Ruby Blazes a Path for Women-Led Businesses, Proves the ROI of DE&I

Management — which is 72% female — is driving industry leadership and growth.

Buffy Naylor, Senior Managing Editor

April 22, 2021

4 Min Read
women leaders, women-led business

Ruby, a provider of live virtual receptionist and chat services for small businesses, is blazing a path for women-led services. Founded in 2003 by Jill Nelson, Ruby built the company on empowering women leaders.

As Ruby has grown, the company has stayed true to its roots. Employees identifying as women today representing 80% of C-level positions, 75% of vice president-level positions, 58% of director or senior manager positions and 77% of manager positions.

In total, women hold 72% of management positions and represent 71% of the entire employee population.

Ruby is an exclusive member of the Telarus partner community and currently serves more than 13,000 small businesses. The company has gained national recognition as a Fortune Magazine Best Small Company to Work for in the U.S., Inc. Best Workplaces, repeat Great Places to Work rankings and a Silver Stevie for Customer Service Training Team of the Year.

Ruby recently announced its expansion into Arizona. They plan to hire 50% of open positions in the state — the company’s first-ever remote-first workforce.

C-Level Promotions

Already an object lesson in the power of women-led businesses and the ROI of DE&I, the company recently promoted four of the company’s women leaders. The promotions include two at the C-level. Women hold four of the top five leadership roles — including CEO.

Stephanie Copeland Weber was promoted to president and chief operating officer (COO). Rebecca Grimes was promoted to chief revenue officer (CRO).


Ruby’s Stephanie Copeland Weber

Weber manages the company’s services team and all people operations. She joined Ruby in July 2017 and most recently served as COO. She has an extensive background in business operations, people leadership and developing customer-centric teams for high-growth businesses. Using these skills, she has scaled Ruby while maintaining the company’s outstanding service and focus on meaningful connections.

In her new role as both president and COO, Weber takes on additional responsibilities. She will manage day-to-day operations across the organization and execution in line with Ruby’s departmental plans. In addition, she will continue to lead the company’s front-line teams and all people operations.

“Stephanie’s passion for balancing customer, employee and business needs is one of her greatest attributes,” said Kate Winkler, Ruby CEO. “As we scale our operations into new markets, solidify our hybrid workforce model and prepare to add new services, her experience in scaling the business while maintaining quality services will help us support more small business customers in need.”


Ruby’s Rebecca Grimes

Grimes joined Ruby as CMO in January 2020. A few weeks later, the company instituted remote work arrangements due to the pandemic.

Grimes managed the sales, partnership and marketing teams through the challenges created by COVID-19. Her 20-plus years of experience in building and scaling sales and marketing teams across multiple SaaS technology companies helped transform Ruby’s go-to-market model, improving how the company attracts, services and retains customers.

Streamlining the Customer Journey

Grimes’ promotion to CRO comes as Ruby seeks to streamline the customer journey.  From the first contact through the ongoing support and management of a business with Ruby, there will be an optimal experience at each touchpoint. A newly created revenue department will oversee all sales, partnership and marketing functions, and will incorporate Ruby’s Customer Happiness Team. Ruby has immediate plans to fill additional roles on the team, including a vice president of revenue operations.

“Consolidating our customer experience and journey under one team is critical to staying ahead of the market’s needs to best serve small businesses across the U.S.,” said Winkler. “I couldn’t ask for a better leader than Rebecca to guide these efforts.”


Ruby’s Tia Bedoya


Ruby’s Marcella Vail

Ruby also announced two promotions at the vice president level. Marcella Vail, formerly senior director of employee engagement, is now vice president of people and culture. Tia Bedoya was promoted from senior director to vice president of human resources.

“Our small business customers have had a tough year; they need every opportunity and every minute in their day to keep their businesses afloat,” said Winkler. “Our entire organization is centered on helping our businesses build trusted relationships within their communities.”

And this champion of women-led businesses is looking for more women to add to its ranks. Ruby has available roles in sales, marketing, product, engineering, employee engagement and more.

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About the Author(s)

Buffy Naylor

Senior Managing Editor, Channel Futures

Buffy Naylor is senior managing editor of Channel Futures. Prior to joining Informa (then VIRGO) in 2008, she was an award-winning copywriter and editor, then senior manager of corporate communications for an international leisure travel corporation and, before that, in charge of creative development and copywriting for a boutique marketing and public relations agency.

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