System Administrator

Phone screen and on-site panel interview

About the client:

Windward Risk Managers is the expert management team behind premier home insurers Florida Peninsula Insurance Company, Edison Insurance Company, and Ovation Home Insurance Exchange. We have been in the business of leveraging our expertise to manage all aspects of an insurer’s operations since 2005, helping our partner carriers provide first-class insurance solutions at competitive prices, along with a superior customer experience. Services we provide include policy management, underwriting services, claims handling, marketing and communications, policyholder customer service, risk management, and agency contracting and licensing.

System Administrator

Boca Raton, FL  •  Onsite  •  Full-Time  •  Information Technology

Position Summary

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.

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.

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)