Kate Winkler wins 2021 ‘Female Executive of the Year’ Gold Stevie® award

Ruby is thrilled to announce that CEO Kate Winkler has been named a 2021 Gold Stevie Award winner in the Female Executive of the Year – Business Services category for companies with 11–2,500 employees. This recognition from Stevie Awards for Women in Business is Winkler’s second leadership accolade since joining Ruby in August 2019 and follows her inclusion on the Portland Business Journal’s list of the top 60 Oregon executives in 2020.

Winkler received the Gold Stevie Award in recognition of her leadership to date in the COVID-19 pandemic. Her achievements in 2020 include moving a 100% in-office operations model with 600-plus employees to a fully remote workforce in 11 days and effectively addressing employee and customer concerns with proactive communication. She also oversaw continued growth and innovation, including the incorporation of additional technology (PureChat) into Ruby’s portfolio. The Stevie Award judges recognized Winkler’s commitment to creating authentic connections with employees, specifically citing her launch of an “Ask Me Anything” weekly video series and open executive office hours as excellent examples of her transparent and vulnerable leadership style.