We’re looking for a true Tier II Help Desk Technician to own complex support issues in a busy, multi-tenant MSP environment. In this role, you’ll handle escalations that Tier I can’t resolve, including advanced troubleshooting across Windows, Microsoft 365, basic server and networking issues, and user onboarding/changes.
You’ll be the person our technicians and clients rely on when things get tricky—digging into root causes, stabilizing environments, and keeping users productive. You won’t be expected to architect Azure or design complex Intune policies (we have engineering roles for that), but you’ll work closely with our Associate Cloud & Endpoint Engineer (Azure / Intune) and project team when issues cross into deeper configuration or project work.
Most support is delivered remotely from our Orlando office. Less than 10% of your time will involve going on-site to client locations for issues that truly require a physical presence. This role also participates in an after-hours on-call rotation. On-call is scheduled in one-week blocks and is compensated with an additional on-call bonus on top of base salary. We’ll walk through how the rotation works and volume expectations during the interview process.
If you love solving tough technical problems, talking directly with users, and being the calm, senior voice on the help desk, this role is for you.
Key Responsibilities
Advanced User & Systems Support
- Own Tier II escalations from the help desk related to Windows workstations, Microsoft 365, basic server services, and line-of-business applications.
- Troubleshoot complex issues primarily via remote tools, with occasional on-site visits (under 10%) when hands-on support is required.
Microsoft 365 & Core Cloud Troubleshooting
- Support Microsoft 365 (Exchange Online, Teams, SharePoint), including mailbox issues, permissions, and access problems.
- Handle everyday Entra / Azure AD issues (user/group access, sign-in problems, MFA issues), escalating deeper policy/architecture changes to engineering as needed.
Network & Server Escalations
- Troubleshoot issues involving network connectivity, VPN, DNS, DHCP, VLANs, and related infrastructure in coordination with senior engineers when necessary.
- Work with servers (on-prem or cloud-hosted) at a Tier II level: service issues, performance checks, and basic configuration fixes.
Ticket, Incident, & On-Call Ownership
- Take full ownership of assigned tickets from intake to resolution, including documentation of findings and updates in the PSA.
- Help monitor queues, prioritize critical issues, and ensure SLAs are met by communicating clearly with both users and teammates.
- Participate in a rotating after-hours on-call schedule (one week at a time), responding to urgent issues and coordinating with teammates as needed; this on-call time is additionally compensated via an on-call bonus.
Collaboration & Knowledge Sharing
- Partner closely with Tier I technicians to provide guidance, answer questions, and help them grow.
- Collaborate with the Associate Cloud & Endpoint Engineer (Azure / Intune) and project team when escalations reveal a need for deeper configuration, automation, or long-term fixes.
- Contribute to knowledge base articles, checklists, and standard operating procedures.
Required Qualifications
- 3–5+ years of professional IT support experience with recent Tier II responsibilities.
- Experience in an MSP or multi-tenant environment strongly preferred.
- Strong skills in:
- Supporting Windows 10/11 workstations and common business applications
- Troubleshooting Microsoft 365 (Outlook/Exchange Online, Teams, SharePoint)
- Handling everyday Entra / Azure AD and user access issues (passwords, groups, MFA, sign-in problems)
- Solid understanding of core networking concepts (TCP/IP, DNS, DHCP, VPN, basic routing/switching) and experience troubleshooting network-related user issues.
- Experience with a PSA and RMM (ConnectWise, Halo, N-able, or similar) for ticketing and remote support.
- Strong problem-solving skills and clear, professional spoken and written English communication with both technical and non-technical audiences, including on phone and video calls with U.S.-based clients and teammates.
- Proven ability to own issues end-to-end, stay calm under pressure, and work effectively in a fast-paced environment.
- Willingness to participate in a rotating after-hours on-call schedule, with additional compensation provided.
Preferred Qualifications
- Prior work in a managed services setting supporting multiple clients.
- Exposure to Intune for device management and policy troubleshooting (you don’t need to be an Intune engineer; we’ll help you grow here).
- Familiarity with firewall/router vendors (Fortinet, Unifi, etc.) at a troubleshooting level.
- Experience mentoring Tier I techs or being the “go-to” escalation person on a service desk.
Location
- This role is based in our Orlando, FL office.
- Day-to-day work is performed remotely via our tools from the office.
- Less than 10% of your time will involve going on-site to client locations in the Orlando area when an issue truly requires a physical visit.
- Candidates must live within commuting distance of Orlando or be willing to relocate.
Salary
Annual salary of $70,000-85,000/year commensurate with experience + on-call stipend as well as paid vacation, health insurance plans, retirement program, disability insurance, and life insurance.
Benefits Include:
✅ Paid Time Off (PTO) – Accrual begins after 90 days, with increasing PTO over time.
✅ Health Insurance – Enterfusion covers a portion of employee premiums; spouse and dependent coverage available. Two plans through Florida Blue.
✅ Life Insurance, Dental & Vision Insurance – 100% company-paid coverage for employees.
✅ Short- & Long-Term Disability Insurance – Income protection benefits provided.
✅ SIMPLE IRA – Enterfusion matches employee contributions up to a set percentage.
✅ Continued Learning – Reimbursement for required or beneficial certifications, plus training support.
Join Enterfusion and be part of a team that invests in your success! 🚀
