Headshot Photographer in Holliston, MA



If you're a Holliston professional looking for a headshot that actually represents you, my studio in Sherborn is just a 10-minute drive down Route 16. No need to fight traffic into Boston.
Every session starts with a conversation about what you need and how you want to come across. From there, I guide you through poses, expressions and small wardrobe tweaks until we land on something that feels authentic — not forced. That coaching is what separates a great headshot from a forgettable one.
I photograph executives, entrepreneurs, LinkedIn professionals and actors — all from my Sherborn studio. The sessions are relaxed, efficient and built around getting you an image that actually works for the way you use it.
Holliston's small-town charm comes with a growing professional community, and the quick drive down Route 16 means you can be in and out of the studio without carving a hole in your workday. Whether you run a business on the town common or commute to a larger office, a polished headshot is easy to check off the list.
During your session I'll coach you through posture, expression and subtle angle adjustments so every frame looks intentional — not like a rigid 'stand and smile' snapshot. You'll review images on screen as we shoot, and most clients are surprised by how much fun the process turns out to be. Every final image is professionally retouched and delivered in high resolution.
Getting Here from Holliston
A quick 10-minute drive west on Route 16 from Holliston center brings you right to our Sherborn studio.
Drive time: 10 minutes
Services
- ✓Executive & Corporate Headshots
- ✓LinkedIn Profile Photos
- ✓Business Portraits
- ✓Actor & Performer Headshots
- ✓Team & Group Headshots (on-location available)
What Clients Say

“Damon was referred to me by a friend who said 'Everyone I know uses Damon.' Now I understand why. He is patient during the shoot but highly efficient, and he understands what makes a good headshot. I highly recommend Damon if you want a great business headshot.”
Jon S.

“Damon is incredibly good at what he does. He knows how to help make the person getting photographed relax and enjoy the process. I highly recommend him.”
Sherry D.
Frequently Asked Questions
How far is your studio from Holliston?
My studio at 80 Maple St in Sherborn is about 10 minutes from Holliston center via Route 16. Easy drive with plenty of parking.
I've never had a professional headshot — what should I wear?
No worries, most Holliston clients are first-timers. Bring 3–5 tops in solid colors — navy, charcoal, burgundy and black photograph particularly well. Avoid busy patterns and logos. We'll look at everything together before we start and pick what works best with your skin tone and the background. For the full guide, see What to Wear for Your Headshot Session.
What if I'm nervous or don't consider myself photogenic?
You're in great company — most of my clients feel exactly this way when they walk in. Coaching you through posture, expression and micro-adjustments 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. For practical tips, read How to Look Confident in Your Headshot.
How often should I update my headshot?
I recommend every 2–3 years, or whenever there's been a noticeable change in your appearance — new hairstyle, glasses, significant weight change. If someone meets you in person and can't reconcile you with your photo, it's time. Read more in How Often Should You Update Your Professional Headshot.
What about AI headshots — are they worth it?
AI-generated headshots have gotten a lot of attention, but they come with real drawbacks — uncanny expressions, inconsistent lighting, and the risk that someone recognizes it as AI. A professional headshot captures the real you with coaching that brings out authentic confidence. For a detailed breakdown, read AI Headshots vs Real Headshots.
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 for different uses — LinkedIn, company website, speaker bio — 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 does the session actually look like?
You'll be in and out in about 30–45 minutes. We start by going through the outfits you brought, then I set the lighting while we chat about what you need the headshot for. The actual shooting takes about 20 minutes — I coach you through every frame so you're never left guessing what to do with your hands or your face. For more detail, read What Happens During a Professional Headshot Session.
Do you come to Holliston offices for team sessions?
Absolutely. I bring my full portable studio — lights, backdrop, the works — right to your Holliston office. All I need is a room with about 10 feet of clear wall space and a power outlet. Most Holliston businesses set me up in a conference room. For tips on getting your team ready, see How to Prepare Your Team for Headshot Day.
What mistakes should I avoid before my session?
The most common ones are wearing busy patterns, waiting until the last minute to plan wardrobe, and trying to look like someone you're not. A great headshot should feel like the best version of you — not a costume. For the full list, see Biggest Headshot Mistakes Professionals Make.
What's the difference between a corporate headshot and a LinkedIn headshot?
They're closely related but not identical. A corporate headshot is typically shot to match your company's brand guidelines — consistent background, lighting and framing across the team. A LinkedIn headshot is more personal and can reflect your individual style. I shoot both and many clients use the same session for both. For a deeper comparison, see Corporate Headshots vs LinkedIn Headshots.
I'm a real estate agent — do you specialize in that?
Yes — real estate headshots are one of my specialties. Your headshot appears on every listing, every mailer and every bus bench, so it needs to project trust and approachability instantly. For tips specific to agents, read Why Your Real Estate Headshot Is Costing You Listings.
What other nearby communities do you serve?
My Sherborn studio is convenient to clients throughout the Metrowest area, including but not limited to Hopkinton, Natick, Sherborn, Medfield, Needham, Wellesley, Weston, Framingham, Newton and Brookline. For team sessions, I bring my full studio setup to offices anywhere in Boston, Cambridge and the greater metro area.