Diane serves as the Global Programs Manager at FounderBoost in Colorado. She previsouly held the position of  Director for the Founder Institute’s Core Program where her leadership has directly contributed to the creation of over $60 million in company value across four cohorts. Under her guidance, the Spring 2022 cohort was ranked as the #1 founder-rated cohort globally among approximately 60 cohorts.

Diane’s expertise extends deeply into early-stage pitching. She has provided insights and advice to over 3,000 founders on crafting compelling pitch decks. Her reputation as a pitch expert is further evidenced by her roles as a Pitch Judge for Go Code Colorado, with $80,000 in prize money, and Unicorn Events, the world’s largest pitch competition. Additionally, she co-organizes 1 Million Cups, where she prepares around 50 founders annually to pitch live to potential investors.

In 2024, Diane Bailey joined forces with Chief of Chaos, a move that strategically combines her deep-rooted expertise in startup development with their innovative, disruptive business methodologies. This collaboration marks a significant milestone, poised to redefine the landscape of startup success by integrating rigorous, analytical startup mentoring with bold, creative disruption strategies.

Diane’s impact on the tech and startup community was recently recognized when she was listed among the “Top 100 Women in Tech” by King Street Ventures, an accolade that highlights her influence and dedication to advancing technology and entrepreneurship. This prestigious recognition can be explored further at King Street Ventures Awards.