Milwaukee Headshots
Milwaukee Headshots™, LLC
featuring the
“Always Up-To-Date Team Photo” ™
“I bring Hollywood to you!”™
“Beautiful, Believable,
and Authentic”™
If your date is not available on my calendar, call me!
414-305-6955
I will do everything possible to arrange other things so I can accomodate your request!
We never get a second chance to make a first impression!
I will help you to
look confident and not awkward;
real, natural, and authentic;
not artificial and plastic.
My expertise will guide you to look professional and “on brand”.
I’m Bill Sargent, a Certified Professional Photographer and owner of Milwaukee Headshots in Milwaukee, Wisconsin.
My headshot photography serves to empower brands, businesses, and individuals with dynamic, impressive photographic images that get attention.
As a specialized expert professional headshot photographer, my expertise extends from creating captivating and distinctive to custom-tailored branding images for organizations and businesses of all sizes.
My corporate clients appreciate my efficiency, reliability, professionalism, and my attention to detail with a personalized method and technique.
Serving the Greater Milwaukee area, Milwaukee Headshots™, LLC provides headshot photography that assists businesses to succeed, grow, and increase their profits.
My headshots serve a variety of clients from conventions, conferences, and events to teams and staff, C-Suite executives, professionals and small business owners.
To best serve my clients, I do everything on location.
I save you production downtime, time, travel, traffic hassle, stress, and money, as I bring my mobile studio to you for your session.
All the headshots in this website were created on location.
I am also available elsewhere in Wisconsin.
What KIND of headshots
are available?
Headshots for Professionals
Convention Headshots
Trade Show Headshots
Event Headshots
Corporate Headshots
Executive Headshots
Team Headshots
New Hire Onboarding Headshots
LinkedIn Headshots
Business Headshots
Staff Headshots
Employee Headshots
Personal & Corporate Branding Headshots and Images
Glamour Headshots
Modeling Headshots
Actors Headshots
Social Media Headshots
AND . . . the ever popular, and totally necessary,
“Dude, if you’re ever going to get a woman to SWIPE RIGHT on that dating app, you have GOT to do better than that!”
Dating Apps Headshots
(Appear as your authentic self on your best day!)
I create impactful headshots for:
Attorneys
Realtors
Doctors
Dentists
Healthcare Professionals
Financial Advisors
Nonprofits
Public Speakers
Authors
Headshots for Job Search
Universities
C-Suite Executives
Life Coaches
Pastors & Church Staff
If your date is not available on my calendar, call me!
414-305-6955
I will do everything possible to arrange other things so I can accomodate your request!
Frequently Asked Questions
Who is the headshot photographer behind Milwaukee Headshots?
I’m Bill Sargent, a Certified Professional Photographer and the owner of Milwaukee Headshots in Milwaukee, Wisconsin. Fewer than 2,500 photographers nationwide hold the CPP designation, and only about 35 are in Wisconsin, according to the Professional Photographers of America and the Wisconsin Professional Photographers Association. I was named to the Wisconsin Top 10 in 2025 and 2026, and I’ve been photographing headshots since 2014.
How do I choose the right headshot photographer in Milwaukee?
Start with the portfolio. Do the headshots look like real people at their best, or heavily airbrushed? Look for a consistent style across many different people and settings. Then check credentials and read client reviews. Finally, get the practical details in writing: what’s included, how many images you’ll receive, how soon you’ll get them, and how you can use them. Also make sure the photographer can work where you need them, whether that’s your office, your home, or an event.
What kinds of headshots do you photograph, and for which professions?
I photograph corporate, executive, business, LinkedIn, staff, employee, new-hire, convention, trade show, event, and team headshots, plus personal and corporate branding images, actor, modeling, glamour, social media, and dating-app headshots. I create headshots for attorneys, realtors, doctors, dentists, healthcare professionals, financial advisors, nonprofit leaders, public speakers, authors, job seekers, university staff, C-suite executives, life coaches, and pastors and church staff. If your field isn’t listed, ask me.
Do you have a studio, or do you come to me?
I come to you. I do everything on location, so I bring my mobile headshot studio to your office, home, or event anywhere in Greater Milwaukee. “I bring Hollywood to you!”™ means you skip the drive, the traffic, and the downtime, and every headshot on this website was made on location. I’ve set up in small homes, living rooms, kitchens, and hallways. When space is tight, I’ll put the backdrop and lights in one room and the camera in another.
Which Milwaukee-area communities do you serve?
I serve all of Greater Milwaukee, including Milwaukee, Waukesha, Wauwatosa, Brookfield, West Allis, Greenfield, New Berlin, Glendale, and Oak Creek. My standard service area covers Milwaukee, Ozaukee, Waukesha, and Racine counties, and I’m also available elsewhere in Wisconsin. Some counties carry a small travel fee, which you’ll find on my Prices page.
What should I wear for my headshot?
Wear plain, muted colors and skip bright colors (fluorescent orange is a good example) and busy patterns. You want people to notice your eyes and expression first, not your clothes. If you’re unsure about an outfit, call or text me at 414-305-6955 before your session.
How long does a session take, and when will I get my photos?
Individual sessions usually take up to 30 minutes, and I’ll give you whatever time you need to get what you want. Team members are typically 5 to 10 minutes each. At conventions and conferences, I can photograph each person in as little as 2 minutes and still get an excellent headshot. Your photos arrive in an online gallery, typically within 48 hours, and sometimes within 24 hours if my schedule allows. Everything I shoot goes in the gallery, which has ranged from about 10 images to as many as 150.
How do I look natural and not awkward in front of the camera?
Natural comes from comfortable. I guide you through posture, angles, and expression one step at a time, so you never have to wonder what to do with your face or your hands. The goal is the confident, real version of you, not stiff and not artificial or plastic. If you tell me what you want your photo to say about you, I’ll steer the session toward that.
Will you retouch my headshot, and will I still look like me?
Yes. Retouching is included for the images you choose, and it’s my Authentic Natural Look retouching: enough to polish the image, never enough to change who you are. The aim is for you to look like you on a great day, so someone who meets you after seeing your photo recognizes you right away.
Do I need a professional headshot for LinkedIn?
If you want people to take your profile seriously, yes. Your headshot is often the first thing a prospective client, employer, or colleague sees, and it shapes the impression before they read a word. We never get a second chance to make a first impression. The same image works on your company website, speaker bio, email signature, and business card. With my license for unlimited use, you can use it everywhere.
