, or requirements automation, I’m obsessed with reducing the gap between what businesses need and what software delivers.Previously, I served in leadership roles at HashiCorp and Red Hat, guiding Fortune 500s through digital transformation, cloud adoption, and platform modernization. From launching Field CTO functions to building new partner ecosystems, I’ve worked across engineering, GTM, and strategy to deliver measurable outcomes at scale.I’ve advised early-stage startups and F500 exec teams alike, combining technical depth with storytelling, market positioning, and sales enablement. My focus areas include: • AI product strategy & vertical agents • DevOps & platform engineering • Software modernization & security • Product marketing & GTM alignment • Executive engagement & enterprise salesI thrive in ambiguous environments and believe deeply in teams that ship, learn, and evolve. Let’s build the future of intelligent software—intentionally.
Experience
Gtm Advisor
Mar 2025 — Present
Helping some very talented groups draft pitch decks and GTM plans; introducing teams to VC backers.
Education
DePaul University
Masters Studies, Distributed Computing
University of Illinois Urbana-Champaign
History, Biochemistry
Skills
- Jdbc
- Distributed Systems
- Apache
- Soa
- Jsp
- Eclipse
- Ejb
- Java
- Tomcat
- Javascript
- Uml
- Eai
- Xml
- Rest
- Weblogic
- Middleware
- Linux
- Hibernate
- Jpa
- Agile Methodologies
- Redhat
- Maven
- Servlets
- Web Services
- Jboss
- Solution Architecture
- Websphere
- Jms
- Saas
- Cloud Computing
- Spring
- Architecture
- Go to Market Strategy
- Application Architecture
- Open Source
- Ant
- Continuous Integration
- Esb
- Architectures
- Java Enterprise Edition
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