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

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 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.

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.

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 having spent 25 years in the technology sector having successfully guided both small and large businesses through various stages of growth 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, so Ruby was a perfect fit.
With small business 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. No plans to recreate Ruby’s purpose, Kate seeks to double down on the human connection and reinforce Ruby’s founding vision by using technology as a super power to enable our Rubys to be that stellar first impression and empower them to build trust and foster long-term relationships between our customers and their clients in a hundred different ways.
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 commitment that Ruby will continue to discover new ways in which we can help small business owners achieve their biggest dreams.

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.

Katharine Nester
Chief Product and Technology Officer
Inspired by Ruby’s mission to create real, meaningful, personal connections in today’s increasingly technology-focused, virtual world, Katharine seeks innovative ways to use products and technology to close the virtual distance that separates us all — and make the world a smaller place.
To the traditionally tech-minded, Katharine’s approach seems ironic for someone who leads product and technology. To Ruby, it’s the driving force behind rebuilding its technology from the ground up to improve features and functionality and empower small businesses to foster long-lasting customer relationships through genuine, personal interactions.
While Katharine’s career path has been varied – from a software engineer to an international MBA at Oxford University to product management roles at AAA and Ancestry.com (and a two brief stints as a small business owner)) — her affinity for organizations that aim to help others has been constant. And it’s a mission she holds true in her personal life as well: Recipient of the first-ever PDX Women in Technology Awards, Katharine has been recognized as the Best Contributor for her work with PDXWIT, App Camp for Girls and the PDX Mentorship Program.

Rebecca Grimes
Chief Marketing 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 sales and marketing, 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.

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 having spent 25 years in the technology sector having successfully guided both small and large businesses through various stages of growth 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, so Ruby was a perfect fit.
With small business 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. No plans to recreate Ruby’s purpose, Kate seeks to double down on the human connection and reinforce Ruby’s founding vision by using technology as a super power to enable our Rubys to be that stellar first impression and empower them to build trust and foster long-term relationships between our customers and their clients in a hundred different ways.
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 commitment that Ruby will continue to discover new ways in which we can help small business owners achieve their biggest dreams.

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.

Katharine Nester
Chief Product and Technology Officer
Inspired by Ruby’s mission to create real, meaningful, personal connections in today’s increasingly technology-focused, virtual world, Katharine seeks innovative ways to use products and technology to close the virtual distance that separates us all — and make the world a smaller place.
To the traditionally tech-minded, Katharine’s approach seems ironic for someone who leads product and technology. To Ruby, it’s the driving force behind rebuilding its technology from the ground up to improve features and functionality and empower small businesses to foster long-lasting customer relationships through genuine, personal interactions.
While Katharine’s career path has been varied – from a software engineer to an international MBA at Oxford University to product management roles at AAA and Ancestry.com (and a two brief stints as a small business owner)) — her affinity for organizations that aim to help others has been constant. And it’s a mission she holds true in her personal life as well: Recipient of the first-ever PDX Women in Technology Awards, Katharine has been recognized as the Best Contributor for her work with PDXWIT, App Camp for Girls and the PDX Mentorship Program.

Rebecca Grimes
Chief Marketing 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 sales and marketing, 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
Meet Cameron
- Virtual Receptionist & Chat Specialist
- Beaverton, Oregon
- Reception Service team member
Rubys live our Core Values. They are not just for show, we embody the spirit of Growing, Innovating, Fostering Happiness, Creating Community and WOWing.
Hello, I’m Cameron

Ruby has been a lifesaver. Best thing we ever did was hire Ruby!
Shawn
Professional and trustworthy.
Bin Xia Zhang
Meet Joanna
- Virtual Receptionist
- Beaverton, Oregon
- Outbound Calls team member
I enjoy seeing how our customers needs are reflected in what we do everyday as receptionists and chat specialists. And I love that Ruby is such a positive force in so many lives.
Hello, I’m Joanna

Great service. Efficient and professional.
Dean
Better than advertised. My clients love it
Mark
Meet Lisa
- Virtual Receptionist
- Portland, Oregon
- Extended Hours & Outbound Calls team member
What I love about Ruby is the benefits and flexibility of the job, as well as all the wonderful people I have met working here!
Hello, I’m Lisa

I love having Ruby on my team!
Gina
Excellent service with a virtual smile.
Kurt

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!



People-powered positivity.
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
View All
Announcements
Ruby Certified as a Great Place to Work for 5th Year

Press Releases
Ruby’s 24/7, HIPAA-Compliant Services Reduce Burden on Healthcare Staff

Press Releases
Ruby Achieves 5 years on Oregon’s Most Admired Companies List

Media
Adapting to the New Business Context

Announcements
13-years on the 100 Fastest Growing Companies

Media
How Ruby Pivoted During COVID

Announcements
Oregon 2019 Philanthropy Awards

Press Releases
Ruby Acquires Pure Chat

Announcements
Ruby Wins 2020 Momentum Award

Announcements
Courageous Marketing Leader Awards 2020
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