On-Site & Remote IT Technician (Level 3) – Hospitality

Job Summary

Job Types: Full time, Permanent

Pay: CA$80,000 – CA$100,000 per year

Benefits: Full employee benefits after successful completion of the 3-month probationary period

Work Location: Hybrid – approximately 70% on-site / 30% remote

Travel: Extensive travel throughout Ontario, including overnight, multi-day, and occasional extended stays

Preferred Base: Brantford / Greater Toronto Area

Candidates must be legally authorized to work in Canada as a Canadian Citizen or Permanent Resident.

About Daryl May & Associates

Daryl May & Associates is a specialized Managed IT Services Provider focused on the hospitality industry since 2005.

Hotels operate 24/7, and when technology fails, the impact can be immediate—from front desk operations and payment processing to Wi-Fi, reservations, staff productivity, and the guest experience.

Our role is to keep hotel technology stable, secure, and operating seamlessly in the background so hotel teams can focus on delivering exceptional guest experiences.

As we continue to grow, we are expanding our regional support model and are looking for an experienced Level 3 IT Technician who is equally comfortable working hands-on at hotel properties, travelling throughout Ontario, and providing professional remote technical support.

About the Role

This is a hybrid technical position consisting of approximately 70% on-site work and 30% remote IT support.

You will support hotel properties throughout Ontario, travelling on-site for technical issues, installations, maintenance, infrastructure work, and projects requiring physical intervention.

This role involves significant travel throughout Ontario. Technicians should be comfortable spending substantial time on the road, with site assignments sometimes requiring 1–3 day overnight stays and, depending on the project, location, or technical requirements, occasional extended stays at hotel properties. Travel is a regular and essential part of this position, not an occasional requirement.

When working remotely, you will be an active member of our technical support team—responding to support tickets, answering customer calls, troubleshooting issues remotely and over the phone, assisting hotel staff, documenting work, and escalating issues when required.

This is not a traditional field technician role, and remote days are not simply administrative days. Your on-site time is active, hands-on technical work at hotel properties, while your remote time is active Level 3 technical support time.

You should be comfortable moving between diagnosing a server, network, or infrastructure issue at a hotel property and remotely supporting users, systems, and technical tickets.

What You'll Do

In office Hotel IT Support – Approximately 70%

- Travel throughout Ontario to support assigned hotel properties
- Perform scheduled and emergency visits to hotel properties
- Complete multi-day assignments and overnight stays when required
- Diagnose and resolve hardware, network, Wi-Fi, connectivity, server, workstation, printer, and peripheral issues
- Troubleshoot technical issues directly with hotel management and staff
- Work efficiently in live, guest-facing hotel environments with minimal disruption
- Support servers, networks, firewalls, workstations, POS systems, printers, and peripheral equipment
- Perform physical diagnostics and hardware component replacements
- Assist with hotel openings, renovations, technology upgrades, migrations, and refreshes
- Support Wi-Fi deployments, adjustments, and troubleshooting
- Assist with structured cabling, patching, labeling, and physical connectivity troubleshooting
- Coordinate with vendors and internal technical teams while on-site
- Complete assigned project and maintenance work according to established standards
- Clearly document time entries, work performed, findings, and next steps

Remote Level 3 IT Support – Approximately 30% When working remotely, you will provide direct technical support to our hotel clients and assist with the day-to-day support queue.

Responsibilities include

- Responding to incoming support tickets
- Answering and responding to customer support calls
- Troubleshooting technical issues with hotel staff over the phone and remotely
- Managing and updating tickets through our PSA/ticketing system
- Providing professional, client-facing technical support
- Troubleshooting laptops, desktops, printers, and peripherals
- Supporting Windows and Mac environments
- Managing users in Active Directory
- Supporting Microsoft 365 / Office 365, including Outlook, licensing, users, and mailboxes
- Troubleshooting network, Wi-Fi, VPN, firewall, DNS, and connectivity issues
- Performing remote diagnostics and follow-up after on-site visits
- Using RMM and monitoring tools to investigate and resolve technical issues
- Coordinating with other technicians, infrastructure, and operations team members when escalation or additional resources are required
- Maintaining clear communication with clients throughout the lifecycle of a ticket




- Ensuring tickets are accurately documented, updated, time-tracked, and resolved
- Supporting scheduled maintenance and urgent technical needs when required

Server & Infrastructure Support You should be comfortable working hands-on with server and infrastructure equipment, including:

- Dell server hardware
- iDRAC troubleshooting and remote management
- RAID and hardware diagnostics
- Hardware component troubleshooting and replacement
- Server maintenance and refreshes
- Windows Server support
- Physical network infrastructure

You will work within established technical standards and escalate architecture-level decisions when appropriate. Networking & Security

You will support technologies including:

- SonicWall firewalls
- Cisco and HP network switches
- Wired and wireless networks
- VLANs
- VPN connectivity
- DNS and DHCP
- Wi-Fi infrastructure
- Structured cabling and patch panels
- Physical network troubleshooting

Depending on your experience and the scope of the work, you may also assist with NAT, VPN, firewall rules, and other configurations within established technical standards and processes. Installations & Projects

You may participate in

- New hotel openings
- Hotel renovations
- Network and Wi-Fi deployments
- Server installations and replacements
- Hardware lifecycle refreshes
- Workstation deployments
- POS and printer installations
- Network equipment replacements
- Cabling coordination
- Technology cutovers
- Equipment labeling, cleanup, and documentation

Projects may require travel, overnight accommodation, multi-day assignments, and occasional extended stays depending on the property location and scope of work. What You Will Not Be Responsible For

This role is focused on technical execution, troubleshooting, client support, ownership, and consistency.

You will not be expected to:

- Make architecture-level technical decisions outside established processes
- Make changes outside approved technical standards and procedures

Must-Have Technical Experience

- Previous Level 3 IT support or equivalent senior hands-on technical experience
- Active Directory experience
- Microsoft 365 / Office 365 administration and troubleshooting
- Strong Windows workstation support experience
- Familiarity with Android, iOS, and Mac environments
- Experience troubleshooting laptops, desktops, printers, and peripherals
- Strong understanding of networking fundamentals, including VLANs, DNS, DHCP, Wi-Fi, VPNs, and firewall concepts
- Experience using a ticketing or PSA system
- Experience providing technical support remotely and over the phone
- Ability to diagnose hardware and physical infrastructure issues on-site
- Strong troubleshooting and problem-solving skills
- Strong time management and ticket documentation skills
- Excellent verbal and written communication skills
- Ability to work independently while knowing when to escalate

Nice-to-Have / High-Value Experience Candidates with experience in the following areas will be given strong consideration:

- Hospitality or hotel IT experience
- Sales or client relationship experience
- Hotel systems such as Opera, Micros, Simphony, Saflok, or similar platforms
- Dell servers, including iDRAC and RAID
- SonicWall firewalls
- Cisco and HP switches
- Microsoft 365 administration
- PSA/RMM platforms such as Halo and Ninja
- Cybersecurity platforms such as Huntress and ThreatLocker
- Structured cabling, patch panels, and telecommunications infrastructure
- Low-voltage cabling vendor coordination
- Server hardware troubleshooting and component replacement
- Supporting live, customer-facing environments such as hotels, retail, healthcare, or restaurants

Requirements – Non-Negotiable

- Canadian Citizen or Permanent Resident
- Valid driver's licence
- Reliable personal vehicle
- Ability and willingness to travel extensively throughout Ontario
- Comfortable working in a role that is approximately 70% on-site and 30% remote
- Comfortable spending significant time driving and travelling between hotel properties
- Ability and willingness to complete 1–3 day overnight assignments and multi-night hotel stays
- Flexibility for occasional extended stays at hotel properties when required by a project, deployment, or technical issue
- Must genuinely enjoy road travel and be comfortable with a travel-intensive position
- Reliable high-speed internet and an appropriate environment for remote technical support
- Comfortable answering customer calls and providing technical support over the phone
- Comfortable managing and responding to a technical ticket queue
- Able to work independently both on-site and remotely
- Strong professional and customer-facing communication skills




- Comfortable working in active, guest-facing hotel environments
- Flexibility for occasional maintenance windows, urgent support needs, or project work outside standard business hours

Who You Are You enjoy technical problem-solving and don't want to be limited to either field service or a remote help desk. You are comfortable with a role where one week may involve significant travel between hotel properties and another may combine project work, site visits, and remote technical support.

You are

- A strong problem-solver
- Comfortable communicating directly with customers
- Confident troubleshooting both in person and remotely
- Self-sufficient and dependable
- Comfortable travelling frequently and working away from home when required
- Calm and professional under pressure
- Organized and detail-oriented
- Comfortable balancing on-site work with a remote ticket queue
- Able to manage multiple priorities and technical issues
- Comfortable taking ownership of an issue through resolution
- Able to follow structured technical processes and standards
- Coachable and interested in continuing to develop technically
- A robust team player who can also work independently
- Professional in guest-facing environments

Most importantly, you understand that technology in a hotel environment is mission-critical. A technical issue can affect check-ins, payments, reservations, hotel staff, operations, and ultimately the guest experience.

Our Core Values

At Daryl May & Associates, our core values guide how we work, how we support our clients, and how we show up as a team.

Accountability

We own every outcome and see it through to resolution.

Transparency

Clear communication, no surprises, and no hidden fees.

Integrity

We do what we say—every time.

Precision Under Pressure

We deliver accurate, high-quality work even when urgency is high.

Client-Centered Service

We make IT seamless so our clients can focus on their business.

What Success Looks Like

Success in this role means:

- On-site issues are diagnosed and resolved efficiently
- Remote tickets and customer calls are handled professionally and promptly
- Clients receive consistent service whether support is delivered remotely or in person
- Technical issues are owned through resolution rather than simply passed along
- Escalations include clear troubleshooting history and documentation
- Site visits and travel assignments are completed efficiently and professionally
- Work and time are documented accurately in the ticketing system
- Hotel teams feel supported and confident
- Communication with clients and internal teams is clear and proactive
- Projects and installations are completed according to established standards
- Guests experience minimal disruption from technology issues

Why Join Us

- A unique hybrid role combining hands-on field IT with Level 3 remote technical support
- Work with experienced IT professionals specializing in the hospitality industry
- Exposure to hotel networks, servers, cybersecurity, Wi-Fi, and specialized hospitality systems
- Opportunity to develop deeper infrastructure, networking, and advanced troubleshooting skills
- Growth opportunities toward senior technical, infrastructure, project, and leadership responsibilities
- Full employee benefits after successful completion of the 3-month probationary period
- Company-provided laptop and required remote-work technology
- Mileage reimbursement for approved business travel
- Paid time off
- Company events
- Casual dress where appropriate
- Work-from-home flexibility during designated remote support time

Why This Role Matters You will play an important role in our regional support model by creating continuity between our hotel properties and centralized technical support team.

You may physically diagnose an infrastructure issue on-site, continue troubleshooting remotely, coordinate with other technical team members, and follow the issue through to completion.

As we grow, this regional model will become part of a broader support structure across multiple hotel properties and regions, creating opportunities for technicians who demonstrate solid technical ability, accountability, client service, and leadership.

How to Apply

Please submit

- Your resume
- A short note outlining your hands-on IT, networking, server, and remote support experience
- The city or region in Ontario where you are currently based
- A brief description of your experience supporting customers over the phone or through a ticketing system
- Languages spoken
- Confirmation that you are comfortable with extensive travel throughout Ontario, including overnight and multi-day stays

If you enjoy the variety of working hands-on at client sites, spending time on the road, and providing professional Level 3 remote technical support, we'd like to hear from you. Pay: $80,000.00-$100,000.00 per year

Benefits

- Dental care
- Extended health care
- Life insurance
- Mileage reimbursement
- On-site parking
- Paid time off
- Work from home

Language:
- English (required)

Willingness to travel:
- 75% (required)

Work Location: On the road

📌 On-Site & Remote IT Technician (Level 3) – Hospitality (Brantford)
🏢 Daryl May u0026 Associates
📍 Brantford