Joshua DeBear is an accomplished sales leader with extensive experience in enterprise sales and leadership roles across various organizations. Currently serving as the Director of Enterprise Sales at Datadog since October 2025, Joshua previously held multiple positions at Twilio from March 2019 to October 2025, including Director of Sales, Enterprise and Regional Manager, where efforts focused on enhancing communication for enterprise organizations through a cloud-based platform. Prior experience includes serving as Vice President of Sales at Clover Imaging Group, managing high-value partnerships, and as Director of Sales at Micro Solutions Enterprises, driving growth initiatives with a sizeable team. Joshua's early career included roles at Future Graphics/MKIC, resulting in consistent revenue growth, effective team training, and impactful presentations.
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