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:

Transition Squad and its sister company Automall Network provide services that help people with some of the more challenging tasks we face. Transition Squad is a project manager that helps seniors downsize and works with families settling an estate. Transition Squad provides a menu of services however its core speciality is helping to find a good home for clients' belongings while maximizing the sale price on their behalf through a proprietary online auction platform. Automall Network is a fully licensed auto dealer, however it doesn't operate like a traditional dealer; it works for the public – just like one would hire a real estate broker to help them buy or sell a home, people who hate car shopping hire Automall Network to help them buy or sell a vehicle. Both companies operate under the same umbrella and share common resources, such as bookkeeping.

We started implementing a primarily work from home environment long before COVID and continue to operate that way with periodic visits to the office when needed. We don't believe in 9-5 and encourage flexible schedules with a focus on getting the job done.

The role will typically be 8-16 hours or more per week. Initially, it will require a more concentrated effort for a few weeks for training and onboarding, after which it will require 16-24 hours per week to become fully up to speed. As you implement and delegate day to day tasks to your team, total hours will normalize to typical levels however increase as volume grows from expansion into multiple markets and new clients.

We have a need for a strategic minded, senior bookkeeper to:

  • Initially handle day to day financial operations of Canadian and US activities
  • Develop, implement and manage an offshore team of virtual bookkeeping assistants for transaction entry, billing, job reconciliations, job and monthly reporting, and expense tracking
  • Assist in developing high level design and automation of financial systems integrating our various ecommerce services with our Quickbooks Online accounts
  • Manage registrations and timely filings in various US states and Canadian provinces where required by law
  • Provide ongoing feedback on processes for cost containment and improved efficiencies
  • Oversee accurate and timely completion of year end requirements and work closely with our accountants to ensure proper tax filings.


  • 5+ years of experience in bookkeeping and accounting.
  • Experience in financial management an asset
  • Excellent computer skills
  • Excellent communication skills, both verbal and written
  • General understanding of computerized accounting systems
  • Good working knowledge of MS Word, Quickbooks Online, Excel and databases
  • Sense of urgency when having to issue refunds or make payments to clients
  • Accuracy and attention to detail while working under tight deadlines
  • Assertive, comfortable communicating with and providing input and feedback to various types of individuals
  • Good interpersonal and customer service skills
  • Billing experience is an asset
  • Good team player
  • Able to build and maintain lasting relationships with corporate departments and key business partners
  • Ability to follow through and complete overlapping projects
  • Good organizational, time management and prioritizing skills
  • Strong problem identification and problem resolution skills
  • Ability to interpret and implement company policies and procedures.
  • Must use a Windows-based PC with at least Windows 10, and a reliable home office setup with high speed internet, cell phone, computers and peripherals.


(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.

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.

Compensation: $17-$25/hr

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 freelance 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.

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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