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

Honor announced as Ruby celebrates its 14th consecutive year as a fastest-growing company in Oregon

Ruby.com, the premier provider of live virtual receptionist and chat services for small businesses, 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.

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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.

“Kate has had a tremendous impact on Ruby in such a short amount of time,” said Ruby president and chief operating officer Stephanie Copeland Weber. “She embodies the perfect blend of pragmatism and idealism in her leadership. And her ability to lead with compassion in times of adversity has kept Ruby growing despite the challenges of the last 18 months.”

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And grow Ruby has. In addition to the Stevie Award, Ruby made the Portland Business Journal’s “2021 Fastest-Growing Private Companies” list for the 14th year in a row. Since January, Ruby has expanded into Arizona and hired 300-plus employees. The company also recently doubled down on employee investment by implementing a progressive wage structure and an extended training program.

The Stevie Awards for Women in Business honor women executives, entrepreneurs, employees, and the companies they run — worldwide. More than 1,500 entries were submitted this year for consideration in more than 100 categories, including Executive of the Year, Entrepreneur of the Year, Company of the Year, Startup of the Year, and Women Helping Women. Gold, Silver, and Bronze Stevie Award winners were determined by the average scores of more than 160 business professionals around the world, working on eight juries.

Winners of the Stevie Awards for Women in Business will be celebrated during a virtual ceremony on January 13, 2022. In addition, Winkler will be leading a panel discussion titled the “Future of Work—Preparing for the Changing Business Landscape” as part of the Stevie Awards’ fourth annual Women|Future Conference on November 3, 2021. The panel will include women leaders from Park Place Payments, Skillsoft, Lions + Tigers, and Corporate Class Inc.

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