About Ruby

We turn first impressions into lasting loyalty.

Ruby’s people, technology, and service come together to deliver one-of-a-kind customer experiences.

Who we are

Ruby is all about making personal connections that help small businesses grow. At the heart of everything we do is a promise to treat every moment of customer communication as an opportunity to make a lasting, positive impression.We are committed to the success of our customers, providing exceptional experiences—and a friendly, human touch—for the people they serve.

What we do

Ruby serves small businesses by delivering exceptional customer experiences over the phone and online via website chat. We’re a team of service-oriented professionals blended with an innovative tech company. Our highly trained receptionists use proprietary software to personalize a caller or website visitor’s experience, answer FAQs, transfer callers and take messages, and collect information that makes it easy for the businesses we represent to follow up.

Who we serve

Even more important than what we do is who we do it for. We believe small businesses are the backbones of our communities and deserve every chance to succeed. By providing small businesses with the services, products, and analytics they need to manage customer interactions, we save them time, reduce stress, and enable them to focus on what they do best.

“Frankly, I love Ruby. As much as they extend the compassion and optimism I try to provide my clients, I’ve also learned even more about the value of good customer service from them. Ruby gives off the aloha spirit that we are so proud of in this state, even if they’re not here.”

Diane Haar

Hawaii Disability Legal

What makes Ruby different?

Our people

We believe happiness has a ripple effect: treat people with kindness, and they’re likely to pass it on. Our team treats every interaction with care, thoughtfulness, and sensitivity in order to create unforgettable experiences for your customers.

Our virtual receptionists go through 120 hours of training in empathetic service, conflict resolution, and active listening before ever interacting with your customers. No matter the topic or type of conversation, our team is able to turn even the most routine interactions into loyalty-winning moments for your business.
We know that the success of your people starts with that of our own. That’s why Ruby is committed to fostering an equitable and inclusive workplace culture that honors the diverse perspectives of our team members while also offering opportunities for personal and professional development.
Our virtual receptionists are more than just communication experts—they’re also experts at helping your business identify and respond to new opportunities. Count on us to provide recommendations and collect insights tailored to your unique goals.

1.1+ million
conversations handled per month

1.6+ million
leads generated per year

14,000+
businesses trust Ruby.

Our technology

Any call—any business

Our proprietary conversation-enabling technology and access to important details about your business ensure that our virtual receptionists sound like a seamless extension of your team. No background noise or unnecessary confusion—we represent your business just like you would.

Zero miscommunications

Our in-house operating system was designed to keep information from slipping through the cracks. Our team can collect and categorize customer details according to your instructions and have it sent to you moments after a call or chat ends.

Streamlined conversations

We know both your and your customers’ time is valuable. That’s why our suite of tools and features works together to streamline the call process and keep each conversation only as long (or short) as it needs to be.

Explore the Ruby app.

Run your business from anywhere with our powerful mobile app. Stay connected, update your availability, and more, in-office or on-the-go.

Our culture

Ruby's vision and mission

Our Vision

We deliver exceptional experiences that build customer loyalty and empower businesses to freely pursue their purpose, cultivating diverse and thriving local economies.

Our Mission

We create meaningful connections and provide actionable insights that capture opportunities and give businesses the freedom over when and how they communicate so they can achieve more.

Ruby's core values

Every day at Ruby begins and ends with how we can serve our customers, which in turn benefits our communities and local economies.

We embrace kindness and empathy by approaching everything we do with compassion, respect, and an open mind. Rooted in transparency and vulnerability, the authentic relationships we build have a ripple effect that reaches far beyond Ruby.

We believe that stepping outside of our comfort zone and being unafraid to take chances can lead to great things. Bold yet thoughtful, we’re invigorated by possibility, undaunted by failure, and see every challenge as an opportunity to learn, adapt and innovate.

We don’t just appreciate our differences, we celebrate them joyfully and honor them with curiosity and respect. When every individual can express themselves fully with honesty and courage, we foster a genuine sense of belonging where everyone feels seen, heard, and valued, enriching us all.

We recognize that every action we take, no matter how big or small, has the potential to build trust, create positive outcomes, and make a difference. We value integrity and accountability in everything we do, celebrating our wins, acknowledging our missteps, and embracing our opportunities.

We are inspired and driven to reach new milestones on our individual and collective journeys of growth and transformation. By always learning, humbly accepting feedback, and supporting each other, we grow and evolve together.

Creating meaningful connections and fostering real relationships is at the heart of our culture and the reason small businesses choose Ruby. We recognize that it takes all of us contributing in small and big ways to build thriving, equitable communities within Ruby and beyond, and we are committed to doing this work.

The Ruby story

It all started with making connections.

In 2003, Ruby started as a small business dedicated to helping other small businesses. We were built on the belief that creating meaningful human connections in our technology-focused world would build trust, foster customer loyalty, and help our customers grow and thrive.

Ruby’s boot-strapped humble beginnings shape every aspect of how we operate—both as individuals and as a company. Our small business beginnings help us understand the needs of the people we serve.

What was once a small, four-person business answering phones in a tiny studio has flourished into what we are today. Ruby employees care not only about the success of our customers, but are inspired by the businesses we serve and share in the joy of their accomplishments.

The Ruby approach

Ruby is the modern version of a hand-written thank you note.

In fact, we still hand-write notes. We could do it all digitally and save a bunch of money on postage, but we don’t. The notes we send don’t even have a price tag. They’re just something we do. And they’re a metaphor for everything we do.

Ruby makes meaningful connections in unexpected ways. We help our customers build great relationships. It’s because we know that first impressions build lasting loyalty, and that builds successful businesses.

Ruby is about doing something because it’s the right thing to do, not the thing we have to do. We’re about doing something because it’ll make someone’s day that much better. We do these little things because, even though they seem insignificant in their own right, they add up. They add up, they multiply, they expand exponentially. We do these things to brighten someone’s day. We do these things to remind our customers that we have their back. We do them all with heart.

The big thing that Ruby does is a hundred little things that make meaningful connections for our customers and that make moments matter.

A dynamic team of leaders, sharing a single vision

Ruby’s leadership team brings together small business expertise and years of experience in delivering operational excellence. Not to mention robust backgrounds in technology with a dedicated focus on customer experience.

Our commitment to equity, diversity, and inclusion

Ruby’s work community is a blend of cultures, genders, ethnicities, and self-identities that we proudly celebrate. We’re committed to creating a welcoming, accepting, and engaging environment for every person.

Ruby Corps

Ruby Corps is committed to diverse and ongoing volunteer opportunities, donation drives, and financial support. Rubys can give their time and effort during monthly and quarterly events, as well as during our annual signature events. When Rubys get together to help the community, great things happen!

 

People-powered positivity

Are you a people person? A gifted gabber? A capable conversationalist? Our team is made up of empathic problem solvers dedicated to supporting the success of our customers and their fellow Rubys. If that sounds like you, let’s chat!

Ready to get started?

Hear why 14,000+ small businesses trust Ruby to answer their calls and chats. 

Kate Winkler

Chief Executive Officer

As the first CEO to take over Ruby’s leadership from its founder, Kate had some big shoes to fill. Jill Nelson, thank you for an amazing 17 years! 

Kate comes to Ruby with 25 years of experience in the technology sector, having successfully guided both small and large businesses through various stages of growth and wearing just about every c-level hat. As a small business leader herself, Kate fell in love with Ruby’s purpose-driven mission to help small businesses survive and thrive through real human connections. 

With small businesses at the heart of our economy and core to the foundation of our local communities, Kate knows that Ruby’s mission is more important than ever. She seeks to empower Rubys by providing them with superpowered technology, helping them create stellar first impressions, build trust, and foster long-term relationships between our customers and the people they serve—in countless ways, big and small. 

Equally committed to Ruby’s culture, Kate believes that the best organizations are decentralized, with passionate leaders working together in company-wide collaboration driven by a holistic sense of pride and ownership. In other words, Kate doesn’t think of Ruby as her company — it’s everybody’s company. You have her word that Ruby will continue to discover new ways to help small business owners pursue their purpose. 

Stephanie Copeland Weber

Chief Operating Officer

Stephanie has always been a people person. Which is a good thing, considering she now oversees the hundreds of people that make up our Services, Customer Success, People Operations and IT teams … essentially, the teams that deliver our best in class service and support, and the teams that support a Ruby along their employee journey.

Throughout her career, Stephanie has served in executive roles in customer success, business operations and people leadership, with a proven track record for driving growth and development for successful start-up companies. Part of what drew Stephanie to Ruby was it’s distinctive people-first operating philosophy: engaged and empowered employees are more likely to deliver a customer experience that makes a difference to the tens of thousands of small businesses utilizing Ruby’s products and services. It is Stephanie’s passion and personal mission to make sure Ruby never wavers from its signature people-centric approach as she continues to implement new practices and programs to help the business grow and scale.

A born-and-bred New Yorker, Stephanie and her family have made their way west from Washington D.C., and now happily call the Pacific Northwest home.

Jace Thompson

Chief Financial Officer

Jace is not your average accounting focused CFO. He’s an analytical-minded creative with a penchant for business intelligence and an eye toward the future — not the next step, the next two steps.

While spreadsheets and KPIs are part of the job, for Jace, they are only as good as the story they tell. That’s why his first order of business when joining Ruby was building a business intelligence team and data machine that delivers real-time insights, empowering Ruby to do more for its small-business customers while investing into technology and scaling the employee culture that drives the main quality differentiator of the legendary Ruby service.

Having started his career at Intel through several strategic Finance positions, he then pivoted to lead finance at a flash sales retail start-up that had to reinvent its marketing tactics and merchandise assortment on a daily basis, all through leveraging data analytics. Jace knows a thing or two about growing a human-powered tech company. And as he seeks new ways to expand what Ruby can do for small business, Jace uses his metrics to ensure Ruby decisions are not just driven by the data — but driven by the heart.

Rebecca Grimes

Chief Revenue Officer

Rebecca is an expert in building and leading teams through unparalleled growth. She has spent her career leading sales and marketing teams, building go-to-market strategies, launching new products and scaling businesses across functional, business and geographic boundaries. Rebecca leads with a human-first approach and has been loyal to small businesses since working for an independent optometrist in high school. Naturally, Ruby was a perfect fit – for a number of reasons from the culture, to the values, and the mission to help small businesses survive and thrive.

As the head of Ruby’s Revenue Team, Rebecca is responsible for creating awareness around Ruby’s unique offerings and their intrinsic value for small businesses. Through partnerships with relevant business associations, Rebecca not only builds deep connections with the small business communities Ruby serves, she continually looks for new ways to address their challenges, meet their needs and help them be successful at every stage of their business journey.

Rebecca’s passion for driving success and giving back extends into her off-hours as well. In addition to her philanthropic work for the American Cancer Society and supporting several local charities in her hometown, she recently co-founded and launched a Chicago-based non-profit called Building Up, a professional community of women for women dedicated to building each other up through mentoring, education, knowledge sharing and giving.

Wendy E. Miller

SVP, Customer Success

We’re often told that the customer is always right—but never that they’re always “happy” or “thriving.” Wendy wants to change that, which is why she’s spent her career building teams and products that meet and exceed the needs of small business customers. 

That experience serving the SMB community is what drew her to Ruby, where she now leads multiple teams dedicated to the ongoing success of our customers. She found that many others out there claim to be “customer-centric” but fail to back it up. With Ruby, she knows we don’t just talk the talk (although we are experts at that!)—we also walk the walk. 

Originally from the Midwest, Wendy started her career in NYC and worked her way to Oregon, where she and her husband (and very large dog Larry) continue to explore the city’s unique physical and cultural landscape by taking hikes and enjoying live music. 

Roger Demuth

SVP, Technology

When it comes to leveraging technology to drive business innovation, Roger is a jack-of-all-trades and master of…well, all of them. His previous experience as CTO at two tech-driven companies had him overseeing internal development, networking architecture, business intelligence, and countless other areas related to network and system security. 

However, Roger’s true passion isn’t in the development of programs—but of people. He’s seen firsthand how digital tools can be used to power and elevate human connections, which is why he’s on a mission to continually improve the efficiency and effectiveness of Ruby’s people and systems in order to better help our customers. To Roger, the combination of people and industry-leading technology is almost indistinguishable from magic. 

Modern devices and conveniences haven’t always been part of Roger’s life: the midwestern farmhouse he grew up in didn’t have running water until he was 7, and he learned self-resiliency and independence working on the farm. Nowadays, he lives just outside of downtown Portland (now with access to water and modern conveniences) and enjoys woodworking in his spare time.