Senior Helpdesk Engineer - Pathway to Technical Lead

Senior Helpdesk Engineer — Pathway to Technical Lead

Are you the engineer others turn to when a problem needs deeper investigation? Can you take ownership of a complex issue, communicate confidently with customers and help other engineers improve?

CyberAgency Group is seeking a Senior Helpdesk Engineer with broad technical expertise, a strong service mindset and the ambition to grow into a Technical Lead role.

This is a hands-on opportunity for an experienced MSP all-rounder who enjoys solving problems across cloud, infrastructure, networks and security—and wants greater influence over how support is delivered.

The opportunity

You’ll own escalated support issues, support a diverse range of customer environments and contribute to projects and service improvements. You’ll combine technical depth with practical judgement: understanding business impact, prioritising effectively and keeping customers informed.

As you demonstrate technical leadership, sound decision-making and the ability to develop others, there is a pathway to Technical Lead.

What you’ll do

• Resolve complex Level 2 and Level 3 incidents across Microsoft 365, Windows, identity, endpoints, servers and networks.
• Own issues from investigation through to resolution, coordinating with customers, vendors and colleagues.
• Troubleshoot Microsoft 365 services, including Exchange Online, Teams, SharePoint and OneDrive.
• Administer and support Entra ID, Active Directory, Intune, device compliance and access controls.
• Diagnose networking issues involving firewalls, VPNs, DNS, DHCP, switching and Wi-Fi.
• Support backup and recovery, endpoint security, patching and reliable day-to-day operations.
• Contribute to cloud migrations, customer onboarding, infrastructure upgrades and other technical projects.
• Identify recurring issues and address root causes through documentation, standardisation and automation.
• Maintain accurate tickets, time entries, technical notes and customer documentation.
• Mentor other engineers, share knowledge and help improve the quality of escalations and resolutions.

What you’ll bring

• Proven senior helpdesk or systems engineering experience in an MSP supporting multiple customer environments.
• Strong hands-on capability across Microsoft 365, Windows Server, identity, endpoint management and networking.
• A structured troubleshooting approach and the ability to work through unfamiliar problems.
• Experience managing competing priorities while meeting service commitments and maintaining quality.
• Clear, professional communication—you can explain technical issues in plain language and set realistic expectations.
• A security-conscious approach to administration, access, change management and customer information.
• Commercial awareness: you understand the importance of accurate time recording, scope boundaries and escalating additional work.
• The independence and accountability to work effectively in a remote team.
• A willingness to coach colleagues, take initiative and raise the standard of service.

Bonus experience

• Hands-on cloud migration delivery, such as Microsoft 365 tenant migrations, email migrations, SharePoint/OneDrive migrations or Azure workload migrations.
• ConnectWise PSA experience, including ticket management, service boards, time entries and reporting.
• PowerShell scripting, RMM platforms and practical support automation.
• Azure administration, virtualisation or hybrid cloud environments.
• Relevant Microsoft, networking or cybersecurity certifications.

Your pathway to Technical Lead

Progression will be based on demonstrated capability and business needs, with a focus on:

• Becoming a trusted escalation point for complex technical issues.
• Improving team capability through coaching and knowledge sharing.
• Leading technical delivery and coordinating effective incident resolution.
• Strengthening documentation, technical standards and service quality.
• Building customer confidence through reliable advice and follow-through.

This role suits someone who wants to remain hands-on while growing into technical leadership.

Why join CyberAgency Group?

• Work remotely from within Australia.
• Gain exposure to varied customer environments across managed IT and cybersecurity.
• Have a direct influence on service improvements and technical delivery.
• Build your leadership capability through meaningful responsibility.