Technical Support Team Lead, Dedicated Team

Flagler Technologies LLC; Oregon; Hybrid; USD 85,000 - 110,000; Full time

Benefits offered by this job

PTO – 3 weeks

Health insurance

Dental & Vision

Group life insurance

401k with 4% match

Professional development support

Company equipment provided

Internet and cell stipend

Job summary

Flagler Technologies LLC is seeking a Technical Support Team Lead for a dedicated customer environment. This full‑time remote role blends hands‑on technical work with team leadership, service‑delivery oversight, and proactive customer communication.

You’ll guide a dedicated support team, escalate and resolve complex issues, and drive improvements across Microsoft 365, AD, MFA, and hybrid infrastructure while maintaining SLA performance and customer satisfaction.

Qualifications

• Three to five years of experience troubleshooting system infrastructure and networking environments.

Responsibilities

• Coordinate daily workloads, assign tasks, and prioritize requests across the dedicated support team.
• Monitor ticket queues, backlog, and SLA performance to keep service delivery on track.
• Serve as first escalation point for technical assistance, guidance, or issue resolution.
• Provide advanced troubleshooting across Microsoft 365, Active Directory, hybrid infrastructure, networking, and MFA environments.
• Use PowerShell scripting to automate administrative work and improve efficiency.
• Act as primary operational contact for customer stakeholders with updates on priorities and risks.
• Participate in regular customer meetings to review performance and upcoming initiatives.
• Review ticket notes and documentation for accuracy and compliance.
• Coach and mentor team members, support onboarding, and reinforce service-delivery standards.
• Identify workload imbalances and escalation needs, coordinating with other teams as required.
• Develop and maintain SOPs, technical documentation, and knowledge-base content.

Skills

Microsoft 365

Active Directory

Networking

PowerShell

Team leadership

Customer-facing communication

Time management

ITIL knowledge

Tools

PowerShell

Job description

Technical Support Team Lead - Dedicated Team FLAGLER TECHNOLOGIES Managed Services United States | Full-Time | Remote

Who Are We?

We're more than just an IT support provider - we're a team committed to delivering exceptional service while fostering growth and development within our ranks. Our mission is to empower the next generation of IT professionals by creating opportunities for leadership and career advancement. When you join us, you become part of a team that's as invested in your success as we are in providing top-tier support to our clients. For this position, we're looking for an experienced technical leader who can guide a dedicated support team, serve as a trusted operational contact for the customer, and remain actively engaged in resolving complex technical issues.

What Does a Typical Day Look Like in This Role?

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.

A typical day may include:

• 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.

This is a full-time remote position supporting a dedicated customer environment. The role requires consistent availability, ownership, and the ability to shift comfortably between technical escalation, team leadership, and customer‑facing responsibilities.

What Qualifications or Experience Do I Need?

We're looking for someone who combines strong Microsoft and infrastructure support experience with the judgment, communication skills, and organizational discipline needed to lead others effectively. Candidates should bring:

• 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.

Just as importantly, we're looking for someone who is 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.

What Will Help You Stand Out?

While not required, you'll stand out if you have:

• 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.

What Else Should You Know About Us?

• 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.**Devices that access company resources will need to be managed by us while being used for work purposes. A company computer and peripherals will be provided. You'll need a personal cell phone for multi‑factor authentication and a reliable internet connection – we even provide a stipend for this.