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Thomas Winfield has a diverse work experience in the field of analytics and metrics. Thomas started their career in 2014 as an intern at HughesWattersAskanase and worked in the same role for consecutive summers in 2015 and 2016. In 2018, Thomas interned at WPA Intelligence. Since 2019, Thomas has been working at the Republican National Committee (RNC), where they have held various positions. Thomas started as a Data Analyst before progressing to roles such as Field Analytics and Metrics Analyst, Deputy Director of Field Analytics and Metrics, and Director of Field Analytics and Metrics. Currently, Thomas holds the position of Director of Analytics at RNC, which they started in 2023.

Thomas Winfield attended Washington and Lee University from 2015 to 2019 where they earned a Bachelor's Degree in Business Administration and Management, with a focus on General Political Science.