Executive Headshots in Boston
The Executive Photographer.
Authentically catching you in the act of being your best self.
The only Boston photographer who spent 35 years as a sales and marketing executive and a decade as a leadership consultant and coach.
Headshots Built for the C-Suite
Most headshot photographers can take a sharp, well-lit photo. I can do that — and I can also tell you exactly why your posture is signaling something you don't intend, or why your expression reads as guarded rather than confident, or how a two-degree change in chin angle changes what the camera sees. That's not photography knowledge. That's 35 years of sitting across from executives, coaching them on presence, and watching how confidence actually reads in a room.
My background as a corporate executive and certified executive coach is the reason sessions here produce superior results for executives than a standard headshot studio does. I've been in the chair my clients sit in. I know what boards look for. I know what a LinkedIn photo is supposed to communicate to a search committee or a board chair. The difference is that I understand what presence actually is — how behavior, bearing, and the way someone carries themselves gets read by other people. That's what executive coaching is. And it's exactly what determines whether a headshot works.
As you research photographers, you'll find some with hundreds of five-star reviews — and that's great. Social proof is a real consideration, and you should weigh it. I'd just ask you to consider what else matters for an executive headshot. For much of the last 35 years I wasn't behind a camera collecting reviews — I was in the room: a sales and marketing executive, then a decade as a leadership consultant, coaching leaders on exactly the executive presence you're here to capture. I've sat in your chair. So when I direct you, I'm not guessing what reads as credible to a board or a client — I spent 35 years as a corporate leader and a decade as a leadership consultant coaching executives on executive presence, so I know what engages, aligns, and inspires a room, and how to bring it forward in front of the camera.
My studio is in Sherborn, about 30 minutes west of Boston. Sessions are private, unhurried, and built around getting you the one image — or two or three — that actually represents how you carry yourself at your best. Not a stock-photo smile. Not a forced formal pose. The version of you that walks into the room, owns it, and connects — before you say a word.
I work with C-suite executives, managing directors, partners, and senior professionals across industries — finance, law, consulting, healthcare, technology, and beyond. Many clients come through referrals from other executives who noticed a difference in their headshot results and wanted to know who photographed them. While my studio is in the Boston area, I also travel nationally to photograph leadership teams and boards of directors on-site — so if your executives are spread across offices, or you want a consistent look for a national leadership page, that's work I regularly take on.
Photographing your whole leadership team or board? See how a corporate headshot day works.
Getting Here from Boston
Take the Mass Pike (I-90) west to Route 16 south — about 30 minutes from downtown Boston to the studio in Sherborn.
Drive time: 30 minutes
Services
- ✓C-Suite & Board-Level Headshots
- ✓LinkedIn Executive Portraits
- ✓Speaker & Conference Bios
- ✓Annual Report Portraits
- ✓Company Website & Brand Headshots
- ✓Executive Presence Coaching During Session
What Clients Say
“Damon has the rare ability to master the technical while keeping the experience intimate. He immediately knew how to optimize my look — from wardrobe to lights to positioning. Everyone in my network is complimenting me on my new headshot.”
David D.
“Amazing experience with Damon. He draws you out in a very subtle and effective way that can only come from years of experience. His work has already had great impacts on my career.”
Paul C.
Frequently Asked Questions
What makes an executive headshot different from a standard professional headshot?
The stakes are higher and the audience is more discerning. A senior executive's headshot is reviewed by board members, search committees, institutional investors, and C-suite peers — people who read presence and authority in a photograph the same way they read it in a room. A standard professional headshot communicates competence; an executive headshot communicates leadership. If you're after a polished business image rather than a board-level portrait, my corporate headshots in Boston page covers that session. Getting the executive version right requires more than good lighting — it requires coaching on the specific signals of authority, approachability, and gravitas that land differently at the senior level. That's where the 35-year executive background in my coaching changes the result.
How long is an executive session?
Sessions run 30–45 minutes. Executives often find that's enough time to move through two or three wardrobe changes and cover different expressions — formal, approachable, authoritative. The session doesn't feel long because we're working the entire time, not waiting around.
What about LinkedIn specifically — does the session produce a LinkedIn-ready headshot?
Absolutely. Most executive clients use their session for three things at once: a formal headshot for the company website or annual report, a LinkedIn image, and a conference or speaker bio photo. These can all come from the same session — we just vary the framing and expression during the shoot. For the full breakdown, read Corporate Headshots vs. LinkedIn Headshots.
Where are you located?
My studio is at 80 Maple St in Sherborn, MA — about 30 minutes west of downtown Boston via the Mass Pike. There's free parking at the studio. I also photograph executive teams on-location throughout Greater Boston, including Boston, Cambridge, Wellesley, Newton, and Framingham.
What is the ExPI framework and how does it apply to a headshot session?
The ExPI (Executive Presence Index) is a framework that organizes executive presence across three dimensions — Character, Substance, and Style — and the specific observable behaviors within each. I am a certified ExPI coach. In a headshot session, that means I can help you identify and surface the elements of executive presence that matter most in a photograph and bring them forward deliberately. Most photographers tell you to relax and smile. I can coach you into the presence you want to project. Read my deeper piece on executive presence and the ExPI framework, or learn what happens during a session.
Do you work with both individual executives and leadership teams?
Yes. Individual sessions take place at my Sherborn studio — private, controlled, no rushing. Team sessions are on-location at your office anywhere in Greater Boston — I arrive one hour before the first session to set up a full studio (professional lighting, backdrop, tethered display) and photograph each person in 8–10 minutes. Both approaches produce consistent, high-quality images. See team session pricing and details here.
What should I wear?
Classic executive wardrobe — navy, charcoal, dark gray, or deep blue. Solid colors photograph better than patterns. I do a wardrobe review at the start of every session and advise on what will and won't work with the lighting setup and background. Bring 3–4 options and we'll choose together. For more guidance, read what to wear for your headshot session.
How much does an executive headshot session cost?
Sessions start at $395, which includes one fully retouched high-resolution image. Additional images are $125 each. Most executives select 2–3 final images. There are no packages, no pressure — you choose the number of images that makes sense after you see the results. See the full individual session pricing page.