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Jackie Weinstein has a diverse range of work experience in various industries. Their most recent position was as a Data Annotator at Skit.ai, starting in July 2022. Prior to that, Jackie worked as a Transcriptionist at Rev.com from November 2021 to June 2022, where they edited AI-generated transcription documents and collaborated with a global team to meet deadlines.

From November 2016 to November 2021, Jackie worked as a Transcriptionist at TranscribeMe, where they transcribed audio files, researched industry-specific terms, and were promoted to the First Draft team, ensuring a 24-hour turnaround for clients.

Before their transcription roles, Jackie was Co-Owner of David's Pretzel Company from April 2012 to November 2016. In this role, they led all hiring efforts, analyzed sales data, and managed payroll using QuickBooks. Prior to that, they were a Manager at a former concessions business at Revere Market from August 2010 to April 2012, where they filed permits, assisted with bookkeeping, and coordinated hiring. They also worked as a Sales Associate at Richie's Classic Italian Slush at the Revere Flea Market from April 2004 to August 2010, where they focused on customer communication and obtaining necessary permits.

Additionally, Jackie has experience in the education sector, working as an Assistant Teacher at the YMCA of Greater Boston from August 2011 to January 2012, supervising and developing after-school curriculum for first and second grade students. They also volunteered as a Tax Preparer at Bunker Hill Community College from December 2009 to April 2010, helping low- and middle-income individuals and families with tax preparation.

Earlier in their career, Jackie worked as a Concession Salesperson at Aramark, selling concession items at Fenway Park during Red Sox home games from September to December 2009. They also volunteered as a SciCORE Volunteer at the Museum of Science, Boston, where they authored a newsletter, conducted museum tours for students, and participated in a program focused on alternative sources of transportation.

Jackie Weinstein obtained an Associate of Science (A.S.) degree in Accounting from Bunker Hill Community College, where they studied from 2008 to 2011. Jackie then pursued a Bachelor's Degree in Political Science from the University of Massachusetts Boston from 2012 to 2014. In October 2016, they obtained a certification in Building Self-Confidence from LinkedIn.