Have you ever had to wait on a client’s photos to finish your web design projects? Like, you've done everything else… the strategy, the copy, the layout… and then you're just stuck, waiting for your client’s photo shoot, waiting for the photographer to get the photos processes, for the client to choose them, and then when you finally do get them – you don’t even have the sizes or orientations you need to make your designs work? Or the vibe is just all wrong? I’m totally having flashbacks right now of all the terrible photos I had to edit and figure out how make work back in the day…
But what if you could just create the photos yourself – AI portraits, brand photo shoots, the whole thing – and turn it into a profitable add-on service that makes your projects move faster AND gives your clients better images than they'd ever get from a traditional photo shoot?
If you've been in business for more than five minutes, you already know: aside from waiting on logins and copy, waiting on client photos is one of the most maddening parts of running a web design project.
You do everything right. You build a gorgeous layout, nail the copy structure, dial in the strategy… and then you're stuck. Waiting on the client’s photographer to come through. Holding your breath that the photos are horizontal.
Diane Whiddon, founder of AI Designer's Academy and Sway Rise Creative has a completely different solution – and it turns one of the biggest project bottlenecks in web design into a profitable, strategic add-on service that clients are actively asking for.
Diane teaches designers how to use AI with the eye and judgment of a creative director – so they can deliver better client results faster and stay indispensable as the industry evolves.
Scaling a WordPress Agency Almost Broke Her
Diane has been in web design since 2006. She built a full WordPress agency – employees, in-person office, systems, the whole thing. She hired business coaches, followed the advice, scaled the way everyone told her to scale.
And she burned out completely.
“Scaling to me has become like a four-letter word,” she told me. “I did everything that everyone was telling me to do. And what I didn't realize was getting me was I didn't understand myself and how I really wanted to work.”
What Diane discovered – the hard way – is that scaling often means handing over the parts of your business you actually love (the design, the strategy, the one-on-one client work) and replacing them with the parts that drain you (HR, management, meetings, overhead). She sold the agency and walked away.
She eventually found her way back to web design through Squarespace, and this time she built it completely differently. Boutique. White-glove. On her terms. No in-person office. Minimal phone calls (her clients use WhatsApp and, as it turns out, most of them prefer it that way).
“Can I build a business where I never get on the phone?” she asked herself. Turns out, you can.
This is something we talk about a lot inside our Next Level Mastermind – the difference between building a business that looks successful on paper and building one that actually works for your life. Diane lived the cautionary tale, rebuilt from scratch, and now has the receipts.
How She Stumbled Into AI Portraits
Diane wasn't looking to pivot into AI imagery – she was just trying to solve a very annoying client problem.
A client hired a photographer, the photographer took terrible photos, and the whole web design project became a headache around how to make a professional-looking website with images that weren't working. So Diane decided to try something different – she used AI to create portraits for the client.
The client loved them, and Diane immediately thought: “I think this is a service…”
She validated it fast. She told herself if six people bought, she'd consider it a real thing. Twenty-four people bought. The AI Photo Factory (which eventually became AI Designer's Academy) was born.
The Two AI Imagery Services You Can Offer Right Now
Diane breaks AI imagery for web design clients into two distinct services, and she recommends starting with both on your menu.
1. AI Headshots
This is the easier entry point – and the easiest upsell she has ever offered in 20 years of web design.
The process: you ask for 20-30 photos of the client, train a model in Flux (her preferred tool for character consistency and likeness), and produce a small suite of professional headshots. Diane charges $600 for a basic headshot package of three to four images, with additional images available at $50-75 each. From start to finish, a typical project takes her four to six hours.
The easiest sales question in the world? At the end of a discovery call: “Do you need headshots?” Diane says 90% of people say yes. That $600 upsell is, in her words, like cake.
And the clients who have even a little experience with AI imagery already understand why it takes skill and why it's not cheap. The ones who don't? They usually aren't Diane's clients.
2. Full Brand Photo Shoots
This is where it gets strategic – and where your design and brand thinking skills give you a real edge.
A full brand photo shoot package from Diane includes around 50 images: portraits, lifestyle shots, stock-style backgrounds, textures, and even B-roll video clips for social media. She charges $3,300, and projects typically take 20-25 hours.
The intake process is extensive. She wants to know what world the client wants to live in inside their brand photos. Do they want to be in Paris? A warm home office? What does the furniture look like? What are they wearing? How do they want their hair? And then they get into the deeper stuff: who do they serve, what's their USP, what problem do they solve, how do they help clients get from A to B?
“I want it to look like you went to Paris and had a $30,000 photo shoot with a creative director,” Diane said. “And everything matches.”
Think about what you're actually selling here: you're not just delivering images. You're solving a problem that your client has been putting off, stressing about, or settling for with bad results. The value of eliminating that problem – the photographer hunt, the uncomfortable shoot day, the waiting, the hoping the photos work for a horizontal website layout – is enormous.
This is the kind of thinking we dig into a lot inside the Web Designer Academy, where we help you package your services around the outcomes you create, not just the deliverables you hand over.
Who Buys AI Photography Services (It's Not Who You Think)
Here's something that surprised me in my conversation with Diane: a lot of the people buying AI brand photo shoots are NOT people who would have hired a traditional photographer.
They're people with problems that only AI can solve.
Diane told me about a client who was launching her book and had a fancy photo shoot booked out of town. Then she got a really difficult health diagnosis and couldn't fly. She called Diane: “What am I going to do? I have this book launch, I need photos.” AI portraits to the rescue.
Another client initially said no to AI headshots – it felt weird, she wasn't sure about it. Two weeks later she called back. She had just landed a major speaking gig and they needed headshots immediately for the event website. She was eight and a half months pregnant. All her existing headshots were ten years old. “Okay, I need headshots. Can you help me?”
These are the clients who are specifically looking for what AI imagery can do. Not because it's a shortcut. Because it's the only option that actually works for them.
The Ethics of AI Imagery (And Why Clients Ask for More Wrinkles)
I was genuinely curious how Diane handles the ethics side of this, and she shared the three-part pledge she has her students make inside AI Designer's Academy.
First: they don't use copyrighted work to train models or produce images. Second: they never use AI to mislead audiences or clients – so no TED Talk stage if you haven't given a TED Talk, no awards you haven't received, no meetings with people you haven't met. Third: transparency – they encourage designers to disclose on their sales pages that they use AI imagery.
On the client disclosure side, she has a nuanced take. Some clients ask specifically not to have their images in her portfolio. Given the sensitive reasons some people come to her – health situations, life transitions – she respects that completely. And she pointed out something I hadn't thought about: there's not a lot of difference between AI imagery and what a photographer does with lighting, posing, makeup, and Photoshop. You're still putting someone in their best light.
And in her experience? Clients are NOT coming to her asking to be made unrecognizable. “I can't tell you how many clients have come back and said, nope, make me heavier. That doesn't look like me. I need more wrinkles. Where's my gray hair?”
They want to look like themselves – just in the photos they actually needed.
Visual Claims: The Strategic Edge AI Gives Web Designers
This is the part of the conversation that genuinely lit me up – because it connects AI imagery directly to what we do as web designers and strategists.
Diane talked about something she calls “visual claims” – using AI to intentionally design images that build trust and address visitor objections before a single word is read.
She gave a great example. A lot of her clients are ex-C-suite executives starting their own consulting businesses. They come from a very corporate world – marble, glass, navy, power poses, the whole thing. And that branding can actually work against them when they're trying to attract clients who want someone warm, approachable, and enjoyable to work with.
With AI imagery, you can design the contrast in. Give them the polished, expert shot AND the relaxed conversation shot. Add a plant. Soften the lighting. Put them in an elegant home office instead of a glass high-rise. That contrast is what builds trust – because you're not sitting at either extreme on the seesaw.
And on sales pages? You can now design the before-and-after feeling right into the imagery. Cluttered, warm, slightly chaotic images at the top when you're in the problem. Clean, structured, minimalist images at the bottom when you're in the solution. Your website's visual language starts doing persuasive work before anyone reads the headline.
“We're designers,” Diane said. “We understand intuitively that a bunch of silver glass, all vertical, all in a row – we understand that looks masculine and expertise. But we also understand, girl, you need a plant in the background.”
AI Is Not Going to Kill Web Design
Diane had a scary moment last summer when she was genuinely worried the industry was about to disappear. She is not in that place anymore.
“Web design is very sophisticated on its own,” she said. “There's a reason that some big corporation hasn't been able to swoop in and productize this and sell it to the masses. It's almost like interior design. There are so many things we're having to juggle.”
Client satisfaction, brand expression, niche fit, customer journey, website function, 3D machine vs. 2D brochure – these are not things an AI can handle consistently and well. They require a person. They require judgment. They require the kind of thinking that only comes from years of experience and genuine understanding of the client's business.
What IS coming, according to Diane, is that the websites themselves are going to get significantly more sophisticated. Designers who are already thinking strategically about how imagery builds trust and handles objections are going to be ahead of the curve. And they're going to be able to charge accordingly.
About AI Designer's Academy
Diane's community started as a narrow course on AI portraits and quickly evolved into something much bigger. Her students are not just learning how to use tools – they're having sophisticated conversations about branding, design strategy, visual alignment, and how to make AI imagery actually work inside a real web design project.
The membership includes a Skool community platform, regular calls (including open coffee chats where students bring real client situations), and detailed walkthroughs of Diane's actual client projects – prompts, feedback, edits, the whole messy, real process.
There’s a VIP membership, and there's a free tier if you want to come check out the community before you commit. Weekly prompt challenges, tool discussions, and a community of designers who are actively figuring this out together.
And as Diane pointed out, if you sell even one headshot package, the annual membership pays for itself.
Resources Mentioned
- AI Designer's Academy – aidesignersacademy.com (free tier available)
- Swayrise Creative (Diane's web design agency) –
- swayriscreative.com
- The Rabbit Hole – rabbithole.swayrisecreative.com
- Grab our High-Converting Proposal Template and learn what to include (and what to leave out) to turn more of your proposals into higher-paying clients: webdesigneracademy.com/proposal
- Web Designer Academy Programs: webdesigneracademy.com/programs
- Simply Profitable Designer Summit: simplyprofitabledesigner.com
Related Episodes
- Episode 197: Building Visual Trust in an Artificial World with Pippa Tanko
- Episode 198: How To Make More With Less Web Design Clients
- Episode 191: How To Choose the Right Web Design Business Model
About Shannon Mattern
Shannon Mattern is a pricing strategist, creator of the Package Matrix™ and the founder of the Web Designer Academy, where she helps experienced women web designers package, price, and sell their services so they can build profitable, sustainable businesses without burnout.
Website: webdesigneracademy.com
YouTube: @profitablewebdesigner
LinkedIn: shannonmattern
Can web designers offer AI portrait services without photography experience?
Yes - and Diane Whiddon built a whole membership around teaching them how. The key skill you already have as a designer is understanding visual strategy, brand alignment, and what makes an image suite work. You just need to learn the tools and prompting process, which Diane walks students through step-by-step inside AI Designer's Academy.
How much can web designers charge for AI headshots?
Diane Whiddon charges $600 for a package of three to four AI headshots, with additional images available a la carte. A full brand photo shoot package - 50 images, B-roll video, stock suites - is priced at $3,300. A basic headshot package typically takes four to six hours from intake to delivery.
Is AI imagery ethical for web design clients?
Diane Whiddon’s position is yes, with clear standards around it: no copyrighted work in model training, never use AI to fabricate achievements or misleading scenarios, and be transparent with audiences about using AI imagery. Clients retain full creative control over how they look, and in Diane's experience, they consistently ask for their images to look more like themselves, not less.
Will AI replace web designers?
According to Diane Whiddon, no - and she spent a lot of last year working through that fear herself. Web design requires too many moving parts that AI can't consistently replicate: client alignment, brand expression, customer journey, conversion strategy, and the judgment that comes from real human experience. What IS changing is how sophisticated website imagery can become, and designers who get ahead of that will be able to charge significantly more.
What is the AI Designer's Academy?
AI Designer's Academy is Diane Whiddon's membership community for designers who want to use AI tools with the eye and judgment of a creative director. It started as a course on AI portraits for web design clients and evolved into a community covering AI imagery strategy, branding alignment, client management, and more. There's a free tier to explore and a VIP membership.
