Boston Headshot Photographer
Boston Executive & LinkedIn Headshots
Most photographers pose you. I coach you — because I spent 35 years in corporate leadership and as an executive coach, and I know exactly what confidence looks like on camera. You'll leave with an image that reads as credible, approachable, and unmistakably you.
Book Your SessionBoston Team Headshots
Coordinating headshots for a team doesn't have to be a production. I bring a full studio setup to your office, photograph everyone efficiently, and deliver a consistent look that holds together across your website, directory, and pitch deck.
Learn More & Get a QuoteBoston Business Portraits
For speakers, authors, and executives whose work puts them in front of an audience, a standard headshot leaves too much on the table. Business portraits give you a more complete visual story — your presence, your environment, your authority.
Book Your SessionBoston Actor Headshots
Casting directors make decisions in seconds. Your headshot needs to do the casting for them — showing the range of characters you can play before they ever read your résumé. We shoot multiple looks in one session so you walk out with a portfolio, not just a photo.
Book Your Session
Book
Choose a date, book your session online, and you'll receive a wardrobe and prep guide. No back-and-forth, no waiting on a quote.

Shoot
We start with wardrobe, then move into lighting and coaching. I direct every expression and adjustment in real time — you see the shots on a monitor as we go, so you always know where we are.

Select
We review your shots together before you leave. You choose your favorites, order any additional images you want, and walk out knowing exactly what you're getting.
The Experience
Frequently Asked Questions
What should I wear?
Once you've booked and paid for your session you'll get an email confirmation with wardrobe and accessory guidance. Generally dark and / or neutral colors work best for headshots, though sometimes bright bold colors can be fun for certain applications. Bring a range of wardrobe options and we'll experiment and see what works best for you. Remember though, if it isn't in my studio I can't shoot it!
Do I need professional hair and makeup?
I do not recommend makeup for men. For women, however, professional hair and makeup services can make a significant difference in image quality. The makeup is done with a light but very intentional touch. For reference, all the women on my website engaged my pro hair and makeup services. I have several hair and makeup artists I work with and their fee starts at $400. This is in addition to session and image fees. If you would like to engage their services please contact me prior to booking your session so I can coordinate our 3 schedules. Plan on about an hour for hair and makeup in my studio prior to the session and then about another hour for our shoot.
Does the session include retouching?
Yes, your session and image fees include basic color correction and retouching. This may typically include skin tone adjustments, removal of fly away hairs and blemishes, lint on clothing, etc. Heavy retouching, which I strongly advise against, may incur an additional fee.
What forms of payment do you accept?
Your session fee, which must be pre-paid upon booking on this site, can be paid with Visa, Master Card, American Express or PayPal. Additional images may be paid for at the time of your session with the above credit cards, Venmo, PayPal or cash.
When will I receive my final images?
Retouching usually takes about two weeks. Once I get them back from my retoucher, I make final adjustments and get them yo you within 24 hours via email.
How will you help me look my best?
My entire process is designed to help you look your best! It starts with wardrobe selection, then pro hair and make up for the ladies and then lighting, posing and expression. The look I go for is something I call 'approachable confidence.' If you've spent any time at all on my site you probably already have a good idea what that looks like! I'll coach and direct you through our shoot and you'll see your images get better and better through out our session.
How long does a headshot session take?
A typical individual session runs about 30–45 minutes. That includes wardrobe review, lighting setup and the shoot itself. Team sessions vary depending on group size — generally about 10–15 minutes per person once we're set up.
Where is your studio located?
My studio is in Sherborn, MA — about 30 minutes west of Boston. It's easy to get to from anywhere in the metro area. For team sessions, I come to your office or location anywhere in the greater Boston area.
What other nearby communities do you serve?
My Sherborn studio is convenient to professionals throughout the Metrowest area and greater Boston, including but not limited to Holliston, Hopkinton, Natick, Needham, Wellesley, Weston, Newton, Concord, Lincoln, Brookline, Framingham, Dover, Sudbury, Westwood and Boston. I also specialize in actor headshots in Boston, Cambridge and Somerville. For team sessions, I travel to offices in Boston, Cambridge, Wellesley, Newton, Framingham, Waltham, Burlington, Worcester and beyond.
Can I use my headshot for LinkedIn?
Absolutely — LinkedIn is one of the most common uses for my headshots. The images I deliver are high-resolution and formatted to look sharp on LinkedIn, your company website, speaker bios and print materials.
What's the difference between a headshot and a business portrait?
A headshot is typically shoulders-up against a clean background — ideal for LinkedIn, company directories and email signatures. A business portrait is more editorial, often incorporating environment, body language and more of your personality. I offer both.
How often should I update my headshot?
I recommend updating your headshot every 2–3 years, or whenever there's been a significant change in your appearance. If someone meets you in person and can't reconcile you with your photo, it's time for a new one.
Do you travel to offices for team sessions?
Yes. For team sessions I bring my full studio setup to your office or location. I just need a room with about 10 feet of depth and access to a power outlet. I handle all the setup and breakdown.
What if I'm nervous or don't consider myself photogenic?
You're in good company — most of my clients feel exactly this way when they walk in. Coaching you through the process is a core part of what I do. By the time we're a few minutes in, you'll be relaxed and we'll be getting great shots.
Can I bring multiple outfits?
Yes, please do! I encourage you to bring 3–5 options. We'll review them together at the start of the session and choose the ones that work best on camera. Variety gives us more to work with.
How many final images do I receive?
Your session includes one fully retouched, high-resolution image. Many clients end up wanting 2–4 additional images to suit different professional and personal applications, which can be purchased at the time of your session. You'll see all your shots during the session so you can choose your favorites.
What Clients Say
“We provide professional services to high net worth clients and image is important for our website. Damon's photo sessions are professional, detail oriented yet efficient; he captures the very best of his subjects. We will use Damon again!”
Anna S.
“Damon made me feel comfortable and I really could see the difference between shots, he was really focused on the micro expressions. He really pulled the rabbit from the hat! He went above and beyond my expectations and the results are stunning!!!”
Jorge A.
“Damon was a true pleasure to work with. The shoot was swift, professional, friendly, and it delivered way past our expectations. We would happily go back to Damon if we needed additional photos, and would highly recommend him!!!!”
Mona I.
“Damon is a true professional and I could not be happier with the results. He is uniquely gifted as a photographer (with superb artistic and technical skills) and he made the photo session interesting and fun. I recommend him without reservation.”
Tim F.
About Damon
Photography is the family business. Three generations: my grandfather with the 82nd Airborne in WWII, my father, who ran the Macy's photo studio, and me — after 35 years in corporate leadership — behind the camera full-time.
That background changes everything about how I work. I spent three decades reading how people present themselves — what reads as approachable versus closed, what makes someone look credible versus just well-dressed. I bring that into every session. I'm not just looking for a technically correct exposure. I'm looking for the version of you that your clients, colleagues, and hiring managers will respond to.
Most clients tell me afterward that the coaching was the part they didn't expect — and the part that made the difference.
My studio is in Sherborn, MA — an easy drive for executives and professionals across Greater Boston and MetroWest.