Toby O'Brien

Toby O'Brien is an accomplished sales leader with extensive experience in technology and advisory roles. Currently serving as a Sales Advisor at Omlet Stack since December 2024, O'Brien also holds positions on the Bronco Bench Board of Trustees and as a Limited Partner at Red Shepherd Ventures. Notably, O'Brien has led strategic sales teams at Chainguard, managing significant partnerships with Fortune 150 companies, and achieved remarkable results at Datadog, where responsibilities included overseeing a $127 million ARR business with exceptional performance metrics throughout multiple fiscal years. O'Brien's career includes key positions at companies like Castlight Health and Jive Software, where outstanding sales achievements led to numerous accolades. Educational credentials include a Bachelor's degree in Accounting from Santa Clara University and International Studies from the Institute of European Studies in London.