Himalayas logo
OS

Senior Technical Lead – Helpdesk & Projects

Outsourced Staff
Philippines only

Stay safe on Himalayas

Never send money to companies. Jobs on Himalayas will never require payment from applicants.

About the Company

Our client is not your average IT company, they are a team of passionate tech wizards who love solving problems, streamlining business operations, and delivering top-notch IT solutions that make life easier.
They believe IT should be affordable, stress-free, and tailored to your needs. That’s why they 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!

About the job

Apply before

Posted on

Job type

Full Time

Experience level

Senior

Location requirements

Hiring timezones

Philippines +/- 0 hours

About Outsourced Staff

Learn more about Outsourced Staff and their company culture.

View company profile
Claim this profileOS

Outsourced Staff

View company profile

Similar remote jobs

Here are other jobs you might want to apply for.

View all remote jobs

19 remote jobs at Outsourced Staff

Explore the variety of open remote roles at Outsourced Staff, offering flexible work options across multiple disciplines and skill levels.

View all jobs at Outsourced Staff

Remote companies like Outsourced Staff

Find your next opportunity by exploring profiles of companies that are similar to Outsourced Staff. Compare culture, benefits, and job openings on Himalayas.

View all companies

Find your dream job

Sign up now and join over 100,000 remote workers who receive personalized job alerts, curated job matches, and more for free!

Sign up
Himalayas profile for an example user named Frankie Sullivan
Outsourced Staff hiring Senior Technical Lead – Helpdesk & Projects • Remote (Work from Home) | Himalayas