Senior Systems Engineer

About Us:

We're a fast-growing, privately held insurance company on a path to become a leading U.S. retail platform. We believe every client and customer relationship holds the potential to grow into something greater, and the same is true for our people. As we grow, we're redefining how great talent connects with meaningful work, enabling our ambitious strategy while building a culture of high performance, creativity, and partnership. If you're driven by building reliable, secure infrastructure that supports critical financial operations, and you enjoy blending technical expertise with real-world business impact, you'll thrive here!

About the Role:

We're looking for a Senior Systems Engineer who brings deep infrastructure expertise, a problem-solver mindset, and a passion for building and maintaining resilient, secure systems. In this role, you'll own and advance our data center, Cloud, and Microsoft 365 environments, with a strong focus on server infrastructure, identity, data protection, and disaster recovery.

You'll play a key role in provisioning, configuring, and optimizing infrastructure across Nutanix HCI, Windows Server, AWS, and Microsoft 365 platforms-while ensuring seamless integration across systems, identity services, and proprietary applications. You'll lead efforts to modernize legacy infrastructure, harden identity and policy controls, and maintain robust backup, recovery, and monitoring capabilities.

This role partners closely with IT teams and business stakeholders to ensure our environment remains scalable, secure, and built for the future-bringing together technical expertise and practical execution to drive meaningful impact across the organization.

What You'll Do:

Build and Maintain Core Infrastructure

• Own and optimize Nutanix HCI infrastructure, including cluster upgrades, health monitoring, and capacity planning
• Own Windows Server environments spanning legacy (2003+) through current versions, including hands-on upgrade and migration projects
• Deploy, configure, and maintain Microsoft Failover Clusters and SQL Server deployments in clustered and standalone configurations
• Support AWS infrastructure and services as a strong complement to on-premises workloads
• Perform ongoing performance tuning, capacity planning, and resource optimization to support business growth
• Lead legacy-to-modern server upgrade initiatives, ensuring minimal disruption and full documentation of the migration path

Data Protection and Disaster Recovery

• Design, implement, and maintain data protection strategies, including backup policies, replication, and retention management
• Own disaster recovery planning, testing, and execution to ensure business continuity across all critical systems
• Support and optimize Wasabi object storage for backup targets and archival workloads
• Leverage Nutanix-native data protection features, including snapshots, replication, and DR runbooks

Identity, Directory, and Access Management

• Serve as the subject matter expert for Active Directory-including AD Sites and Services, OU structure hardening, Group Policy design and enforcement, and schema management
• Support hybrid Active Directory environments, including synchronization between on-premises AD and Entra ID
• Support and troubleshoot Entra ID for SSO, SAML-based application integrations, Conditional Access policies, and identity governance
• Own the enterprise PKI and certificate infrastructure, including CA hierarchies, certificate lifecycle management, renewal processes, and integration with public certificate authorities such as DigiCert
• Support and troubleshoot Intune device management policies, including compliance, configuration profiles, and patch management

Microsoft 365 and Cloud Productivity

• Serve as the escalation point and subject matter expert for Microsoft 365, including Exchange Online, SharePoint Online, Teams, and OneDrive
• Provide deep technical support and guidance on SharePoint architecture, permissions, and content governance across the organization
• Troubleshoot, validate, and support Conditional Access policies aligned to Zero Trust principles
• Act as the escalation owner for Mimecast email security, including policy troubleshooting, threat protection, DMARC enforcement and monitoring, and continuity services

DNS, Networking, and Security

• Serve as the DNS authority for both public and private DNS-managing zones, records, delegation, split-horizon configurations, and DNS security practices
• Design, implement, and support network infrastructure, including routers, switches, firewalls (including Fortinet), and connectivity solutions
• Leverage deep knowledge of TCP/IP, routing protocols (BGP, OSPF, EIGRP), and network architecture to maintain a stable and resilient infrastructure
• Support and optimize storage, compute, network, and security resources across on-premises and cloud environments
• Troubleshoot complex network, system, and application issues-resolving connectivity and performance challenges across the environment
• Implement and support security tools, protocols, and controls to protect infrastructure and data
• Partner on vulnerability remediation efforts, system hardening, and ongoing monitoring of security risks

Monitoring, Automation, and Continuous Improvement

• Leverage Site24x7 for deep infrastructure and application monitoring, alerting, and uptime reporting
• Lead efforts to evaluate, test, and deploy infrastructure upgrades, patches, and enhancements
• Identify opportunities to improve system performance, scalability, and reliability through proactive analysis and innovation

Collaborate and Support Across the Organization

• Partner with IT teams and system administrators to maintain and troubleshoot the environment
• Provide support for network-related issues impacting the user community, ensuring timely resolution and minimal disruption
• Create and maintain clear documentation of systems, configurations, and processes to support knowledge sharing and operational efficiency

What You'll Bring:

• BS in Computer Science or related discipline, advanced degree desirable.
• 7+ years of experience as a Systems, Infrastructure, or Senior Network Engineer in an enterprise environment
• Broad hands-on experience across server infrastructure, networking (LAN/WAN/WLAN), identity, and cloud platforms

Required Experience:

• Nutanix: Hands-on experience with Nutanix HCI infrastructure, cluster upgrades, and data protection features
• Windows Server: Deep expertise in administering, troubleshooting, and upgrading Windows Server from 2003 through current versions
• Active Directory: Extensive experience with AD design, AD Sites and Services, OU hardening, Group Policy management, and hybrid AD architecture
• Certificate Services: Strong PKI and certificate lifecycle management experience in enterprise environments, including public certificate authorities such as DigiCert
• Entra ID: Proven experience with SSO, SAML integrations, Conditional Access, and identity governance
• Intune: Experience managing device compliance, configuration, and patching policies across Windows and mobile platforms
• Microsoft 365: Solid M365 administration including Exchange Online, SharePoint, Teams, and OneDrive
• SQL Server: Experience deploying and maintaining SQL Server in standalone and clustered configurations
• Microsoft Failover Clustering: Experience designing and maintaining Windows Server failover clusters
• DNS: Expert-level understanding of public and private DNS, split-horizon configurations, and DNS security
• Networking: Strong understanding of TCP/IP, routing protocols (BGP, OSPF, EIGRP), LAN/WAN/WLAN architecture, and enterprise network hardware, including routers, switches, and firewalls; hands-on experience with Fortinet platforms (FortiGate, FortiManager, or FortiAnalyzer)
• Data Protection & DR: Experience designing and maintaining backup, replication, and disaster recovery solutions
• Mimecast: Experience supporting Mimecast for email security, policy troubleshooting, DMARC enforcement and monitoring, and continuity
• Site24x7: Experience configuring and managing infrastructure monitoring, alerting, and reporting
• Wasabi: Familiarity with Wasabi object storage for backup and archival use cases

Strong Plus:

• AWS infrastructure experience spanning compute, containers, networking, and storage (EC2, Workspaces, ECS/Fargate, ECR, ALB, S3, Direct Connect, CloudFormation); comfortable operating in multi-region, multi-account AWS Organizations environments with an understanding of security boundary design.
• Redwood ActiveBatch for enterprise job scheduling and automation
• Experience leading legacy-to-modern server platform migrations

Core Competencies:

• Execution Excellence: Delivers high-quality infrastructure solutions while balancing speed, reliability, and operational stability
• Technical Depth: Demonstrates strong expertise in networking, cloud (Azure), and infrastructure technologies to solve complex challenges
• Problem Solving: Analyzes and resolves complex system, network, and performance issues with a proactive, solutions-oriented mindset
• Security & Risk Awareness: Prioritizes system security, data protection, and adherence to regulatory and compliance standards
• Communication: Clearly translates technical concepts and issues to both technical teams and business stakeholders
• Collaboration: Works effectively across IT and business teams to maintain and improve system performance and reliability
• Ownership & Accountability: Operates independently with sound judgment, taking full ownership of systems, issues, and outcomes
• Adaptability: Thrives in a dynamic environment, managing multiple priorities and evolving infrastructure needs
• Continuous Improvement: Identifies opportunities to enhance system performance, scalability, and resilience through innovation and optimization

What We Offer:

• A collaborative, inclusive environment that values authenticity, accountability, and partnership
• The opportunity to join the company at an exciting stage of growth, where colleagues are empowered to build what's next
• A variable compensation package with a base range of $100k-$147k
• A competitive benefits package including comprehensive medical, dental, and vision coverage; an HSA and 401(k) company match; paid time off; and employer-paid life and disability insurance
• Remote/hybrid work arrangement with significant travel

At Prosperity, we are committed to equal employment opportunities and encourage people from all backgrounds to apply. We make hiring decisions based on merit and do not discriminate on the basis of race, religion, color, national origin, gender identity, sexual orientation, age, disability, or any other protected status.

We strive for a meaningful interview experience for all candidates. If you need an adjustment or accommodation due to a disability or medical condition during the hiring process, please let your recruiter know.