Ruby - Female Executive of the Year

Company: Ruby, Portland, OR
Company Description: Ruby® provides small businesses with the services, products, and analytics they need to manage customer interactions and deliver exceptional experiences. Trusted by 13,000+ business owners, our remote receptionists and chat specialists create meaningful human connections supported by proprietary technology—building trust and helping win new business 24/7/365.
Nomination Category: Individual Awards Categories
Nomination Sub Category: Female Executive of the Year – Business Services –11 to 2,500 Employees

Nomination Title: Kate Winkler

Kate Winkler joined Ruby in 2019, stepping into the role of CEO held by Jill Nelson—Ruby founder and company leader for 17 years. Kate quickly built on Ruby’s foundation, incorporating a new technology acquisition into the company structure, rebuilding and filling key leadership roles, and shifting Ruby’s service to a 100% remote workforce.

Kate prioritizes our company’s livelihood, and also the livelihood of every one of the 13,000+ business owners that rely on our platform to handle the phone and web chat operations, fueling revenue and customer service operations at their respective companies. With this spirit, Kate acted decisively to reforecast, replan, and prepare Ruby for up to 18 months of economic impact in early March 2020. She pivoted all organizational operations to be equipped to deal with the major economic impacts that our customer base—small businesses—have faced due to the pandemic. She also focused on ensuring our team and company culture not only remained intact, but that we found ways to thrive—and even surpass what we were doing before the new remote work world.

Stepping into Ruby’s 17-year culture while positioning the company for its next stage of growth is not easy. Kate did it.

Kate implemented new programs and protocols to get Ruby and our customers through the many crises of 2020, and shifted approximately 400 receptionists to WFH status over a 96-hour period.

She has managed to move Ruby along an optimistic and pragmatic path, remaining committed to her vision of expanding Ruby from a one service provider (virtual reception) into a customer engagement solution for small businesses. During the pandemic, Kate quickly identified the changing needs of our customers and worked with our Product team to accelerate the launch of our 24/7 receptionist services and get our customers the support they needed.

Kate also led the acquisition of Pure Chat in early 2020, an Arizona-based self-chat and AI-enabled chatbot software company, which has been key for developing Ruby’s full chat service and will be a multiplier for overall growth. The acquisition was a great achievement in preserving and perpetuating real meaningful connections while also providing a second channel for our customers to capture new business.

Internally, Kate holds weekly office hours to assist in breaking down internal communication barriers, shorten the timeframe to implement suggested changes from frontline workers, and provide professional development conversation opportunities. To accommodate employees working outside of normal hours, Kate makes herself available starting at 5:30am during the week and on Saturdays. Kate also films a weekly “Ask Me Anything (AMA)” video series. Topics are sourced from her one-on-one office hour meetings with employees. These internal communications initiatives have led to greater employee support and growth.

Kate’s challenge coming into her role has been leading the changes needed to grow Ruby into its next incarnation. She honors the foundation that contributed to Ruby scaling its current size, while also demonstrating how new strategic shifts are aligned with Ruby’s culture. Ruby is now leading the next iteration of customer engagement by integrating live chat into our line of business, which Kate helped grow and formalize this past year.

While addressing crises this past year, Kate led from a place of courage and empathy. She wrote an employee-facing statement and wrote to all of our customers, outlining where Ruby stands on issues of equity. Every customer who responded to the email received a response back. These actions evolved into both a doubling down on our evolving Equity, Diversity, and Inclusion (EDI) strategy and formalizing our commitment to helping underserved minority and women-led businesses succeed in 2021. This included hiring an EDI business partner focused on improving our internal efforts, investing in empathy trainings for managers, and telling the stories of small business owners that have faced issues of discrimination and hardship during the pandemic.

Employees have felt her presence, too. In a recent Culture Amp engagement survey, employees cited Kate’s initiatives as helpful additions to Ruby’s internal communications and increased transparency around decision-making, with more clarity around the company’s long-term vision. She has expanded the value impact we bring to our customers and our employees.

Kate took a 17-year history and readied the company for the changing future.

Reference any attachments of supporting materials :

Employee Email: Kate sent to Ruby employees just one week into the pandemic. In it, Kate thanks employees for their swift change to a remote working environment; most importantly, Kate transparently details Ruby’s plan for the possible sustained impact of COVID-19 on our small business community and on employees. She talks about the economic impact plans, and how theirtop priority was to retain jobs and wages for all employees. This letter demonstrates Kate’s vulnerability, transparency, and honesty as a leader.
Black Lives Matter Email: This communication was sent to all of Ruby’s customers after the murder of George Floyd, demonstrating Ruby’s and Kate’s commitment to sharing our values and helping our communities.
Press releases: These releases share major news and initiatives that happened as a result of Kate becoming CEO of Ruby. They demonstrate how her vision and leadership are bringing Ruby into its next phase.
Article: This article highlights Ruby’s growth and trajectory under Kate’s leadership, as we announced the hiring of 100 employees. This was a result of our new presence in Arizona with Ruby’s acquisition of Scottsdale-based Pure Chat in August 2020.