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Kendall Trenchard has a diverse range of work experience. As a Business Development Representative at Workhuman, Kendall began in 2022 and is currently in the role. Before that, Kendall worked at Toast, Inc. as an Inside Account Executive from March 2021 to July 2022. Kendall also served as a Fellow at Sseko Designs from August 2019 to December 2021, where they utilized social media to communicate the brand's story and mission and hosted online events to engage the target audience and generate sales. Prior to that, Kendall worked as an Account Representative at the American Red Cross Connecticut Chapter from March 2019 to March 2021, implementing strategies to recruit, retain, and manage sponsor organizations, as well as identifying areas of expansion and executing sales strategies. Kendall's other experiences include working as a Beauty Advisor at Ulta Beauty from October 2018 to March 2019, a Sales Associate at Gap Inc./Old Navy from June 2015 to May 2018, a Media Relations Specialist intern at the American Red Cross from September 2017 to March 2018, and a Campus Representative at Serengetee LLC from January 2015 to May 2015.

Kendall Trenchard obtained a Bachelor's degree in Communication and Media Studies from Quinnipiac University between 2014 and 2018.