Proudly serving the Durham Region, Peterborough and Surrounding Areas

Team/Group Headshots & Portraits Whitby

For organizations and professional teams throughout Whitby and the wider Durham Region, Darian Drake Photography offers refined on-site photography services thoughtfully designed to present your people with clarity, distinction, and cohesion. Whether you represent a corporate office, a creative collective, a professional practice, or an emerging entrepreneurial enterprise, a unified visual identity conveys confidence, professionalism, and a quiet pride in one’s work.

Our team and group photography sessions are carefully arranged to produce a complete gallery of portraits that feel consistent, polished, and appropriate to the character of your industry. Rather than a collection of mismatched images, each session results in a cohesive body of photographs—portraits that sit comfortably alongside one another across company websites, marketing materials, professional directories, and social media profiles. The outcome is a visual presence that honours both the individuality of each member of your team and the shared standards of the organization as a whole.

On-site sessions are conducted at your workplace or chosen location within Whitby and the surrounding communities of the Durham Region. This approach allows your team to remain at ease within their own professional environment while ensuring the least possible disruption to the day’s affairs. Particular care is given to lighting, background, and composition so that each portrait maintains a consistent aesthetic while still appearing natural and authentic to the individual being photographed.

For organizations arranging portraits for larger groups or entire teams, we are pleased to extend preferred team rates, offering a practical advantage for businesses and institutions wishing to create a complete and unified gallery of portraits in a single sitting. The result is a distinguished and enduring collection of images—one that represents your team with the professionalism, character, and quiet confidence it so rightly deserves.

The On-Site Advantage

There is a distinct advantage in conducting team portrait sessions within the familiar surroundings of one’s own place of work. An on-site photography session allows colleagues to remain in an environment where they feel naturally at ease, surrounded by the rhythm and character of the setting in which they spend their professional lives. This comfort often reveals itself in the portraits themselves — expressions are more genuine, posture more relaxed, and the resulting images possess an authenticity that is difficult to replicate in an unfamiliar studio setting.

Practical convenience is, of course, another considerable benefit. By bringing the studio to your workplace, team members are spared the need to travel or rearrange their schedules. Portraits can be conducted efficiently throughout the day, allowing individuals to step briefly away from their work before returning without disruption. For larger organizations, this thoughtful approach ensures that every member of the team can participate without sacrificing valuable time.

Beyond convenience, on-site photography can also foster a quiet sense of unity within a team. When colleagues participate together in the creation of a cohesive gallery of portraits, it reinforces the shared identity of the organization. Each individual image contributes to a larger visual narrative — one that reflects the professionalism, character, and collective spirit of the people behind the work.

The resulting photographs are not merely portraits of individuals, but a refined and harmonious representation of the team itself — an enduring visual record of the people who together form the heart of the organization.

How Our Team/Group Sessions Work

Step One: Get Your Free Quote

Every service we offer starts by us learning a little about your project (i.e., number of people, location etc.) and then providing your representative with a quote for the service. We offer competitive scaled pricing, so the more people we photograph, the less it costs per person. We are confident you will love your quote!

Click here to get a free quote now!

Step Two: Book In

Here we coordinate with your representative to select the perfect date and time for your photoshoot. We offer one photoshoot per day to guarantee our clients get the exact time which works best for their needs. Once you are booked in, we will send you materials to set up your photoshoot and to distribute to your team. Our best practices guide for headshots will have your team look great on the big day!

Step Three: Photoshoot Day

The big day! Darian will arrive at the predetermined location to set up for your photoshoot. Set up is quick and quiet, so you won't even know we're there and your normal daily routine can go uninterrupted. We will run through our sign up sheet, filled out by your representative, to quickly and efficiently photograph your entire team. Our sessions usually photograph up to 12 people per hour, allowing each person to have a sizable gallery of images they will love. Once the photoshoot is over, we tear down quickly and leave without any disruption to your day. The whole process is neat, professional and efficient.

Step Four: You Get Your Images

Your representative will be sent a private online gallery for your team to view their headshots. Once they have been selected, the final edited images will be added to your gallery for download and use. Our turn around time depends on the size of your team, but most businesses will have their edited images within 48 hours.

Trusted by Professionals Across The Durham Region

Starks Barbershop - 5 Stars

Darian is very professional, worked around our teams schedule and had our pictures to us very quickly. Would highly recommend for all of your photography needs.

Jaclyn Hamblin - 5 Stars

Darian did our company headshots. It was very professional and made us all feel comfortable confident.

Kosu Boudreau - 5 Stars

Convenient, friendly and affordable service. Darian set up his portable studio effortlessly and then helped me choose from a variety of options to get the perfect headshot. Highly recommend!

D.M. Wills - 5 Stars

Our team had an excellent experience from start to finish. Darian was professional, efficient, and delivered high-quality headshots that represent our organization beautifully.

Whitby Team/Group Session

An excellent choice to turn any team into a trustworthy brand. You get the choice to do headshots, portraits (up to 3/4 body), or both.

One background.
Five minutes of camera time for each team member.
Minor wardrobe changes.
Posing and expression coaching.
Two edited images returned per team member. Images are returned as maximum resolution .JPEG files.
Option to do headshots and/or portraits (1/2 body or 3/4 body).
Competitive scaled pricing - the larger your team, the less it cost per person.
Options to purchase additional images.
Option to select full body portraits (at an additional cost).

Your Investment:

Teams of 2-4: Starting at $199/person

Teams of 5-8: Starting at $179/person

Teams of 9-12: Starting at $159/person

Teams of 13-15: Starting at $149/person

Teams of 16+: $129/person

Add Ons:

Additional Edited Images - $50/images

Priority Editing (Receive your images within 24 hours of selection) - $20/image

Logo Overlay (Place your logo on your images) - $10/image

F.A.Q.

01. How Long Does A Team Headshot Session Take?

This depends largely on the size of your team, but you should plan on about 1.5 - 2 hours for set up and tear down plus 5 minutes per team member.

02. Where Do You Set Up Your Studio?

I can set up our on site studio in any space. We generally need about 7'x7' for headshots and 1/2 to 3/4 body portraits. More space will be required for full body portraits. Typically, a board room, lunch room or other similar area works just fine for our purposes.

03. Do You Travel Outside Whitby?

Absolutely! We travel everywhere in Southern Ontario.

04. How Soon Can I Get My Edited Images?

Once you have finalized your selection, our turnaround time is generally between 1-7 business days. We also offer 'priority' editing at an extra cost, which can guarantee you receive your images within 24-48 hours after selection.

05. Do You Charge A Deposit Fee?

Yes. We require a 50% non-refundable down payment to secure the date for your photoshoot.

06. Do You Provide Any Guidance For Our Team?

Definitely! We will send you a PDF to send out to your team members. This file will go over best practices for how to dress, make-up, jewelry and more. You'll have the best looking team in Peterborough!