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Rick Naylor has a diverse work experience. Rick started their career as a Sales Representative/HP Intern at Carahsoft in 2014, where they were responsible for building complex software quotes, increasing webinar attendance, and organizing reseller information. From 2016 to 2017, they worked as a Real Estate Salesperson at Anchor Associates Group. In 2017, they joined Mason Frank International as a Recruitment Consultant, specializing in providing Salesforce.com permanent resource solutions. In 2018, they transitioned to CloudHealth by VMware, where they first worked as an Inside Sales Representative, managing IT service management for cloud platforms. Rick later became an Account Executive, focused on cost, visibility, and optimization of cloud services. In 2021, Rick joined Fairwinds as an Account Executive, offering Kubernetes enablement services. Currently, they are working at Device42 in the role of Enterprise Sales, providing comprehensive agentless discovery system solutions for hybrid IT infrastructure.

Rick Naylor attended Trinity College-Hartford from 2012 to 2016, where they earned a Bachelor's degree in American Studies.