Rob Reynolds is a founder and former developer with nearly two decades in software and over a decade focused on infrastructure automation, particularly for Windows. He created Chocolatey and leads Chocolatey Software/RealDimensions, blending open source community stewardship with commercial product direction. Known for pragmatic simplicity, he delivers low-maintenance automation and CI/CD practices that reduce total cost of ownership while mentoring teams and fostering community growth. An eight-time Microsoft MVP, Rob combines systems-level vision with the willingness to dive into code and test-driven development. He also has a track record of building developer tooling and community projects (NuGet contributions, Puppet Windows work) that have materially advanced Windows automation.
9 years of coding experience
14 years of employment as a software developer
Diploma, Diploma at Neodesha High School
Bachelor’s Degree Business Management, Bachelor’s Degree Business Management at Kansas State University
AA Art Agriculture, AA Art Agriculture at Coffeyville Community College
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