Kate Winkler wasn’t even a year into being CEO when she oversaw the transition to remote work of about 650 people at Ruby. Yet the company completed the task in just 11 days. What’s more, the company didn’t really even have a remote working transition plan set in stone before COVID-19 arrived.

How did Ruby manage such a feat in such a short time? Kate tells Ramon Ray two things the company practices made this quick transition to remote work possible. Kate and Ramon also talk about being a new CEO and finding senior talent for your business. She also has two things small businesses need to have an eye on.

From CEO to investment banker to CEO

Kate Winkler is a CPA. She’s ran two high-growth technology companies. She also spent a decade in investment banking, rising to managing director of the technology group at Piper Jaffray.

She went into investment banking as she was settling down to be a parent. That allowed her to step back from the day-to-day responsibility of being a CEO. She was also able to spend a decade being around smart entrepreneurs building some of the best small businesses in the world.

Kate was named CEO of Ruby last year, after founder Jill Nelson retired. However, the two met about four years ago.

Kate knew the investors backing Ruby. Nonetheless, she did not know what Ruby was all about.

The banker was under the impression that the company was simply an answering service. As she walked through a Ruby reception center in Portland, she understood that it was much more. Ruby empowers its employees to do a hundred things for clients, Jill came to realize.

Kate then spent months helping Jill with strategies to grow the business. She then moved on. Fast forward to February of last year, Jill called Kate to say she was retiring. Kate thought Jill was asking for connections to possible CEOs, but she was asked to run the whole thing.

Open Communication high five office happy colleagues

What looking for senior talent should be about

“We should always look at hiring as an opportunity to build more skill sets around ourselves,” Kate says. However, you can’t always find someone who has skills that combine well with your own.

Plus, entrepreneurs can get awfully emotional in the process of hiring someone who will take the reins after them.

“As entrepreneurs – naturally, as we all are – we want to protect what we’ve built,” Kate says. “It’s a very risk-associated decision that we’re making.”

We should always look at hiring as an opportunity to build more skill sets around ourselves

That leads to a tendency to potentially be more emotional than when trying to take a step back and evaluating someone’s skills against yours. When she was asked, Kate told Jill to not choose her because she is the easy decision. She asked to be put through the hiring process, to ensure that the fit and skills were right. Nonetheless, it was evident after the process that she was a great fit.

Start with open communication

If there’s a fit, it becomes a question of communication, Kate says.

Misunderstandings happen in the first step of communication. It can be an accusation. Sometimes it’s an assumption. It can be a number of things that hinder an open and honest conversation.

At Ruby, she came in and people were expecting that she will revamp the business. People feared that she was a technology CEO and a banker. She may come in and suddenly pivot the business to become solely focused on technology.

Instead, she told the Ruby team that what she really wanted to do first was to have a conversation. She was finding out what people love, where change was needed, and what were sacred things in the company that can’t be touched.

Misunderstandings happen in the first step of communication

“Let’s look at them with the same open eyes, and where you have to be willing to allow that open conversation to happen, to be able to actually ensure that we’re both walking in the same direction on day one,” Kate says.

“What I found is that the biggest fear was, are we all of a sudden not going to become a purpose driven organization?” she adds.

By having the conversations, the company’s core solidified in Kate’s mind.

“The one thing that is absolutely spectacular about Ruby, is 100% of the employees know that our vision, our mission, our purpose, is to help small businesses survive and thrive 100 different ways. And we do that through these very meaningful human connections. We are a human business,” she says.

Empowerment two women talking office business meeting boardroom

Thrive through empowerment

Kate’s first task at Ruby was actually to get everyone to recommit to purpose, vision, and mission. She knew from the start that there is a lot of talent in Ruby. However, all of the decisions were being made by four people, she says.

That’s can be just the nature of entrepreneur-run companies. But the ability of the company to scale was dependent on accessing and unleashing the talent that is already in the company, she explains.

So she got to work to find out what people were doing. She also asked on one-on-one sessions what one thing they love and hate about their job. Through this process, she found out that Rubies were working on 1,183 individual tasks. Only half were essential to the business, she tells Ramon.

There is nothing but opportunity in front of us, particularly as quickly as the world is evolving right now

“The world changes fast. We need to be more nimble,” she says. If something doesn’t work, just set it aside and pick up the next opportunity. “There is nothing but opportunity in front of us, particularly as quickly as the world is evolving right now,” she says.

More importantly, Ruby didn’t need a new direction or vision, Kate realized. It just needed more communication and empowerment. “Within a three-month period of time, we were really able to empower our extended leadership team,” Kate explains.

She made it a point for her executive team to not be the sole decision-makers anymore. “Our job is to remove blockage and our job is to make sure we’re all running in the same direction,” she says. That is important, even if everybody is going in the same general direction. If you stray a little bit, that gets to be a wide gap over time, Kate says.

11-day transition to remote work

Open communication and empowerment where what made Ruby’s transition to remote work possible in just 11 days, according to Kate.

The company was already working on cross-team collaboration, project-based activities, and cohesive teams across different departments when COVID arrived. If it was not doing these, the company would not have transitioned to remote working as fast as it did.

When the company was bracing for the effects of the pandemic, there were many ideas. They could share these ideas on how to transition to remote work because they build a culture of open communication.

As the plan took shape and it came time to implement, people acted decisively. That’s all because Ruby had empowered their people to act.

 In her own work, Kate reflects these practices. One way is by not having an assistant. She wants to be accessible, because she believes it’s best to have her ear on the ground.

“Particularly as businesses get large, the best way to stay in-touch with the health and well-being of the organization is to talk to the organization.”

Kate spends about half of her time communicating and collaborating with her executive team, her extended leadership team. She believes in the spirit of transparency. She knows that people know where it’s going good in the company. People also know where it’s bad and what’s being done about it.

“If everyone needs me to make every decision in the company, we’re screwed,” she says. “So I want to empower everyone to be helpful.”

Home office transition to remote work woman smiling employee

Two themes for small businesses

Beyond the transition to remote work, Kate thinks small businesses should take note of two themes in the current business landscape. These are financing and data.


Kate says that for the first time, financial institutions are finally giving the small business community the attention that they deserve. These institutions are also providing realistic opportunities to get sustainable financing for small businesses.

Even before the pandemic, Kate says 7 of 10 businesses were failing in their first decade. Only under a third of business owners paid themselves regularly.

So what does that mean for the small business? Kate says it’s all about the passion.

She explains: “They started these businesses because they knew they could do a better job on their own.”

These business owners are passionate about what they can do. Now, they just need the opportunity to focus on that passion. Part of that is having stable financing to smooth out the peaks and valleys in the business models, she says.

Kate recommends looking beyond PPP but also new programs launched by Main Street banks.


“Data is your best friend,” Kate says. “Any and every bit of data possible.”

Ruby first saw the impact of COVID-19 in mid-March when the community went into shelter in place. Overnight, call volume dropped 40%, Kate says.

What Ruby did was to reach out to customers. They were telling customers that the decline was across the board. They were also reminding them to think about how their businesses should manage the coming storm. How should they transition to remote work? What were the other necessary decisions to make?

Ruby was actually proactively asking clients whether they wanted to downgrade to save money. They also found out that there were opportunities some businesses were missing. For example, 60% didn’t have a website. Some haven’t thought about chat support for their customers.

By looking at these data, Ruby is building the relationships to be the eyes and ears of customers across all channels of communication. It’s directly connected to the core of the business. Ruby aims to help small businesses manage customer relationships regardless of where customers are making contact.

“Data doesn’t lie. It’s very factual. You need to use it as almost a superpower,” Kate says.

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Source: Smart Hustle