About the Position
We are looking for an experienced Senior Systems Engineer / Technical Lead to join our Managed Services team in Tampa, Florida.
This is a hands-on senior engineering position with some leadership responsibility. We aren't looking for someone who wants to sit back and manage a ticket board all day. We need someone who can jump into a difficult issue, figure out what's actually going on, get it resolved, and help the rest of the technical team get better along the way.
The right person will have solid experience working for an MSP and understand what that environment is actually like. You're going to work across multiple clients, multiple networks, and different configurations. Priorities change, escalations happen, and sometimes you're walking into an environment you didn't build.
You should be comfortable troubleshooting a Windows Server problem in the morning, reviewing a FortiGate configuration after lunch, handling a Veeam restore, working through an escalation with a technician, and keeping the work properly documented in ConnectWise.
If you have only worked internal IT in one environment, this probably isn't the right position.
What You'll Be DoingSenior Engineering & Escalations
You will serve as the primary senior escalation point for our helpdesk and engineering team.
That includes troubleshooting and resolving issues involving:
- Cybersecurity and Compliance
- Windows Server
- Active Directory and Group Policy
- Microsoft 365 and Entra ID
- DNS and DHCP
- Networking and VPNs
- Fortinet/FortiGate
- Virtualization
- Backup and disaster recovery
- Endpoint management
- Security-related issues
We expect our senior engineers to troubleshoot the whole problem.
"This is a networking issue" or "this is a Microsoft issue" isn't where troubleshooting stops. You should be able to work across the stack, determine the root cause, and either resolve the issue or clearly identify what needs to happen next.
You'll also be involved in projects including server replacements, infrastructure upgrades, Microsoft 365 migrations, firewall and network deployments, virtualization projects, and other client technology initiatives.
Our Core MSP Platforms
We're looking for someone with strong, real-world experience with the tools we use every day.
Expert-level experience is expected with:
- ConnectWise
- Cybersecurity
- Business compliance
- NinjaOne
- Veeam
- Fortinet / FortiGate
- Microsoft Windows Server
When we say expert, we mean you've actually administered and troubleshot these platforms in production. Having logged into ConnectWise or deployed a FortiGate a couple of times isn't what we're looking for.
Experience with Proxmox is also important. You don't need to be a Proxmox guru on day one, but you should understand virtualization well enough to become comfortable with it quickly.
VMware and Hyper-V experience is also useful.
Microsoft Experience
You should have strong hands-on experience with:
- Windows Server
- Active Directory
- Group Policy
- Microsoft 365
- Entra ID
- Exchange Online
- SharePoint
- Microsoft Teams
- DNS and DHCP
- File and print services
- Identity and access management
We support both traditional on-premises infrastructure and modern Microsoft cloud environments, so you need to be comfortable working in both.
Networking
Strong networking fundamentals are a must.
You should understand:
- TCP/IP
- VLANs
- Routing and switching
- DNS
- DHCP
- NAT
- Site-to-site VPNs
- Remote-access VPNs
- Firewall policies
- Compliance and Cybersecurity regulations
- Network troubleshooting
Strong Fortinet/FortiGate experience is required. Experience with FortiSwitch and FortiAP is a plus.
Backup & Disaster Recovery
Strong Veeam experience is required.
You should be comfortable troubleshooting backup failures, performing restores, validating backups, and helping plan and test disaster recovery.
We aren't interested in someone who considers a green checkmark on a backup job the end of the conversation. Backups need to be recoverable when they are actually needed.
Helping Lead the Technical Team
This position isn't strictly management, but you will be one of the senior technical resources the team relies on.
That means:
- Helping technicians work through difficult tickets
- Handling higher-level escalations
- Mentoring junior and mid-level technicians
- Reviewing ticket quality
- Improving troubleshooting habits
- Making sure work is properly documented
- Identifying recurring problems
- Helping improve technical processes and standards
- Holding technicians accountable for completing their work correctly
We don't want someone who takes every difficult ticket away from the helpdesk.
A good technical lead helps the technician understand why something broke, how to troubleshoot it, and how to handle it themselves the next time.
Documentation Matters
Good documentation is part of the job.
If you spend three hours figuring something out, the next engineer shouldn't have to spend another three hours figuring out the exact same thing six months later.
Client environments, configurations, network information, troubleshooting steps, and completed work should be documented clearly enough that another engineer can pick up where you left off.
Automation & Scripting
PowerShell experience is strongly preferred.
We're also interested in engineers who naturally look for ways to make things more efficient.
If you're doing the same task manually every week, we'd rather have someone who asks why we're still doing it manually.
Experience using scripting or automation for deployments, monitoring, remediation, maintenance, or other MSP tasks is a big plus.
Required Experience
- Strong previous MSP experience
- Expert-level ConnectWise experience
- Expert-level NinjaOne experience
- Expert-level Veeam experience
- Expert-level Fortinet/FortiGate experience
- Expert-level Windows Server experience
- Strong Active Directory and Group Policy experience
- Strong Microsoft 365 and Entra ID experience
- Strong networking knowledge
- Tier 3 / senior escalation experience
- Strong troubleshooting and root-cause analysis skills
- Experience mentoring or leading helpdesk technicians
- Strong documentation habits
- Good client communication skills
Nice to Have
- Proxmox
- VMware
- Hyper-V
- PowerShell
- Azure
- FortiSwitch / FortiAP
- Microsoft security technologies
- Backup and disaster recovery planning
- Infrastructure migrations
- Microsoft 365 migrations
- Firewall and network deployments
- Cybersecurity or compliance experience
Certifications from Microsoft, Fortinet, Veeam, or other relevant vendors are certainly a plus, but we're more interested in what you can actually do than how many certifications are listed on your resume.
What We're Really Looking For
Technical ability matters, but so does ownership.
If an issue gets escalated to you, we expect you to take responsibility for getting it to a resolution. That doesn't mean you personally have to know the answer to everything. It means you know how to troubleshoot, research, involve the right resources when necessary, communicate what's happening, and keep things moving.
We want someone the helpdesk can depend on when they get stuck and someone management doesn't have to chase down to find out whether something got finished.
If you're a strong MSP engineer who likes solving difficult problems, enjoys helping other technicians improve, and wants to have a real impact on how a technical team operates, we'd like to talk to you.
Work Location
This is a full-time hybrid position based in Tampa, Florida.
Candidates should live in the Tampa Bay area or within reasonable commuting distance of Tampa. This is not a fully remote position.
The position will include a combination of office, remote, and occasional onsite client work depending on support and project needs.
Pay: $95,000.00 - $105,000.00 per year
Benefits:
- Dental insurance
- Health insurance
- Life insurance
- Paid time off
- Tuition reimbursement
- Vision insurance
Work Location: Hybrid remote in Tampa, FL 33610
