Senior Systems Administrator

Remote (United States)

Job Details

Employment Type: Full-time

Department: Operations

Compensation: $135,000-$150,000 per year, plus equity compensation

About the Role

This opportunity is for a Senior Systems Administrator who will help build and scale a unified, secure IT infrastructure across a rapidly growing organization. The environment is expanding from approximately 500 to 2,500 employees while integrating multiple acquired entities, creating a need for scalable systems, strong security controls, reliable infrastructure, and efficient IT operations.

The role combines defensive security design, greenfield infrastructure architecture, and frictionless operational security. The Senior Systems Administrator will help consolidate fragmented systems, strengthen security and compliance, and build infrastructure that enables clinical, technical, and operational teams to work efficiently without compromising security.

This position offers significant ownership and requires close collaboration with leadership, engineering, HR, operations, security partners, and other internal teams.

What You’ll Do

Security Posture and Systems Protection

• Own and strengthen the security posture across business systems.
• Implement and enforce cybersecurity controls, including multi-factor authentication, conditional access, endpoint detection and response, vulnerability scanning, and secure remote access.
• Lead incident response activities and coordinate with external or internal security partners.
• Maintain HIPAA-aligned technical safeguards.
• Support CMS and state audits.
• Create and maintain security documentation, policies, system diagrams, and other records needed to maintain visibility into the technology environment.
• Design security controls with both prevention and breach containment in mind, including reducing potential blast radius and enabling rapid incident detection.

Cloud and Systems Infrastructure

• Architect, deploy, administer, and maintain Microsoft 365, Entra ID, Intune, VPNs, and virtual desktop environments.
• Manage backups, disaster recovery, infrastructure monitoring, and patch management.
• Lead system upgrades, migrations, and integrations as business units and technology environments are consolidated.
• Help design scalable, secure infrastructure rather than relying solely on legacy systems and incremental fixes.

M&A Systems Integration

• Lead post-acquisition IT integration initiatives.
• Consolidate directories across acquired organizations and business units.
• Lead email migrations.
• Standardize endpoints and device environments.
• Integrate networks and related infrastructure.
• Decommission legacy systems when appropriate.
• Participate in IT due diligence for acquisitions, including system inventories, security posture assessments, and risk identification.
• Develop repeatable IT integration playbooks to support an ongoing acquisition strategy.

Endpoint Management

• Secure and administer Windows, macOS, and mobile devices across a distributed workforce.
• Use MDM platforms such as Microsoft Intune, Jamf, and Knox to manage devices.
• Standardize device configurations, encryption requirements, and compliance policies.
• Own asset tracking and lifecycle management for field-based and corporate staff.

Business Systems and Operational Support

• Support and administer business-critical platforms, including HRIS and payroll systems such as ADP and Rippling.
• Support EHR and EMR systems such as Homecare Homebase.
• Support compliance platforms such as Relias.
• Partner with HR to provide secure employee onboarding and offboarding.
• Work toward same-day account and system provisioning for new employees and immediate access revocation when employees leave.
• Provide escalation support for complex technical issues affecting remote and field-based staff.
• Partner with operations and other teams to enable fast, secure organizational growth.

Qualifications

• 7+ years of enterprise systems administration experience.
• Demonstrated experience working in HIPAA-regulated or other highly compliant environments.
• Strong hands-on experience with Microsoft 365.
• Strong hands-on experience with Microsoft Entra ID.
• Strong hands-on experience with Microsoft Intune.
• Experience administering macOS environments.
• Experience managing iOS devices.
• Experience working across mixed-platform technology environments.
• Proven ability to manage VPNs.
• Proven ability to manage firewalls and network security.
• Proven experience managing backup and disaster recovery systems.
• Excellent documentation skills.
• Excellent troubleshooting skills.
• Excellent communication skills.
• Ability to take ownership of outcomes and solve problems independently rather than waiting for others to act.
• Ability to move quickly and take action in a fast-paced environment.
• Strong security-first mindset focused on prevention, breach preparedness, containment, and minimizing the impact of security incidents.
• Ability to turn complex or ambiguous problems into clear documentation and actionable solutions.
• Comfort working with ambiguity and helping define solutions when requirements are not fully established.
• Ability to work collaboratively with a low-ego, hands-on approach.

Preferred Qualifications

• Experience in healthcare or multi-site clinical operations.
• Experience with M&A systems integration, including migrating or consolidating IT environments following acquisitions.
• Experience administering Jamf.
• Experience with Apple Business Manager.
• Experience with Knox or other enterprise device management platforms for tablets and mobile devices.
• Experience with virtual desktop infrastructure.
• Microsoft Azure or Microsoft 365 certifications are a plus.
• CompTIA Security+ certification is a plus.
• Jamf certification is a plus.
• CISSP certification is a plus.

Working Conditions

• This is a fully remote position.
• Reliable high-speed internet access is required.
• Occasional travel to branch offices or data centers may be required for major deployments or audits.
• On-call or after-hours work may be required during outages or critical system changes.

Benefits

• Equity compensation.
• Opportunities for professional growth within a fast-growing organization.
• Collaborative work environment focused on innovation and problem-solving.
• Flexible paid time off policy, with an expectation that most employees take at least three weeks of vacation per year.
• 401(k) retirement plan with employer contribution.
• Comprehensive health insurance.
• Dental benefits.
• Commuter benefits.