Careers

Help Desk Technician

Posted: November 2025.

Deadline: When we find the right person. If this post is up, we are taking applications.

Title: Help Desk Technician
Company: Inderly – IT for Law Firms
Location: Primarily remote, with occasional on-site client visits. Our offices are in Toronto, Hamilton, and Stratford. You must reside in the GTHA/KW area. A co-working desk can be provided near your location should you prefer to work outside the home. 

Required experience: > 1 year

Salary: Starting $50k/year, or $55k/year if you have more than 3 years of help desk experience (plus the opportunity for occasional paid On Call time), plus health benefits. 

We are seeking a new help desk technician to help our growing list of legal clients with their IT support and hosting. 

Who are we? 

Inderly is a family-owned managed IT services and hosting provider with a focus on the legal sector. We want you to come here, learn, and stay with us as we grow. 

We offer only fully managed service agreements. We apply an extremely high level of standardization to our services. 

We pride ourselves on having great relationships with our clients, many of whom are longstanding. We do this by holding both ourselves and our clients accountable to our core values – doing what we say we are going to do; engaging in respectful and productive communication; and transparency (“clear is kind”). 

We are committed to creating an environment that supports equal opportunity, inclusion, and nondiscrimination for all staff and contractors at our company, regardless of race, ethnicity, religion, sex, age, sexual or gender identity, gender expression, marital status, national origin, or disability. 

Who are you? 

You are a great communicator and like helping people first. Technology is second.  

You have fluent written and spoken communication skills in English. 

You are looking for an opportunity to expand your expertise and level up your career. 

You have been working in the IT sector or providing some level of technology support for at least a year. 

You have experience helping others with some (but does not have to be all) of the below technologies: 

  • Windows 11 desktop support 
  • Office 365 
  • Active directory 
  • Remote Desktop 
  • A ticketing/RMM system 
  • Veeam backup 

Further requirements: 

  • You are physically capable of carrying and installing a desktop computer (approximately 35 lbs) and able to crawl under a desk. You will not be asked to climb a ladder or use any power tools. 
  • You reside in the GTHA or KW area. 
  • You have a valid driver’s license (a car is not required). 
  • You have a quiet, dedicated place to work at home or remotely. 
  • You are available for approximately 2 On Call days per month (more info on that below). 

What does the job look like? 

This is a remote-first position with on-site visits to our clients as needed. You must be available to attend client sites as required in the GTHA, sometimes same-day. We cover your travel either by Uber, transit, or mileage reimbursement if you have your own vehicle. You can expect to be on site with a client 1-2 times a month. 

You will primarily be joining our help desk manager to provide day-to-day support to our clients. In a typical week you will: 

  • Set up new user accounts and help new users get to work on their systems. 
  • Set up new computers. 
  • Assist users with accessing their systems (password resets, troubleshooting network issues). 
  • Make account changes upon request such as Office 365 delegations, printer settings, assigning access to 3 third party software such as Adobe. 
  • Triage issues with software such as PCLaw and work with third-party support to resolve issues. 
  • Investigate automated alerts such as low disk space, performance alerts and backup alerts by following our established processes. 
  • Record the time you spent on these issues so we can figure out what to automate next. 

In addition, you will work with our CEO and technical lead to help with our hosting environment by setting up new clients and performing ongoing maintenance tasks and checks. Training will be provided for this portion of the role. 

What’s in it for you? 

We want this to be the place you come to level up your career but stay around because we’re taking care of you. 

This is not a “hit the ground running” position. You will be trained on our processes and work closely with the CEO and help desk manager as you ramp up with us and we onboard new clients. 

Over time you will learn how a private cloud hosting environment is built and maintained. 

Our regular working hours are 9 AM-5 PM. We don’t bleed into overtime. 

Compensation: 

Salary starts at $50k/year, or $55k/year if you have more than 3 years of help desk experience. 

Expect winter holiday bonuses and annual increases over and above inflation as you grow in the role. 

Health, drug, dental, and wellness benefits coverage. 

There will be the opportunity for approximately 2 On Call days per month, paid at $35/day, plus $131/hour for any time spent actually working (minimum 1 hour). Our On Call utilization is very low, expect to be paged for On Call work less than 20% of the time you are on call. 

10 vacation days (starting). 

5 sick days. 

1 pre-scheduled “mental health/disconnect” day off per month, usually a Friday. 

1 half-day per month for “human maintenance” (doctor, dentist appointments, etc.). 

How to apply: 

While we do not believe in making applicants jump through hoops, due to the overwhelming number of AI-generated applications we receive, applications that do not meet the below requirements will not be considered: 

  1. Subject line: Include the word “BlueJays” somewhere in the subject line, but not as the first or last word. (Example: “Application – BlueJays – IT Technician”)
  2. Attachment: Attach your resume as a PDF named exactly: Lastname_Firstname_BlueJays.pdf
  3. In the body of your email: In 2–4 sentences, describe a technical problem you personally solved in the last 6 months. Please focus on your thought process and how you approached the problem, not the final outcome.
  4. In the body of your email: The city in which you currently reside.
  5. Email your application to: helpdeskcareers@inderly.com