Bailey Douglass

Bailey Douglass is an experienced operations and people strategy leader, currently serving as an Expert in Residence at First Round Capital and CEO of Second Principles, where the focus is on building operational practices for venture-backed companies. Previously, Bailey held the role of VP People at EvenUp, the first HR leader at a high-growth AI startup, and has an extensive background at Mode in various capacities, including VP of People and Places and Senior Director of People Operations. Additional experience includes technical recruiting roles at Affirm and Ripple, alongside operations and special projects at Airware. Bailey holds a BA in Politics and Government from the University of Puget Sound and has contributed to startup growth and organizational development throughout a diverse career.