Senior IT Support Specialist (Level 2), Grimsby

Information Technology - Managed Services

Full-time, Permanent, Hybrid

Grimsby, ON

Expert Troubleshooter. Trusted Advisor. Problem Solver. If that sounds like you, you will fit right in.

At AOS, every team member plays a role in our success and culture. We value curiosity, coachability, and an entrepreneurial mindset, paired with dedication, resilience, and high performance. Collaboration, accountability, and exceptional client service are at the core of everything we do.

We’re looking for a Senior IT Support Specialist (L2) who thrives on solving complex problems, supporting teammates, and building trusted relationships with clients.

About Us At AOS, we specialize in providing office technology and managed services to businesses of all sizes. Our mission is to help organizations boost productivity, streamline workflows, and manage costs with ease.

We apply technology to drive profit, productivity, and peace of mind for our clients. Through reliable solutions and top-notch customer service, we ensure our clients can focus on what they do best.

We hire with the future in mind. With strong career growth opportunities, AOS fosters a dynamic environment where teams are challenged, supported, and continuously learning. If you’re excited to make an impact and grow with a forward-thinking, tech-driven team, we’d love to meet you.

About The Role As our Senior IT Support Specialist (L2), you will serve as a trusted technical advisor and escalation expert. You will take ownership of complex issues, support our L1 team, and drive proactive improvements that strengthen system reliability and client experience.

You’ll combine advanced technical skills with leadership, strong communication, and a client-first mindset.

What You’ll Do

Serve as the primary escalation point for complex and high-impact issues

Own problems from start to finish, ensuring strong outcomes for clients

Provide expert-level support across hardware, software, networking, and cloud systems (remote and onsite)

Troubleshoot Advanced Issues Related To

Windows environments

Microsoft 365 and SaaS platforms

Networks, firewalls, and security controls

Manage and maintain core IT systems, including:

Patching and updates

Backup and recovery

Antivirus and endpoint protection

Monitoring and alerting tools

Collaborate on projects, solution design, and IT initiatives

Support client onboarding and ongoing service improvements

Identify recurring technical or operational patterns and recommend proactive solutions

Document all work thoroughly in our PSA system

Mentor and support L1 team members through coaching and hands‑on problem solving

How Success Is Measured

Escalation resolution efficiency

Customer satisfaction (CSAT) scores

Proactive issue identification and prevention

Contribution to long‑term system stability and reliability

Proactive Improvement Expectations

Provide leadership with a monthly update on recurring trends and risks

Deliver at least one proactive solution per quarter that improves stability, efficiency, or client experience

What We Expect

Take full ownership of assigned issues until resolved or properly escalated

Remain calm, focused, and solution‑oriented under pressure

Communicate clearly and collaborate effectively

Demonstrate empathy, adaptability, and strong critical thinking

Be a positive role model for the service team

Required Experience And Certifications

3-5 years of IT support or systems administration experience, with a strong background in troubleshooting complex hardware, software, networking, and cloud environments.

Proven experience providing mentorship or guidance to junior team members and supporting escalations

MSP experience preferred.

ITIL Intermediate or ITIL Foundation, CompTIA A+, CompTIA Network+ or CompTIA Security+, Microsoft 365 Certified: Administrator Expert are required

Why Join Us? At AOS, you will be part of a collaborative, growth‑focused team where your expertise truly matters. You will have the opportunity to

Make a visible impact on client success

Mentor and develop junior team members

Grow into senior technical and leadership opportunities

Work on meaningful projects and initiatives

Be recognized for your contribution and performance

You are not just resolving escalations, you are shaping how we deliver exceptional service.

How To Apply If you’re passionate about technology, love solving complex problems, and enjoy helping both clients and teammates succeed, we’d love to hear from you.

Please submit your resume and a cover letter explaining why you’re a great fit for the Senior IT Support Specialist (L2) role at AOS.

Our Commitment to Inclusion We are an equal‑opportunity, affirmative action employer. We value and welcome diversity and are committed to creating an inclusive environment where everyone feels they belong.

We provide reasonable accommodations throughout the recruitment process. If you require assistance, please let us know. We celebrate diverse backgrounds, experiences, and perspectives and encourage all qualified candidates to apply.

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