Systems Administrator Supervisor

Job Summary

The Systems Administrator Supervisor is a hands-on technical leader who manages and mentors a team while continuing to contribute at a senior technical level. This role is ideal for an experienced Systems Administrator ready to step into leadership—balancing advanced system administration expertise with guiding team performance and driving best practices.

Remote Work Qualifications

• Access to a reliable and secure high-speed internet connection. Cable or fiber internet connections (at least 75mbps download/10mbps upload) are preferred, as satellite connections often cannot support the technologies used to perform day-to-day tasks.
• Access to a home router and modem.
• A dedicated home office space that is noise- and distraction-free. The space should have strong wireless connection or a wired Ethernet connection (wired connection is preferred, if possible).
• A valid, physical address (apartment, suite, etc.). PO Boxes are not supported, as a physical address is required for you to receive your computer equipment.
• The desire and ability to work and communicate with other team members via chat, webcam, etc.
• Legal residents of one of the following states: (AK, AL, AR, AZ, CT, DE, FL, GA, IA, ID, IN, KS, KY, LA, MD, ME, MI, MN, MO, MS, NC, ND, NH, NM, NV, OH, OK, PA, SC, SD, TN, TX, UT, VA, VT, WI, WV, and WY).

We only accept W-2 candidates, H-1B sponsorship is not available.

Responsibilities

• Lead and mentor Systems Administrators while actively managing complex technical tasks.
• Manage day-to-day team operations, including workload prioritization and alignment with organizational goals.
• Conduct regular 1:1s and performance reviews; provide coaching for technical and career development.
• Oversee installation, configuration, and maintenance of Windows/Linux servers and Domain Services.
• Guide the team in implementing best practices for system administration, automation, and security.
• Collaborate with IT Operations and Security teams to design and deploy secure, scalable systems leveraging Infrastructure as Code (IaC).
• Act as an escalation point for advanced troubleshooting and incident resolution.
• Ensure accurate documentation of systems, processes, and standards.
• Participate in project planning, scope design, and high-level architectural decisions.
• Ensure systems and processes adhere to PCI DSS standards and other relevant security compliance requirements.

Physical Requirements

• Work is performed while sitting/standing and interfacing with a personal computer.
• Requires the ability to communicate effectively using speech, vision, and hearing.
• Requires the regular use of hands for simple grasping and fine manipulations.
• Requires occasional bending, squatting, crawling, climbing, and reaching.
• Requires the ability to occasionally lift, carry, push, or pull medium weights, up to 50lbs.

Qualifications

Experience

• Minimum of 5 years of enterprise systems administration experience (Windows/Linux environments).
• Experience providing technical guidance, mentoring peers, or leading projects.
• Advanced technical understanding of virtualization (preferably VMware), Active Directory, domain services, and server administration.
• Experience with scripting (PowerShell, Bash) preferred.

Education

This role does not require a degree. We value relevant skills and experience and alignment with our core values above all else.

Desired Traits & Skills

• Strong leadership and coaching skills with the ability to develop team capabilities.
• Advanced proficiency in system administration, networking, and IT security best practices.
• Excellent problem-solving and analytical skills.
• Strong verbal and written communication skills; able to explain technical concepts clearly.
• Ability to manage multiple priorities in a fast-paced environment.
• Customer-focused mindset with a commitment to operational excellence.
• Familiarity with Infrastructure as Code and automation tools preferred.