Anna Cillan Photography – Headshots

High-End Headshots and Timeless Creative Portrait Photography

>> It's not just a headshot, it's the most authentic version of you <<

On paper you are an industry leader, but does your headshot communicate the same? A headshot that portrays the best version of you makes a killer first impression and elevates your overall brand messaging to the next level.

Ughh...I need professional headshots, stat!

Ever find yourself in a position where you are in need of a headshot for work or for that acting audition you were waiting for but need to submit a photo asap?  I think we can all agree that its never too early to have a headshot ready to go but it can be too late if you're searching for one last minute and when rushed, the personal brand you were looking to accomplish....well it's just not met.  This is where I enter the pun intended. 

Your Headshot Session Agenda - Spoiler's fun and easy!

Free Phone Consultation

When you work with me you are entering not only a photo session where we capture photos and send you on your way but a holistic branding experience.  From the moment you inquire, I'll set up a phone consultation to review your goals of the shoot.   

Step in Front of the Lens

During your session, tunes will be going which helps set the tone for your shoot.  I will be coaching you on head angles, expressions, positioning, re-positioning. So I'm there to guide you the entire time.  I'm not a hair stylist, but I do know when hair should be repositioned in your don't worry about that.  We'll take breaks in between to see how we're doing and tweak any shots that will give you that WOW factor. 

Break Time!

After your session, we'll sit down have a coffee, tea...or wine and go through your photos together because it can be overwhelming to do this on your own.  This is called the "culling" process.  I'll give you as much input as you like on one photo vs. another and after it all, you will have chosen the number of images that meet your personal brand objectives. 

Gallery Delivery in 2 Weeks!

Within 2 weeks from your selections at the close of your session, you will receive high-resolution JPEGs via WeTransfer or Password Protected Web Gallery, I'll also make sure you receive the same shots that are custom size and crops for social media platforms like LinkedIn which will save you time to re-size and crop the shots after you receive them.

Ok I understand the process, now what?

Allow yourself at least 2-4 weeks to prepare for your headshot. This accounts for any Covid-19 Haircuts.

Day of Session: hair and makeup artist is available upon request

Click the calendar to choose your session -->


Have a larger group of 5+ for Headshots?

Perhaps you are hosting a conference or a summit meeting for your organization and are offering Headshots Photography as a special perk?

Contact me for a custom quote

I’m a Chicago Headshot Photographer

originally from the Pacific NW starting my professional career in computer programming moving into Testing financial software and capping off my IT career with Project Management for software implementations.  It wasn’t until a major layoff back in 2016 that jump started my journey back into the world of photography and so happy I did!  I specialize in High-End Corporate and Acting Headshots most notably used for LinkedIn and performer portfolios for Musical Theater, Acting, Modeling, and Dance.

I’ve had the privilege to train 

under the direction of world-renowned educators Scott Robert Lim, JB Sallee and am a verified member of world-class Headshot Educator Peter Hurley’s Headshot Crew. I’ve been published in the April 2019 edition of Shutter Magazine, one of the leading professional photography Magazines to date!


and don’t you forget it.  I would love for the opportunity to direct and capture you being the most authentic version of you.  I know the lights and camera gear can be intimidating, but never fear, it’s just me, a friend that may make you share in a few belly laughs throughout your session. Oh did I say that I can sing too?  How well you ask?  That’s for me to know and you to find out.