Technical Support Team Lead, Dedicated Team

Flagler Technologies LLC • Jacksonville, FL

2h • $55,000 - $65,000 • Remote

About The Position

Flagler Technologies Managed Services is hiring a Technical Support Team Lead to guide a dedicated customer support team while remaining hands-on with complex technical issues. The role balances technical escalation, team coordination, service-delivery oversight, and customer communication. The Team Lead helps maintain focus and accountability, removes roadblocks, and ensures responsive, consistent customer support.

This full-time remote position supports a dedicated customer environment and requires consistent availability, ownership, and the ability to move comfortably between technical troubleshooting, team leadership, and customer-facing responsibilities. The role coordinates work across the support team and collaborates with Managed Services, Engineering, Project Management, Customer Success, account management, and third parties as needed.

Requirements

• Three to five years of experience troubleshooting system infrastructure and networking environments.
• Advanced experience administering and supporting Microsoft 365 environments.
• Advanced experience administering and supporting Active Directory and hybrid identity environments.
• Experience administering and troubleshooting multi-factor authentication solutions.
• Intermediate proficiency with PowerShell scripting and automation.
• Ability to independently troubleshoot complex technical issues and engage engineering teams or third parties when appropriate.
• Previous experience in a lead, supervisory, or management role involving technical professionals.
• Ability to prioritize work, coordinate multiple assignments, and guide others in a fast-moving support environment.
• Strong organizational and time-management skills, including balancing hands-on technical work with leadership and administrative responsibilities.
• Excellent written and verbal communication skills and ability to work effectively with technical personnel and customer stakeholders.
• Strong customer-service instincts, sound judgment, and ability to manage expectations while remaining aligned with contractual scope and service standards.
• Experience reviewing operational metrics, recognizing service or performance concerns, and recommending practical improvements.
• Careful attention to ticket documentation, time-entry accuracy, operational reporting, and follow-through.
• Ability to work independently, take ownership, and escalate concerns appropriately.
• Personal cell phone for multi-factor authentication and a reliable internet connection.

Nice To Haves

• Experience supervising or leading a team of IT support professionals.
• Experience working within a managed services provider or supporting a dedicated customer account.
• Familiarity with IT service-management platforms, ticketing systems, SLA reporting, and operational dashboards.
• Working knowledge of ITIL principles, incident management, problem management, and service-delivery best practices.
• Experience participating in customer-facing service reviews and operational meetings.
• Relevant Microsoft, Cisco, ITIL, or comparable technical and service-management certifications.

Responsibilities

• Coordinate daily workloads, assign tasks, and prioritize service requests, incidents, and operational activities across the dedicated support team.
• Monitor ticket queues, backlogs, work assignments, resolution times, and SLA performance.
• Serve as the first escalation point for technical assistance, operational guidance, and customer concerns.
• Provide advanced troubleshooting and root-cause analysis across Microsoft 365, Active Directory, hybrid infrastructure, networking, and MFA environments.
• Use PowerShell scripting to automate administrative work and improve operational efficiency.
• Serve as a primary operational contact for customer stakeholders and communicate priorities, outstanding issues, risks, and ongoing activities.
• Participate in recurring customer meetings to review service performance, open items, upcoming initiatives, and improvement opportunities.
• Review ticket notes, technical documentation, and employee time entries for accuracy, completeness, and compliance with company standards.
• Coach and mentor team members, support onboarding and knowledge transfer, and reinforce accountability and service-delivery expectations.
• Identify workload imbalances, performance concerns, coverage gaps, recurring incidents, and resource constraints, and address or escalate them appropriately.
• Coordinate with Managed Services, Engineering, Project Management, Customer Success, account management, and third parties when broader support is required.
• Develop and maintain standard operating procedures, technical documentation, and knowledge-base content.

Benefits

• Three weeks of paid time off, with vacation and sick time accrued subject to manager approval.
• Healthcare options with 75% of the premium covered.
• Dental and vision services.
• Group life insurance.
• 401(k) with up to 4% matching and immediate vesting.
• Professional development support, including training and certification reimbursement.
• Stipend for a reliable internet connection.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed