Medical Transcriptionist, Remote jobs in Ontario

Who are we?

We are a growing Managed IT Services Provider in central Toronto. For over 30 years we have delivered managed IT, cybersecurity, cloud, and data protection services to businesses across the GTA. A lot has changed in three decades, but our commitment has not: we exist to deliver the best IT support experience in the city, and to do that we hire people who genuinely care about doing the job right.

The values we hire for

These are not wall art. They are the standard every person on our team is measured against, and they are the standard you will be measured against here. If they resonate with you, we want to hear from you.

• Reliability comes first (our number one). Above everything else, you show up prepared, on time, you communicate clearly with everyone involved, and you keep your commitments. If you say it is handled, it is handled. This is the value that matters most to us: a brilliant technician who cannot be relied on is not someone our clients can trust.
• A can-do, client-first attitude. You bring energy to every problem and stay focused on the client's experience, not just the ticket.
• Respect for people. You treat colleagues, clients, and vendors with care, because everyone deserves it, and because it makes us better at what we do.
• A drive to keep improving. You stay curious, you learn from mistakes, and you keep sharpening your skills.

What you’ll do

As a Level 2 Technical Support Specialist you provide both remote and on-site support to our clients, and you act as an escalation point for more junior technicians. Day to day, you will:

• Diagnose and resolve escalated issues across desktops, servers, networks, security platforms, and cloud services, keeping the client informed at every step.
• Install, configure, and maintain client environments including Windows Server, Microsoft 365, networking, Wi-Fi, and firewalls.
• Own your tickets end to end in our PSA tool, documenting your work clearly so the next person (and the client) always knows where things stand.
• Create and improve standards, procedures, and documentation so we deliver consistent, repeatable results.
• Meet response and resolution commitments (SLAs) and juggle several clients and projects at once without letting anything slip.
• Make sure client data is backed up and recoverable, and flag risks before they become problems.
• Understand each client’s business and help translate technology into outcomes that matter to them.
• Participate in team meetings and initiatives to keep raising our service standard.
• Take part in a rotating after-hours / weekend on-call schedule.

What you need to be strong in

You do not need to have touched every technology we use. You do need to be genuinely strong across the fundamentals below, and comfortable communicating them to non-technical people:

• Windows desktop and Windows Server administration, including Active Directory, DNS, DHCP, and file/print services.
• Microsoft 365 administration: Exchange Online, SharePoint/OneDrive, and Entra ID (Azure AD).
• Networking fundamentals: TCP/IP, VLANs, VPN, DNS, and Wi-Fi, with the ability to troubleshoot connectivity methodically.
• Firewall administration on at least one major platform (for example Sophos, SonicWall, Fortinet, Meraki, Cisco, or Palo Alto).
• You possess strong written and verbal communication skills and are able to explain technical concepts to lay people. You bring a calm, clear, client-first manner to your end-user support, and this matters to us as much as your technical skill.
• Working with a PSA/ticketing system and an RMM tool, with disciplined documentation and time tracking.

Great to have, or things you’ll grow into with us

• Virtualization (Hyper-V or VMware).
• Cloud beyond Microsoft 365 (Azure, AWS, Google, Backblaze) and backup / disaster-recovery platforms.
• VoIP systems, particularly Asterisk / FreePBX.
• Linux (Ubuntu / CentOS), plus iOS and Android support.
• Certifications such as A+, Network+, CCNA, Microsoft, or Azure. Nice to see, not required.
• Structured cabling (Cat 5e / Cat 6, patch panels).

Experience

At least 3 to 5 years of hands-on experience supporting end users, ideally in an MSP or other multi-client environment where you have juggled competing priorities across several businesses. What we care about most is that you are a strong, reliable, well-rounded L2 who communicates well, not that you tick every box above.

Where and when you’ll work

• This role is in our central Toronto office every day to start. After you successfully complete probation, we offer 1 to 2 days per week of remote work.
• Core coverage is between 8:00 am and 6:00 pm, Monday to Friday. The workday is 8.5 hours, including a 30-minute paid lunch break, plus the rotating on-call schedule noted above.
• The role requires local travel to client sites, so a valid Ontario driver’s licence and access to a vehicle are required.
• This is primarily an office and client-site role. You will sit and use a computer for extended periods and occasionally lift or move IT equipment (up to roughly 50 lbs). Reasonable accommodations are available to enable individuals with disabilities to perform the essential functions of the role.

Compensation & benefits

The salary range for this role is $82,000 to $95,000 per year, based on experience and fit. On top of base salary, we offer:

• Profit sharing and an employee incentive program.
• A benefits program including dental and life insurance.
• Paid time off.
• A training allowance so you can keep building your skills.

How we hire

• This is a live vacancy for an immediate hire.
• We use an AI-assisted tool to help us organize and screen applications. Every hiring decision is made by our team, not by software.
• We respond to every candidate we interview, either way, so you are never left wondering.
• A criminal background check is part of our process because our clients trust us with confidential data. If you are selected for an interview, we reimburse the cost of the check.

Sound like you?

If the values above describe how you already work, and the fundamentals are squarely in your wheelhouse, we would love to hear from you. Please apply through this posting and tell us a little about why this role interests you.

Job Type: Full-time

Pay: $82,000.00-$95,000.00 per year

Benefits:

• Company events
• Dental care
• Extended health care
• Life insurance
• On-site parking
• Paid time off
• Profit sharing

Flexible language requirement:

• French not required

Application question(s):

• Do you have a valid Ontario driver's licence and access to a vehicle?
• This role is in-office in central Toronto every day to start, moving to 1-2 remote days after probation. Can you work on-site daily to begin?
• Briefly, how would you explain what a VPN is to a non-technical client?
• Briefly describe your hands-on experience with Windows Server / Active Directory, Microsoft 365, networking, and firewalls.
• What are your salary expectations?

Experience:

• end-user IT support: 3 years (required)

Work Location: In person