Family Options Inc.
Employment Type: Full-Time
Department: Information Technology / Technology Services
Location: Toronto (hybrid)
Experience: 3–5 years
Certification: Microsoft 365 certification required

Compensation: $65,000-75,000 per year, commensurate with experience and qualifications, plus a benefits package and professional development opportunities.

About Family Options (FO)

FO is a small but growing organization with a strong sense of purpose and a people-first culture. We support youth and adults with complex care needs, helping individuals achieve their developmental goals while promoting dignity, independence, inclusion, and a meaningful sense of belonging.

As our organization continues to grow, so does our reliance on technology. We currently support more than 100 end users across our organization, and we are entering an exciting period of technology transformation. We are moving away from a legacy technology platform and establishing Microsoft 365 as the foundation of our modern technology environment.

This transformation is more than a technology upgrade. It is an opportunity to rethink how our people collaborate, communicate, access information, and deliver services. Following the successful transition to Microsoft 365, our technology roadmap will evolve toward the development of custom applications and digital solutions designed specifically around our business needs.

The Level 2 Technology Helpdesk Specialist is a new position that will play an important role in this transformation. You will be joining at a pivotal point in our technology journey, with the opportunity to help build a stronger, more secure, and more effective technology environment from the ground up.

Because we are a relatively small organization, your work will be visible, your ideas will matter, and your ability to take ownership will have a direct impact on our organization. The successful candidate will have the opportunity to work across a broad range of technologies, participate in strategic technology initiatives, and grow alongside the organization.

Position Summary

The Level 2 Technology Helpdesk Specialist will provide hands-on technical support for hardware, software, Microsoft 365, networking, user accounts, and other technology services across FO.

This is a Level 2 support role, requiring the ability to independently diagnose and resolve issues that cannot be addressed through basic first-line troubleshooting. The successful candidate will be comfortable working directly with users, investigating complex technical problems, documenting solutions, and escalating issues appropriately when required. Since we are small organization, the position will also play a role in addressing first-line troubleshooting.

The ideal candidate combines strong technical knowledge with patience, professionalism, excellent communication skills, and a service-oriented approach.

Key Responsibilities

Technical Support

- Provide Level 2 technical support to staff through phone, email, remote support, and in-person assistance.
- Diagnose and resolve hardware, software, connectivity, printing, authentication, and application issues.
- Troubleshoot Windows workstations, laptops, mobile devices, peripherals, printers, and related technology.
- Support Microsoft 365 applications and services, including Outlook, Teams, OneDrive, SharePoint, and Microsoft Office applications.
- Troubleshoot Microsoft 365 user access, licensing, permissions, MFA, and account-related issues.
- Manage and troubleshoot user accounts, password resets, access permissions, and security-related support requests.
- Investigate recurring technical issues and identify opportunities for permanent solutions.
- Escalate complex incidents to senior IT resources, vendors, or third-party service providers when appropriate.

Microsoft 365 & Cloud Administration

- Assist with the administration and support of the Microsoft 365 environment.
- Support Microsoft Entra ID/Azure AD user identities, groups, authentication, and access.
- Assist with Microsoft 365 licensing and user provisioning/deprovisioning.
- Support Microsoft Teams, SharePoint, OneDrive, Exchange Online, and related services.
- Assist with implementing and maintaining Microsoft 365 security and productivity best practices.

Security & Compliance

- Follow organizational policies and procedures relating to information security, privacy, confidentiality,



and acceptable technology use.
- Assist with endpoint security, antivirus/EDR, patching, and device management.
- Identify and escalate potential security incidents, phishing attempts, suspicious activity, or unauthorized access.
- Handle confidential organizational and personal information with discretion and professionalism.
- Support technology practices that protect the privacy and dignity of the individuals and families served by our organization.

FO emphasizes privacy, dignity, accessibility, and compliance with applicable legislative and regulatory requirements.

Documentation & Continuous Improvement

- Maintain accurate records of incidents, service requests, troubleshooting steps, and resolutions.
- Develop and maintain knowledge-base articles and user documentation.
- Identify recurring issues and recommend improvements to systems, processes, and user training.
- Assist with technology deployments, upgrades, migrations, and organizational projects.
- Provide basic technology training and guidance to staff as required.

Required Qualifications

- 3–5 years of progressive experience in an IT helpdesk, service desk, desktop support, or technical support environment.
- Current Microsoft 365 certification required (such as Microsoft 365 Certified: Administrator Associate or another relevant Microsoft 365 certification).
- Strong working knowledge of Microsoft 365 administration and troubleshooting.
- Strong knowledge of Windows operating systems and Microsoft Office applications.
- Experience troubleshooting hardware, software, network connectivity, printers, peripherals, and user-access issues.
- Experience with Microsoft Entra ID/Azure AD and cloud-based identity management.
- Familiarity with multi-factor authentication, endpoint security, and common cybersecurity practices.
- Experience using a ticketing/service management system.
- Strong analytical and problem-solving abilities.
- Excellent verbal and written communication skills.
- Solid organizational skills and attention to detail.
- Ability to prioritize competing requests and manage incidents through to resolution.
- Ability to work independently while collaborating effectively with a multidisciplinary team.
- Demonstrated commitment to confidentiality, privacy, professionalism, and respectful service.

Assets / Preferred Qualifications

- Microsoft certifications beyond the required Microsoft 365 certification.
- Experience with Microsoft Intune and endpoint/device management.
- Experience supporting Microsoft Teams, SharePoint, OneDrive, and Exchange Online.
- Knowledge of networking fundamentals, including TCP/IP, DNS, DHCP, Wi-Fi, VPNs, and VLANs.
- Experience with cybersecurity tools and practices.
- Experience supporting organizations operating across multiple locations.
- Experience in a healthcare, social services, developmental services, or other regulated environment.
- Familiarity with privacy and accessibility requirements in Ontario.
- Desirable: Interest in AI, automation, low-code development and emerging technologies, with a desire to develop these skills as FO builds custom applications and digital solutions.

What We're Looking For

The successful candidate will be more than a technical troubleshooter. You will be someone who:

- Treats every user with patience, respect, and professionalism.
- Takes ownership of problems and follows through to resolution.
- Can translate technical concepts into clear, understandable language.
- Understands that technology supports people—not the other way around.
- Is comfortable working with staff who have varying levels of technical knowledge.
- Looks for practical solutions when barriers arise.
- Values accountability, collaboration, integrity and responsible compassion.
- Understands the importance of protecting confidential information.

These qualities align closely with FO's Core Values of accountability, collaboration, integrity and responsible compassion, as well as its commitment to individualized support and community inclusion.

Working at FO





Working at FO means joining a small, collaborative, and growing organization where technology has a direct and meaningful impact on the people we serve.

Our technology environment is at an important inflection point. With more than 100 end users and continued organizational growth, we are actively transitioning from a legacy platform to Microsoft 365, creating a modern foundation for communication, collaboration, security, and information management.

This role will be at the centre of that transition.

In the immediate term, you will help support our users and ensure a successful adoption of Microsoft 365. You will have opportunities to contribute to the migration, configuration, documentation, user education, troubleshooting, and ongoing optimization of our new environment.

But the vision extends beyond Microsoft 365.

Once our Microsoft 365 foundation is established, FO intends to develop custom applications and technology solutions that address our unique operational needs. This creates an exciting chance for a technically curious individual who wants to do more than close helpdesk tickets. The successful candidate will be able to contribute ideas, identify opportunities for improvement, participate in technology projects, and potentially grow into broader systems, application, automation, or technology administration responsibilities as our environment evolves.

Because our IT team is lean, this position requires someone who is comfortable rolling up their sleeves, solving problems independently, learning new technologies, and taking ownership from start to finish. You will interact directly with employees across the organization and work closely with leadership and other stakeholders to understand needs and turn them into practical technology solutions.

Career Evolution & Future Growth
While your core immediate responsibilities focus on standard IT support and stabilizing our Microsoft 365 foundation, FO is a growing organization entering a major digital transformation. For the right candidate, this role offers a distinct pathway to expand into emerging tech.

As part of this evolution, FO will support ongoing professional development and upskilling in AI and emerging technologies, providing the successful candidate with opportunities to develop the skills needed to help design, build and support custom AI-enabled applications that can improve how hundreds of employees work, collaborate and deliver services across Canada.

Hybrid Work Environment

This is a hybrid position that combines remote work with regular opportunities for in-person collaboration at our Head Office in Toronto, located near Yonge Street and Lawrence Avenue.

The successful candidate will be expected to visit Head Office occasionally when in-person support, collaboration, meetings, technology projects, or other organizational needs require it. Employees also can work from Head Office at least 1–2 days per week, providing flexibility while maintaining regular face-to-face connection with colleagues and the broader organization.

Given the hands-on nature of Level 2 technology support, the ability and willingness to attend the office when required is an important part of the role. Rarely, travel may be required to our local sites around the Golden Horseshoe in southern Ontario.

For the right person, this is an opportunity to join FO at the beginning of an important technology journey—helping us move from legacy systems to Microsoft 365 today and toward purpose-built digital solutions tomorrow.

If you are looking for a role where you can combine strong Level 2 technical support skills with the opportunity to help shape a growing organization's technology future, this position offers significant room to contribute, learn, and grow.

Application

If you are an experienced IT professional with strong Microsoft 365 expertise and a passion for providing excellent technical service, we would like to hear from you.

Please submit your resume and cover letter outlining your relevant experience and Microsoft 365 certification.

FO is committed to accessibility, dignity, independence, integration, and equal opportunity, and is committed to preventing and removing barriers to accessibility.

Pay: $65,000.00-$75,000.00 per year

Benefits:

- Employee assistance program
- Life insurance
- Paid time off
- Work from home

Work Location: Hybrid remote in Toronto, ON (Toronto District)

📌 IT Support & Microsoft 365 Specialist (Toronto)
🏢 Family Options
📍 Toronto