The Future of Communication Technology: Jason O’Neill of LiveHelpNow On How Their Technological Innovation Will Shake Up How We Connect and Communicate With Each Other

Every website you go to these days has a bot. Sometimes it’s obviously not human, sometimes you’re not sure and more often than not the bot can’t get your customers the information they need. Businesses that are trying to replace the live human conversation with a bot are turning away the opportunity to build a relationship with a buyer or existing customer. LiveHelpNow certainly builds bots for our customers to handle simple tasks or to help direct inquiries to the right place. But we always keep the live conversation really easy to access as it is our top priority. LiveHelpNow is going to ensure the person-to-person conversation is here to stay. So, we might change the world by keeping it human.

The telephone totally revolutionized the way we could communicate with people all over the world. But then came email and took it to the next level. And then came text messaging. And then came video calls. And so on…What’s next? What’s just around the corner?

In this interview series, called ‘The Future Of Communication Technology’ we are interviewing leaders of tech or telecom companies who are helping to develop emerging communication technologies and the next generation of how we communicate and connect with each other.

As a part of this series, I had the pleasure of interviewing Jason O’Neill, Chief Operating Officer for LiveHelpNow and HelpSquad, organizations that deliver software and services for customer support teams, help desks, and contact centers. Jason oversees company strategy development and implementation, marketing, sales, customer success, and product development. He’s the father of two girls who push him to constantly look for better ways to communicate and not be ignored. Jason has a BS in Business Logistics from Penn State University’s Schreyer Honors College and an MBA from Drexel University.

Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

I’ve had a lot of different jobs and roles during my career. A LOT. Golf caddy, intern, industrial weed control, purchasing, manufacturing, supply chain, warehousing operations, product marketing, product management, regular old marketing, inside sales, outside sales, customer service. I served on boards of directors, started a non-profit, coached baseball, softball and soccer. And, of course, I’m a dad and a husband, which are my most important jobs. All these experiences have helped shape who I am today. And each of them have in some way developed how I communicate with people.

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

When I graduated from college, I moved from State College, PA to Chicago, IL to start a coding/software job with Accenture. Right before I was set to start, September 11, 2001 happened and my start date was delayed and eventually my offer rescinded. The world was just in turmoil. So I was in a city 750 miles from home. It turns out my family’s business, an industrial weed control company, just had the head of the operation leave the company and my dad needed help. I became head of operations covering 6 midwestern states, managing a fleet of trucks and multiple employees, doing sales, managing inventory, etc…and I had almost no experience in any of these things. Along with those challenges, I was also the boss’s kid which came with its own set of issues. After 4 years of 90 hour work weeks, the region’s revenue doubled in size, I learned an incredible amount about business and life, and I was burned out. Fast forward 20 years, I joined LiveHelpNow and finally got the job in software that I wanted. Everything happens in its right time.

As for the most interesting story?

Well, I delivered my second daughter in the front seat of our car in the parking lot of an Ace Hardware.

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

It’s super lame to reference my high school yearbook quote, but it means a lot to me. “Life is 10% what happens to you and 90% how you handle it.” It’s been true in every stage of my life and career. I didn’t get the job I wanted out of college. I didn’t get into the MBA program I wanted. My wife and I had to move far from family to get her career started. I got passed over for promotions. We’ve been stuck in the house for the past year during COVID. There are always lots of challenges. But all along the way I have learned to make the best of the situation, kept my glass half filled, built a great network of colleagues and friends, and worked really hard to get where I am.

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?

No one has ever had better bosses than me. I’ve been so fortunate throughout my career to report to people that cared about me, saw my potential, coached me up, and went to bat for me when there were opportunities. But no one has been more influential in my career than my wife, Jen. She’s really smart, an incredible listener and gives great advice. We are also really different but we compliment each other well. I’m more prone to being the one to talk too much in work meetings but I’ve watched her be really successful in her career in pharmaceuticals by listening, thinking, analyzing, and then talking. There is a lot that chatty people like me can learn by turning to the quiet person in the room and asking their opinion…and then shut up and listen.

How have you used your success to bring goodness to the world?

I worked with some family members and close friends to start a non-profit fundraising event for Cystic Fibrosis research. The event has raised over $700,000 the past 10 years and is in honor of a lifelong friend that has CF, a terrible genetic disease. My ability to organize and implement an idea has proven really helpful. It has also been an honor to recently join the Advisory Board of the Penn State Smeal College Tarriff Center for Social Responsibility and Business Ethics. It will give me an opportunity to work with a group of really impressive business leaders to advance ethical business practices globally.

Ok wonderful. Let’s now shift to the main focus of our interview. Can you tell us about the cutting edge communication tech that you are working on? How do you think that will help people?

LiveHelpNow’s mission is to connect businesses to their customers by any type of communication channel — web chat, SMS, Facebook, web forms, email, voice, etc — and provide a great customer experience for both the business and customer. Our software platform seeks to do this for customer service representatives and sales people so they can seamlessly navigate between many customer conversations all on one screen with as few clicks as possible. Picture an ecommerce business that is getting flooded with customer questions. People might ask about a product during the sales process, the status of their order, a broken item, troubleshooting an issue, etc. Many of these businesses don’t have a huge call center or enough people to create separate phone, chat and social media teams. They need their reps to handle all inquiries no matter the channel and regardless of the type of question. Businesses can do it with LiveHelpNow and be up and running in one day. Our software allows for multitasking and serving more customers in a more efficient way.

How do you think this might change the world?

Every website you go to these days has a bot. Sometimes it’s obviously not human, sometimes you’re not sure and more often than not the bot can’t get your customers the information they need. Businesses that are trying to replace the live human conversation with a bot are turning away the opportunity to build a relationship with a buyer or existing customer. LiveHelpNow certainly builds bots for our customers to handle simple tasks or to help direct inquiries to the right place. But we always keep the live conversation really easy to access as it is our top priority. LiveHelpNow is going to ensure the person-to-person conversation is here to stay. So, we might change the world by keeping it human.

Keeping “Black Mirror” in mind can you see any potential drawbacks about this technology that people should think more deeply about?

The more efficient our software is, the fewer humans businesses might need to engage customers. I’m picturing some business taking this to an extreme and expecting their customer service reps to handle 10 customer conversations all at once. It’s not possible. A great end-user customer experience always needs to be top of mind and an overwhelmed customer service representative can’t provide that. It’s important to always put quality over quantity. Building strong relationships with customers using our software is the intended goal we have for our clients.

Was there a “tipping point” that led you to this breakthrough? Can you tell us that story?

When I started with LiveHelpNow last year, I went on a listening tour (via Zoom of course) and met with dozens of existing and prospective customers. Instead of telling them why they should buy from LiveHelpNow, I asked them what they wanted and needed and the types of challenges they faced. It changed our thinking midway through a pretty big development project about what we want the future of our software to look like. The voice of our customer (and seeing which direction our competition was pointed) changed the way we’re planning to achieve our mission.

What do you need to lead this technology to widespread adoption?

We’ve heard the need, now we need to develop the platform to meet that need. We need to find the use cases where our software really helps the most, focus on those customers, and clearly communicate the value for them. Lots of our competitors’ software has many features, some of which we don’t have. We’ll get to our goals by understanding the value the software can bring to each business. Serving each customer’ unique need is what will help us reach more customers in the long run.

The pandemic has changed so many things about the way we behave. One of them of course, is how we work and how we communicate in our work. How do you think your innovation might be able to address the new needs that have arisen as a result of the pandemic?

The days of the 500 person call center with all those folks jammed in one room could be a thing of the past. Using software like ours, businesses have realized they can hire great people, keep them at home, allow them to work from their own computer equipment, and do their jobs really effectively. Telling a customer service rep or sales person who has been successfully working from home for the past year to all of a sudden add a long commute back onto their day will be a hard sell. Our software can support the “work-from-anywhere” movement that is here to stay.

Fantastic. Here is the main question of our interview. What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

  1. Reward failure. At a previous company, I managed a salesperson that was nervous to meet with clients by himself. He felt like he needed technical support or a senior leader on the phone with him so that he didn’t mess up. I coached him around all the things he needed to be successful on his own, told him to go screw up, and shoved him off the diving board. A few bombs later, he started to see that he could do it on his own and started winning. We can’t get successful without failing first. That’s the only way.
  2. Shut up and listen. When I stop talking in meetings, listen more, and find ways to engage the quietest people in the room, I learn more and teams function better. I still have work to do there.
  3. Pay people what they’re worth before it’s too late. I worked for a company that was losing people who were able to go find lateral jobs for more money. After resigning, the boss would offer them more money to stay. If he had just paid them what they were worth, they wouldn’t have been looking to leave in the first place.
  4. Don’t push send on that email when you’re mad. I sent an email to a colleague years ago when I was angry. The person had really ticked me off and I fired off an email that I later regretted. I’m not sure our relationship was ever the same. When emotions are high, take 15 minutes or 2 hours to respond, whatever it takes to cool off, then figure out how to communicate your feelings.
  5. Learn how to ask great questions. My time at Kepner-Tregoe, a pioneer in critical thinking, taught me the skills to ask better questions and ask more questions. It’s helped me provide better customer service, sell more, communicate with my wife, coach softball, etc. Seriously, study how to ask questions and the types of questions to ask (or take a KT workshop) and it’ll change your life.

You are a person of great 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. 🙂

My 9-year old daughter is passionate about climate change and actively looks for ways to raise awareness. When we talk about it, she just can’t understand how people don’t believe in it or care that it’s happening. We’re not perfect at home by any means, but we talk a lot about it and try and do good. If I could inspire people to turn their energy towards the climate crisis, I’d do it for her, my other daughter, and all the kids today that will be left with the damage done to our planet by older generations.

How can our readers further follow your work online?

I’m most active on LinkedIn at and send the occasional tweet @jbon14. You can also always contact me through our website at

Thank you so much for the time you spent doing this interview. This was very inspirational, and we wish you continued success.

Thank you. It was my pleasure and got me thinking.

About The Interviewer: David Liu is the founder and CEO of Deltapath, an award-winning unified communications company that liberates organizations from the barriers of effective communication. Liu is known for his visionary leadership, organic growth strategies, and future-forward technology. Liu is highly committed to achieving a greater purpose with technology. Liu’s business insights are regularly featured in Forbes, Entrepreneur Magazine, Tech Crunch, and more.


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