Edelson

Executive Portraits for the CEO of a Billion-Dollar Startup

When Forbes named Ossium Health one of its 2026 Next Billion-Dollar Startups, CEO Kevin Caldwell did something most executives do too late: he built his image library before the press requests started arriving.

Kevin booked an executive portrait session at Ossium Health’s San Francisco office with exactly that brief: a deep library of press-ready photographs he can hand to any journalist, conference organizer, or publication for years, without ever scrambling for a photo again.

Kevin Caldwell, CEO of Ossium Health, walking portrait with jacket over shoulder in San Francisco, photographed by Josh Edelson
Kevin Caldwell, CEO of Ossium Health. (Photo by Josh Edelson for Ossium Health)
Ossium Health CEO Kevin Caldwell, relaxed executive portrait in the office
The environmental look inside the office. (Photo by Josh Edelson for Ossium Health)

How the session worked

I arrived with an assistant and scouted the office and the block around it, settling on four distinct setups: a studio-lit look against a brick wall, a portrait at a reclaimed wood beam, a warm environmental look inside the office, and editorial frames on the street outside. Kevin changed outfits between setups, from a knit polo to a camel blazer to an open-collar white shirt, and every look was photographed in a range of framings.

Kevin Caldwell of Ossium Health, editorial portrait on a San Francisco street
The camel blazer, editorial street setup. (Photo by Josh Edelson for Ossium Health)
Kevin Caldwell of Ossium Health, relaxed executive portrait in the office
Relaxed executive, same session. (Photo by Josh Edelson for Ossium Health)
Kevin Caldwell, CEO of Ossium Health, executive portrait in a camel blazer against brick, photographed in San Francisco by Josh Edelson
The reclaimed wood beam setup. (Photo by Josh Edelson for Ossium Health)

Why a library beats a headshot

A CEO photo works harder than anyone else’s in the company. It runs next to funding announcements, in conference programs, on podcast covers, in trade press features, and every outlet wants something slightly different. A magazine wants an environmental frame with room to crop. A byline wants a tight headshot. A speaker bio wants something in between. One session covering multiple looks, settings, and framings means the answer to every request is a file, not a reshoot.

Kevin Caldwell of Ossium Health, candid walking portrait on a tree-lined San Francisco sidewalk
Editorial walking frames give editors options a headshot cannot. (Photo by Josh Edelson for Ossium Health)
Kevin Caldwell, Ossium Health CEO, arms-crossed portrait at a reclaimed wood beam against brick
Same beam, different outfit and mood. (Photo by Josh Edelson for Ossium Health)
Kevin Caldwell, Ossium Health CEO, candid editorial portrait outdoors in San Francisco
Not every frame needs a smile at the camera. (Photo by Josh Edelson for Ossium Health)

The timing is the strategy

Ossium Health is a bioengineering company whose profile is rising fast, and that is precisely the moment to build the reservoir. The week a reporter asks is the wrong week to book a photographer. Kevin’s library is done, edited, and sitting ready, so as coverage of the company grows, every article gets a strong, current, consistent image of its CEO.

Kevin Caldwell, CEO of Ossium Health, environmental portrait inside his San Francisco office
The warm office look. (Photo by Josh Edelson for Ossium Health)
Kevin Caldwell, CEO of Ossium Health, candid lifestyle portrait walking outside the office
One session, a full press-ready library. (Photo by Josh Edelson for Ossium Health)

About executive portrait sessions

I photograph CEO portraits and executive headshots across San Francisco and the Bay Area, and I travel nationwide for multi-office companies. An executive portrait session like this one is the deeper version of a headshot: multiple looks, settings, and framings in a single session, built for founders and executives who need press-ready photography for funding announcements, speaking engagements, and media features. For leadership teams rather than individuals, see this leadership team headshot refresh or the corporate headshots page, and for founders building a public presence, personal branding photography works the same way.

If your company’s profile is rising and your CEO needs a press-ready image library, reach out for a quote! Tell me your timeline and I will send pricing the same day: josh@edelsonphotography.com or 650-515-0999.