Cierra Kriese

Cierra Kriese is a seasoned professional with extensive experience in management, learning and development, and customer experience optimization. Currently serving as the Senior Manager of Agent Success at Headway since November 2025, Cierra leads the strategy for Enablement, Knowledge Management, and Quality within CX teams, focusing on AI-powered solutions. Prior to this role, Cierra was the Director of Learning and Development and Quality at Lemonade, where responsibilities included enhancing enablement strategies for over 700 employees and integrating data-driven practices. Cierra's career at GEICO encompassed various roles, including Sales Operations Manager and Customer Operations Manager, where a strong emphasis was placed on performance improvement and leadership development. Cierra holds a Bachelor of Business Administration degree from the University of San Diego, earned in 2018.