Jobs at Windward Risk Managers

Provides advanced Level 2 and Level 3 help desk support for Windows and macOS endpoints, Microsoft 365, identity, networking, VPN, and endpoint management issues. Owns complex incidents through resolution, performs root-cause analysis, supports onboarding and device lifecycle activities, contributes to migrations and deployments, maintains documentation, mentors junior analysts, and improves help desk processes. This is an onsite senior individual-contributor role in Boca Raton, Florida.

A 10–12 week corporate internship with a homeowners insurance carrier. Interns rotate through four to six departments, support leadership, follow work instructions, gain exposure to insurance operations, and collaborate with peers to present their key learnings. The role is designed for students pursuing relevant bachelor’s degrees and emphasizes communication, initiative, adaptability, critical thinking, and professional development.

Develops sales for homeowners insurance products by supporting, training, and communicating with assigned agencies. Provides new-business assistance, completes quote data, supports sales campaigns and managers, identifies market opportunities, and may assist with catastrophe response efforts. Requires an insurance license, homeowners insurance industry experience, strong communication and organizational skills, and proficiency with Microsoft Office.

Develops sales for assigned agencies by providing training, support, and resources for WRM insurance products. The representative contacts agencies about market opportunities, facilitates quotes and applications, supports sales campaigns and new business issues, and assists Sales Development Managers. The role may support catastrophe response efforts and requires strong customer service, communication, organization, problem-solving, and computer skills.

Operates and improves enterprise LAN, WAN, wireless, firewall, cloud, storage, and connectivity infrastructure across data centers and Azure. Administers Palo Alto security platforms, Cisco switching and compute fabrics, dynamic routing, VPNs, NetApp networking, monitoring, and network access controls. Responsibilities include troubleshooting incidents, root-cause analysis, maintenance windows, documentation, hardware lifecycle support, security remediation, and on-call participation.

Administer and optimize Microsoft SQL Server and Azure SQL environments across hybrid infrastructure. Design and maintain high-availability, disaster-recovery, backup, recovery, security, and performance-tuning solutions. Validate recoverability, support compliance and business continuity, automate administration with PowerShell and T-SQL, manage capacity and costs, and serve as the escalation point and subject matter expert for database operations.

Administers hybrid on-premises and Azure infrastructure focused on backup, disaster recovery, business continuity, and high availability. Designs and optimizes Veeam environments, manages VMware and enterprise storage, validates restores, leads DR planning and testing, monitors backup health and SLA compliance, supports audits, and automates verification and reporting with PowerShell.

Manages day-to-day accounting, including accounts payable, commissions, claims billing, general ledger activities, and month-end close. Leads preparation of financial statements, budgets, variance analyses, cost allocation methodologies, audit support, and internal control activities. Supervises and mentors accounting staff, reviews reconciliations and journal entries, partners with department leaders, and supports process and reporting improvements.

Lead Agile/Scrum project delivery for homeowner's insurance initiatives: plan and track schedules, manage scope, risks, dependencies, and resources; run Scrum ceremonies; communicate status to stakeholders; maintain documentation; and drive continuous improvement to ensure on-time, on-scope delivery.