Happiness is

A real, happy person, happy to take every call and chat.

Ruby's core values.

At the heart of everything we do is a promise to treat every call and chat as an opportunity to make a lasting, positive impression.


It all started with making connections.

small pink rectangle shape

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 win new business.

Ruby’s boot-strapped humble beginnings shape every aspect of how we run our business and deliver our services. Our small business beginnings help us understand the needs of our customers.

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 growth of our business customers, but are inspired by the businesses we serve and share in the joy of their success.



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

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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.


On Diversity

Ruby is all about growing and celebrating our diverse people-powered culture. We embrace and encourage all of our many varied, wonderful differences. Together we cultivate human connections that empower each of us to bring our unique selves to work every day.

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!

About - Ruby Corps

People-powered positivity.

Ruby provides thousands of great first impressions every day. Want to help?

Awards & Recognition

Fastest Growing

Fastest-Growing Private 100 Companies

Portland Business Journal, 2007 – 2019

Top 10

Top 10 Oregon Most Admired Companies, Across All Industries

Portland Business Journal, 2016

Top 5

Top 5 in Oregon’s Most Admired Companies, Technology & Technology Manufacturing

Portland Business Journal, 2017-2019

100 Best

100 Best Green Companies in Oregon

Oregon Business Magazine, 2010 – 2013

Inc. 5000

Inc. 5000 Top Telecommunication Companies

Inc., 2012 -2019

Top 25

Top 25 in Oregon’s Most Admired Companies, Across All Industries

Portland Business Journal, 2016-2018

Ruby News

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Sales Support

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.

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*Ruby is delighted to offer a money-back guarantee to first time users of both our virtual receptionist service and our chat service. To cancel your service and obtain a full refund for the canceled service (less any multi-service discount), please notify us of the service you wish to cancel either within 21 days of your purchase of that service or before your usage exceeds 500 receptionist minutes/50 billable chats, as applicable, whichever occurs sooner. Some restrictions may apply.