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Matt Bailey has a diverse work experience in various roles. Starting in 2015, they worked as a Key Account Sales Representative at Alleson Athletic. From 2016 to 2018, they were a Real Estate Agent at Key Realty Group, LLC, specializing in representing both landlords and tenants in the rental market. In 2018, Matt joined Starry, Inc. as an SMB Account Executive, then transitioned to being an Enterprise Account Executive and later a Channel Sales Manager. At Starry, they contributed to building the company's first channel partnership program and achieved increased sales leads and net new subscribers. In 2019, they worked as an Account Manager at Join Digital, focusing on managing current partnerships to expand product and service offerings.

Matt continued their career at Starry, Inc. in 2020, becoming a Subscriber Sales Team Manager and later the SMB Business Development Team Manager. In 2021, they participated in the Techstars Company Class of '21 as part of Trova, a startup they co-founded in 2020. Trova aims to enhance employee experiences in corporate workplaces, promoting a sense of belonging and fostering connections among co-workers. In 2022, Matt joined Compt as a Senior Account Executive.

Matt Bailey attended John Carroll University from 2011 to 2015, where they earned a Bachelor's Degree in Business, Management, and Marketing.