Transition Squad® Employment Opportunities

At Transition Squad®, we're always keeping our eyes open for good people to join our team. We don't want employees, we want driven, energetic go-getters that want to be part of building something great, and to grow professionally and personally along with it.

Successful candidates must provide a clear criminal background check as a condition of employment as you are dealing with seniors and their belongings. If you feel you are a serious contender for the following roles, please send us this application along with your resume in MS-Word format to We appreciate everyone's efforts in applying, however due to time constraints only those chosen for interviews will be contacted. THOSE WHO DO NOT SUBMIT AN APPLICATION WILL NOT BE CONSIDERED.

We are now hiring for the following positions:

For any family, a parent transition to a retirement home or dealing with an estate can be an overwhelming, emotionally draining and physically challenging ordeal. Typically, the home has to be sold and all the contents cleared out. One of the biggest physical challenges is "what do I do with all the contents?" This isn't just stuff, it is people's lives, their memories and their emotions. They have loved and cherished many of their treasures and enjoyed their use for many years.

Transition Squad does online estate and downsizing auctions and estate sales to help seniors downsize and families settle an estate. We also offer clear out services, donation management and move management.

We are looking for territory project managers (independent contractors) that love to get their hands dirty, rummage through clients' premises, pull together items for photography, write descriptions and manage the pickup of items that are won.

The successful candidate with work primarily from their home office, visit prospective clients to present and sell our services, assemble and schedule a small team of freelance helpers upon approval of contracts, execute the projects and reconcile the paperwork after an auction.

You must be a detail oriented leader who is comfortable managing clients, staff and vendors. You must be able to work independently from your home office which you will equip with the necessary tools of the trade (primarily a PC-based system, appropriate laser printer, high speed internet, folding tables, bins, signs, vests, a toolkit and general supplies). You must be able to handle the full project cycle including sales, management, execution and administration of projects. You must be empathetic and genuinely concerned about the clients' results. And you must be reliable and flexible to work non-regular hours to manage the pickup of items won at the auction. For example, we hold pickups during a 4-5 hour window on a Saturday or Sunday, subject to your schedule. You'll need to be at the premises to get ready for the pickup one to two hours in advance to get organized and post signs.

You will set up your own business as an independent contractor (we can make recommendations on how to do this if needed). We will qualify customers and feed you leads to go visit. Compensation will be higher of an attractive hourly wage or 50% profit share. We will provide you with training, ongoing support and marketing to generate leads on your behalf. You are also expected to network in your area to generate awareness and business.

Do you love estate sales? Do you love thrifting? Do you love negotiating on second hand items? Want to get paid for it? Then join our team. Get paid to shop. Get paid to sell.

Transition Squad is now hiring independent contractors in all markets to shop for, acquire and consign second hand items on our behalf. Successful candidates must be willing to learn or already have an eye for value and for what is resellable with a reasonable profit margin.

Successful candidates will be paid a flat fee per auction plus a hefty commission on sold items to shop, set up auction listings, post items on our online auction platform and manage the pickup of items that are won. This job is fully remote and you will operate on your own schedule with interaction with head office through Zoom and phone.

You must have a decent camera and computer. Training and support are provided to applicants that are hired.


(Partially Remote)

Are you a fun, enthusiastic person who loves dealing with people and capturing the beauty of household decor? Do you enjoy rummaging and getting your hands dirty? Our Online Estate and Downsizing Auctions help previously loved belongings find love again in a new home. To do this, they have to look their best online so people will buy them.

We are looking for freelance photographers to help with our online estate and downsizing auctions. Whether it is for a Transition Squad franchisee or for one of our clients using our do-it-yourself platform, items have to be photographed and uploaded to our website where they are catalogued, briefly described and priced before an auction launches.

Our Transition Squad Managed auctions typically require two or three people, including the project manager, to go into a home, pull everything out of cupboards, basements and the like, set them up into "lots" and photograph them from various angles while making notes on the condition and dimensions. Photos must then be uploaded from your home or office and updated with the notes taken.

Our client managed Do-It-Yourself Auctions require one or more photographers to work directly with the client, typically a senior citizen or their family member, and take photos and catalog as above on their behalf. We handle all billing with the client.

You must be comfortable with e-commerce still product photography and the use of computers and websites. You must have your own transportation and camera or smartphone.

While we appreciate everyone's submissions, only those that are being considered will be contacted.

Are you good at packing fragile items? Do you have experience in the moving industry with packing the contents of people's homes?

Transition Squad does online estate and downsizing auctions. We are preferred service providers for various highrise condos. Due to logistics, most condos and townhouse complexes do not allow pickups on site. Therefore, all items that are won must be packed and transported to offsite venues for pickup.

We are building a roster of specialists who are fast but good at packing fragile items so they are safe and secure during transport. The successful candidates will be called upon with one or more weeks' notice as jobs happen. Each job will typically require two packing specialists, reporting to the team leader, for 6-8 hours each depending on what the client has and the amount of bidding activity that took place. Additional freelance hours could also be available in other roles. Job sites will be throughout the GTA and maybe beyond, in which case travel will be paid.

A vehicle is handy but not necessary. A clean criminal background check will be required as you will be dealing with people's belongings in their home.

For the safety of our senior citizen clients, only those fully vaccinated with proof of vaccination will be considered.


Transition Squad is an equal opportunity employer and values diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.


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