[Hiring] Technical Support Team Lead @Flagler Technologies LLC

Role Description

As the Technical Support Team Lead for a dedicated customer environment, you'll balance hands-on technical work with team coordination, service-delivery oversight, and customer communication. You'll help the team stay focused, remove roadblocks, maintain accountability, and ensure the customer receives responsive and consistent support.

• Coordinating daily workloads, assigning tasks, and prioritizing service requests, incidents, and operational activities across the dedicated support team.
• Monitoring ticket queues, backlogs, work assignments, resolution times, and SLA performance to keep service delivery on track.
• Serving as the first escalation point for team members who need technical assistance, operational guidance, or support resolving customer concerns.
• Providing advanced troubleshooting and root-cause analysis across Microsoft 365, Active Directory, hybrid infrastructure, networking, and MFA environments.
• Using intermediate PowerShell scripting to automate administrative work, streamline repeatable processes, and improve operational efficiency.
• Serving as a primary operational contact for customer stakeholders and providing clear updates on priorities, outstanding issues, risks, and ongoing activities.
• Participating in recurring customer meetings to review service performance, open items, upcoming initiatives, and opportunities for improvement.
• Reviewing ticket notes, technical documentation, and employee time entries for accuracy, completeness, and compliance with company standards.
• Coaching and mentoring team members, supporting onboarding and knowledge transfer, and reinforcing accountability and service-delivery expectations.
• Identifying workload imbalances, performance concerns, coverage gaps, recurring incidents, and resource constraints, then escalating or addressing them appropriately.
• Coordinating with Managed Services, Engineering, Project Management, Customer Success, account management, and third parties when broader support is required.
• Developing and maintaining standard operating procedures, technical documentation, and knowledge-base content that improve consistency and customer outcomes.

Qualifications

• 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.
• The 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.
• Demonstrated ability to prioritize work, coordinate multiple assignments, and guide others in a fast-moving support environment.
• Strong organizational and time-management skills, with the ability to balance hands-on technical work with leadership and administrative responsibilities.
• Excellent written and verbal communication skills and the ability to work effectively with both technical personnel and customer stakeholders.
• Strong customer-service instincts, sound judgment, and the 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.
• The ability to work independently, take ownership, and escalate concerns appropriately.

Requirements

• Humble, hungry, and people-smart - a leader who supports the team, communicates directly, protects the customer experience, and remains willing to step into the technical work when needed.

Benefits

• 3 Weeks of Paid Time Off (vacation and sick time accrued, subject to manager approval).
• Healthcare Options with 75% of your premium covered.
• Dental & Vision Services.
• Group Life Insurance.
• 401k with up to 4% matching and immediate vesting.
• Professional development support, including training and certification reimbursement.