Systems Engineer

Jobtailor; Honolulu (HI); On-site; USD 90,000 - 140,000; Full time

Benefits offered by this job

Intense on‑site client engagements

Job summary

Jobtailor is seeking a Systems Administrator in Hawaii to manage client environments, perform migrations, and lead deployments with strong emphasis on security compliance (CMMC/NIST 800-171). The role requires mentoring junior staff, driving automation, and onsite client visits.

Ideal candidates will have深 extensive Windows Server/AD/M365 experience, Azure and virtualization expertise, and MSP tooling proficiency. Hawaii residency and local travel are required.

Qualifications

• Must live in Hawaii and have a valid driver’s license.
• Strong Windows Server/AD/M365 administration experience.
• Experience with Entra ID, conditional access and MFA rollouts.
• Solid Azure infrastructure knowledge with Hyper‑V/VMware.
• Experience with endpoint management, Intune and EDR.
• Familiar with SPF/DKIM/DMARC and security basics.
• Knowledge of SAN/NAS high‑availability storage.
• RDS/RD Gateway and remote session hosting experience.
• PowerShell scripting and MSP tooling automation.
• Documentation of networks, runbooks and configs.

Responsibilities

• Run migrations for client environments.
• Handle escalated tickets from the service desk.
• Build and clean up client environments.
• Advise clients on next steps.
• Teach and mentor Systems Administrators.
• Take projects from quote through deployment and own them.
• Work on project and escalation tasks.
• Contribute to automation initiatives.
• Build and manage secure enclaves meeting CMMC/NIST 800-171.
• Attend planned and unplanned client‑site visits.

Skills

DNS

DHCP

Routing

Subnetting

VLANs

Windows Server

Active Directory

Group Policy

DFS

Domain migrations

Microsoft 365

Entra ID

Conditional access

MFA

Azure

Hyper‑V

VMware

Intune

EDR

RDS / Remote Desktop Services

RD Gateway

PowerShell

Automation

Dell hardware

Documentation

Tools

Intune

EDR

Remote Desktop Services

RD Gateway

SAN

NAS

Job description

• Run migrations
• Handle escalated tickets from the service desk
• Build and clean up client environments
• Advise clients on next steps
• Teach and mentor Systems Administrators
• Take projects from quote through deployment and own them
• Work on project and escalation tasks
• Contribute to automation initiatives
• Build and manage secure enclaves for clients meeting CMMC and NIST 800-171 requirements
• Attend planned and unplanned client‑site visits

Requirements

• Must live in Hawaii
• Valid driver's license required
• Car required for planned and unplanned onsite visits
• Working knowledge of DNS, DHCP, routing, subnetting, and VLANs
• Working knowledge of Windows Server, Active Directory, Group Policy, DFS, and domain controller migrations
• Working knowledge of Microsoft 365 administration, migrations, and tenant management
• Working knowledge of Entra ID, identity, conditional access, and MFA rollouts
• Working knowledge of Azure infrastructure and architecture
• Working knowledge of Hyper‑V and VMware virtualization
• Working knowledge of endpoint management and security baselines, including Intune and EDR
• Working knowledge of SPF, DKIM, DMARC, and multi‑factor providers including Entra MFA and Duo
• Working knowledge of SAN and NAS high‑availability technologies
• Working knowledge of Remote Desktop Services, RD Gateway, and session hosts
• Working knowledge of PowerShell scripting and automation inside MSP tooling
• Working knowledge of server hardware quoting and troubleshooting; Dell environment
• Working knowledge of documentation including network diagrams, runbooks, and configuration records
• Microsoft certifications are valued, especially MD‑102, SC‑300, and AZ‑104; AZ‑305 is relevant later
• Network+ and Security+ are nice to have
• Certifications are not required to apply
• Ability to work methodically, seek help when stuck, investigate independently, and document technical issues

Core Competencies

Demonstrates expertise in managing client environments, including migrations and security compliance with CMMC and NIST 800-171 standards. Proficient in Windows Server administration, Azure infrastructure, and automation using PowerShell, while effectively mentoring Systems Administrators.

Highest-signal resume keywords

• Windows Server Administration
• Azure Infrastructure
• PowerShell Scripting
• CMMC Compliance
• Client Environment Management

Hard Skills

• DNS
• DHCP
• Routing
• Subnetting
• VLANs
• Active Directory
• Microsoft 365 Administration
• Entra ID
• Hyper‑V
• VMware

Soft Skills

• Mentoring
• Methodical Work
• Independent Investigation

Certifications & Qualifications

• MD-102
• SC-300
• AZ-104
• Network+
• Security+

Industry Keywords

• CMMC
• NIST 800-171
• Client-Site Visits
• Escalated Tickets
• Automation Initiatives

Tools & Technologies

• Intune
• EDR
• Remote Desktop Services
• RD Gateway
• SAN
• NAS