System Administrator

Windward Risk Managers is seeking a highly skilled System Administrator to serve as the primary administrator for backup, recovery, and cloud infrastructure across the company’s on-prem and cloud environments. The ideal candidate will have deep expertise in Veeam, vCenter, and Microsoft Azure, with a focus on continuously improving, optimizing, and validating data protection and high-availability architecture. This role leads disaster-recovery planning and testing in partnership with the Systems, Network, Database, and Security teams to keep business-critical systems protected and recoverable., This is a full-time, in-person position based at our Boca Raton, Florida office. Remote and hybrid work arrangements are not available for this role., Continuously improve and evolve the company’s disaster-recovery environment across our data centers and Azure; lead DR planning, runbooks, and failover testing, engaging the Systems, Network, Database, and Security teams; configure fault-tolerant features and maintain Recovery Time Objective and Recovery Point Objective documentation. Design, implement, and optimize the Veeam Backup & Replication environment, including job architecture, repositories, replication, retention and immutability policies, and storage usage. Administer the VMware vSphere / vCenter environment as it relates to data protection, including replication and recovery validation, along with the supporting SAN / NAS storage (NetApp, Tintri), deduplication appliances (ExaGrid), and immutable backup repositories. Validate backup integrity through regular restore testing and automated verification; confirm all critical systems are covered, configurations follow best practices, and gaps are remediated. Contribute to the company’s business continuity program, supporting business impact analysis, recovery strategies for critical business functions, and the ongoing maintenance and testing of business continuity plans as infrastructure and systems change. Manage and expand the company’s Microsoft Azure footprint, building out cloud infrastructure to support business continuity, backup, and DR targets while maintaining storage, access control, and cost governance as adoption grows. Monitor backup health, capacity, and SLA compliance; perform root cause analysis on failures and implement preventive measures. Support compliance and audit requirements related to data protection, backup retention, and recoverability, including evidence gathering and remediation of audit findings. Automate verification and reporting with PowerShell; maintain runbooks and documentation; serve as the escalation point for backup and recovery issues. Serve as a subject matter expert for data protection, storage management, and recovery operations.

Why Windward Risk Managers

5 to 8 years of systems administration experience in a hybrid (cloud and on-premises) environment. Hands-on production experience designing and managing Veeam Backup & Replication and VMware vSphere / vCenter environments. Administrator-level experience with Microsoft Azure (resources, access control, storage, cost governance). Solid understanding of backup and disaster-recovery concepts, including Recovery Point Objective and Recovery Time Objective, replication, snapshots, immutability, and DR testing. Practical PowerShell scripting skills; working knowledge of Windows Server and enterprise storage (NetApp and / or Tintri preferred). Strong problem-solving skills, the ability to prioritize effectively, and clear written and verbal communication.

Preferred Qualifications:

Veeam Certified Engineer (VMCE) VMware Certified Professional (VCP) or Microsoft Azure Administrator (AZ-104)

Due to current business and operational considerations, we currently hire employees residing in the following states at this time: AL, AR, CA, CT, FL, GA, KY, MO, NC, NV, OH, SC, TN, TX, VA, and WI.

Candidates must be authorized to work for any employer in the U.S. without requiring visa sponsorship now or in the future.

Windward Risk Managers is proud to be recognized on Fortune’s 2026 Best Medium Workplaces list, ranking #28 among the Top 100 companies 100% employer paid health insurance for employees Up to 6% 401(k) match with immediate vesting Long-term and short-term disability insurance 3 weeks PTO to start + generous paid holidays Tuition reimbursement and continuing education support Collaborative and growth focused culture, * 401(k) matching

• Dental insurance
• Employee assistance program
• Health insurance
• Life insurance
• Paid time off
• Parental leave
• Referral program
• Tuition reimbursement
• Vision insurance