Technical Support Specialist (Lead)

Sherpa 6•Ashburn, VA

5d•Onsite

About The Position

The Technical Support Specialist Lead supports the U.S. Customs and Border Protection (CBP) Operational Technology Operations Center (OTOC) and the build-out, integration, and operation of the Office of Information and Technology (OIT) ISS OTOC. This position serves as the working lead for a team of four IT Support Specialists responsible for a 24x7x365 help desk supporting network operations, cybersecurity operations, helpdesk/call-center support, and the deployment and sustainment of the Watchtower Mobile Device Management (MDM) platform for operational technology (OT) assets. The Lead is responsible for day-to-day help desk operations coordination, including shift and coverage coordination, workload prioritization, ticket quality, escalation management, operational reporting, knowledge management, and continuity between shifts. The position provides technical leadership and mentoring to support personnel while remaining hands-on in the deployment, operation, provisioning, monitoring, troubleshooting, and sustainment of OT and tactical devices across connected, offline, and edge environments. The position also serves as a primary coordination point among help desk personnel, technical teams, program leadership, and government stakeholders for incident, problem, and change management activities, including escalation, root cause analysis, technical support, documentation, planned changes, and continuous service improvement.

Requirements

Associate's or Bachelor's degree in Information Technology, Computer Science, Cybersecurity, Network Engineering, Communications, Business Technology, or a related field; equivalent directly relevant experience may be substituted for a degree.
5+ years of progressively responsible experience in technical support, customer support, help desk/service desk operations, systems administration, customer success, technical training, or a related customer-facing technical role.
At least 1-2 years of demonstrated experience leading, coordinating, mentoring, or providing senior-level technical direction to an IT support or service desk team.
Demonstrated experience coordinating a 24x7x365 or shift-based technical support operation, including workload prioritization, shift handoffs, escalation management, and operational continuity.
Experience using help-desk or IT service management systems (e.g., ServiceNow) to manage incidents, service requests, escalations, and operational reporting.
Demonstrated ability to troubleshoot software, device, account, connectivity, and configuration issues in a structured manner.
Experience supporting Windows and/or macOS desktop environments and Android and/or iOS mobile devices.
Strong customer service, leadership, and communication skills, with the ability to coordinate effectively with both technical and non-technical users and stakeholders.
Experience conducting customer or staff training, onboarding, product demonstrations, technical instruction, or knowledge transfer.
Ability to explain technical concepts, operational status, risks, and escalation needs clearly in written and verbal communications.
Strong organizational skills, attention to detail, and the ability to manage multiple priorities, incidents, customer requests, and team activities in a mission-oriented environment.
Ability to create and maintain customer-facing and internal documentation, training materials, SOPs, troubleshooting guides, escalation procedures, and knowledge articles.
Ability to work independently in a desk-based support environment while coordinating effectively across product, engineering, cybersecurity, network operations, program management, and support teams.
Strong working knowledge of: Windows Server and Desktop Operating Systems, Linux Operating Systems, Android and iOS Mobile Platforms, Mobile Device Management (MDM) Solutions, Active Directory and LDAP Administration, Microsoft Azure Cloud Services, AWS Cloud Services, Virtualization Technologies (Hyper-V, VirtualBox, VMware).
Knowledge and experience supporting Tactical Awareness Kit (TAK) software applications, including: TAK Server Administration, ATAK/WinTAK Client Configuration, TAK Infrastructure Deployment and Support, Tactical Data Distribution and Network Integration.
Experience with: Public Key Infrastructure (PKI), X.509 Certificates, Certificate Authorities (CA), Client and Server Certificate Lifecycle Management, Secure Communications Architectures.

Nice To Haves

Experience supporting a SaaS, mobile technology, mobile device management (MDM), public safety, situational awareness, field operations, or communications platform.
Experience with customer relationship management (CRM), help-desk, ticketing, or knowledge-base systems.
Experience supporting commercial sales teams through technical demonstrations, trials, pilots, or pre-sales customer discussions.
Working knowledge of mobile device management, networking fundamentals, VPN technologies, identity and access management, certificates, or cloud services.
Experience with Watchtower or a similar situational awareness, mobility, or operational technology platform.
Experience developing or delivering structured technical training programs.
Relevant technical certifications such as CompTIA A+, Network+, Security+, or comparable certifications.
Experience supporting government, public safety, defense, or other mission-oriented customers is beneficial but not required for the role.

Responsibilities

Lead and coordinate the daily activities of four IT Support Specialists supporting a 24x7x365 Operational Technology Operations Center (OTOC) help desk.
Coordinate shift coverage, workload distribution, ticket ownership, priorities, and operational continuity to maintain continuous support.
Establish and maintain effective shift-turnover practices so open incidents, escalations, outages, planned changes, and priority activities are communicated between shifts.
Monitor help desk queues and operational workload; identify aging, stalled, high-priority, or mission-impacting tickets and coordinate appropriate action.
Provide technical guidance, mentoring, and escalation support to IT Support Specialists and assist with onboarding and knowledge development.
Coordinate team activities and day-to-day priorities with program leadership and government stakeholders.
Identify staffing, coverage, workload, process, or service-delivery risks and elevate issues requiring management attention.
Promote consistent customer service, documentation, troubleshooting, and ticket-handling standards across all shifts.
Coordinate 24x7x365 incident management, escalation, root cause analysis, and technical support activities.
Ensure incidents and service requests are appropriately categorized, prioritized, assigned, documented, escalated, and tracked through resolution using government-furnished systems (e.g., ServiceNow).
Lead or coordinate response activities for high-priority and mission-impacting incidents and maintain situational awareness of active operational issues.
Coordinate technical resources and stakeholder communications during complex incidents, outages, and escalations.
Develop and maintain incident, problem, and change management processes, including SOPs, escalation procedures, knowledge management, and lessons learned.
Coordinate and document root cause analysis and maintain a repository accessible to authorized government personnel.
Support release and change management, including planning, validation, communication, reporting, and support for on-premise and cloud migrations.
Track corrective actions and recurring issues to support problem management and continuous improvement.
Develop and maintain help desk SOPs, shift-turnover procedures, escalation matrices, troubleshooting guides, knowledge articles, and operational documentation.
Track and report operational metrics such as ticket volume, response and resolution performance, aging tickets, recurring issues, escalations, and service trends.
Conduct periodic reviews of ticket quality, documentation, prioritization, and closure practices to promote consistency and accountability.
Prepare operational status updates and support briefings for program leadership and government stakeholders.
Identify recurring technical or process issues and recommend improvements to workflows, documentation, training, tooling, or support procedures.
Capture lessons learned from significant incidents and operational events and incorporate improvements into team procedures and knowledge resources.
Deploy and operate the Watchtower MDM platform for OT and tactical devices, including Android, Windows, Linux, iOS, radios, sensors, and wearables.
Automate device provisioning, configuration management, and remote updates with minimal human intervention.
Support secure certificate distribution, remote wiping, device compliance monitoring, and over-the-air (OTA) updates.
Enable offline/edge deployments and support for disconnected operations.
Integrate Watchtower's analytics for device usage, compliance, and operational metrics.
Manage device lifecycle, including onboarding, configuration, and decommissioning.
Ensure all MDM operations comply with CBP's security and operational policies.
Serve as a primary operational coordination point among help desk personnel, engineering, cybersecurity, network operations, product teams, program management, and government stakeholders.
Communicate operational impacts, risks, outages, escalations, and resolution status clearly to technical and non-technical audiences.
Coordinate planned maintenance, releases, migrations, deployments, and other changes that may affect help desk operations or supported users.
Ensure support personnel receive the information, procedures, training, and documentation required to support new capabilities and operational changes.