For years, "safe" was smart strategy for headshots and executive portraits. Clean background. Even lighting. Pleasant expression. Nothing that could possibly work against you.

Now that same formula works against everyone — because AI mastered it overnight.

Why did safe headshots stop working?

AI learned professional photography by studying millions of images. It absorbed every rule: proper exposure, flattering angles, neutral expressions, corporate-appropriate styling. It can now generate technically flawless executive headshots faster and cheaper than any photographer.

The result: technical perfection became the floor, not the ceiling.

When everyone's headshot hits the same standard of polished professionalism, none of them stand out. Your carefully crafted image blends into a sea of equally careful images. Safe became synonymous with forgettable.

And forgettable is expensive when you're trying to attract clients, investors, or opportunities.

What do Silicon Valley founders actually need from a headshot now?

Connection. Not just recognition. There's a difference.

Recognition confirms you exist: "I've seen this person's face before." Connection sparks something: "I want to meet this person."

Most executive and corporate headshots optimize for recognition. They communicate competence, professionalism, approachability — all valuable signals. But they rarely trigger the deeper response: I trust this person. I'd want to work with them. I feel like I'm seeing who they actually are.

The founders and executives I work with in San Francisco and Silicon Valley have started asking different questions. Not "does this look professional?" but "does this make someone want to reach out?"

That's a fundamental shift.

What creates connection in a portrait?

The experience someone is having with the photographer. That's the real answer. When you feel comfortable, safe, and genuinely enjoying the process, your guard drops — and that's when something real shows up. After almost 2 decades behind the camera, I've learned the images that land aren't the ones where everything went technically perfect. They're the ones where something real and genuine was happening in the room.

The in-between moments:

• The half-second before the professional smile locks in

• The laugh that escaped when you weren't “ready”

• The flicker of genuine thought crossing your face

What actually makes an image work:

• When I see it on screen, it creates a deep human reaction or feeling in me — emotional, not analytical

• It feels endearing, charming, or authentically fun — depending on what you need to communicate

• It makes me connect with your human spirit first and want to meet you, even though I already have

I still bring technical craft to every shoot — precise lighting, editorial color grading, thoughtful retouching. That foundation matters. But I've shifted my focus to what happens between the frames everyone expects.

How do you get an in-between moment on purpose?

You don't. That's the point.

What you can do is create the conditions for it. This is where the photographer matters more than the camera. Reading the room. Knowing when to direct and when to step back. Managing the energy so the person in front of the lens can stop performing and start being present.

I manage the energy. That's the job.

Most people freeze when lights and lenses point at them. They armor up, default to a rehearsed expression, become a version of themselves they think they should be. Getting past that armor — earning the real moment — requires skill that AI can't replicate because AI isn't in the room.

What should you actually look for in an executive portrait photographer?

Ask to see the images with character, not just the headshots.

Any competent photographer can deliver the boardroom-appropriate image. A.i. can create one in 30 seconds. The question is whether they can also capture the moment that creates connection — and whether they understand why that matters now more than it did five years ago.

The best executive portraits in 2026 do both. They're polished enough for the professional context, human enough to cut through the noise. They check the box and they move the needle.

I like the phrase "polished enough for the boardroom. Human enough to be remembered."

That's not a contradiction. It's the whole point.

Frequently Asked Questions

How much does an executive portrait session cost in San Francisco?

Executive portrait sessions in San Francisco and the Bay Area typically range from $1,500 to $3,500, depending on scope, location, and usage rights. This includes professional lighting, editorial-quality retouching, and both boardroom-appropriate and character portraits.

What's the difference between a headshot and an executive portrait?

A basic headshot is just a checkbox — and AI does checkboxes now. An executive portrait is a strategic asset. It makes someone want to meet you. When you see a person's guard drop — even for a split second — you feel like you're seeing who they actually are. That triggers something: trust, warmth, curiosity. A headshot says 'I exist.' An executive portrait says 'here's who I am.' And it's still polished enough for any professional context.

Can AI generate headshots that look as good as professional photography?

AI can generate technically perfect headshots — that's actually the problem. When perfection is free and instant, it stops being impressive. AI-generated headshots often look "too perfect" in a way that feels uncanny or generic. What AI can't replicate is the authentic human moment: the real laugh, the genuine expression, the split-second where someone's guard dropped. Those require a photographer in the room reading the energy.

How long does an executive portrait session take?

Most executive portrait sessions take 30-90 minutes. This allows time to work through the initial stiffness most people feel in front of a camera, find the angles that work best for your face, and capture both the polished boardroom headshot and the more authentic editorial portrait with genuine personality and character that can create real connection.

Brian DeSimone is an executive and editorial portrait photographer based in Oakland, California. With a background in hospitality and over two decades behind the camera, he's photographed hundreds of founders, C-suite executives, and creative teams throughout San Francisco, Silicon Valley, and the Bay Area. His specialty: directing people who aren't used to being directed, and making it look natural. Corporate portraits, teams and executive headshots that are polished enough for the boardroom, human enough to be remembered.