IT Help Desk Supervisor- In Office

About us:

Windward Risk Managers is a homeowner’s insurance company based in Boca Raton, FL. We offer a casual, family-oriented work environment with a long-term focus on shared success. Our full-time employees enjoy a comprehensive benefits package that includes medical, dental, vision, disability, life insurance, FSAs, a Safe Harbor 401k, tuition reimbursement, paid time off, and holidays.

Position Summary

We are seeking an accomplished IT Help Desk Supervisor to provide strategic leadership for our technical support team while collaborating extensively with our Systems, Network, and Database departments. This position offers an exceptional opportunity for an experienced IT professional to advance their career through cross-functional expertise development in a dynamic enterprise environment.

The ideal candidate will demonstrate both technical proficiency and management excellence, overseeing daily help desk operations while building effective partnerships across specialized IT disciplines. In this role, you will drive operational excellence through process optimization, team development, and the delivery of exceptional technical support services that enable business success.

Key Responsibilities

Technical Leadership & Operational Excellence

• Strategic Help Desk Management: Direct all technical support functions including request prioritization, resource allocation, and escalation management. Deliver comprehensive support for both on-site and remote employees across all technology platforms while analyzing performance metrics to optimize service delivery and demonstrate quantifiable business impact.
• Process Development & Team Leadership: Establish and maintain best-practice policies, procedures, and knowledge management systems. Provide hands-on leadership through effective training, performance coaching, and career development while managing user lifecycles and technology deployment processes in collaboration with cross-functional partners.
• Project & Quality Management: Lead Help Desk initiatives including hardware/software implementations and cross-functional projects with disciplined planning and execution. Monitor service level metrics, develop targeted improvement strategies, and deliver executive reporting that drives continuous enhancement of support services and operational efficiency.
• Cross-Functional Collaboration: Partner closely with Systems, Network, and Database teams to implement integrated solutions that advance enterprise technology capabilities. Coordinate technical requirements, escalation protocols, and service transitions to ensure seamless support across technology domains.

Qualifications

Experience & Education

• 3-6 years of progressive experience in IT Help Desk roles with demonstrated technical expertise
• 1-2 years of leadership experience in a technical support environment
• Bachelor's degree in Information Technology, Computer Science, or related field preferred (equivalent experience considered)

Technical Knowledge

• Comprehensive understanding of Windows operating systems, Office 365, Active Directory, and networking fundamentals
• Proficiency with enterprise ticketing systems, remote support platforms, and IT asset management tools
• Experience with IT service management methodologies and best practices

Leadership Capabilities

• Demonstrated ability to lead technical teams while driving measurable performance improvements
• Excellent communication skills with the ability to translate complex technical concepts for diverse stakeholders
• Strong analytical thinking with systematic approach to problem identification and resolution
• Exceptional customer service orientation with commitment to continuous improvement

What We Offer

• Competitive compensation and comprehensive benefits package
• Professional development opportunities and clear advancement pathways