Headshot Photographer in Winter Garden and Orlando
We bring studio lighting to your office, or meet you in downtown Winter Garden or near Lake Eola. You'll review your photos on the camera before we pack up.
Photographing Central Florida since 1996
Licensed and insured
You need a new headshot for LinkedIn, your company bio, or your website, and you need a convenient location near your home or work instead of wasting your time traveling across Orlando. Maybe you don't love having your picture taken either and we understand. As a headshot photographer based in Winter Garden and serving Orlando, we keep the session relaxed and efficient, and we come to you. Jason Cannon has photographed people across Central Florida since 1996, and he photographs every individual session himself.
A headshot photographer near you, because we come to you
There's no studio for you to drive to. We set up professional studio lighting wherever works best: your office, a conference room, or your home office. If you'd like natural light, we'll recommend an outdoor spot close by. You can choose indoor studio lighting, outdoor natural light, or both in one session.
Headshots in Winter Garden
Winter Garden is home for Cannonfire Photography. Our administrative office is here, and we're longtime members of the West Orange Chamber of Commerce, which named us Small Business of the Year. We photograph professionals at offices across Winter Garden, Horizon West, and Windermere. For natural light, downtown Winter Garden near City Hall is a favorite, with brick streets and tree-lined walkways a short walk apart.
Headshots in Orlando
We also photograph professionals across Orlando, from downtown offices to Lake Nona and Dr. Phillips. For an outdoor headshot, the area around Lake Eola puts greenery and the downtown skyline close together. Somewhere else? We travel throughout Central Florida and beyond, so ask about your location.
How your headshot session works
Every professional headshot session follows the same simple plan, so you always know what comes next.
1. Tell us what you need. Share where your headshot will be used and when you need it. We aim to reply within one business day of your inquiry.
2. Plan your look together. On a quick phone call, we'll talk through clothing, background, and whether you'd like studio lighting, natural light, or both.
3. Your session with Jason. Jason Cannon guides your posture and expression, so you’ll know how to pose, and you will look relaxed and confident in your photo.
4. Review your photos on the spot. You'll look through your images on camera with Jason before you leave, so you know you have one you like.
5. Natural retouching. We refine the details and keep you looking like you.
6. Delivery. Your finished headshot typically arrives in 3–5 days. Rush turnaround is available upon request in advance.
A few days later, your new headshot is ready for LinkedIn, your website, and your next speaker bio, and it looks like you on a good day.
What's included
Every individual headshot session includes:
• An on-location session with Jason Cannon at your office or a recommended outdoor spot
• Professional studio lighting, natural light, or both
• Live image review before you leave
• One professionally retouched, high-resolution headshot, with additional images available
• Delivery typically in 3–5 days, with rush turnaround available on request
Professional headshot pricing
Individual headshot sessions start at $250. That covers the on-location session and one retouched headshot. Your final quote depends on how many images and looks you want and where we meet.
Photographing your whole team? We offer half-day and full-day sessions. See our on-location corporate headshots.
Tell us where your headshot will be used, because that shapes the lighting and background we recommend.
Not a fan of having your picture taken?
Most people tell us they aren't photogenic. We hear it frequently, and it's never a problem. You don't need to know how to pose. Jason coaches you through small changes in posture and expression, and the session feels more like a conversation than a photo shoot.
Jason learned photography on film, back when every frame counted. He still works to get the shot right in camera, because that means less time posing for you.
“My husband and I had an incredible experience with headshots with Cannonfire Photography. From the very first contact, everything was smooth, professional, and stress-free.
Jason made us feel so comfortable during the session and knew exactly how to capture natural, beautiful moments. The photos turned out stunning- better than we could have imagined. We will definitely be booking again!”
— Thayssa
What to wear for your headshot
A little planning goes a long way. We'll talk through your options on our call, and here's a head start:
• Choose solid colors or subtle textures. Busy patterns and large logos pull attention from your face.
• Pick tops, blouses, jackets, and suits that fit well through the shoulders.
• If you wear glasses everyday, wear them for your headshot so it looks like you.
• If you wear makeup, keep to your usual everyday look.
• Schedule haircuts and grooming a few days before your session, not the same morning.
Who we photograph
Our headshot clients include entrepreneurs, real estate agents, attorneys, finance and insurance professionals, healthcare providers, creatives, and hospitality leaders. Some need a fresh LinkedIn photo. Others are updating a company bio, a speaker page, or a listing. Either way, the goal is the same: a headshot that looks like you on a good day.
Meet your headshot photographer, Jason Cannon
Every individual session is photographed by Jason Cannon, who founded Cannonfire Photography in 1996.
A note from Jason
I've been photographing people in Central Florida since I founded Cannonfire in 1996. Before that, I earned my journalism degree at the University of Florida, shot college sports, and traveled the world for a sport fishing and diving magazine. I learned on film, when every frame counted, so I still work to get the shot right in camera. For you, that means less time posing and more time getting back to your day.
I'll plan your session with you, guide you through it, and review your images with you before you leave.
What clients say
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“Jason is a true professional in the industry. I appreciate that he made the entire process simple and stress free! Thank you for your honest feedback along the way and of course a quality headshot! I look forward to working with him again in the near future.”
Monika
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“Had Jason and the team update my headshot for 2025 and these guys knocked it out of the park. Could not be happier with the results, and a good and fun team to boot. Thanks again to their team!”
Michael -
“I cannot thank Jason at Cannonfire Photography enough for the work he did on my professional headshot. I had an “impossible” deadline to submit a new photo in a tight turnaround window and he was able to meet me locally around my work hours for a shoot and provided an edited final within 24 hours ( no easy feat!). I would recommend this service for any corporate, team or professional photography and am grateful for the professionalism, speed, and quality of the service I received! Thank you again, Jason!”
Taryn
See headshot sessions in action
Take a quick look at Cannonfire headshot sessions, from setting up the lights to reviewing images on screen.
Headshot Photographer FAQs
We come to you. There's no retail studio to drive to. We bring professional studio lighting to your office or home office, or we meet you at a recommended outdoor location in Winter Garden or Orlando.
Do I come to you, or do you come to me?
Do you serve my part of Orlando?
Very likely. We photograph clients across Orlando and West Orange County, from downtown and Lake Nona to Dr. Phillips, Windermere, and Horizon West. We also travel beyond Central Florida. Tell us where you are, and we'll let you know.
Where can we take outdoor headshots?
Downtown Winter Garden near City Hall and the area around Lake Eola in Orlando are two favorites. On our planning call, we'll suggest a spot based on the look you want, the time of day, and where you're coming from.
How much does a professional headshot cost?
Individual headshot sessions start at $250. That includes the on-location session and one retouched headshot, and you can add more images. Your quote depends on how many images and looks you want and where we meet. Tell us what you need, and we'll send a custom quote.
Who will photograph me?
Jason Cannon, Cannonfire Photography’s founder, photographs every individual headshot session himself. He's photographed people in Central Florida since 1996. He'll plan your session with you, coach you through posing and expression, and review your images with you before you leave.
Will I see my photos during the session?
Yes. You'll review your images on screen with Jason before the session ends, so you leave knowing you have a headshot you like.
How soon will I get my headshots?
Most headshots are delivered in 3–5 days. If you're working against a deadline, rush turnaround is available. Just ask when you reach out.
We keep retouching natural and authentic. Your headshot should look like you on a good day, so the person clients meet matches the photo they saw on your website or business card.
How much retouching do you do?
How often should I update my headshot?
Update it when your look changes noticeably, such as a new hairstyle or new glasses, or when you change roles. A refresh every few years keeps your photo current, so people recognize you when you meet in person.
How do I choose a headshot photographer?
Look at their headshot portfolio, read their reviews, and ask how they help people who feel awkward on camera. Ask about turnaround, too, and whether they come to you. Our professional headshot portfolio shows our style, and we've photographed Central Florida professionals since 1996.
Can you photograph my whole team?
Yes. We offer on-location half-day and full-day sessions for teams, with a consistent look for everyone. See our corporate headshots page for details.
What's it like to work with you?
Clients tell us that they feel relaxed throughout the entire headshot process and love their images. We try to have fun, but if you are in a time crunch then we’ll be as efficient as possible.
What happens next
1. Tell us what you need your headshot for and when.
2. We aim to reply within one business day. Cannonfire Photography’s owners Jason or Kara will be in touch to plan the details.
3. We schedule your session at your office or a spot we recommend.