Gary Osborn

Gary Osborn is an experienced sales leader with a strong background in enterprise sales and customer experience management. Currently serving as Regional Vice President of Enterprise Sales at Udacity since August 2025, Gary also acts as an Advisor for PinPoint Workforce. Previous roles include Area Vice President of Sales at Sitecore, Vice President of Sales & Customer Experience at Allied BioScience Inc., and Senior Vice President of Global Sales at Firefly Educate. At Skillsoft, Gary held various leadership positions, including General Manager and Senior Vice President of Sales for North America Enterprise, managing significant sales organizations and driving revenue growth. Gary's career began at Thomson Reuters/NETg, where outstanding performance as Regional Vice President of Sales earned recognition as the top Regional VP multiple times. Gary holds a degree in Business from Wichita State University.