Holly Weaver

Director of Sales Enablement

Holly Weaver is director of sales enablement at October Three, where she works across sales and marketing to help turn big ideas into practical strategies that drive growth. She joined October Three after more than a decade at CBIZ, drawn to the opportunity to help build something new at a growing company and to work alongside a team that values curiosity, collaboration, and creative problem-solving. Holly’s career has never followed a perfectly straight line, and she considers that one of its greatest strengths. Her experience spans marketing, business development, product strategy, sales operations, and enablement, giving her a unique perspective on how the pieces of a growing business fit together. At October Three, she focuses on connecting people, processes, tools, and ideas to make it easier for teams to do great work and grow together. She especially loves solving messy problems, creating something where nothing existed before, and finding smarter ways to get things done. Holly earned her B.A. in International Relations and Comparative Politics from Kent State University. She also serves on the Board of Directors of Rainey Institute, a Cleveland nonprofit that expands access to arts education for young people. Outside of work, Holly is usually reading, cooking, traveling, or spending time with her husband and two children. She’s endlessly curious, loves a good problem to solve, and firmly believes there’s almost always a better way to do something.