Tier 2 IT Support Engineer / Help Desk Lead

Massive IT; Tampa (FL); On-site; USD 65,000 - 95,000; Full time

Job summary

Massive IT, LLC in Tampa, FL seeks a Tier 2 IT Support Engineer / Help Desk Lead for a full-time, on-site role. Candidates should have a minimum of 5 years of IT experience and a passion for improving service delivery and mentoring junior technicians.

You will oversee daily Help Desk operations, develop SOPs, document procedures, and drive automation to reduce tickets while maintaining SLA compliance. This is not just ticket work; you will shape our support processes.

Qualifications

• Minimum 5 years of professional IT support experience, preferably within an MSP environment.
• Strong experience troubleshooting Microsoft-based business environments.
• Hands-on experience with Microsoft 365 administration, Active Directory, networking, and endpoint management.
• Experience working with PSA/ticketing and remote monitoring tools.
• Demonstrated ability to troubleshoot and resolve complex technical problems independently.
• Strong organizational skills and attention to detail.
• Ability to prioritize competing requests in a fast-paced environment.
• Excellent written and verbal communication skills.
• Ability to develop and document technical procedures.
• Experience mentoring or providing technical guidance to other technicians.

Responsibilities

• Provide advanced Tier 2 technical support for business customers.
• Troubleshoot complex workstation, server, network, Microsoft 365, and cloud-related issues.
• Serve as an escalation resource for Tier 1 technicians.
• Diagnose recurring technical issues and implement long-term solutions.
• Support Microsoft 365, Entra ID, Active Directory, Exchange Online, and Intune environments.
• Troubleshoot VPN, firewall, wireless, and network connectivity issues.
• Assist with cybersecurity incidents, system outages, and other critical service issues.

Skills

5+ years IT support

MSP experience

Microsoft 365, AD, networking

PSA/ticketing tools

Troubleshooting complex issues

Documentation & procedures

Mentoring/leadership

Communication skills

Tools

ConnectWise PSA

RMM tools

PowerShell scripting

Job description

Tier 2 IT Support Engineer / Help Desk Lead

Massive IT, LLC | Tampa, FL

Full-Time | On-Site Only | Minimum 5 Years of IT Experience

About Massive IT

Massive IT is a growing Managed Services Provider (MSP) based in Tampa, Florida. We provide managed IT services, cloud solutions, cybersecurity, infrastructure support, and technology services to businesses across multiple industries.

We are looking for an experienced Tier 2 IT Support Engineer / Help Desk Lead who combines strong technical troubleshooting skills with organization, initiative, accountability, and a passion for improving IT service delivery.

This is not simply a position where you work tickets all day. We are looking for someone who can help strengthen our Help Desk operations, develop processes, mentor junior technicians, and proactively identify opportunities to improve efficiency and the customer experience.

If you are someone who sees a problem, takes ownership, and works toward a solution without waiting to be told what to do, we want to hear from you.

What You'll Be Doing

Technical Support & Escalations

• Provide advanced Tier 2 technical support for business customers.
• Troubleshoot complex workstation, server, network, Microsoft 365, and cloud-related issues.
• Serve as an escalation resource for Tier 1 technicians.
• Diagnose recurring technical issues and implement long-term solutions.
• Support Microsoft 365, Entra ID, Active Directory, Exchange Online, and Intune environments.
• Troubleshoot VPN, firewall, wireless, and network connectivity issues.
• Assist with cybersecurity incidents, system outages, and other critical service issues.

Help Desk Leadership & Service Delivery

• Help oversee daily Help Desk operations and ticket workflow.
• Monitor ticket queues, priorities, response times, and resolution progress.
• Identify tickets requiring escalation or additional attention.
• Ensure tickets contain accurate documentation, troubleshooting notes, and resolutions.
• Mentor Tier 1 technicians and provide technical guidance.
• Help maintain service quality, customer communication, and SLA compliance.
• Identify recurring customer issues and recommend permanent solutions.

Process Development & Operational Improvement

• Develop, document, and improve Help Desk processes and standard operating procedures (SOPs).
• Identify gaps in existing workflows and recommend improvements.
• Establish troubleshooting guides, technical documentation, and knowledge base articles.
• Identify opportunities for automation and ticket reduction.
• Help standardize how technical issues are diagnosed, escalated, resolved, and documented.
• Recommend improvements that increase technician productivity and customer satisfaction.

What We're Looking For

Required Qualifications

• Minimum 5 years of professional IT support experience, preferably within an MSP environment.
• Strong experience troubleshooting Microsoft-based business environments.
• Hands-on experience with Microsoft 365 administration, Active Directory, networking, and endpoint management.
• Experience working with PSA/ticketing and remote monitoring tools.
• Demonstrated ability to troubleshoot and resolve complex technical problems independently.
• Strong organizational skills and attention to detail.
• Ability to prioritize competing requests in a fast-paced environment.
• Excellent written and verbal communication skills.
• Ability to develop and document technical procedures.
• Experience mentoring or providing technical guidance to other technicians.

Preferred Experience

• ConnectWise PSA and RMM tools.
• Microsoft Azure and hybrid environments.
• Microsoft Intune and endpoint security.
• Firewall and network administration.
• PowerShell scripting and automation.
• IT documentation platforms and knowledge base development.
• MSP service delivery processes and SLA management.
• Microsoft, CompTIA, or other relevant industry certifications.

The Person Who Will Succeed Here

• Takes ownership: Follows issues through to resolution and doesn't wait for someone else to take responsibility.
• Is self-driven: Recognizes what needs to be done and takes initiative.
• Is organized: Can manage multiple priorities while maintaining accurate documentation and follow-through.
• Thinks beyond the ticket: Identifies root causes, recurring problems, and opportunities for improvement.
• Creates structure: Can develop practical processes and procedures that help the entire team operate more effectively.
• Leads by example: Supports teammates, shares knowledge, and maintains high standards.
• Communicates effectively: Keeps customers and internal team members informed.

Work Location & Schedule

• Tampa, Florida
• Full-time, in-office position
• Monday-Friday, during standard business hours
• This is not a remote or hybrid position.

Why Join Massive IT?

This is an opportunity to play an important role in a growing IT services company where your ideas, technical expertise, and initiative can make a direct impact.

You will have the opportunity to help shape our Help Desk operations, improve service delivery, and contribute to building a stronger technical team.