Site Support Specialist

Our Toronto Canada office has the opportunity for an experienced Site Support Specialist to join the Firms expanding technology department. The Site Support Specialists primary responsibilities include providing 1st and 2nd level technology support for attorneys and staff on a variety of hardware and software. As part of a Regional support team provide technology support for other offices in the region including travel to these locations as needed. The candidate will participate in firm and department technology initiatives as needed.

• Windows OS and application software installation repair and support.
• Imaging deployment and support of desktops laptops and peripherals including user profile provisioning.
• Hardware installation repair and support including printers conference room A/V equipment wireless access points and server room equipment.
• Keeps accurate inventory of supported offices equipment.
• Troubleshooting network connectivity from desktop and laptop computers.
• Mobile device setup and support.
• Telephone administration setup and support. Including moves/adds/changes.
• Provide excellent customer service and practice total contact ownership from acknowledgement to closure. Document problem description and resolution using ITSM system. Participate in ticket creation escalation and follow-up.
• Keep current on the firms needs with regular communication with Office Administrator; be proactive in identifying technology solutions and preventing potential problems; act as the local office liaison and end-user advocate as it relates to technology.
• Work with other technology department teams including Service Desk Endpoint Administration Applications team and Infrastructure team.
• Consistently act in support of overall firm and department initiatives goals and objectives.

• Four-year technical degree from an accredited college or university or equivalent work experience.
• Minimum of four years experience in a technical support position. Law firm experience a major plus.
• Working knowledge of Dell and Lenovo laptops and desktops Microsoft Windows OS Microsoft Office Suite Document Management System Mobile devices and enterprise network.
• Independent analysis and strong problem solving skills.
• Strong customer service and communication skills (face-to-face phone and email)
• Law firm experience a major plus
• Microsoft Office and Azure certifications preferred
• Help Desk Institute ITIL Foundation and CompTIA A certification preferred
• Document Management System support experience a plus
• SCCM experience a plus
• Mobile Device Management experience preferred

Please note we are not working with outside recruiters for this position.

Ogletree Deakins offers a robust suite of benefits for staff including: Paid Time Off Sick Time RRSP matching program TFSA reimbursement of commuting expenses including TTC or Go Transit Paid Holidays Paid Parental Leave Health and Life Insurance including Dental and Vision coverage Tuition Reimbursement and an Employee Assistance Program.

If you have questions please e-mail Megan Becker at with Site Support Specialist in the subject line. Please note applications submitted via e-mail will not be considered.

Ogletree Deakins is one of the largest labor and employment law firms representing management in all types of employment-related legal matters. Best Law Firms has named Ogletree Deakins a Law Firm of the Year for 14 consecutive the 2025 edition the publication named Ogletree Deakins its Law Firm of the Year in the Litigation Labor and Employment category. Ogletree Deakins has more than 1100 attorneys located in 60 offices across the United States and in Europe Canada and Mexico. The firm represents a diverse range of clients including many of the Fortune 50 companies in the U.S.

We are fully committed to the importance of diversity within the legal profession as well as all workplace environments.

Equal Opportunity Employer.