Happiness is Contagious.

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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.


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 diverse 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

Reliable, meticulous, and hard-working—Kate meets the description of an “Operator”-style personality to a “T.” With a background spanning finance, product, operations, and more, Kate can get under the hood of virtually any business and make sure it’s running like a well-oiled machine. As CEO, Kate is responsible for guiding the continued trajectory of Ruby, exploring new ways in which we can add value to the small businesses. Kate has 25 years of experience in technology, telecom, and finance, and has helped over 75 companies build and capture over $4Bn in enterprise value. Her previous roles include Managing Director of the Technology Group at Piper Jaffray, Director of the Technology Media & Telecom Group at Houlihan Lokey, and CEO roles at both Jentro and Centerpost Communications, Inc. When not at work, you can find Kate in a co-ed soccer game, climbing a17,000-foot peak, crossing the Everest icefall, tackling a 550-mile bike ride, or adding another passport stamp to her collection of more than 60 countries.

Stephanie Copeland Weber

Chief Operating Officer

If it keeps the Ruby ship moving forward, it’s probably Stephanie’s doing. As COO, she’s responsible for the legendary Ruby employee experience, and for developing systems that ensure our company’s continued growth. Stephanie brings deep experience in developing high performing teams and scaling businesses. She’s a music lover (and former acapella group leader), a great outdoors lover (she’s all about hiking in the Pacific NW with her family), and a graduate of the University of Virginia (in the state for lovers).

Jace Thompson

Chief Financial Officer

As an endurance athlete, every day you’ll find Jace running or biking somewhere around Portland. As CFO, most days you’ll find him running numbers around Ruby. Jace develops enterprise business analytics to help shape Ruby’s future growth, as well as managing day-to-day tactical business execution. If it sounds complicated, it is. But he’s been doing it for over two decades, working in strategic finance at Intel, and as Finance Director in the retail e-commerce sector. We still don’t know how he finds time to squeeze in all the running and biking.

Molly Moore

Chief Marketing Officer

Experience could be Molly’s middle name (it’s not). For over 20 years, she’s been a sales and marketing leader. Before Ruby, her experience included executive-level roles in telecom at companies like Zayo and Integra. As CMO, Molly focuses on building exceptional customer experiences and meaningful engagements with prospects. It all helps to grow businesses, win trust, and build loyalty. And she knows a thing or two about loyalty. She’s a regular fixture at University of Oregon Ducks games (her alma mater). When she’s not donating her time to the American Heart Association, she’s donating her energy to chasing her 7-year-old son around.

Katharine Nester

Chief Product and Technology Officer

Technology moves at the speed of innovation. Katherine seems to move just a little bit faster than that. From degrees in Computer Science at UC Berkeley, to an MBA from Oxford, she moved into roles in product management at Ancestry.com and AAA. Her work at Ruby focuses on designing products and services that put the human connection first and foremost. As if that wasn’t enough, in 2017 Katharine was recognized with the Best Contributor Award by PDX Women in Tech for her contributions to PDXWIT, App Camp for Girls, and the PDX Mentorship Program. She makes the rest of us look like we’re going in slow motion.

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.

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

  • 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, 2017-2018

  • 100 Best

    100 Best Green Companies in Oregon

    Oregon Business Magazine, 2010 – 2013

  • Growth Award

    Growth Stage Company Award

    Oregon Entrepreneurs Network, 2016

  • Top 25

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

    Portland Business Journal, 2016-2018

Ruby News

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Press Releases

Ruby Receptionists rebrands to reflect 16 years of growth!

Press Releases

Ruby Receptionists’ board names Kate Winkler as new CEO!


Want to grow your business? Focus on customer experiences.


Ruby breaks another fastest-growing companies record—12 years running!


Why connections matter more than ever in customer service.


How to roll out the red carpet for your customers.


Help your small business stand out with a memorable domain name.


Practice management tips for lawyers.


Good old fashioned customer service.


Jill Nelson on the Life After Business podcast.

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