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.
Executive headshots in Boston for C-suite leaders, board members, managing directors, and senior professionals — the presence-focused portrait a board, search committee, or investor reads before they meet you. Individual sessions start at $395 and include one fully retouched, licensed image, with additional images $125 each, at the Sherborn studio about 30 minutes west of Boston. Damon Bates spent 35 years as a corporate executive and leadership consultant, and trained with Peter Hurley in 2013 — so the session is coached, not just photographed. Leadership teams and boards are also photographed on-location across Greater Boston.
Damon Bates — by the numbers
- ✓35 years as a corporate sales and marketing executive
- ✓A decade coaching leaders on executive presence as a leadership consultant and certified Bates ExPI executive-presence coach
- ✓Trained with Peter Hurley in 2013 — among the first headshot photographers in Boston, refreshed 2025
- ✓MBA, Boston University
- ✓The only Boston photographer who has been a senior executive — 35 years in senior leadership
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.
Executive Headshots by Role
At the senior level, the read isn't generic — a founder's photograph is doing a different job than a board director's, and a newly promoted VP has a different problem to solve than a managing partner. Here's how I approach the roles I photograph most.
CEOs & Founders
At the top, your headshot is inseparable from the company's story — it runs on the leadership page, the annual report, the press release, the conference program. The read has to project the confidence that reassures a board and an investor without tipping into the polish that reads as manufactured. People are deciding whether to trust the organization by looking at the person who runs it. That's the read we build — and after 35 years as an executive myself, it's the one I understand from the inside.
Board Directors & Nominees
A board photograph is scrutinized by people who serve on boards — governance committees, fellow directors, institutional investors, proxy advisors. It has to signal judgment, independence, and steadiness, not personality. The frame that works for a startup founder is wrong here; board-level presence is quieter, more composed, and more deliberate. If you're being put forward for a seat, the photograph is part of how the room sizes you up before the vote.
Managing Directors & Partners
In finance, law, private equity, and consulting, the partner photograph carries the weight of the firm's brand and your personal book of business at once. Clients and prospects read it for the same thing they'd read across a conference table: does this person have the seniority, discretion, and command to handle what I'm bringing them? The session is tuned to that specific read — the composure a client hands their most sensitive matters to.
Newly Promoted & Rising Executives
The hardest headshot to get right is the one where the title just changed. You've earned the seat, but the old photo still reads as the person you were two levels down — and stepping into the role means the image has to catch up fast. This is where the coaching matters most: adjusting how you carry authority so the frame reads at your new altitude, not your old one. It's the exact transition I spent a decade coaching leaders through.
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.
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. From my years leading teams, you may also like Do You Bring Light or Heat? Grace Under Pressure and 6 Lessons on Building a Great Team.
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 Boston team headshots for how on-location group sessions work, or team session pricing and details here.
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.
Why not just use an AI headshot generator?
For a board or C-suite portrait, an AI generator is the wrong tool — and the room can increasingly tell. AI doesn't photograph you; it averages your selfies into a composite and idealizes it, smoothing the very signals of judgment and steadiness a board reads a leader for. When the executive who walks into the meeting doesn't quite match the polished image on the leadership page, trust takes a hit before a word is spoken. A coached session does the opposite: I direct your expression, posture, and presence in real time until the frame reads as you at your most composed and credible — the read an algorithm can approximate but never earn. More on this in AI Headshots vs. Real Headshots.
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.
Are you insured for on-site work at our offices?
Yes. I carry $1 million in professional liability insurance through the Professional Photographers of America (PPA) member program, administered by Lockton Affinity, LLC. For on-location leadership-team or board sessions I can provide a Certificate of Insurance (COI) naming your company, building, or facility as certificate holder ahead of the shoot — a requirement many corporate offices and law firms have for outside vendors. Just let me know who the certificate holder should be.
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.