Headshot Photographer in Weston, MA

Professional headshot
Professional headshot
Professional headshot

Weston professionals — my studio in Sherborn is about 25 minutes southwest, an easy drive down Route 30 to Route 16. Far closer than downtown Boston and a far more relaxed experience.

My sessions are part photography, part coaching. I'll guide you through posture, expression and wardrobe choices so you walk out with a headshot that projects the right mix of confidence and approachability for your industry.

I work with executives, business owners, attorneys, financial advisors and actors. Each session is tailored to your goals — whether that's a polished LinkedIn photo, an updated corporate headshot or new acting headshots.

Getting Here from Weston

Take Route 30 west to Route 16 south — about 25 minutes to our Sherborn studio. Easy parking right at the door.

Services

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

What Clients Say

John W.
Damon's ability to put the photographee at ease enables him to create portraits that reflect the person's personality.

John W.

Jon S.
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.

Frequently Asked Questions

How far is your studio from Weston?

My studio at 80 Maple St in Sherborn is about 25 minutes from Weston center via Route 30 and Route 16. Plenty of free parking.

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

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 Weston offices for team sessions?

Absolutely. I bring my full portable studio — lights, backdrop, the works — right to your Weston 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?

My Sherborn studio is convenient to clients throughout the Metrowest area, including but not limited to Wellesley, Lincoln, Concord, Newton and Natick. For team sessions, I bring my full studio setup to offices anywhere in Waltham, Cambridge, Boston and the greater metro area.