19 years, 19 lessons: insights from helping small businesses grow since 2003

Title card with text: Happy 19th birthday Ruby!

Happy birthday, Ruby!

This month marks our 19th year in business, and we have a lot to celebrate. We’re feeling fortunate to have been in the game for nearly two decades—a milestone few businesses achieve.

And that brings me to the real reason we’re here. This isn’t just about how far Ruby has made it; it’s about the thousands of small businesses we’ve supported along the way. After all, our customers’ success is our success, and it’s something we celebrate every day.

Still, 19 years is a lot of days—about 7,000, in fact—and we’ve learned a lot along the way. What better excuse than our birthday to reflect on some of those insights, so you can apply them to grow your own business?

Don’t worry, this isn’t a list of 7,000 things (we’re saving that for next year, ha!). We’ve distilled the last 19 years of Ruby experiences and insights into 19 key takeaways. Here’s what we’ve learned about small business success, customer communication, employee engagement, navigating disruptions, and more:

Table of contents

1. The importance of personal connections

This is our hit single—if you work at Ruby, it gets stuck in your head. We hire and train our people to turn every moment into a meaningful, personal connection.

It starts with “hello,” but the interaction entails so much more. We know there’s no second chance at a first impression. And when it comes to making a positive impression and establishing trust, nothing beats friendly, immediate, and compassionate service that ensures people feel your business truly understands their needs. Plus, when you consider the value of every conversation, great experiences for callers and website visitors are truly priceless.

2. The value of a small business’s time

Another priceless asset? A small business owner’s time. That’s why we’ve set industry-leading standards over the last 19 years to enable our customers to make the most of their workdays:

  • On average, Ruby answers calls in one ring cycle—that’s less than 10 seconds! Or the time it takes Usain Bolt to run the 100-meter dash.
  • We filter over 20,000 robocalls per month on behalf of our customers— giving you back time in your day and only warm leads at your fingertips.
  • This adds up to over 1,000 hours(!) saved each day for the businesses Ruby serves.

We’ve seen our customers do some amazing things with those extra hours—from expanding their business and services offered to putting themselves to work for their community.

3. The secret behind an award-winning company culture

Knowing what you stand for, hiring people who stand for the same, and inspiring and empowering your staff are key to creating an outstanding company culture. We’ve worked hard to do that by:

  • Taking the right approach to hiring and onboarding
  • Having a Vision, a Mission, and set of core values our team understands and believes in
  • Providing industry-leading training and opportunities for professional growth and development
  • Regularly assessing and refining all the above, as we acknowledge we’re all human—we evolve, we make mistakes, and we grow better together

We recognize that there’s always room for improvement, and have taken steps to ensure that everyone here at Ruby feels comfortable sharing their ideas, perspectives, concerns, questions, and experiences.

4. What it takes to optimize customer experience

Customer expectations are constantly shifting, which means that improving their experiences starts with improving dozens of little things (and a few big ones) when it comes to your service.

This could be something as simple as returning emails in less than 24 hours, or something more involved, such as mapping out and gaining insight into your customer journey from start to finish.

Looking to improve your customers’ experience but aren’t sure where to begin? We’ve got a comprehensive list to inspire you.

5. How to build the right ecosystem

Customer experience is a team sport—as is nearly every aspect of running a business.

That’s where partners and vendors come in.

You don’t always need to build or buy capabilities to grow your business. You can join forces with complementary people and companies in your market—like we’ve done with organizations such as Clio, Scorpion, and bar associations throughout North America—not to mention our wonderful affiliates.

The same goes for third-party vendors—we’ve learned to look for experts who support us and reflect our business’s values. Shoutout to RLM Media, Simple Smart Marketing, Future Work Design, and the other phenomenal teams we’ve worked with!

That said, it’s important to remember what you do best, and what you need to do in-house, as we’ve explored together with Hire an Esquire in our guide to legal outsourcing.

6. What a billable hour really means to a lawyer

Speaking of doing what you do best, we’ve learned that many professionals wish they had more time to focus on their work.

It’s more difficult than ever for attorneys, for instance, to balance productivity with daily tasks. The result: only 2.5 hours billed in a typical 8-hour workday. By minimizing distractions and allowing them to stay focused on the task at hand, we’ve been able to help attorneys and other legal professionals grow their business while strengthening their relationships with their clients.

In the words of one of our customers, attorney Diane Haar:

“Ruby's extended hours translated into a boom for my business. I did not realize how many potential clients moved on to someone else when they got my after-hours voicemail. Now with Ruby on the line, even if I cannot pick up, many more potential clients are sticking around to become actual clients.”

7. The amount of money a single new customer can bring for a home services business

Did you know that using virtual receptionists to capture opportunities 24/7 can boost a roofer’s bottom line by $17,989 per year?

How about $24,261 for a plumber?

Every single lead matters. Seriously. Take it from our customers:

“Ruby’s receptionists answer the phone as if they are in our office. Customers have no idea it’s an answering service! It has saved us time; we don’t miss any new potential customer calls. Communication with our current customers is very important and they want to speak to a human being when they call. We’re very happy with the service.”

See how much your business could stand to earn by taking on more projects.

8. The many ways live chat can grow a business

These days, a business’s online presence is its new front door. After years as a company focusing solely on answering calls, we introduced live chat in 2019, and we’ve seen firsthand how powerful multichannel communication can be for businesses.

Why is live chat important? Because these days, when people are conditioned to use technology to communicate, it’s crucial that your website provides the right experience.

Live chat makes it easy for them to connect with a friendly professional at the touch of a button—someone who can answer their questions while collecting information and representing your brand.

The bottom line: chat bridges your business with your audience. It’s an essential service and sales tool, helps you learn more about your online audience, and—most important of all—it’s many customers’ preferred method of communication with small businesses.

9. That every business has unique needs and opportunities…

From lawyers to home services professionals, from marketing agencies to accountants to candlemakers to tattoo parlors and everyone in between, each business we serve is unique. Every business has a fascinating story, its own personality, and customers or clients with unique needs.

Being adaptable to these realities is in Ruby’s DNA. Everything we do is in service of our customers. It’s why we’ve invested in a technology platform and award-winning team training that enables any Ruby receptionist to capably represent any business, for example. It’s also why we continually optimize various elements of our interactions with customers, such as our emails, our website, and the Ruby app, down to details such as the paper choice for handwritten notes.

Want to optimize your customer service journey? Start with our checklist.

10. …and there’s always more to learn.

In recent years, we’ve dug in even deeper to learn more about our customers, from conducting surveys and communicating with them at multiple touchpoints. Just this year, we launched a customer council to gain even more regular and feedback from small businesses.

These efforts play an important role in our organization’s equity, diversity, and inclusion initiatives. Ruby’s team is comprised of people of all cultures, genders, ethnicities, and self- identities, and we’re committed to creating a welcoming, accepting, and engaging environment for every employee. That same commitment extends to our small business customers. We proudly represent numerous local businesses, woman-owned businesses, Black-owned businesses, veteran-owned businesses, and other people and organizations who serve our communities.

Beyond our services, we also endeavor to use our platforms—including the Ruby blog—to provide free resources on topics such as intersectionality, funding for women-owned businesses, dismantling barriers faced by Hispanic and Latinx businesses, respecting others’ pronouns, providing accommodations to those with disabilities, and more.

This work is never over, and we understand there’s always room for improvement. There’s a direct correlation between empathy and our own success, and that requires practicing vulnerability.

11. Customer communication is vital in uncertain times

Ruby has navigated multiple economic downturns and grown through them—making it possible for our small businesses to grow through them, too. When the 2007 recession occurred, we doubled down, focusing our efforts on our customer service experience and the way we continue to deliver personal, meaningful experiences for customers. When the pandemic hit in 2020, we launched 24/7 service so businesses could stay nimble and meet changing expectations around the clock.

Whenever our customers face new challenges, we put our team and technology to work on new solutions.

We find strength in being able to empathize with the businesses we serve, seeing uncertainty as a challenge to handle with grace. It may not always be easy, but with honest, thoughtful communication, your business can make it through any challenge.

12. How to take a company virtual in 11 days…

When COVID-19 hit, Ruby responded quickly, transitioning hundreds of employees to a virtual, distributed setup in a matter of days—without letting anyone go. We optimized our team’s equipment and internet connections to ensure continuity of service, providing accommodations to those who needed them.

As it turned out, this setup made for a more productive and flexible Ruby. We learned that working remotely made life easier for employees who need more flexibility in their schedules or were interested in relocating. It also positioned us well to launch 24/7 service and expand our workforce in areas beyond our headquarters in Portland and Beaverton, Oregon and Kansas City, Missouri to more than 14 states.

13. …and the secret to keeping a virtual team happy

Like so many businesses, we had to learn a lot about managing, motivating, and empowering people to do their best in a virtual environment, and we’re learning more every day.

For Ruby, it’s all about intentional leadership and self-awareness. We keep our employees engaged by doing things like…

  • Rethinking training to make it digestible and more interactive for a remote team
  • Acknowledging awkwardness, internet outages, and interruptions with humor and understanding
  • Finding new ways to make human connections in a virtual setting, such as one-upping each other with GIFs, playing improv games, hosting costumed dance parties, making videos and Padlet boards (So. Many. Padlet boards.) to celebrate one another, and so much more

14. All about each other's kids, partners, and pets

We see the remote or hybrid work environment as a challenge and an opportunity—a chance to bond with our co-workers’ loved ones and families as well.

We’ve all learned so many more names over the past couple of years. Louisa, Andrew, Milo, Danielle, Buddy… Can you guess which ones are people and which are pets?

One really cool thing about working as part of a remote team is you not only get to know your co-workers, but also all the people and creatures who cohabitate with them. We literally have windows into each other’s lives—it’s one way we can make even deeper connections in a digital world.

15. How to own our failures

Navigating these times means figuring things out together—and owning our mistakes.

For example, have I ever referred to someone’s spouse by their pet’s name?

You bet I have.

But beyond the small flubs, it’s important to make space for larger moments of growth and humility. No business can make the right decisions 100% of the time.

There’s no simple way to avoid or fix these kinds of mistakes, but it’s always a good idea to ask for help (see lesson 5), admit what you do and don’t know (lesson 10), and communicate openly (lesson 11). I’m also a firm believer in acknowledging mistakes quickly, apologizing for them sincerely, and making a good faith effort to do better and move forward

At the foundation of all this is earning your team’s trust. And that means trusting them. Remember: you hired them for a reason. As leaders, we’re most effective when we empower our employees to bring their best selves to work, lead in service of them, and otherwise get out of their way.

16. How to say hello​

This isn’t about saying hello over the phone—we mastered that 19 years ago—but about welcoming new employees, new customers, and new experiences. As I mentioned earlier on, first impressions are critical, and so is intentionality. Growth is constant for a successful business, but it doesn’t automatically lead to sustained momentum. We’ve learned to grow in an equitable, authentic, and welcoming way.

It all comes back to culture. It’s not enough to create a welcoming, positive space, but to regularly reflect on and improve culture. It means continually asking your business:

  • What do we do?
  • Why do we do it?
  • Who do we do it for?

Earlier this year, we posed these questions for ourselves to reimagine our Vision and Mission. Learn how a similar exercise could transform your business.

17. How to say goodbye

Hellos go hand-in-hand with goodbyes. Establishing a new Vision and Mission, for instance, means letting go of the old set.

That said, it’s no secret that goodbyes are more difficult than hellos. (I mean, have you ever tried to end a phone call with a talkative friend or client?) But to move forward—or at least eat lunch before it goes cold—we need to learn how to say goodbye.

I’m guessing you already have some experience here. We’ve all said goodbye to people and things we weren’t ready to let go of. It’s a consequence of change.

Everything changes. Priorities change. Technology changes. Teams change. And just as change leads to new beginnings, it brings about endings, too.

Remember: your business can’t be everything to everyone. So, as you grow and continue to work toward your value and purpose, practice your hellos and goodbyes. You know what’s best for your business, and you can’t afford to wait for the other person to (metaphorically or not) hang up first.

18. To be thankful for all the special moments we’ve had

When I think about what it means to succeed as a business for close to two decades, I come back to a phrase we’ve used often at Ruby:

And when we look back on how far we’ve come since 2003—or even just since 2019—our team doesn’t think in terms of beginnings and endings. We think about all those moments.

Like this moment. Or this one. Or that one. Or the time we talked to Adele (not really). Or all those Space Kitten Pizza Parties (really).

Financial, commercial, or creative success is certainly worth celebrating, but sharing unforgettable moments with people you love working with? That’s a special kind of success—and one every business should strive for every day.

Just remember, when they happen, to recognize and practice gratitude for those moments. It’s good for you and your team.

19. That the best is always yet to come

It’s hard to believe it’s been 19 years since Ruby started, but here we are—and I can’t imagine a more exciting time for our small business community and us.

We’re so thrilled to share more wins, learnings, growth, connections, and memorable moments in the weeks, months, and years to come with all of you. And we can’t wait to let you in on some exciting things we have in store very soon.