Canada only | Remote | Task-based | Long-term collaboration

I run an established Canadian document services company and am looking for someone based in Canada to become a long-term part of our processing team.

Our work primarily involves Canadian record suspension applications, U.S. entry waiver applications and related document processing.

I'm not looking for a traditional hourly administrative assistant or someone who wants a few tasks and then moves on.

I'm looking for someone I can personally train on an established process, who can start by working through files alongside me and eventually become someone I can confidently hand a client file to and know it will be handled properly.

You do not need previous experience with record suspensions or U.S. entry waivers. I'll teach the right person.

What matters much more to me is that you're careful, dependable, organized, comfortable dealing with clients and genuinely interested in becoming part of the team long term.

How the role starts

We will start on a per-task basis while you learn the process.

Each file consists of a series of specific tasks. You'll initially complete individual pieces of the file while I remain actively involved, provide instructions, answer questions and review your work.

During this learning stage, the tasks associated with a fully completed file will total approximately:

US$35 / CAD$50 per completed file

This is the starting structure while we're working through files together and I'm providing hands-on training. It is not intended to be the long-term rate.

Progression to US$100 per file

Once you demonstrate that you:

- Understand our processes and systems

- Consistently produce accurate work

- Can communicate professionally with clients

- Know when you can proceed independently and when something should be escalated

- Can move a file forward without requiring me to supervise every step

I can begin handing files off to you directly.

At that point, compensation increases to:

US$100 per completed file

There isn't an arbitrary number of training files required to reach that point. If you pick things up quickly and demonstrate that I can trust you with the work, you'll progress quickly.

The goal is to develop this into consistent ongoing file volume and a long-term working relationship.

What you'll actually be doing

Depending on the file and where it is in the process, tasks can include:

- Reviewing client files and determining what remains outstanding

- Preparing application forms using information already collected

- Speaking with clients to obtain missing information

- Taking detailed client notes and organizing client-provided information into draft documentation

- Preparing requests for supporting documents

- Following up on outstanding court, police and government documents

- Reviewing returned documents for completeness and inconsistencies

- Maintaining organized digital client files

- Following established checklists and procedures

- Identifying anything unusual and bringing it to my attention

- Preparing completed packages for final review

You'll be dealing with sensitive personal information, so confidentiality and good judgment are essential.

Who would be a good fit

You may have experience as a legal assistant, law clerk, paralegal/paralegal student, caseworker, government administrator, immigration/legal-services administrator, document processor or another detail-oriented administrative professional.

But legal experience isn't required.

I'd rather train someone intelligent, careful and dependable who wants to learn than hire someone with extensive experience who isn't interested in our way of working.

I've been involved in this type of work for more than a decade. We already have established processes, templates, instructions and checklists.

I absolutely expect you to ask questions. If something doesn't make sense, something in a file doesn't match, or you have a genuine concern, I want you to raise it.

What I'm looking for in return is someone who is willing to learn and understand the existing process first, become proficient at it, and then help us improve things as they gain experience.

What I'm ultimately looking for

I'm not trying to hire someone for five files.

I'd like to find someone who can become a genuine part of the processing side of the business.

Initially, you'll work closely with me.

Over time, I should need to be involved less and less.

Eventually, I'd like to be able to assign you a file, have you move it through our system, deal with the normal issues that arise, escalate the things that actually require my attention, and bring the file to completion.

If you're looking for a short-term freelance project, this probably isn't the right opportunity.

If you're interested in learning a specialized area of document processing, becoming very good at it and building a longer-term working relationship with consistent work, I'd like to speak with you.

To apply

Please answer these questions in your proposal:

1. Where in Canada are you located?

2. What experience do you have working with sensitive, administrative or document-heavy client files?

3. Tell me about a role where you had to learn and consistently follow an established process where accuracy mattered.

4. Are you comfortable starting on a task-based structure totaling approximately US$35 / CAD$50 per completed file while you're learning alongside me, with compensation increasing to US$100 per completed file once you demonstrate that you can reliably manage files within our system with minimal supervision?

5. What are you looking for over the next 1–2 years, and why does a long-term collaboration like this interest you?

If you have experience with legal files, record suspensions, pardons, U.S. entry waivers, immigration matters, court documents, government applications or case management, please mention it.

Please don't send me a generic proposal. I'd much rather understand who you are, how you work and what you're looking for.

I'm looking for someone dependable who wants to learn the process, become excellent at it and grow into a trusted long-term member of the processing team.

Back to blog

Other Jobs To Apply

No other job posts for this day.

Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...