Executive Headshots That Work for LinkedIn, Press, and Fundraising

The short answer: an executive headshot isn't one photo — it's a small system. LinkedIn wants a tight, warm square. Press wants high-res verticals and horizontals with clean backgrounds. A fundraise announcement wants both, on 24 hours' notice. A proper session ($350, 20 post-produced images with press-ready crops) covers all three jobs at once, which is why founders should book it before they need it — not the week TechCrunch asks.

I shoot these constantly for NYC founders, and the booking trigger is almost always the same: something got announced, someone asked for a photo, and the best available option was a 2019 conference badge crop. Here's what to have ready instead.

The three jobs

• LinkedIn: the most-viewed image of you in your professional life, full stop. It renders at thumbnail size in feeds — which means tight crop, clear eyes, real warmth. Serious-face reads as unapproachable at 48 pixels.

• Press: journalists need high-resolution files, vertical and horizontal, with backgrounds that survive being cropped into any layout. When the story is moving, "can you send a hi-res portrait in the next hour" is a literal email you will receive.

• Fundraising and speaking: announcement graphics, conference speaker pages, podcast cover art, the About page. Each wants a slightly different frame — which is why a session delivers twenty images, not two.

What separates an executive portrait from a team headshot

Time and range. A team session gives each person ten minutes and two finished images — right for its job. An executive session is a focused hour: multiple backgrounds and setups, seated and standing, tight and environmental, serious and warm. The goal is a folder that answers every request for the next two years without a reshoot. Here's a behind-the-scenes look at how one of these portraits comes together.

Timing it around a raise

If a fundraise announcement is on the calendar, shoot at least two weeks ahead: it leaves room for selects, retouching, and the inevitable "can we also get one with a different background" — and it means your comms plan launches with visuals instead of scrambling for them. The same session feeds the launch-day LinkedIn posts, the press kit, and the investor update. Announcements are visual events now; founders who treat the portrait as infrastructure move faster when the moment comes.

Prep that actually moves the needle

Sleep matters more than anything cosmetic. Come with two wardrobe options in solid mid-tones (full wardrobe guide here), skip the brand-new haircut, and plan for the first ten minutes to be warm-up — nobody's best frame happens in minute one. The photographer's direction does the rest; not being "photogenic" is a myth about people who haven't been directed well.

FAQ

What does an executive session cost?
$350 for a dedicated session: 20 post-produced images, professional retouching, and LinkedIn, bio, and press-ready crops, shot at your office or a studio. Full NYC headshot pricing is here.

How often should executives reshoot?
Every 2–3 years, or after any meaningful change in appearance. The test: would a stranger recognize you from the photo in a coffee shop?

Office or studio?
Office environmental portraits tell more story and double as About-page material; studio gives maximum press flexibility. A good session at your office captures both looks.

Can the rest of the leadership team piggyback?
Yes — back-to-back executive sessions on one day is the most efficient way to refresh a leadership page, and consistency across the portraits comes free.

Raise or press push coming? See the photography packages, or book a free 20-minute call — tell me the announcement date and I'll work the session backward from it.