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Ryan Gessay has worked in a variety of roles in the tech and government sectors. In 2022, they began working as a Scrum Master and Software Tester at Obscurity Labs. In 2020, they began working as a Scrum Master at Jacobs, where they were responsible for ensuring project goals were clearly defined and that team members could execute their responsibilities without impediment. From 2015-2020, they worked at Novetta as a Technical Support Engineer, providing Tier 1 support for technical issues and account management. In 2014, they began working at Technical and Project Engineering (TAPE), LLC as a Customer Service Representative for the Office of Intelligence and Analysis' TSA PreCheck program. Ryan also worked at Universal Consulting Services, Inc. as a Helpdesk Technician for the Financial Crimes Enforcement Network's BSA E-Filing system. In 2013, they began working at Novetta Solutions as an IMSMA Program Tester, providing Quality Assurance Testing for each build the development team produced. From 2012-2011, they worked at FGM, Inc. as a System Administrator SKIWeb Tier II Support and a Program Planning and Control Analyst. Finally, in 2010, they worked at the Loudoun County Assessor's Office as a Real Property Data Collector.

Ryan Gessay graduated from James Madison University in 2010 with a Bachelor of Arts (B.A.) in Geographic Science. Ryan has also obtained several certifications, including CKAD: Certified Kubernetes Application Developer from The Linux Foundation in 2022, Certified Scrum Master from Scrum Alliance in 2016, AWS Certified Solutions Architect Associate from Amazon Web Services (AWS), AWS Certified SysOps Administrator Associate from Amazon Web Services (AWS), Certified SAFe 4 Agilist from Scaled Agile, Inc., LPIC-1 from Linux Professional Institute, Linux+ from CompTIA, and Security+ from CompTIA.