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Ashley Cummings has worked in a variety of roles since 2011. Ashley began their career as a Bartender at Buffalo Wild Wings in 2011. In 2014, they joined QuickSpark Financial as a Sales Associate, where they worked with small to medium sized business owners with their financial transactions via phone and email. Ashley was later promoted to Training Specialist and then Sales Manager, where they nurtured and mentored the top performing reps to ensure targets were exceeded and maintained and cultivated large equipment seller relationships. In 2020, Ashley moved to Superlative RM as a Client Service Supervisor. In 2021, they joined TimePayment as a Broker Account Manager, and in 2022 they became a Sales Manager at Faastrak.

Ashley Cummings attended Arizona State University from 2010 to 2014, where they earned a Bachelor of Arts in Women, Gender and Communication.