How to Plan a Startup Team Headshot Day at Your Office

A startup team headshot day is one weekday visit: I set up a backdrop in your office and each person steps away for 5 to 10 minutes. It costs $99 a person, with a $495 minimum covering up to 5. Below: the math, the dress code, the room and the running order.

This guide is for the small, casual team: the founder, a few engineers, someone in ops, and two people who joined last month. If you want the general manager's checklist, read how to prepare your team for a headshot day first. This post covers what's different when the team wears hoodies and keeps growing.

What a startup team headshot day costs, for 5, 8 and 12 people

The price on my team headshots page is $99 per person, with a $495 minimum that covers up to five people. Travel in the Bronx and lower Westchester, the setup and two retouched headshots per person are included. Payment in full holds the date.

Here is the arithmetic for three common team sizes:

Setup time comes on top of that. A team of five is usually done in under an hour, so most people are back at their desks before their coffee gets cold.

Casual but consistent: one dress code everyone can follow

Startups don't need suits. They need everyone to look like they belong on the same page. The simplest rule I give casual teams: solid colors, no logos, one layer.

• A quarter-zip, a crewneck sweater or a plain tee under an overshirt all work.
• Avoid big graphics, company swag with text, and thin stripes, which shimmer on screens.
• Pick a lane as a team: either everyone casual or everyone in a blazer. A mix looks like two companies.

If people argue about hoodies, send them my guide to hoodie, quarter-zip or blazer for tech headshots. The short version: a clean hoodie can work for engineers, but a quarter-zip reads as "casual on purpose" for almost everyone.

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Where in your office the setup works

Most startup offices have three options, and each one works for a different reason:

1. A conference room. The easiest choice. A door, a quiet room and room to step back from the backdrop.
2. A window wall. Soft daylight is lovely, as long as nobody needs that corner for calls during the session.
3. A quiet corner of the open floor. Fine for small teams. Expect a few curious coworkers, which can actually help people relax.

What the setup needs is simple: enough space for a portable backdrop, a stool, and a few steps of distance between the person and the camera. It also needs to stay put for the whole session. Moving the backdrop halfway through changes the light, and the photos stop matching.

Pick the room a week ahead and book it on the shared calendar. The fastest way to lose 20 minutes is finding a standup already in there.

How to run the day so nobody leaves their desk for long

On site, I come on a weekday, in the morning or after work. The goal is that each person disappears for one short block and goes back to work.

1. Send a time slot to each person a few days before: name, slot, room.
2. Leave a short buffer every few people, for the one call that runs long.
3. Put the founder or team lead in an early slot. Once people see one relaxed portrait, the rest of the team stops dreading theirs.
4. Keep one person as the runner who taps the next person on the shoulder.

Each person gets several angles and expressions, then picks with the team later. Nobody waits in a hallway, and nobody has to perform in front of a crowd.

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Remote and future hires: keeping the new people's photos matching

This is the part startups underestimate. You'll shoot eight people in November, then hire three more by spring. If the new photos look different, the team page drifts.

Three habits keep it consistent:

• Write down the look on the day: backdrop color, crop, and dress code. Keep it with your brand files.
• Plan a catch-up date for people who were remote, sick or not hired yet. A short second visit, or a solo session matched to the same look, keeps the page uniform.
• Ask for the same editing style for every batch, so color and skin tone match across shoots.

I wrote a full system for this in keeping team headshots consistent as people join. If your team is spread out, it's worth reading before you pick a date.

Matching the founder's portrait to the team page

Founders usually need more than a team-page square. Press, investor decks and conference bios want a portrait with a bit more personality. That's a separate session, covered on my headshots for founders page.

The trick is to make the founder's team-page photo from the team day, on the same backdrop as everyone else. Then shoot the more personal portrait on its own. If you're raising, my notes on Series A founder headshots cover tone and what investors notice.

For the company page, everyone should match, founder included. For startup headshots used on LinkedIn and press, the founder can stand apart a little.

Booking it: what I need from you

Send me three things on the team headshots page: how many people, your office address, and a few weekdays that work. I'll confirm the total and the date. Book at least two days ahead so everyone has time to get ready.

If a few people would rather shoot outdoors, I also photograph teams in Riverdale and Van Cortlandt Park in the Bronx on weekends. Offices in lower Westchester get the same price and included travel.

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FAQ

Do you come to Manhattan offices? Travel in the Bronx and lower Westchester is included. For an office elsewhere, ask me on the team headshots page before you book and I'll tell you what works.

How many images does each person get? Two retouched headshots per person, in a private online gallery, in formats ready for your website and LinkedIn.

Can people who are out that day be added later? Yes. Tell me when you book, and we'll plan a catch-up so their photos match the rest of the team.

How is a team day paid? Payment in full holds the date: $99 per person with a $495 minimum, which covers up to five people. Rescheduling is free with 48 hours' notice.

What if we have more than 15 people? Ask me first. Bigger groups can be split across two dates or planned as a longer day. Send your headcount and I'll confirm the total.