CEO Connect: Cliff Scott talks about landing a major client, the robot invasion and slowing down to enjoy life

Cliff Scott established Career Match Solutions out of his home on a computer that his wife, Velma, purchased for him. At the time, he was still reestablishing his life. 

On that computer, he would go on to build his business, which is now a $20 million company that operates in 37 states. 

The Scotts have opened a handful of assisted-living facilities, two of which he gave away.

He’s involved in his church. He sings and plays guitar. He was ordering turkeys the day Tampa Bay Business and Wealth visited him so he could pass them out to families before Thanksgiving.

Bridgette Bello, chief executive officer and publisher of TBBW, interviewed Scott in front of a live audience, at the Humane Society of Tampa Bay. This interview has been edited for length and brevity. 

View photos from Cliff Scott’s CEO Connect here.

What has it been like being on the cover of TBBW?

It has been absolutely been amazing. A lot of people have reached out to me with encouraging words and telling me how the story affected them. I’m a researcher, by habit, so I took some time and read up on TBBW and I realized just how amazing your magazine is. I knew about it but I didn’t know the details of it until I really sat down and realized how many lives you affect, on a monthly basis, on a daily basis. People read your stories about this region and we get a real understanding of what it looks like to live in paradise, which is where I think we are.

Did you get your 200 turkeys? 

I did get my 200 turkeys. I’m just really excited about being able to bless some people in the area, let them know that we care about them and that we’re here for them. People may look at a turkey as just a small thing, but it’s not really the turkey – it’s the feeling behind the turkey. It’s letting people know that they’re not alone in this world and that there’s opportunity for them. 

You signed the biggest client that you have ever signed –Emirates Airlines – because they read your cover story. Is that accurate? 

We now have an active contract with Dubai, Abu Dhabi, in the Arab Emirates, along with Qatar. And all of that is wrapped around Emirates Airlines. They’re going to be expanding throughout the country. They’re going to be hiring some 22,000 people and we’re now their prime vendor. 

The person who connected me with the person in Dubai saw my Facebook post of the story. So I want to let you know that you no longer have just a Tampa Bay regional reach, you have an international reach.

That made me so proud when you shared that with me, I had to make sure that we shared that tonight. So many of us in this room are small business owners. Talk about some of your growing pains and what you’ve learned from them.  

I think that most people in this room probably have similar growing pains with their businesses, especially when you look at the amount of time and the energy you put into your business. There will always be money issues. You’re always looking for more liquidity and more capital to be able to advance your business. You’re looking for opportunities. And I’ll tell you, most small business owners, including myself, have no idea what we’re doing. I was just banging my head against brick walls. But some of the things that we are still dealing with, and going through, really just revolve around trying to understand the culture of what’s going on in the country today. 

There are so many different changes and the way things are being handled, as far as business relationships and B2B. Look at the new advancements in AI, which is going to completely change the landscape. When you look at the way individual businesses are trying to fund themselves and find ways to integrate to modern technology, it’s difficult. I’m an old school guy. I still pick up a pen and I sit down at my desk with a telephone and I work. I really can’t stand iPads. I like a computer, a desktop. I need a big screen and I can’t see very well. I’m getting old. So, for all of us who are just trying to make sure we stay up to speed and keep our heads above water, in this current landscape, and the way the economy is, it’s difficult. But I am a forever optimist. I believe that we were all meant to do great things and, as long as we keep our heads on right, we will. 

Do you see AI impacting your business?

I have a feeling that within the next, I would say, seven to 10 years, 80% of my business will be done by AI. I believe that. I think that it’s going to impact an enormous amount of businesses across the landscape. If it’s customer-generated or a business that has an administrative capacity to it, that’s going to disappear. I truly believe that. 

How are you going to deal with that?

Well, the same way we’ve always dealt with it. America is a country where we adjust. AI will be integrated into everything that we do. However, AI will still need us. We will find a way to keep it within the scope of where we need to. We are a great country. We didn’t just pick up yesterday and become a great country. We’ve been this way for a long time and we will be as long as we don’t allow the singularity. The singularity is when AI no longer needs us. If we keep them, needing us to keep the power on, to keep the lights going, keep things going, to keep them out of the areas they shouldn’t be in, we’ll be fine.

You’ve seen the movies where the robots are coming and how that ends, right?

Listen, my all-time favorite movie is The Matrix. 

You’ve had amazing growth. How did you first navigate that? 

Poorly. [laughter] I started hiring good people. I am an old Ronald Reagan fan and Reagan said, “Hire smart people and get out of the way and let them do the job.” And I had to learn that very quickly because as business owners, we want to keep our hands in every detail because we are afraid that what we built, someone is going to take away. But the reality is you can’t grow unless you let smart people do smart things. That’s what I’ve learned along the way. 

We started just at the crux of the pandemic. We were a very small $1.5 million to $2 million company, but we were blessed tremendously because we started out, as a virtual company, and we maintained our virtual infrastructure over that 10 to 12-year timeframe. And when everybody was scrambling, trying to get themselves set up [virtually], we just kept going. Nothing was stopping us at that point. 

Fortunately, the growth hasn’t slowed down. You reach that time in your company where it’s kind of fueling itself. And that’s what I think we all want, as entrepreneurs; to get your company to that position, running without you having to be the one doing all the work. And I feel like the company is getting there now. I’ve got good people, young folks who are doing amazing things in the company. With this new contract, the estimate was $25 million, now we’re going to take it to $35 million to $40 million, probably by the end of the next two years. 

How are you handling the success? 

[My wife, Velma] keeps me humble. This is the boss, guys. And, all jokes aside, she is an amazing woman and I have to give her kudos because without her, I wouldn’t be sitting up here today. And that’s just being honest. 

You’re launching something that’s called the Awake Coalition, in April of 2024. What is that and why are you launching it? 

The Awake Coalition is a nonprofit that I’m developing that’s going to be specifically targeted toward homelessness and poverty in the Tampa region. And I look forward to expanding out, but I’d like for each individual group coalition to target the community that they’re in. Unfortunately, a lot of our nonprofits, and organizations, are spread so thin across the country that they really don’t have the impact upon the region that they really started out trying to make. 

I hope that everybody in this room puts their arms around you and supports you. 

There are a lot of smart people in this room and I’d like to become a very smart person. And the way you do that is by listening to smart people. If you have a comment or advice you want to give, I’m open to hear every word of it. ♦


TBBW’s “CEO Connect” series is an exclusive, invitation-only, event that brings together the Tampa Bay area’s top business leaders to meet and mingle. CI Group, CLA  and Shumaker were presenting sponsors. The host sponsor was the Humane Society of Tampa Bay. 

TBBW’s video partner is Empowering Creative.

The evening begins with a cocktail reception for about 120 guests, followed by an interview with that month’s cover CEO.

Partnering with TBBW on future editions provides an opportunity to network with the area’s business elite, generate new business opportunities and increase brand awareness.

For information about event sponsorship opportunities, email Jason Baker at [email protected].

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