Windows System Administrator

Windows System Administrator

Location: Remote (Preference for San Francisco Bay Area candidates)

Duration: Minimum 1-Month Contract with Potential Extension

Pay Rate: $50-65/hr (DOE)

Work Schedule: Monday–Friday, standard business hours; occasional extended hours as needed

Travel: None anticipated

LHH Recruitment Solutions is seeking an experienced IT Systems Administrator / Microsoft 365 Project Specialist for a long-term contract opportunity supporting a growing organization undergoing significant technology modernization and integration initiatives.

This role is ideal for a technically strong systems professional who combines deep Microsoft 365 expertise with project execution experience, documentation skills, and the ability to operate effectively within regulated IT environments.

The selected consultant will lead and deliver critical infrastructure, collaboration, security, and application management projects while partnering closely with a small, highly collaborative IT team.

This position offers the opportunity to work on a variety of strategic initiatives, including Microsoft 365 optimization, enterprise application administration, process improvements, and emerging technologies such as Microsoft Copilot.

Position Overview

The IT Systems Administrator will serve as a senior technical contributor responsible for managing and executing IT projects, improving operational processes, and supporting technology initiatives across the organization.

This individual will inherit projects from existing administrators, drive implementations from planning through execution, and help scale IT operations as the company continues to grow. Success in this role requires a blend of technical expertise, independent project ownership, strong communication skills, and the ability to create sustainable solutions within a compliance-focused environment.

Key Responsibilities

Microsoft 365 Administration & Modern Workplace Projects

• Administer, configure, and optimize the Microsoft 365 ecosystem, including:
• Entra ID (Azure AD)
• Exchange Online
• SharePoint Online
• Microsoft Teams
• OneDrive
• Microsoft Defender
• Microsoft Intune (where applicable)
• Microsoft Copilot technologies
• Lead Microsoft 365-related initiatives from planning and design through implementation and support.
• Evaluate new Microsoft technologies and recommend solutions that align with business objectives.
• Support ongoing modernization and platform optimization efforts.

IT Project Management & Technical Delivery

• Take ownership of infrastructure and systems projects transitioning from other administrators.
• Manage project plans, timelines, technical requirements, testing, implementation, and post-deployment support.
• Perform technical research and solution evaluations to support business and IT objectives.
• Coordinate implementation activities and communicate project status to stakeholders.
• Assist with application onboarding, administration, and vendor-supported system management.

Regulatory & Compliance-Focused Technology Support

• Design and implement solutions within a regulated IT environment.
• Ensure projects align with internal security standards, governance requirements, and compliance-driven processes.
• Work closely with IT leadership to evaluate risks and maintain appropriate controls.
• Support environments operating under established compliance frameworks such as ISO 27001 or similar governance standards.

Documentation & Technical Writing

• Create and maintain technical documentation including:
• System configuration guides
• Operational procedures
• Administrative runbooks
• End-user instructions
• Maintenance and support documentation
• Develop clear documentation suitable for both technical administrators and non-technical users.
• Maintain knowledge repositories within SharePoint and other collaboration platforms.

Team Collaboration & Support

• Partner closely with system administrators, service desk staff, and IT leadership.
• Delegate appropriate operational and lower-level technical tasks while maintaining focus on strategic project work.
• Provide guidance and mentorship where appropriate.
• Serve as a technical resource during planning, deployment, and troubleshooting activities.

Required Qualifications

• 5+ years of progressive experience in Systems Administration, Infrastructure Administration, Microsoft 365 Administration, or related IT roles.
• Advanced experience administering Microsoft 365 technologies in enterprise environments.
• Strong understanding of:
• SharePoint Online
• Microsoft Teams
• Exchange Online
• Entra ID (Azure AD)
• Identity and access management
• Collaboration technologies
• Demonstrated experience leading technical projects from requirements gathering through deployment.
• Experience working in compliance-focused, security-conscious, or regulated environments.
• Strong technical writing and documentation skills.
• Ability to conduct technical research, evaluate solutions, and make implementation recommendations.
• Excellent organizational, communication, and stakeholder-management skills.
• Proven ability to work independently in a remote environment.

Preferred Qualifications

• Experience supporting Microsoft Copilot deployments or adoption initiatives.
• Exposure to ISO 27001, SOC, NIST, HIPAA, or similar governance and compliance frameworks.
• Experience with third-party application administration and vendor management.
• Background in growing organizations, acquisitions, integrations, or enterprise transformation initiatives.
• Experience creating knowledge management content in SharePoint Online.

Work Environment

• Fully remote position with occasional optional in-person meetings.
• Standard 40-hour work week.
• Limited planned overtime may be required during project cutovers, migrations, or deployment activities.
• No ongoing on-call responsibilities.
• Collaborative small-team environment with direct interaction across infrastructure and support functions.

What Success Looks Like

• Microsoft 365 initiatives are delivered on time and with minimal operational disruption.
• Technical projects are successfully transitioned, implemented, and documented.
• IT processes become more scalable and efficient through automation and standardization.
• Documentation is accurate, maintainable, and valuable to both administrators and end users.
• Business stakeholders view the resource as a trusted technical expert and project lead.
• Strategic initiatives, including collaboration and AI-enabled productivity solutions, are successfully deployed and adopted.

Benefit Offerings

Benefit offerings include medical, dental, vision, life insurance, short-term disability, additional voluntary benefits, EAP program, and 401K plan. Our program provides employees the flexibility to choose the type of coverage that meets their individual needs.

Available paid leave may include Paid Sick Leave, where required by law; any other paid leave required by Federal, State, or local law; and Holiday pay upon meeting eligibility criteria.

Equal Opportunity Employer/Veterans/Disabled

To read our Candidate Privacy Information Statement, which explains how we will use your information, please navigate to https://www.lhh.com/us/en/candidate-privacy

The Company will consider qualified applicants with arrest and conviction records in accordance with federal, state, and local laws and/or security clearance requirements, including, as applicable:

• The California Fair Chance Act
• Los Angeles City Fair Chance Ordinance
• Los Angeles County Fair Chance Ordinance for Employers
• San Francisco Fair Chance Ordinance