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System Administrator Tier II (80% work from home)

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<p>This Washington, D.C.–based Managed Services Provider delivers modern IT strategy and Microsoft-centric solutions to mid-market clients, nonprofits, and associations. Known for clear communication, deep technical expertise, and responsive, white-glove support, the team blends strategic guidance with hands-on technical problem solving. The culture is collaborative, client-focused, and built for people who love solving complex issues and making a real impact.</p><p><br></p><p><strong>Role: System Administrator Tier II </strong></p><p><strong>Location:</strong> 80% Work From Home, 20% onsite DMV</p><p><strong>Compensation:</strong> $70,000–$90,000 + benefits + bonuses</p><p><br></p><p>This role is <strong>95% true Tier 2 support</strong>—handling escalations involving Microsoft 365, Intune, SharePoint, and Exchange Online. You’ll serve as a trusted technical advisor, an escalation point for the support team, and a familiar voice clients rely on. If you enjoy the combination of technical depth, fast troubleshooting, and strong communication, you’ll thrive here.</p><p><br></p><p> <strong>What You’ll Do</strong></p><ul><li>Own Tier 2 Microsoft 365 escalations: Exchange Online, SharePoint, Teams, Intune, Entra ID, OneDrive</li><li>Perform root-cause analysis and propose long-term fixes</li><li>Mentor Tier 1 technicians and share best practices</li><li>Deliver high-energy, client-friendly phone support</li><li>Document solutions and contribute to internal knowledge bases</li><li>Support occasional networking/server issues (VPN, DNS, firewalls, Windows Server)</li><li>Build strong relationships with clients through consistent, proactive communication</li></ul><p><br></p><p><strong>What You Bring</strong></p><ul><li>4+ years technical support experience (2+ years Tier 2+)</li><li>Hands-on, advanced experience with Microsoft 365 workloads</li><li>Proven ability to resolve multi-user outages, permission issues, and policy conflicts</li><li>Strong phone presence—clear, confident, positive</li><li>Client-service mindset and strong communication</li><li>Mentoring/coaching skills</li><li>Solid networking fundamentals (DNS, DHCP, VPN, TCP/IP)</li><li>Experience with Microsoft Dynamics is a plus</li><li>Current or in-progress Microsoft certifications preferred</li><li>Valid driver’s license + reliable transportation</li><li>Independent, self-driven, high-accountability work style</li></ul><p><br></p><p> <strong>Benefits & Perks</strong></p><ul><li>Health insurance with company contribution</li><li>Dental & vision (company-paid after 1 year)</li><li>401(k) with company match</li><li>PTO + end-of-year bonus</li><li>$50/month wellness stipend (gym, Peloton, etc.)</li><li>Microsoft certification reimbursement</li><li>Company events + supportive team culture</li><li>Clear career tracks: move toward Tier 3, Team Lead, or Projects</li><li>Personalized 30/60/90-day ramp plan</li><li>Home-buying assistance program</li></ul><p></p>

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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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