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Brennan Orlando has a diverse range of work experience. Starting in 2012, they worked as a Sales Associate at The Yankee Candle Company, Inc. They later became a Team Member at Six Flags from August 2012 to July 2015. In 2014, Brennan founded their own company, Steyelr, Inc., and served as its Founder & CEO until February 2016.

Subsequently, Brennan served as a Fulfillment Associate at Amazon from May 2016 to August 2016, and as an Assistant Manager at AM Retail Group from June 2017 to August 2017. They then worked as a Claims Adjuster at GEICO from September 2017 to March 2020.

In 2020, Brennan took on two roles simultaneously. They worked as an Inventory Clerk at ShopRite from March 2020 to April 2020, and as a Claims Adjuster at Plymouth Rock Assurance from July 2020 to August 2022.

Most recently, Brennan worked as a Recruiter at Maxim Healthcare Services (Home Care) from August 2022 to October 2022. They are currently employed as an Inside Sales representative at Turtle & Hughes since October 2022.

Brennan Orlando obtained a Bachelor's degree in Entrepreneurship/Entrepreneurial Studies from Rowan University, where they studied from 2015 to 2017. Before attending Rowan University, they pursued a Bachelor's degree in Financial Economics at the University of Maryland Baltimore County from 2014 to 2015. Prior to that, they studied Chemical Engineering at the University of South Florida from 2013 to 2014. In 2012, Brennan obtained a Tips Alcohol Certification, which trained him in the responsible service, sale, and consumption of alcohol.