Entry Level Help Desk Jobs in Rosedale, MD (NOW HIRING)

Who We Are Looking For:

We’re looking for a seasoned engineer who has been around the block — someone who has seen things break in ways the textbook never covered and figured it out anyway. We don’t hire new folks. You’ll be ready to support whatever our clients have built — no two environments are the same. On any given day that might mean answering a help desk call, managing our clients’ ongoing managed services, contributing to a project deployment, or all three. You own your work from start to finish and bring the experience to back it up.

This is not an entry-level role. We need someone who can hit the ground running, operate with minimal hand-holding, communicate with equal confidence whether you’re walking a frustrated end user through a fix or handling a tough conversation with a client’s senior leadership, and consistently look for ways to fit the right solution to a complex problem — not just resolve the ticket, but leave the client’s business better than you found it.

What You'll Be Doing:

• Handling inbound help desk calls and day-to-day end user support with the professionalism and efficiency that comes from real experience — not a script

• Managing and maintaining client environments under our managed services agreements — proactive monitoring, patching, health checks, and staying ahead of issues before clients feel them

• Supporting our project delivery team on technical deployments, migrations, and implementations across the full range of our service offerings

• Administering and troubleshooting Exchange Online, Teams, SharePoint, Entra ID, Intune, and Microsoft Defender

• Designing, deploying, and supporting Azure infrastructure across IaaS, PaaS, and hybrid scenarios

• Managing and troubleshooting Azure networking — Virtual Networks, subnets, peering, NSGs, route tables, DNS, and Azure Firewall

• Supporting Azure Virtual Desktop (AVD) environments — host pools, session hosts, profiles (FSLogix), licensing, and user experience issues

• Administering Azure Files, Storage Accounts, Azure Backup, and Site Recovery

• Supporting and hardening web-facing workloads using Azure Web Application Firewall (WAF) and Azure Front Door

• Supporting and administering on-premises Windows Server environments — Active Directory, DNS, DHCP, Group Policy, DFS, and file services

• Managing and troubleshooting firewall environments including Sonicwall — policies, NAT, VPN, and routing

• Deploying and troubleshooting Aruba and other enterprise wireless environments

• Designing and managing backup and disaster recovery solutions — assessing client risk, recommending the right tools, implementing and testing recovery plans, and making sure clients can actually get back up when something goes wrong

• Identifying opportunities to improve client environments — going beyond the break-fix mentality to recommend solutions that reduce risk, improve reliability, and make the business run better

• Working across diverse client environments — switches, routers, servers, endpoints, hypervisors — whatever the client has, you figure it out

• Documenting your work thoroughly and communicating clearly with clients at every level throughout the lifecycle of every engagement

• Mentoring and assisting junior staff

What We're Looking for:

We value hands-on experience above all else. A degree or certification list doesn’t tell us whether you can actually do the job. We want to know what you’ve built, what you’ve broken, and what you fixed. Here’s the profile we’re after:

Microsoft 365 & Entra ID

• Deep working knowledge of Exchange Online — mail flow, connectors, spam filtering, DKIM/DMARC/SPF, hybrid configurations, and retention

• Entra ID administration — Conditional Access, MFA, SSO, SSPR, app registrations, and hybrid identity with Entra Connect

• Intune — policy deployment, compliance baselines, device enrollment (Windows, iOS, Android), and troubleshooting

• Microsoft Defender for Endpoint, Identity, and Microsoft 365 — you know what the alerts mean and what to do about them

• Experience with MDR and XDR platforms — you understand the difference between a noisy alert and an actual incident, can work with managed detection and response tooling, and know how to triage, investigate, and escalate endpoint and identity telemetry across an XDR platform (Microsoft Defender XDR, SentinelOne, CrowdStrike, or similar)

• SharePoint Online and OneDrive — site architecture, permissions, sharing policies, content types, and sync troubleshooting; OneDrive Known Folder Move, and Teams/SharePoint integration beyond the basics

Azure Infrastructure

• Compute: Virtual Machines — deployment, sizing, availability sets, scale sets, extensions, and performance troubleshooting

• Networking: Virtual Networks (VNets), subnets, VNet peering, VPN Gateway (site-to-site, point-to-site), ExpressRoute concepts, Network Security Groups, User Defined Routes, and Azure DNS (public and private zones)

• Azure Firewall: Policy management, DNAT/SNAT rules, threat intelligence, and diagnostics — not just “it’s on”; you’ve actually worked through firewall rule logic in Azure

• Web Application Firewall (WAF): Deployed or managed WAF in front of App Gateway or Azure Front Door; familiar with OWASP rule sets, custom rules, and tuning false positives

• Azure Front Door: Routing rules, origin groups, caching, and WAF policy integration

• Storage: Azure Files (SMB shares, AD Kerberos auth, sync), Blob Storage, Storage Accounts, lifecycle policies, and access tiers

• Azure Backup & Site Recovery: Configured and managed backup vaults, recovery plans, and tested restores — not just set it and forgotten it

• Azure Virtual Desktop (AVD): Host pool deployment and management, session host imaging, FSLogix profile containers, RDP Shortpath, licensing (Microsoft 365 / RDS CALs), and user experience troubleshooting

• Hybrid Identity & Connectivity: Entra Connect sync troubleshooting, hybrid Azure AD join, Seamless SSO, and pass-through vs. password hash sync

• Monitoring & Diagnostics: Azure Monitor, Log Analytics, diagnostic settings, and working KQL queries to actually find problems

On-Premises Infrastructure

• Windows Server administration — you’re comfortable across multiple versions (2012R2 through 2022)

• Active Directory — domain administration, GPO design and troubleshooting, OU structure, replication issues, and trust relationships

• DNS and DHCP — split-brain DNS, conditional forwarders, scopes, reservations, and when things break in hybrid environments

• DFS Namespaces and Replication — you’ve diagnosed a DFS replication backlog before and didn’t panic

• File and print services - Permissions, deployment, and the real-world complexity of inherited NTFS ACLs

• Virtualization — VMware vSphere or Hyper-V at a level where you can manage, troubleshoot, and migrate VMs without a wizard holding your hand

• RDS (Remote Desktop Services) — on-prem and hybrid RDS deployments — Connection Broker, Session Hosts, RD Gateway, RD Web, licensing server — you’ve built and fixed these, not just used them

• Backup and DR — you’ve designed and owned recovery solutions end-to-end; you know the difference between a backup that works and a backup that’s been tested, and you understand what RTO and RPO mean in a real business conversation

Networking

• Networking basics - You understand subnetting, routing, VLANs, and NAT at a level where you can troubleshoot without a calculator

• Firewall administration — policies, NAT rules, site-to-site and SSL VPN, logging, and diagnostics

• Wireless — you’ve configured APs, dealt with RF issues, and worked with controllers and instant deployment methodologies

• Basic switching and routing admin — you’re comfortable on a CLI or GUI whether it’s Cisco, HP, NETGEAR, SonicWall, or something else entirely

Communication & Client Engagement

• Communication is non-negotiable. You can engage with anyone in the room — from the employee who just got a phishing email to the executive who needs to understand why their business is at risk. You adjust your language, your tone, and your level of detail to match your audience without being condescending or over-technical. Written communication is just as strong — your ticket notes, emails, and documentation are clear, professional, and something a client can actually read.

• Client-facing confidence built from real experience — you’ve had the hard conversations, managed expectations under pressure, and left clients feeling like they were in good hands

• Strong documentation habits — if it isn’t documented, it didn’t happen

• Multi-Tasking - Comfortable juggling multiple clients and tickets simultaneously in a PSA/ticketing environment

• Self-directed — you don’t need someone telling you what to try next, but you know when to ask

Preferred (But Not Required)

• RMM platform experience — ConnectWise Automate, NinjaRMM, Datto RMM, or similar; comfortable building or working with monitoring, alerting, patch management, and scripted automation at scale across a multi-client MSP environment

• PSA Experience - ConnectWise Manage or similar PSA platform experience

• Scripting – PowerShell / Bash / etc. scripting for automation and administration tasks

• Power Platform — Power Automate flows, Power Apps canvas or model-driven apps, and an understanding of how the platform connects to Microsoft 365 and external data sources; experience troubleshooting connector issues or licensing constraints is a bonus

• Microsoft Purview — information protection, data classification, DLP policies, compliance solutions, and eDiscovery; experience in GCC High environments is a plus

• Barracuda MSP — familiarity with Barracuda’s MSP security and backup portfolio including Email Security, Backup, and PhishLine/Security Awareness Training

• Security Frameworks and auditing - Exposure to security frameworks (NIST, CIS, CMMC) in a practical delivery context

• A.I. – Experience working with some AI platforms and understand how to leverage AI to improve your daily work