Senior Technical Lead – Helpdesk & Projects

Work set-up: 
Full Remote
Contract: 
Experience: 
Senior (5-10 years)
Work from: 

Offer summary

Qualifications:

Proven experience in a senior technical support role, preferably in an MSP or IT services setting., Strong knowledge of Windows 10/11, Windows Server, Active Directory, and Office 365 administration., Working knowledge of DNS, DHCP, MX records, SPF/DMARC, and email tracing., Familiarity with PowerShell scripting and endpoint security tools..

Key responsibilities:

  • Supervise and mentor the technical support team, providing guidance and professional development.
  • Manage the helpdesk ticketing system and ensure effective triage, prioritisation, and resolution of tickets.
  • Lead or assist in technical projects, coordinating with stakeholders and internal resources.
  • Document solutions, processes, and SOPs clearly and share knowledge with the team.

The Outline logo
The Outline https://theoutline.com/
11 - 50 Employees
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Job description

About the Company

Our client is not your average IT company, a team of passionate tech wizards who love solving problems, streamlining business operations, and delivering top-notch IT solutions that make life easier.
We believe IT should be affordable, stress-free, and tailored to your needs. That’s why we take a proactive approach to IT management, ensuring that your business runs smoothly with minimal downtime and maximum performance.

About the Role

We're on the lookout for a Senior Technical Lead—a hands-on, sharp-minded problem solver who thrives on both the technical and people sides of IT. You're the MacGyver of your team, equally comfortable writing PowerShell scripts as you are coaching junior techs. This role blends leadership, technical escalation, client interaction, and process ownership into one dynamic position.


Key Responsibilities

Leadership & Team Management

- Supervise and mentor the technical support team, providing guidance, support, and professional development.
- Lead by example—be the go-to escalation point for complex tickets and projects.
- Promote a culture of ownership, curiosity, and continuous learning.

Helpdesk & Client Support
- Manage the helpdesk ticketing system and ensure effective triage, prioritisation, and resolution of tickets.
- Answer and resolve incoming support requests—phone, email, or ticket-based—with a calm and confident tone.
- Provide L2-L3 support across desktop, server, and cloud environments.

Project & Process Ownership
- Assist and/or lead technical projects, coordinating with stakeholders and internal resources.
- Assist in scoping, designing, and deploying IT solutions, both commercially and technically.
- Improve systems and workflows proactively by identifying recurring problems and bottlenecks.

Documentation & Knowledge Sharing
- Document solutions, processes, and SOPs clearly and share knowledge with the team to lift collective capability.
- Prepare regular reports on ticket trends, resolution times, and client satisfaction.


Technical Skills & Experience
  • Proven experience in a senior technical support role, preferably in an MSP or IT services setting.
  • Strong knowledge of Windows 10/11, Windows Server, Active Directory, and Office 365 administration.
  • Working knowledge of DNS, DHCP, MX records, SPF/DMARC, and email tracing.
  • Familiarity with PowerShell scripting and endpoint security tools.
  • Exposure to macOS and a willingness to explore and troubleshoot unfamiliar systems.
  • Experience with project management tools and helpdesk systems (e.g., SuperOps, ConnectWise, Autotask).
  • Ability to work both autonomously and collaboratively, especially in a hybrid or remote setup.

  • Soft Skills & Attitude
  • Proactive, self-motivated, and constantly looking for opportunities to optimise and improve.
  • Curious and independent—comfortable learning new systems and uncovering functionality without prompting.
  • Strong communicator who can explain technical concepts in plain language.
  • Supportive team player who uplifts others and encourages knowledge sharing.
  • Calm under pressure and comfortable engaging with clients directly and confidently.


  • Perks & Benefits
  • Supportive and flexible work environment with a high-performing team.
  • Opportunities for career growth in a rapidly evolving company.
  • Exposure to innovative tools and real autonomy to lead change.

  • Baseline Software Understanding: Core Technical Software Knowledge
  • Windows 10/11 – in-depth troubleshooting and config
  • Windows Server (2016/2019/2022) – AD, DNS, DHCP, Group Policy
  • macOS (basic to intermediate) – support and user management


  • Productivity & Collaboration
  • Microsoft 365 – admin portal, licensing, mailbox and user management
  • Microsoft Teams / SharePoint / OneDrive
  • Outlook – PST handling, email delivery issues, profile repair

  • Cloud Services
  • Azure AD – user sync, SSO, group assignments, licensing
  • Intune – for device compliance and app deployment
  • Autopilot / Endpoint Manager – desirable


  • Security & Monitoring
  • RMM tools – agent deployment, remote access, alerting
  • EDR/XDR platforms – SentinelOne, Bitdefender, etc.
  • Mail filtering – e.g., Proofpoint, Microsoft Defender for M365
  • Email Authentication – SPF, DKIM, DMARC


  • Scripting & Automation
  • PowerShell – basic scripting, AD/user management
  • Batch scripts – for legacy environments
  • Automation tools – Ninite, Chocolatey, Zapier (bonus)


  • Backup & Disaster Recovery
  • Awareness of Veeam, Acronis, ShadowProtect, etc.
  • Cloud backup platforms like Dropsuite

  • Process & Documentation Tools
  • Ticketing Systems – SuperOps, ConnectWise, Autotask
  • Documentation – IT Glue, Confluence, OneNote
  • Project/Task Management – ClickUp, Monday.com, Asana


  • Nice to Have
  • Networking Tools – Wireshark, NetCrunch, Domotz
  • Password Managers – LastPass, Bitwarden
  • Basic SQL or API experience
  • Virtualisation – Hyper-V, VMware, Azure VMs

  • 💡 Bonus Round: Start your cover letter with your favourite joke - we love a bit of personality!

    Required profile

    Experience

    Level of experience: Senior (5-10 years)
    Spoken language(s):
    English
    Check out the description to know which languages are mandatory.

    Other Skills

    • Calmness Under Pressure
    • Communication
    • Leadership
    • Team Management
    • Curiosity
    • Problem Solving

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