Headshot Photographer in Brookline, MA
Brookline professionals — my studio in Sherborn is about 30 minutes west, a straight shot down Route 9 to Route 16. Free parking, no meters, no garage fees. Just a relaxed session focused entirely on you.
What makes my headshots stand out? Coaching. I walk every client through posture, expression and wardrobe — the kind of guided direction that turns a basic photo into a headshot that actually communicates confidence and approachability.
I photograph professionals across every field — executives, attorneys, physicians, financial advisors, actors. Each session is tailored to your industry and how you'll use the image, from LinkedIn profiles to corporate websites to casting submissions.
Brookline's business hubs — Coolidge Corner, Washington Square and the surrounding neighborhoods — blend urban convenience with a tight-knit community feel. If you work or live in Brookline, my Sherborn studio is about 30 minutes west on Route 9, a far more relaxed setting than a cramped downtown option.
Throughout the session I provide specific direction on posture, shoulder angle, chin position and expression — it's a collaborative process, not a stiff photo line. You'll view frames on screen as we go, which puts most people at ease within the first few minutes. Clients consistently say the experience was genuinely fun. Every final image is professionally retouched and delivered at full resolution.
Getting Here from Brookline
Take Route 9 west to Route 16 south — about 30 minutes to our Sherborn studio. Free parking right at the door.
Drive time: 30 minutes
Services
- ✓Executive & Corporate Headshots
- ✓LinkedIn Profile Photos
- ✓Business Portraits
- ✓Actor & Performer Headshots
- ✓Team & Group Headshots (on-location available)
What Clients Say
“Damon is a great coach for those doing headshots for the first time. The attention to detail is incredible. My husband had his done and I was so impressed I had to get mine done too.”
Janet O.
“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 Brookline?
My studio at 80 Maple St in Sherborn is about 30 minutes from Brookline via Route 9 west. 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 Brookline offices for team sessions?
Absolutely. I bring my full portable studio — lights, backdrop, the works — right to your Brookline 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.