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 [email protected]. 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:

Do you want flexibility in your schedule, in a role that you can be passionate about, that helps people in need, where you can work from home as needed, where you are involved in all aspects of the business and you can make an impact on the organization? Are you tired of the corporate rat-race and just being a number where you do the same thing every day? Do you want something that challenges you physically and stimulates you emotionally and mentally? Our group of companies can provide all of the above with opportunities to advance and freedom to grow.

Transition Squad does online auctions, helps seniors downsize and works with families settling an estate. We also with clearout of the premises, donation management and moving services. Automall Network is an auto broker. Automall is a fully licensed dealer, however doesn't operate like a dealer, they work for the buyer. Just like a real estate broker would help people buy a home, Automall Network helps those that hate car shopping buy to buy or sell a car.

We are seeking an enthusiastic, detail oriented Marketing, Customer Service and Administrative Assistant to provide the following:


  • Social media marketing and blogging with articles of interest to prospective clients
  • Assist with photography of items to be sold

Customer Service:

  • Handle inquiries from clients, review our solutions and send/receive contracts
  • Once trained, train our clients using phone and zoom in how to use our do-it-yourself services
  • Provide inhouse support to team members including attending pickups


  • Reconcile projects and pull together all paperwork
  • Configure and search for vehicles on various classifieds sites
  • Handle logistics of marketing vehicles, coordinating inspections, detailing, licensing, etc. with third party vendors

Requirements to be considered - you must:

  • be legally able to work in Canada for a full time position
  • have a valid driver's license and vehicle
  • have your own Windows based PC with high speed internet access
  • be a very organized individual
  • be able to juggle multiple tasks and projects simultaneously
  • have strong written and oral communication skills
  • excel at customer service
  • be flexible in scheduling and shifting around work hours
  • be very comfortable using technology such as websites, databases, and social media.

Compensation: $15-18/hr plus bonuses

We thank all those who apply but only those that are being considered will be contacted.


Do you like rummaging, organizing and estate sale-ing? Are you a detail oriented leader who is comfortable managing clients, staff and vendors? Can you work independently from your home office? Are you able to handle management, execution and administration of projects?

Do you want to do regular organizing work and get a steady paycheck while at the same time contribute to the growth and success of a team?

Transition Squad does online estate and downsizing auctions to help seniors downsize and families settle an estate. We also offer clear outs of premises, donation management and move management. We are looking for a full time project manager that loves to get their hands dirty, rummage through our clients premises, pull together items for photography, write descriptions and manage the pickup. The successful candidate with work from their home office most of the time and regroup with other team members from time to time to plan and brainstorm. You will visit clients throughout the GTA and maybe beyond to understand the scope of the job, assemble and schedule a team of freelancers, execute the projects and complete the paperwork.

We are launching our service in Burlington, VT and are looking for freelance project managers to perform and oversee the onsite and production aspects of conducting online auctions and clearouts on behalf of clients. This includes photography, uploading, writing descriptions, pricing, managing the pickup, arranging and overseeing the donation and clearout of unsold second hand items, all from the clients' premises.

Working from a home based office, you will be responsible for purchasing the necessary supplies for each job, and scheduling, working with and overseeing a small team of helpers on the various aspects of each job. Training will be provided.

The successful candidate must be comfortable using technology, enjoy getting their hands dirty rummaging through clients' contents as well as basements, attics and crawlspaces, able to handle physical work, detail oriented, have flexible hours and be organized to handle multiple auctions simultaneously. You'll need a suitably sized vehicle to carry around moving supplies and folding tables.

Compensation is $18-20/hour + commission. To apply, see the instructions above.

(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.

Compensation is $18/hr. While we appreciate everyone's submissions, only those that are being considered will be contacted.

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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