System Administrator

Windward Risk Managers; Boca Raton (FL); On-site; USD 100,000 - 140,000; Full time

Benefits offered by this job

Employer-paid health insurance

401(k) match with immediate vesting

Disability insurance

3 weeks PTO + holidays

Tuition reimbursement

Job summary

Windward Risk Managers seeks a senior systems administrator to lead disaster recovery and data protection efforts at our Boca Raton office. You will design, implement, and optimize Veeam and VMware environments, manage Azure infrastructure, and ensure DR readiness across on-premises and cloud data centers.

Ideal candidates bring 5–8 years of hybrid environment experience, strong PowerShell skills, and a solid storage background (NetApp/Tintri).

Qualifications

• 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.

Responsibilities

• Continuously improve and evolve the company’s disaster-recovery environment across data centers and Azure; lead DR planning, runbooks, and failover testing, engaging multiple teams; configure fault-tolerant features and maintain RTO/RPO 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 supporting SAN / NAS storage (NetApp, Tintri), deduplication appliances 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 maintenance/testing of business continuity plans as infrastructure evolves.
• 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 escalation point for backup and recovery issues.
• Serve as a subject matter expert for data protection, storage management, and recovery operations.

Skills

Veeam Backup & Replication

VMware vSphere

Azure Administration

PowerShell

Windows Server

Enterprise Storage

Scripting & Automation

Tools

Veeam Backup & Replication

VMware vSphere

Microsoft Azure

Job description

Job Details: Job Location: Corporate Office - Boca Raton, FL, Position Type: Full Time, Salary Range: Undisclosed, Job Shift: Day, Job Category: Information Technology, Position Summary:

Key Responsibilities:

• 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:

• 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

Qualifications: Required Qualifications:

• 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.

WRM is committed to providing equal employment opportunities to all employees and applicants without regard to race, color, religion, sex, sexual orientation, gender identity or expression, national origin, disability, or veteran status. We take affirmative action to ensure that all employment decisions are based on merit, qualifications, and abilities.