IT Systems Technician (Level 2) - 65887967632

Location: Remote, Philippines

Employment Type: Full-Time, ICA

Schedule: U.S. Business Hours Overlap Required - CST

Compensation: $2,000 – $2,600 USD / month (commensurate with experience)

Reports To: Lead Systems Engineer / IT Operations Manager

Our client is a fast-growing managed IT services provider dedicated to serving a diverse portfolio of healthcare and operating businesses, including senior living, home health, and hospice organizations. Supported by a premier private investment firm, the company possesses immediate committed revenue across 50+ operating entities and is executing a 12-month full-portfolio onboarding sprint.

This is a dynamic startup environment built on real infrastructure, established clients, and a substantial growth trajectory. The team is seeking proactive builders—professionals who thrive on constructing robust IT ecosystems, optimizing processes, and laying the foundation for scalable operations, rather than simply maintaining the status quo.

We are seeking a proactive, highly skilled, and detail-oriented IT Systems Technician (Level 2) to deliver reliable second-level technical support, network administration, and infrastructure management across our portfolio.

In this role, you will play a key part in supporting a high-stakes, 12-month onboarding initiative. You will serve as an escalation point for technical issues, directly managing and troubleshooting multi-OS desktop environments, complex network architecture, Active Directory, server infrastructure, and enterprise security configurations.

The ideal candidate blends strong technical diagnostics with top-tier, customer-focused communication—ensuring system stability, security, and exceptional support standards for our end-users and client operational teams.

• Deliver responsive, second-level technical support across Windows, macOS, and Linux operating systems.
• Diagnose, troubleshoot, and resolve hardware and peripheral issues for desktops, laptops, mobile devices, and core network equipment.
• Conduct swift software diagnostics, deep-dive system analysis, and root-cause troubleshooting to minimize downtime and prevent recurring issues.
• Manage end-to-end service tickets within the help desk system, ensuring accurate documentation, clear communication, and SLA compliance.

• Configure, maintain, and support Windows Server environments, Group Policy Objects (GPO), and Active Directory management (user provisioning, OU management, permissions).
• Assist in deploying hardware and software updates, patches, and system upgrades while ensuring security and system stability across all environments.
• Maintain and update IT documentation, system configurations, and technical standard operating procedures (SOPs).

• Manage, support, and troubleshoot networking protocols and components, including TCP/IP, DNS, LAN/WAN configurations, VPNs, and firewalls.
• Collaborate with the team to enforce organizational security policies, implement firewall rules, and maintain secure VPN access controls.
• Conduct network diagnostic and connectivity reviews to identify and resolve performance bottlenecks across local and remote environments.

• Provide professional, customer service-oriented communication to end-users, guiding them through technical resolutions clearly and patiently.
• Partner with team members during onboarding sprints, contributing to infrastructure setup, system migrations, and operational readiness.

• 2+ years of hands-on experience in a Level 2 IT Support, Desktop Support, or Systems Administration role (MSP or multi-entity support experience is highly preferred).
• Proven experience supporting Windows (10/11) and macOS environments; familiarity with Linux is a plus.
• Hands-on expertise with Active Directory management, user provisioning, GPO configuration, and centralized computer management tools.
• Strong practical knowledge of core networking concepts: TCP/IP, DNS management, LAN/WAN configurations, VPNs, firewalls, and subnets.
• Proven track record of troubleshooting hardware components, system peripherals, and network connectivity.
• Experience managing service tickets in enterprise help desk or ITSM systems (e.g., ConnectWise, ServiceNow, Zendesk, or Freshservice).
• Proficiency with Microsoft 365, Google Workspace, and core business productivity suites.
• Excellent written and spoken English communication skills, with the ability to convey technical concepts clearly to non-technical users.

• Proactive & Self-Directed: Highly motivated to take ownership of tasks, troubleshoot complex problems independently, and follow through to resolution.
• Strong Analytical Mindset: Excellent critical-thinking and diagnostic skills to quickly isolate root causes in fast-paced environments.
• Detail-Oriented & Methodical: Meticulous with system configurations, security standards, and help desk documentation.
• Adaptable & Agile: Thrives in a high-growth startup atmosphere, handling shifting priorities during major onboarding sprints.
• Customer-Centric Focus: Patient, professional, and dedicated to delivering a frictionless IT experience for users.

The ideal candidate is a well-rounded Level 2 IT Technician who takes pride in solving non-trivial technical challenges and building scalable systems.

You are someone who looks past surface-level symptoms to find the true root cause of a technical problem. You can comfortably transition between configuring a GPO, diagnosing a DNS resolution failure, supporting an executive on macOS, and helping a remote user configure VPN access.

You are excited by the opportunity to join a startup backed by real infrastructure and committed growth, where your day-to-day work directly contributes to building a world-class IT service organization.

As our client executes a 12-month onboarding sprint across 50+ operating entities, this role serves as a backbone for IT operational reliability. Your technical expertise will directly empower healthcare workers, operating teams, and corporate staff to stay connected, secure, and productive—ensuring that essential healthcare and operational services run smoothly without technical disruption.