Small business headshots have more work to do than most. The same photos need to sit on your website, your Google listing, Instagram, LinkedIn, a press mention and maybe a printed flyer, and they need to look like the person customers will actually meet. The efficient way to get there is one planned session with a few different looks. Many headshot photographers on Book Holiday Photos offer short sessions with several looks, and the profile shows the length, the number of retouched images and the usage terms.
One session, three jobs
Why owners need more than one headshot
A single corporate-style photo is fine for an employee. For an owner, the photo is part of the brand, and different places ask for different moods:
- Website about page: warm, personal, often a looser crop with space for text.
- Google business profile and review sites: friendly and recognizable, tight crop.
- Instagram and Facebook: more relaxed, sometimes a bit of personality.
- LinkedIn: polished, a step more formal.
- Press, podcasts, speaking: a clean, editorial image that editors can crop.
- Print: business cards, flyers, packaging inserts. Needs a high-resolution file.
Using the same face across all of these, in slightly different looks, makes a small business feel established and personal at once.
Planning 3 looks for 3 jobs
Before the session, decide what each look is for. A plan that works for many owners:
- The trust look: your most polished outfit, light gray or white backdrop, a warm smile. LinkedIn, Google listing, press.
- The personal look: something you would wear on a normal workday, the same or a softer backdrop, more relaxed expression. Your website's about page and social media.
- The brand look: a top in your brand color, or a darker backdrop for something more editorial. Speaking, podcasts, a feature article, or your homepage.
If your business has a strong visual identity (a bakery's warm tones, a law practice's navy and gray), let your outfits carry it. Neutral and dark backdrops let a brand-colored top stand out. More on that in which headshot backdrop to choose.
What to wear, by type of business
There is no dress code, but there is a simple test: wear what your best customer expects to see when they meet you, one step smarter.
- Professional services (accountants, consultants, lawyers, therapists): jackets or structured tops in navy, charcoal, soft blue.
- Creative businesses (designers, florists, studios): your own style, solid colors, texture over pattern.
- Food and hospitality: clean, simple clothes. An apron can work for one look if it is part of your brand, but keep a non-apron version too.
- Wellness and fitness: relaxed, fitted, soft colors. Avoid gym logos.
- Trades and home services: a clean polo or shirt, possibly with your own logo, plus a plain version.
Solid colors, no busy prints, no other brands' logos. Bring options on hangers and decide with your photographer. Our full guide: what to wear for headshots.
Expression and retouching
Approachable owner, not stock photo
Customers buy from people they like. The goal is a face that says "I'm good at this and I'm nice to deal with". A good photographer coaches toward that in small steps, with posture tweaks and light prompts ("think about your favorite customer"), and short bursts so nothing looks held.
If you are not comfortable in front of a camera, you are in good company. Tell your photographer, and they can start slower. Most people relax by the second look.
Retouching that stays honest
Customers will meet you, so your photo should match. Good retouching:
- Cleans up skin: blemishes, redness, shine.
- Tidies stray hairs.
- Balances color and light.
- Does not reshape faces or bodies.
You on a good day, recognizable at the door.
Usage rights and team photos
Usage rights: the part owners should check
When you run a business, headshots go on paid ads, packaging, brochures and press releases. That is commercial use, and with some photographers it costs extra or is not allowed.
Before you book anyone, ask directly whether commercial use is included and which file sizes you receive, web and print. Many profiles state the usage terms, and how booking works explains how to message a photographer first.
Adding your team
If you have a few employees, consistent photos for everyone make a small business look bigger and more trustworthy. Ask the photographer about back-to-back sessions or an on-location team day, and note in each booking that you want matching photos. See team headshots in NYC.
Getting the most out of your photos
- Update everything in one week: website, Google listing, LinkedIn, Instagram, email signature.
- Keep a folder with the web and print files clearly named, so you can send them to a journalist or a printer in seconds.
- Use the looser crops on your website, where a designer can place text next to you.
- Rotate looks on social media so your profile does not feel stale.
- Refresh every couple of years, or when your look or your business changes.
If you are in real estate, our realtor headshots guide covers signs and listing portals in more detail.
How booking works
- Browse headshot photographers and pick a profile, a session and an open time.
- Pay online when you book. Your card is only charged once the photographer accepts, usually within 48 hours.
- Tell the photographer in your message what the photos are for and what your business does.
- Your photographer confirms the location and a short wardrobe guide.
- You spend the session on your looks.
- Delivery time and the number of retouched headshots vary, so check the profile.
Quick answers
How many headshots does a small business owner need?
Usually three different looks: a polished one, a personal one and a brand one. Look for a package that includes several looks and a handful of retouched images.
Can I use the photos in ads and on packaging?
Only if the photographer's terms allow commercial use. Check the profile or ask before you book.
How long does it take?
Many headshot sessions run 30 to 60 minutes. Read our full guide to professional headshots in NYC for what makes a headshot work.
Find a photographer
Pick a time that suits your business hours, and browse headshot photographers in NYC and Long Island.