Senior Remote IT Systems Administrator (PST Hours)

Senior Remote IT Systems Administrator (Contractor – PST Hours)

Location: Remote (Philippines only)
Type: Independent Contractor
Hours: 9:00 AM – 5:00 PM Pacific Time (Night shift PH)
Pay: Competitive, paid twice monthly

ABOUT THE ROLE
We are a Canadian Managed IT Services Provider supporting multiple small business clients in Windows-based environments. We are hiring a senior-level remote IT professional who can operate independently with minimal training and take responsibility for real production systems.

This is not a junior helpdesk or VA role.

RESPONSIBILITIES
- Monitor and remediate backup alerts and failures (Datto)
- Review and act on Huntress security alerts
- Administer Microsoft 365 (Exchange Online, Entra ID, licensing, MFA)
- Administer Google Workspace (users, mail, security settings)
- Remote troubleshooting via ScreenConnect
- Windows 10 / 11 support (workgroup and domain-joined systems, troubleshooting-focused)
- Application-level troubleshooting (Microsoft Outlook, PST/OST issues, browsers, and common business software)
- Strong understanding of DNS, static IPs, WAN/LAN networking, port forwarding, and RDP
- VPN administration and troubleshooting (WireGuard, OpenVPN)
- Installing / configuring printers (Brother, Ricoh, Xerox, HP)
- Datto- and Ubiquiti-based hardware (WAPs, switches, routers)
- Windows Server administration (Active Directory, DNS, GPO)
- Basic Linux administration and troubleshooting (asset)
- User onboarding/offboarding and computer setup
- Installing, updating, and maintaining end-user software in managed environments
- Client communication via email and chat
- Proper escalation when appropriate
- Documenting work to technical sheets and for invoicing

Over time, this role will expand to inbound support calls and increased ticket ownership.

REQUIRED EXPERIENCE (READ CAREFULLY)
Please apply only if you meet these requirements:
- 5+ years professional IT support or systems administration experience
- Hands-on experience with Windows Server and Active Directory
- Strong Microsoft 365 administration experience
- Experience supporting multiple clients or tenants (MSP experience preferred)
- Comfortable working independently without step-by-step instructions
- Clear, professional written English
- Prior experience working US or Canadian hours
- Reliable internet and professional work environment

THIS ROLE IS NOT
- Entry-level
- A training position
- Data entry or VA work

We are looking for someone who can analyze, troubleshoot, and make sound decisions.

SCREENING QUESTIONS (REQUIRED)
Applications without clear answers will be ignored.

1. Describe your experience with Windows Server and Active Directory.
Include examples such as user management, GPOs, DNS issues, or real problems you have resolved.

2. What Microsoft 365 admin tasks do you perform regularly?
(Examples: mail flow issues, MFA problems, licensing, account compromises, etc.)

3. Have you worked in an MSP or multi-client environment before?
If yes, briefly describe the type of clients and tools you supported.

4. This role requires working 9:00 AM – 5:00 PM Pacific Time (night shift in the Philippines).
Are you able to commit to this schedule long-term? (Yes/No)

5. What is your expected monthly compensation (PHP) for a full-time contractor role?

6. Describe a production IT issue you handled independently from start to resolution.

SCHEDULE & PAY
- 9:00 AM – 5:00 PM Pacific Time
- Independent contractor
- Paid twice monthly
- Long-term role for the right person

FINAL NOTE
We value reliability, good judgment, and clear communication. If you are looking for a stable, long-term role where your experience is respected, we want to hear from you.

If you do not have hands-on Windows Server and Active Directory experience, please do not apply.