Windward Risk Managers
Job Details
Job Location Corporate Office - Boca Raton, FL
Position Type Full Time
Description
** This position will report daily to our corporate Headquarters in Boca Raton, Florida. **
We are seeking a motivated and detail-oriented Junior System Administrator with strong leadership qualities to manage daily helpdesk operations while collaborating closely with our Systems, Network, and Database teams. This is a hybrid role that blends technical support, team management, and cross-functional coordination, offering a growth path toward mid-level system administration and IT leadership.
The ideal candidate will bring a combination of hands-on technical skills and people management capabilities, with a proactive approach to support delivery, operational improvement, and cross-departmental collaboration. In this role, you'll be responsible for overseeing the helpdesk team's performance, conducting daily stand-up meetings, managing ticket workflows, and serving as a key liaison between frontline support and infrastructure teams.
Key Responsibilities
Help Desk Operations & Oversight Supervise day-to-day operations of the IT Help Desk, ensuring timely and effective resolution of service tickets for both onsite and remote users. Conduct daily team meetings to review open tickets, set priorities, and communicate relevant updates. Enforce SLAs and ensure ticket queues are actively managed and escalated when necessary. Perform routine performance assessments, coaching, and training sessions for the Help Desk team to support individual and team development. Monitor support metrics and KPIs, identifying service trends and recommending improvements to boost efficiency and user satisfaction. Technical Support & Escalation
Serve as the final escalation point for complex helpdesk incidents requiring advanced troubleshooting or coordination with infrastructure teams. Ensure consistent knowledge sharing and documentation of common issues and solutions within the helpdesk knowledge base. Participate in hardware/software deployment projects, patching cycles, and endpoint lifecycle management. Cross-Departmental Collaboration
Act as a liaison between the Help Desk and the Systems, Network, and Database teams, facilitating clear communication and coordinated support for IT projects. Assist with server administration, basic networking tasks, and infrastructure support under the guidance of senior sysadmin or network engineers. Help plan and execute cross-functional IT projects, ensuring proper hand-offs, resource coordination, and timely updates. Process Improvement & Reporting
Develop and refine Help Desk procedures and onboarding documentation to standardize support practices. Generate periodic reports on helpdesk performance, ticket resolution trends, and user feedback to inform leadership decision-making. Maintain compliance with internal IT policies, user access controls, and operational documentation. Qualifications
Qualifications
Education & Experience
Bachelor's degree in Information Technology, Computer Science, or a related discipline preferred (or equivalent experience/certifications). 3-5 years of experience in a helpdesk, desktop support, or junior sysadmin role, with at least 1-2 years of leadership or team coordination responsibilities. Prior experience in a regulated industry such as insurance, finance, or healthcare is a plus. Technical Skills
Proficient with Windows OS, Office 365, Active Directory, and basic networking (DHCP, DNS, VPN, LAN/WAN). Experience with ITSM/ticketing platforms such as Jira, ServiceNow, or Zendesk, ServiceDesk Plus. Familiarity with scripting, endpoint security tools, and virtualization technologies (VMware, Hyper-V) is a plus. Soft Skills
Strong leadership, organizational, and communication skills. Proven ability to coach and support team members in a fast-paced IT environment. Comfortable translating technical concepts into user-friendly language for end-users and non-technical stakeholders.
Job Location Corporate Office - Boca Raton, FL
Position Type Full Time
Description
** This position will report daily to our corporate Headquarters in Boca Raton, Florida. **
We are seeking a motivated and detail-oriented Junior System Administrator with strong leadership qualities to manage daily helpdesk operations while collaborating closely with our Systems, Network, and Database teams. This is a hybrid role that blends technical support, team management, and cross-functional coordination, offering a growth path toward mid-level system administration and IT leadership.
The ideal candidate will bring a combination of hands-on technical skills and people management capabilities, with a proactive approach to support delivery, operational improvement, and cross-departmental collaboration. In this role, you'll be responsible for overseeing the helpdesk team's performance, conducting daily stand-up meetings, managing ticket workflows, and serving as a key liaison between frontline support and infrastructure teams.
Key Responsibilities
Help Desk Operations & Oversight Supervise day-to-day operations of the IT Help Desk, ensuring timely and effective resolution of service tickets for both onsite and remote users. Conduct daily team meetings to review open tickets, set priorities, and communicate relevant updates. Enforce SLAs and ensure ticket queues are actively managed and escalated when necessary. Perform routine performance assessments, coaching, and training sessions for the Help Desk team to support individual and team development. Monitor support metrics and KPIs, identifying service trends and recommending improvements to boost efficiency and user satisfaction. Technical Support & Escalation
Serve as the final escalation point for complex helpdesk incidents requiring advanced troubleshooting or coordination with infrastructure teams. Ensure consistent knowledge sharing and documentation of common issues and solutions within the helpdesk knowledge base. Participate in hardware/software deployment projects, patching cycles, and endpoint lifecycle management. Cross-Departmental Collaboration
Act as a liaison between the Help Desk and the Systems, Network, and Database teams, facilitating clear communication and coordinated support for IT projects. Assist with server administration, basic networking tasks, and infrastructure support under the guidance of senior sysadmin or network engineers. Help plan and execute cross-functional IT projects, ensuring proper hand-offs, resource coordination, and timely updates. Process Improvement & Reporting
Develop and refine Help Desk procedures and onboarding documentation to standardize support practices. Generate periodic reports on helpdesk performance, ticket resolution trends, and user feedback to inform leadership decision-making. Maintain compliance with internal IT policies, user access controls, and operational documentation. Qualifications
Qualifications
Education & Experience
Bachelor's degree in Information Technology, Computer Science, or a related discipline preferred (or equivalent experience/certifications). 3-5 years of experience in a helpdesk, desktop support, or junior sysadmin role, with at least 1-2 years of leadership or team coordination responsibilities. Prior experience in a regulated industry such as insurance, finance, or healthcare is a plus. Technical Skills
Proficient with Windows OS, Office 365, Active Directory, and basic networking (DHCP, DNS, VPN, LAN/WAN). Experience with ITSM/ticketing platforms such as Jira, ServiceNow, or Zendesk, ServiceDesk Plus. Familiarity with scripting, endpoint security tools, and virtualization technologies (VMware, Hyper-V) is a plus. Soft Skills
Strong leadership, organizational, and communication skills. Proven ability to coach and support team members in a fast-paced IT environment. Comfortable translating technical concepts into user-friendly language for end-users and non-technical stakeholders.