Jenna Chaplinsky is a Customer Acquisition Strategist at Toast, a position held since June 2025. Previously, Jenna served in various roles at Datadog, initially as an Enterprise Sales Development Representative and then as a Commercial Sales Development Representative from April 2024 to June 2025. At Verkada, Jenna was part of a sales training program and later promoted to the West Select team as an Associate Account Executive, focusing on Tier 1 accounts within SLED. Additionally, Jenna worked as an Associate Account Executive for Growth Accounts at Aply from November 2022 to April 2023 and completed an internship in Marketing at Uvaro in summer 2022. Jenna holds a Bachelor of Science degree in Advertising and Business from the University of Colorado Boulder, completed in 2023.
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