Boston Headshot Photographer

Professional headshot
Professional headshot
Professional headshot

Boston professionals — skip the overpriced downtown studios. My dedicated headshot studio in Sherborn is about 30 minutes west of the city. The drive out is a scenic escape past horse farms and stone walls — clients tell me it puts them in a relaxed headspace before we even start shooting. Free parking, zero stress, and a session that's all about you.

As a headshot photographer, I bring a coaching-first approach — guiding you through posture, expression and wardrobe to capture a look that's confident and approachable. No stiff corporate cutouts. You'll walk out with a headshot you're genuinely proud to put on LinkedIn, your company site or anywhere else.

For team sessions, I come to your Boston office with my full studio setup. For individual headshots, executive portraits and actor headshots, you'll make the short trip out to my studio — and you'll be glad you did.

Whether you work in the Financial District, Back Bay or the Seaport, a 30-minute drive west trades crowded downtown studios and inflated pricing for a dedicated space built specifically for headshot photography. Executives across Boston's business community choose my studio for the quality, the convenience and the calm environment.

Expect real direction throughout your session — I'll adjust your posture, shoulders and expression shot by shot so every frame has purpose. You'll see the results on screen in real time, which takes the guesswork out of the process entirely. Clients who came in skeptical routinely tell me it was the most enjoyable professional photo experience they've had. Every image is retouched and delivered at full resolution.

Getting Here from Boston

Take the Pike (I-90) west to Route 16 south — about 30 minutes to our Sherborn studio. Free parking right at the door. For team sessions, I come to your Boston office.

Services

  • Executive & Corporate Headshots
  • LinkedIn Profile Photos
  • Business Portraits
  • Actor & Performer Headshots
  • Team & Group Headshots (on-location in Boston)

What Clients Say

Rebecca G.
My partner and I both find taking photos unnerving, but Damon spoke to our individual concerns and set us both at ease. The hardest part was choosing our favorites because even the runner-ups were better than any headshots we've ever had.

Rebecca G.

Mike M.
Damon knows his stuff. He walked me through the headshot process and knew how to get me to show off my best self. Quick and painless, but also fun and educational.

Mike M.

Frequently Asked Questions

Do you shoot on-location in Boston?

For team sessions, absolutely — I bring my full studio setup to your Boston office. I just need a room with about 10 feet of depth and access to a power outlet. For individual sessions, you'll come to my Sherborn studio about 30 minutes west of downtown. The scenic drive past horse farms and stone walls is a great way to decompress before your shoot.

I've never had a professional headshot — what should I wear?

It depends on your industry. Finance and law: dark blazer, solid shirt, no tie unless it's your style. Tech and startups: a clean button-down or structured casual look works. Creative fields: express yourself, but keep it simple on camera. Bring 3–5 options and I'll help you choose the winner. The goal is to look like the best version of your everyday professional self. 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 Boston offices for team sessions?

Absolutely. I bring my full portable studio — lights, backdrop, the works — right to your Boston office. All I need is a room with about 10 feet of clear wall space and a power outlet. 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?

I photograph professionals from across the greater Boston area. My Sherborn studio is an easy 30-minute drive from downtown, and I also serve clients in Hopkinton, Natick, Sherborn, Medfield, Needham, Wellesley, Weston, Newton, Lincoln, Concord and Brookline. For team sessions, I come to your office anywhere in Cambridge, Newton, Wellesley and beyond.