Headshot Contests
Headshot of the Month
Every month, we host a free, public Headshot of the Month Contest open to everyone.
Submit your best shot to be critiqued live by Peter Hurley and Headshot Crew mentors. All entries are reviewed during our public Crew Cast, where Peter selects a grand prize winner. We also typically award a second prize to one randomly selected participant—so anyone has a shot at winning! Sponsored prizes and expert feedback make this a can't-miss opportunity to grow and get noticed.
Past Winners
Headshot of the Week
Every week, we run a Headshot of the Week (HOTW) contest exclusively for coaching members. These contests rotate through three different formats, giving members at all levels a chance to shine.
- Standard HOTW: Open to all coaching members who have won fewer than two prior HOTW contests. Once you’ve won twice, you’re no longer eligible for this category.
- Winners Circle Edition: For past winners of HOTW and HOTM (Headshot of the Month). Expect stiff competition—these members are Associates or well on their way to becoming one.
- Associate Showdown: Exclusive to Headshot Crew Associates. This is the best of the best facing off. Everyone in this contest should be producing top-tier, Associate-level work.
The rotation goes like this: Standard, Winners Circle, Standard, Associate Showdown—then it repeats. That means a Standard contest runs every two weeks.
Past Winners
Portrait Contests
The Headshot Crew isn’t just about headshots—we also have a dedicated Portrait Track for photographers who want to explore expressive, creative portraiture beyond the standard headshot format.
Led by London-based portrait specialist Ivan Weiss, the Portrait Track focuses on developing your personal style, improving technical skills, and capturing more nuanced, compelling portraits. Whether you’re just beginning to branch out from headshots or you're already an experienced portrait shooter, this is where you can take your work to the next level.
Portrait of the Month
Portrait of the Month (POTM) is open to all coaching group members and reviewed live during our Wednesday Portrait Track Crew Casts. There are no strict rules — just submit a portrait you’ve taken in the past month. We review the entries together as a group, offering live critiques and professional feedback in a supportive, learning-focused environment.
Past Winners
Portrait Probe
Portrait Probe is our monthly themed portrait challenge, open to all coaching group members. Each month, a theme or concept is announced to spark new ideas and push your portrait skills further. Entries are reviewed live during the Wednesday Portrait Track Crew Casts, where you'll get real-time feedback and direction from Ivan Weiss and the Crew.
Past Winners
