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“Have an amazing product”, With Douglas Brown and Natalie Ruiz of ‘AnswerConnect’

Have an amazing product. We understood early on that missed calls result in missed opportunities. Through amazing people and technology, we are able to provide our clients with a live, professional voice on the other end of every phone call 24/7/365. The benefits of our service are real and measurable. We deliver real ROI and […]

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Have an amazing product. We understood early on that missed calls result in missed opportunities. Through amazing people and technology, we are able to provide our clients with a live, professional voice on the other end of every phone call 24/7/365. The benefits of our service are real and measurable. We deliver real ROI and an impact to results that matter to business leaders.


As a part of my series about “Lessons From Inspirational Women Leaders in Tech”, I had the pleasure of interviewing Natalie Ruiz, CEO of AnswerConnect. Her company provides people-powered services and technology that support small and mid-sized businesses and help them work anywhere.

AnswerConnect is a remote-first company that made the switch from co-located to a work-from-anywhere model in 2007, and Natalie is passionate about the model not just because she gets to work barefoot, but because the work-from-anywhere model has positively impacted her company’s triple bottom line: people, planet and profit.

When she’s not working, she loves spending time with her family, getting outside, and volunteering.

Natalie is also an award-winning executive who has been recognized with an award for Female Executive of the Year and for Women Helping Women by the Stevie Award Association. She advocates for women and other marginalized groups at work and as a volunteer. She is passionate about equity and belonging and works to create an environment at her company where people from all backgrounds can thrive. Natalie also volunteers as a mentor, lends her voice to speaking engagements, and is a published thought-leader and writer.


Thank you so much for joining us in this interview series! Before we dive in, our readers would love to learn a bit more about you. Can you tell us a story about what brought you to this specific career path?

My background is pretty unconventional for a CEO of a global technology company. Prior to finding my current company and career, my work history was extremely varied. For example, I have sold cars, I managed a restaurant and worked in retail. All of these roles taught me lessons and skills, but inevitably, I left each position because I didn’t see a long-term future for myself. I was never quite sure WHAT I wanted to be when I grew up, but I have always had a strong sense of WHO I wanted to be. Career wise, I was searching for a place where I could be the best version of myself.

When I found AnswerConnect in 2006, I initially thought it would be the same story I had encountered before, and I didn’t expect to stay. I had been placed through a staffing agency as a salesperson, and was not prepared for how much of a startup I had walked into. I wasn’t given any formal training or even a real orientation to the company, and there were no defined sales goals. I didn’t see how I could be successful.

Fortunately, during my first week with the company, I had a chance encounter with the founder and then CEO. He asked me how things were going, and instead of giving him the answer I would typically give in that situation — which would be to say everything was amazing and thank him for the opportunity — I actually leveled with him. I shared feedback on the aspects of the job that were not working for me and I discussed insights based on what I had noticed in my first days.

The way he handled my critiques changed my life: he listened intently and asked me if I could help improve any of the things I had mentioned. From that point on, I saw how using my voice could lead to positive change, and I became completely committed to improving everything I could. As the company grew, so did I, and in 2015, I was offered the position of CEO. It has been one of my life’s greatest honors and adventures to lead my company.

I think it is important to note that when I started, I was young and inexperienced. I think I had internalized the expectation that someone who was a boss, a founder or a CEO would have all of the answers. Those early days showed me that no one person knows it all and that learning and experimenting has to be continuous. I’ve carried the lessons around lifelong learning and humility with me since then and it has helped shape my approach to leadership.

Can you share the most interesting story that happened to you since you began at your company?

A few years ago, I was at a trade show for one of our bigger franchise clients. As we were setting up our booth, I noticed a woman sending people our way. Before we were even fully set up, we had a line of people waiting to speak with us about our services. After the crowd dissipated a little, I went to meet this woman and thank her for sending so many prospects our way. I was floored by what she told me.

She let me know that she had been a franchise owner for a couple of years. She had cashed out her 401K to buy her franchise business, and the same day that she was supposed to sign the paperwork to officially become an owner, she was served with divorce papers. In an instant, her world had been turned upside down, and with 3 kids depending on her, she told me she felt like she was drowning. Navigating a brand new business, a divorce and the responsibilities of being a single-mother pushed her to the point of breaking. She shared that she after she found AnswerConnect, for the first time in months, had been able to enjoy dinner with her kids without checking her phone or answering calls. She started seeing appointments rolling in while she was focusing on growing her business, and she told me she started to breathe easier. She then grabbed my arm, looked me in the eye and said, “Natalie, AnswerConnect saved my life.”

We aren’t building rockets or conducting life-saving surgeries, so being told with absolute sincerity that you’ve saved someone’s life isn’t something I had gone to work expecting. Remembering this story gives me chills. So many of our clients are small business owners, entrepreneurs and enterprising people who are stretched thin. The ability to give someone back some time and peace of mind can have a bigger impact than we may know.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

My daughter was born in 2014 and I was promoted to CEO in 2015. Like most new parents, I was definitely not getting enough sleep, and I never felt like there was enough time in the day to handle everything that was on my calendar. I remember showing up to an event for work just barely on time after a frantic morning of getting my daughter up, fed, ready and dropped at daycare — only to discover that I was wearing two different shoes. They were not only different styles entirely, but also different colors. Initially, I was horrified.

After a deep breath, I realized that I worked with many other parents and people who had lived through times when they were juggling too much — so, I called it out. I doubled-down on being real and being honest and let everyone know that I was thrilled to be at the event, even if it had been a harried morning and looked a little silly. We all laughed moved on. Being there mattered — my footwear didn’t. I think it is extremely important for leaders to be real about their struggles and missteps because it creates space for everyone else to do the same. In my experience, bringing authenticity and vulnerability to work has been a key to building high performing teams.

Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

In 2007, our business was growing quickly and we were running out of space in our building. We had choices to make — invest in bigger real estate or try something new. Technology was just coming available that would allow us to experiment with running our business virtually. We embarked on transforming our business to a remote-first model and began moving our teams home. This was a big leap, and there were risks in making this switch from a co-located business model to remote work.

In the midst of our transformation, the ’08-’09 recession happened. There was a lot of uncertainty during that time. Many of our clients had to radically change the way they worked, some had to close their doors forever, and more still found us for the first time, as they looked to operate their businesses virtually.

Leading change can be challenging. Not only were we completely changing the way we worked, the world was also changing around us. I never considered giving up because I recognized how many people were counting on our success and this cemented my resolve to show up and give my company everything I had. I’m grateful to be surrounded by people who do the same in the face of challenging times — and this also keeps me going.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

When it comes to mentors, I have been extremely fortunate to have so many people who have helped me grow and also held me up when things were extremely difficult.

There’s no chance I would be as strong of a leader as I am without the help of Lorissa Bowersox. She is the Director of People Operations at our company, and her guidance has helped me navigate countless situations. She is the second set of eyes on communications I write, the sounding board for crazy ideas I may have, and someone who I look up to because of her generosity, drive and professionalism in all that she does.

I have to also highlight my boss, Michael Payne, who is the founder of my company. He gave me a chance during those first days with the company when I couldn’t see a path forward. He’s continued to believe in me and give me opportunities to learn and grow.

Truly, there are more people than I can name here — I am an extremely lucky person with a rich life and a full cheering squad. My family and friends love me and also hold me accountable and keep me grounded. What good is success if you don’t have people around you to enjoy it with?

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

I am a huge fan of Dr. Maya Angelou’s work, and so many of her quotes. One that is resonating now is, “Success is liking yourself, liking what you do, and liking how you do it.” I have learned that there are many paths to achievement and happiness — and that this is going to look different for everyone.

At the end of our lives, we will have spent 30% of our time working. I want to do something that matters, something that leaves the world a little better than I found it and gives my daughter and the people around me a positive example. It is easy to get distracted by outside measurements or someone else’s idea of what your life or work should look like — I work hard to stay true to myself, my values and my why, and to me the ability to do this is the definition of success.

Ok super. Thank you for all that. Let’s now shift to the main focus of our interview. We’d love to learn a bit about your company. What is the pain point that your company is helping to address?

AnswerConnect understands small and mid-sized business needs because we started out as a small business. Our clients are often crazy-busy and need a solution that they can rely on. We are that solution! We partner with our clients 24/7/365 to take care of their callers, schedule appointments, handle web-chats and more. We provide answering service, contact center solutions and technology that free up business leaders so they can multiply themselves and thrive, no matter where their business takes them.

I remember working in our sales department and continually trying to reach a prospect who had requested information on our service. Every time I called him, he would answer, hear who I was, shout at me and then hang up. It was a rough cycle! Finally, I was able to catch him before the inevitable yelling followed by the click of the phone to ask if he really wanted information or would prefer I stop calling. He quickly explained that he was under a building in a crawlspace, that the previous day when I had called he was in a heating vent, and another time I called, he was re-wiring an electrical box — he said he did need our help — here he was answering his own business calls in these precarious situations — but he didn’t have time for the details. Long story short, we made it easy for him — we started handling his HVAC business calls that day, scheduled his appointments for him on a shared calendar, and got him set up with our mobile app. If I had been a little less tenacious, that guy may still be stuck under a building trying to conduct business! No matter the industry, the pain points are similar. The value of a phone call from a possible client is large, and AnswerConnect helps by ensuring that every call is handled well by someone who can fully focus on providing the best customer service.

What do you think makes your company stand out? Can you share a story?

My answer to this question has not changed in 15+ years. Our people and our technology are what sets us apart.

Answering service is not the sexiest industry to be in. It doesn’t immediately lead to visions of cutting-edge tech or innovation, yet our business uses the best technology paired with amazing people to support our clients. In many ways, we have been disruptors in our industry.

Because of our remote-first model, we are able to attract the best talent — not just the closest. One of my favorite things to do is to meet our new hires. I join our virtual training classes on a video call and we get to know more about each other and I take all of their questions. In any given class, we might have people from across the nation and a wide range of demographics. Everyone is bringing with them unique perspectives, previous work and educational history and their own voice.

We are all extremely different, which is where our strength lies. We rally around our core values, which are learning, sharing and giving back and have a mission to help the world work anywhere. With this in mind, we have cultivated an environment where everyone plays a role in us leveling up and delivering value to our customers. This level of commitment and engagement is what makes us special and allows us to be positioned as the company our clients trust with their businesses.

Are you working on any exciting new projects now? How do you think that will help people?

Small businesses create a special kind of magic. There’s innovation, creativity and grit that I believe enriches our world. AnswerConnect wants to continue to support that magic by providing the right people and amazing technology to help those businesses flourish.

We know that our services can be the difference between success and failure, strained and thriving, profit and loss. We will continue to look ahead and work to anticipate the needs of our clients so that we can support them, no matter what comes next.

We’ve doubled down on our desktop and mobile applications, which help individuals and businesses stay connected in their offices, from home or from anywhere. We are also continuing to expand and grow our business, and we are looking at Canada as a possible next step in our expansion.

Let’s zoom out a bit and talk in more broad terms. Are you currently satisfied with the status quo regarding women in Tech? What specific changes do you think are needed to change the status quo?

Absolutely not. In order to be satisfied with the reality of women working in tech, I would need to see at least 50% of all roles held by women and true equity in opportunities and compensation. We have a long way to go. COVID has created even more of a disparity for women at work, as many of us are juggling increased unpaid work at home and schooling responsibilities for our children, while also trying to thrive in our careers. This is creating a massive setback, and a disproportionate number of women are leaving the workforce. We are losing ground.

As employers, leaders and hiring managers, we need to do several things to address this. First, we must challenge our expectations on where great tech hires come from. If we want to change the makeup of our workforce, we have to change the ways we recruit, hire, support and promote diverse talent. We need to give women a chance, which means it is time to consider hiring unconventional backgrounds and grow people in our organizations. I am an advocate for paid internships, mentoring and paid learning time at work — all of these help extend opportunities to women and other underrepresented groups. More than anything, senior leadership has to admit that there is a problem and then commit to taking measurable actions toward solving it.

In your opinion, what are the biggest challenges faced by women in Tech that aren’t typically faced by their male counterparts? What would you suggest to address this?

The big challenges that women in tech face all tend to be related to each other. Women are taken less seriously in their roles, paid less and still encounter a glass ceiling when it comes to advancement. Each of these issues feeds the rest. Women are still underrepresented in tech, especially in senior and executive roles. As such, there’s a lack of representation, and this influences unconscious bias that can lead to fewer opportunities and disparity in compensation. The problems are complex, but not unsolvable.

As a mother to a young girl, I would advocate that we start working to solve this problem long before women enter the workforce or even university. Girls are losing interest in STEM at age 15, and while we may not know all of the reasons, I am a big believer that we can’t be what we can’t see. Girls need mentors, role models and a well-lit path to careers in technology. As female leaders in tech, we have a responsibility to use our voices, to show up and to help lift the next generation of women in technology.

Once women enter the workforce, it is also our responsibility to continue to advocate and mentor them so they can navigate and ascend their careers. Executives and leaders need to commit to initiatives that improve equity and then be accountable to their results.

What would you advise to another tech leader who initially went through years of successive growth, but has now reached a standstill. From your experience do you have any general advice about how to boost growth or sales and “restart their engines”?

My first suggestion would be to identify if it is an issue with marketing or the product itself. If prospects don’t know about you or can’t find you, you can’t sell to them and you can’t grow. The world changes quickly, as do the ways consumers and businesses shop. When it comes to marketing and selling, keep experimenting and keep learning.

On the other hand, it is a good idea to examine your product or service offering with fresh eyes and ensure it hasn’t fallen flat or been outmoded. Work to understand your customers and target customers, understand the problems they’re facing and the options they have to address their challenges — then be real with yourself about how your offering stacks up. If it isn’t where you want it to be, get to work improving it. If you can’t or won’t improve it, consider sunsetting that offering and trying something new. Talk to the clients you do have; work to understand their business, pain points and how they use your product. A conversation with a client can be extremely valuable.

Do you have any advice about how companies can create very high performing sales teams?

Sales can be a grind. To create and maintain high-performing sales teams, take care of your people. Even the best salespeople get rejected every single day. Cultivate a company culture that is values based, inclusive and is about more than just the bottom line. Have a little fun while you’re at work — a little levity and whimsy goes a long way to fuel up a team.

Invest in great leaders, training and support to help the team thrive. Beyond that, have an amazing service or product that your team believes in. Help them connect to how what they’re selling is making a difference for the client or user.

Finally, communication is key to success. Performance, expectations and anything that is new or changing should be communicated clearly and often. I suggest a quick daily standup to stay on the same page, transparency of KPIs and regular one on ones to hold and open dialogue about goals and growth.

In your specific industry what methods have you found to be most effective in order to find and attract the right customers? Can you share any stories or examples?

One of our favorite ways to gain a new customer is through a referral. Of course, we rely on advertising and marketing as well, but there is no substitute for a business owner telling their friends and colleagues about our business and sending them our way. When one of our clients uses their platform to tell true stories about how AnswerConnect has helped their business grow, we know that the relationships we are making are meaningful. We have grown large segments of our business through word of mouth and referrals, and I’m forever grateful for our sales and support teams for taking great care of our clients so that this is possible.

Based on your experience, can you share 3 or 4 strategies to give your customers the best possible user experience and customer service?

Absolutely! My first piece of advice is to know where each of our expertise lies. Each of our clients is an expert on their particular business and industry. There’s no way we will know as much about their business as they do. If we can call that out right away, things tend to go smoother! The great news is, we are experts at setting up our client accounts in such a way that we’ve got fast access to all of the information we need to do a great job for our clients. In short, the first strategy is to trust us! Once we have a new client set up and begin working for them, it’s common that we will want to make changes and adjustments. We expect this, and know that how we support our clients will continue to evolve. Therefore, my second strategy is to regularly provide feedback and updates to us. Treat us like a business partner so that we can do our best work for you. Finally, my third strategy is to suggest that our clients use all of our tools to get the optimal user experience. Many of our clients find us through a search for one product or service. However, we offer an entire suite of services that are aimed at supporting our clients and allowing them to take their business with them — wherever they may be working.

As you likely know, this HBR article demonstrates that studies have shown that retaining customers can be far more lucrative than finding new ones. Do you use any specific initiatives to limit customer attrition or customer churn? Can you share some of your advice from your experience about how to limit customer churn?

In most cases, customers fire you when they no longer see value in what you’re doing for them, and they’ll stay in a long-term partnership if the relationship is fruitful. Therefore, we first look to ensure that we are doing what we set out to do and delivering value. We talk to our clients, heed their feedback and suggestions and expect to continue iterating on deliverables until we get it right. To further limit churn, we try to look at every touchpoint in our client’s journey and ensure that the experience is what we intend. We have amazing teams who are invested in taking care of our clients, and we are open and transparent about retention and churn. I am a big believer in inviting more voices and experts into a conversation to yield better results, and this approach to taking care of our clients for long-term partnerships has worked.

Here is the main question of our discussion. Based on your experience and success, what are the five most important things one should know in order to create a very successful tech company? Please share a story or an example for each.

  1. Have an amazing product.

We understood early on that missed calls result in missed opportunities. Through amazing people and technology, we are able to provide our clients with a live, professional voice on the other end of every phone call 24/7/365. The benefits of our service are real and measurable. We deliver real ROI and an impact to results that matter to business leaders.

2. Invest in the right people

We believe that the right people make all the difference. When you find folks who will put in the work to grow and learn as your business needs evolve, you have to take care of them. When you take care of people, they’ll take care of your business. The CEO cannot be in the room for every discussion or decision. By staffing your business with the right people, you are able to grow, scale and multiply your efforts successfully, while staying true to your values and mission.

Stay true to your values

3. Commit to lifelong learning

We have added a paid learning benefit at our company. By adopting a growth-mindset and prioritizing on-going learning, we have seen notable advances among individuals and teams. To stay relevant as a technology leader, we all have a responsibility to continue learning.

4. Iterate, experiment and stay nimble.

In life and in business, things rarely go exactly as planned. Mistakes and redirects happen, and they can be a big opportunity to level-up, if we stay nimble and open minded. We are big advocates of smaller experiments to test ideas. This allows us to either succeed or fail faster, which helps us keep moving.

Wonderful. We are nearly done. Here are the final “meaty” questions of our discussion. You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

Goodness, no pressure, right?

This year, I have been focusing a lot on what I can personally do to make a positive impact. So, I will speak to the things I have centered on. If I could inspire a movement, I would love to see more mentorship and outreach to girls and women to help them navigate career and life. We should build in the ability to give back in our educational programs and our businesses. Let’s normalize sharing expertise and experience.

I have struggled with Impostor Syndrome in life and career, and for some time I felt like I wasn’t qualified to mentor others… Once I started, I realized I had a lot to offer; I wished I had gotten started earlier. When I look back at my teens and twenties, I know that a mentor could have made overcoming the trials and tribulations of life a smoother experience and helped me find my confidence, voice and success earlier.

The future of business needs to be more equitable. Mentoring, outreach and volunteering with women and girls can help address many of the problems keeping us from true equity, and everyone reading this article has the ability to be part of the solution.

We are very blessed that very prominent leaders read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them 🙂

There are so many amazing people who come to mind, but for today, I will give Sara Blakely a shoutout. I have been so inspired by her story and continued tenacity. She had a background in sales and became an inventor and a huge success. She famously suggests that we hire for our weaknesses, which is something I have seen the value in and adopted. She’s a mother, leads Spanx and somehow makes shapewear something to get excited about. Sara, if you are reading, I really want you to make me a dinosaur shaped pancake!

Thank you so much for this. This was very inspirational, and we wish you only continued success!

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