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Richard Cutinello has a diverse work experience in various roles and industries. Richard began their career in 1993 at VASCO Data Security, where they worked as a Technical Support Engineer, providing help desk and phone support services. In 1996, they joined Technology Advisors as a Senior Consultant until 1999.

From 1999 to 2005, Richard worked at Willow Creek Association as a Senior Consultant. Richard then moved on to Consultus, where they served as a Project Manager from 2006 to 2007. At Allstate Insurance, Richard worked as a Project Manager from 2007 to 2008, managing mid-size projects focused on integration and middle-layer projects in a J2EE environment.

Starting in 2008, Richard joined McDonnell Investment Management as a Manager of Software Development, where they transitioned the development team and implemented key IT policies and procedures. Richard later became the Vice President of Information Technology, overseeing business-focused solutions, software development, and procurement functions.

In 2016, Richard joined Rival Systems as a Project Manager, responsible for managing projects. Richard then moved to Golub Capital in 2017 as the Vice President of Portfolio Management and Data Warehousing. Richard later transitioned to the role of Associate Director of Application Development in February 2020.

Richard Cutinello has a Masters of Science in Information Systems from Northwestern University. Richard also holds a Bachelor of Science in Business Administration (BSBA) with a focus on Finance from Roosevelt University. In addition to their degrees, Richard has additional certifications including the CISSP (Certified Information Systems Security Professional) from (ISC)² and the PMP (Project Management Professional) from the Project Management Institute. The specific months and years in which Richard obtained their certifications are not provided.