After-Hours IT System Administrator (Tier 1) – Remote(Part-Time)

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After-Hours IT System Administrator (Tier 1) – Remote (Part-Time, Potential Full-Time)

FLAGLER TECHNOLOGIES MSP Team
United States (Remote)


Who Are We?

We’re more than just an IT support provider—we’re a team committed to delivering exceptional service while fostering growth and development within our ranks. Our mission is to empower the next generation of IT professionals by creating opportunities for leadership and career advancement. When you join us, you become part of a team that’s as invested in your success as we are in providing top-tier support to our clients.


What Does a Typical Day Look Like in This Role?

This is an after-hours role focused on ensuring smooth IT operations while minimizing impact on production environments.

As an After-Hours IT System Administrator (Tier 1), your evenings will consist of both end-user support and scheduled maintenance on core infrastructure. You’ll work directly with clients to resolve technical issues, document solutions, and escalate when needed.

Your responsibilities will include:

  • Performing after-hours maintenance and applying firmware updates to core infrastructure (hosts, firewalls, switches, wireless APs).
  • Troubleshooting PCs, printers, and peripherals.
  • Resetting passwords, assisting with MFA, and resolving account access issues (Active Directory, Office 365).
  • Supporting standard applications and assisting with installs.
  • Documenting all work thoroughly in our ticketing system.
  • Collaborating with senior technicians and team leads to learn and grow in your role.


Schedule & Work Environment

This role is remote (no longer tied to Boca Raton).

  • Part-Time (20 hours/week): Primarily Mon–Fri, 5 PM – 9 PM Central (fixed).
  • Full-Time (40 hours/week): Primarily Mon–Fri, 4 PM – 1 AM Central (some flexibility possible).
  • Note: This position is primarily part-time, but could expand to full-time based on business needs and candidate fit.


What Qualifications or Experience Do I Need?

For this role, you should have 1–2 years of hands-on IT experience specifically performing after-hours maintenance tasks such as firmware updates, infrastructure patching, and scheduled changes on production systems. Help Desk or MSP background is strongly preferred.

We’re looking for people who can demonstrate:

  • Direct experience performing maintenance and updates to infrastructure (switches, firewalls, wireless APs, servers/hosts).
  • Ability to follow structured change plans for firmware and patch updates.
  • Basic troubleshooting of Windows and/or Mac systems.
  • Familiarity with networking concepts and devices.
  • Familiarity with Microsoft 365 applications.
  • Clear written and verbal communication skills, with thorough documentation practices.
  • Ability to work independently and stay detail-oriented during after-hours shifts.
  • A strong willingness to learn and grow.

Preference will be given to candidates with:

  • IT-related coursework or certifications (CompTIA A+, Network+, or equivalent).
  • Previous MSP or Help Desk experience.

Above all, we value candidates who are humble, hungry, and people smart—qualities that allow us to help you grow your career in IT systems administration.


What Else Should You Know About Us?

Part-Time Employee Benefits

  • Paid Time Off (accrued, subject to manager approval).
  • Company-provided computer and peripherals.
  • Internet stipend to ensure reliable connection.
  • Access to training resources and potential certification reimbursement.

Full-Time Employee Benefits

  • 3 Weeks of Paid Time Off (vacation and sick time accrued, subject to manager approval).
  • Healthcare Options with 75% of your premium covered.
  • Dental & Vision Services.
  • Group Life Insurance.
  • 401k with up to 4% matching and immediate vesting.
  • Access to training and certification reimbursement to support your growth.
  • Company-provided computer and peripherals.
  • Internet stipend to ensure reliable connection.
  • Devices that access company resources will need to be managed by us while being used for work purposes. You'll also need a personal cell phone for multi-factor authentication.

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...

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