A conversation with Ray Donnelly reveals why real photography beats everything else in today’s digital world
Ray Donnelly had a problem. His IT team at Umbrella IT Solutions was scattered all over Jacksonville, and he needed professional headshots for everyone. You know the drill – trying to get a remote team together for photos is like herding cats.
But here’s the thing: it turned out to be way easier than he thought it’d be. We figured out how to make it work without shutting down his business or making his team take a whole day off.
In my latest episode of Chat with Clients, I discuss headshots for Ray Donnelly‘s team, but we also cover what Umbrella IT does in its own business and how it serves clients in Jacksonville and beyond.
Getting a Remote Team Together? Good Luck With That
Jacksonville’s huge. Like, really huge. Ray put it: “We were just searching because my guys work all over town, right? They’re working remotely all over town. Jacksonville is a very big city spatially, right? Like just the amount of time it takes to travel from one side to the other side of Jacksonville.”
So instead of forcing everyone to show up at the same time, we did something to make it a lot easier. Each person booked their own slot throughout the day. Simple. And, they could book it in their calendars and come over to my studio.
Why Professional Headshots Actually Matter
Look, I get it. Professional headshots can seem like overkill for small businesses. But Ray’s got a point here that’s worth listening to.
“For us in the service industry, especially our services are our bread and butter. Most of the stuff we do for our clients is face-to-face in some way or another. It’s on a Teams call. It’s, you know, we’re talking to them, we’re picking up a phone, we’re emailing them,” Ray explained.
Think about it. When you’re in tech, there’s already this wall between you and your clients. Computers. Jargon. Technical stuff they don’t understand. Why make it worse by being faceless too?
“I think when you can make your experience working remotely and working through these computers as personable as possible, you end up in a situation where people remember you and they appreciate you more. And you’re not just this person that’s telling them they need to do things or that they call when they have a problem,” Ray said.
Boom. That’s it right there.
The Money Talk (It's Not What You Think)
Here’s where most people stop reading because they think professional photos cost a fortune. Ray’s got news for you.
“I don’t, for me, the cost of the headshot is a negligible cost. When you compare the cost of the web development, you compare the cost of the branding. I mean, we paid four times what we paid for headshots with you guys, just for our basic branding for our logo package,” Ray said. Four times more for a logo. Let that sink in.
When you’re already spending money on your website and marketing, headshots are actually a bargain. Ray put it this way: “From a marketing standpoint, it’s probably the single most powerful thing when it comes to the aesthetic value of the site that we have on there right no
Real People vs. AI: Why Authenticity Wins
AI headshots are everywhere now. They’re cheap, they’re fast, and they make everyone look like a magazine cover model. So why doesn’t Ray want them?
“If I’m going to pay for a headshot, I want it to be a real headshot. I don’t want it to be… if I found out somebody had done the AI headshot thing, in my mind, it’s a corner’s cut because you didn’t cut on a part of a project that could be value engineered. You cut on the human element,” Ray said.
Here’s the thing – people can tell. Maybe not consciously, but they can feel it. There’s something off about perfect AI faces. Ray gets this: “Even if you look a little goofy and the AI makes you look in your mind, you know, better or something, people are going to resonate with the real you better than they’re going to resonate with that AI image.”
Your clients want to work with real people, not digital perfection.
Getting Creative (Because Why Stop at Websites?)
Most businesses take their headshots and call it a day. Website. Email signature. Done. But Ray’s team? They went all out.
They’ve got these QR codes on leather keychains. Someone scans it with their phone, and boom – they’re looking at a bio page with your headshot, contact info, and an “add to contacts” button.
“Each of us has multiple things. We have these QR codes on, have a leather, key ring pad that has a QR code on it. And somebody scans that with their phone, it takes it straight to this embedded bio page where it has the headshot,” Ray said.
Smart, right? Old-school networking meets modern tech.
Why Service Businesses Need Professional Headshots
Manufacturing companies have it easy. Their products do the talking. But when you’re selling services? You’re selling yourself. Your expertise. Your trustworthiness.
“They’re talking to human beings and they need to be able to see how that person looks. That’s super important, especially when you’re in a field like computers, where there’s this layer of abstraction from humans, right?” Ray said.
Doesn’t matter if you’re in IT, consulting, law, or healthcare. Your clients want to know who they’re working with. A face makes all the difference.
The Bottom Line about Professional Headshots
Ray’s experience proves something important: professional headshots aren’t just fancy marketing fluff. They’re essential for building trust in a world where most of our interactions happen through screens.
The investment pays off. Not just in better marketing materials, but in confidence. When you look professional, you feel professional. And that confidence? Your clients pick up on it immediately.
For small business owners still on the fence, Ray’s message is clear: in a digital world, authentic visual representation isn’t optional anymore. It’s essential.
It's a Wrap!
Chris Cottrell is a professional photographer who specializes in corporate headshots and business photography in Jacksonville, Florida. His work focuses on helping professionals and businesses present themselves with confidence through authentic, high-quality photography.
