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Jessica Conway has a background in technical support and customer service. Jessica started their career at Momentum Telecom in 2004 as a Tier 1 Support, and later became a Tier 2 Technical Analyst from 2007 to 2008. Jessica then joined Wachovia, a Wells Fargo Company, in 2009 as a Sales Associate/Customer Service. Jessica returned to Momentum Telecom in 2011 as a Tier 1 support and later transitioned to a Tier 2 Technical Analyst.

Jessica Conway attended Jefferson State Community College from 2002 to 2004, where they earned an Associate degree in Human Resources Management. Prior to that, from 2000 to 2002, they studied at Bessemer Academy and obtained an Advanced Academic Diploma in Vocational studies. From 1996 to 2000, Jessica was homeschooling through the Hope Christian Home Schooling Organization, focusing on vocational studies. Jessica did not receive a degree during this period.