We are seeking a highly accountable and reliable Senior System Administrator to join our internal IT team supporting business-critical systems across a remote/colocated data center and cloud services. This role emphasizes Windows Server 2022, VMware vSphere, and advanced troubleshooting, with a strong focus on PowerShell automation and Tier 2/3 escalation. You will also support a hybrid Microsoft 365 (Office 365) + on-premises Exchange relay architecture, ensuring secure and reliable mail flow for internal applications and business processes. The role requires exemplary customer service abilities when working with our employees.
Job Summary:
Data Center & Core Infrastructure (Remote Site)
- Administer and support infrastructure hosted in a remote data center/colocation environment, coordinating with vendors/remote hands as needed.
- Maintain, patch, harden, and optimize Windows Server 2022 systems (including HA/critical services).
- Manage VMware vSphere (vCenter/ESXi, clusters, HA/DRS, capacity planning, VM lifecycle, performance tuning and troubleshooting).
Identity, Access, and Core Services
- Administer Microsoft Active Directory (GPOs, OU design, permissions, replication, authentication issues).
- Manage and troubleshoot DNS (and DHCP as applicable) and other core infrastructure services.
- Support and maintain MFA and secure authentication workflows.
Messaging (Hybrid Microsoft 365 + On-Prem Relay)
- Administer and support Microsoft 365 Exchange Online and hybrid mail flow.
- Manage on-premises Exchange used for SMTP relay (applications, devices, and line-of-business systems), including:
- Mail connectors, receive/send connectors, transport rules, authentication, and TLS/certificates
- Troubleshooting mail flow issues, message tracing, and relay restrictions
- Maintaining availability and security of relay services
- Use Exchange Admin Center (EAC) and Microsoft 365 admin tools for mailbox, mail flow, and policy administration as applicable.
Automation & Scripting
- Develop and maintain PowerShell scripts (Exchange Online/AD/Windows administration, reporting, onboarding/offboarding, compliance checks).
- Identify repetitive operational tasks and implement automation with clear documentation and safe change practices.
Tier 2/3 Escalation Support (Internal Users)
- Serve as a senior escalation point for complex issues from the help desk (server, virtualization, identity, mail flow, permissions, and infrastructure-dependent application issues).
- Provide clear communication, timely updates, and strong ownership from incident open through resolution.
- Perform root-cause analysis and implement permanent corrective actions where appropriate.
Application & Data Support
- Use SQL scripting for operational support (queries, validation, troubleshooting support, basic security/permissions tasks as applicable).
- Partner with internal application owners to resolve infrastructure-related performance, connectivity, and availability issues.
Citrix / Load Balancing
- Support Citrix NetScaler (ADC) including load balancing, health monitors, SSL certificates, and traffic troubleshooting.
Hardware & Storage
- Support compute platforms including HP Synergy BladeSystem/BladeCenter (remote troubleshooting, firmware planning, vendor coordination).
- Administer HP Alletra storage arrays (capacity planning, performance monitoring, volumes/LUNs, connectivity troubleshooting).
Cloud & Cross-Platform
- Support hybrid services and workloads in Microsoft Azure (VMs, monitoring, identity integration, networking fundamentals).
- Provide administration and troubleshooting in Linux environments (services, logs, permissions, and networking fundamentals).
Accountability & Operational Excellence
- Demonstrate high accountability and reliability—own outcomes, follow through, and document work thoroughly.
- Participate in an on-call/escalation rotation and scheduled maintenance windows as required.
- Maintain accurate documentation (runbooks, diagrams, configurations), and adhere to change management practices.
Required Qualifications
- 5+ years of progressive systems administration experience in an internal IT environment
- Ability to multitask, while still meeting ticket and project deadlines
- Present technical changes during weekly formal Production Change Request meetings
- Strong hands-on experience with:
- Tier 2/3 escalation support and structured troubleshooting
- Windows Server 2022
- VMware vSphere (vCenter/ESXi)
- Cisco and NVIDIA switches ie. OSI model, Layer2 and Layer3 protocols
- Fortinet Firewalls
- PowerShell scripting/automation
- Active Directory, DNS, SMTP, HTTP/S, and IP Subnetting and authentication troubleshooting
- MFA administration/support concepts
- Citrix virtual applications support
- Experience supporting Microsoft 365 Exchange Online and hybrid/on-prem Exchange SMTP relay.
- Experience administering mail flow via Exchange Admin Center (EAC) and Microsoft 365 admin tools.
- Working knowledge of SQL scripting for operational support.
- Strong interpersonal and communication skills; ability to work effectively with both technical and non-technical teams. Ability to describe technology/solutions at the appropriate audience level.
Preferred Qualifications
- Experience with Citrix NetScaler (ADC) load balancing.
- Experience with HP Synergy compute platforms and HP Alletra storage arrays.
- Azure experience in hybrid infrastructure environments.
- Linux administration experience in mixed OS environments.
- Familiarity with monitoring, backup/DR concepts, and formal change control processes.
- Experience with monitoring technologies such as:
- SolarWinds network monitoring
- New Relic application monitoring
To ensure continuous health and performance of systems
Working Conditions
- Supports systems hosted in a remote data center/colocation; coordination with vendors/remote hands for physical access may be required.
- Participation in on-call rotation, quarterly in-house developed portal deployments, and occasional after-hours maintenance windows.
- Must be self-motivated as well as creative and efficient in proposing solutions to complex, time-critical problems.
- Able to work in a collaborative environment, be punctual to team meetings, and have a willingness to share your ideas
- Able to work independently and complete tasks with high quality, but unafraid to seek out suggestions from other team members
- Small, self-sufficient teams with an entrepreneurial spirit with an emphasis on team collaboration
- Casual, collaborative, agile environment which embraces and operates under our shared principles
- Complete transparency with open, honest discussions about our progress and challenges
- Emphasis on customer service with both internal and external customers
- Less than 10% travel expected, if at all
Education and Experience:
Associate’s or Bachelor’s degree in Information Technology, Computer Science, or a related field or equivalent practical experience.
5+ years of progressive systems administration experience in an internal IT environment, including Tier 2/3 escalation
Proven ability to multi-task and prioritize activities and see tasks thru completion.
Ability to work independently and as part of a team.
Strong analytical and diagnostic skills.
Familiar with cloud computing/services (Azure, Office 365).
Familiar with IT security best practices
About Us:
We at Florida Family Insurance are property insurers specializing in providing homeowners, condominium, rental property and flood insurance in the state of Florida. We are one of a select group of Florida insurers that holds a Secure A.M. Best rating. We also have an A Prime, Unsurpassed rating from Demotech. We are among the highest financially-rated Florida homeowners insurance companies.
Florida Family’s mission is to provide outstanding customer service while maintaining a strong financial foundation to meet our policyholders’ needs for years to come.
Working at Florida Family Insurance:
Everyone works together to build a company of which we are extremely proud. Our superior financial strength, solid reputation, integrity, passionate employees, professionalism, and teamwork enable us to attract and retain an outstanding team of employees. We recognize the quality of our talent is one of the driving factors behind our success.
Florida Family Insurance offers a competitive pay and benefits package which includes:
- Medical
- Dental
- Vision
- Life Insurance
- Short Term Disability
- Long Term Disability
- Flexible Spending Accounts
- Health Savings Accounts
- Critical Care Insurance
- Accident Insurance
- Paid Holidays
- Paid Leave Time
- 401(k)
Helping our employees achieve their own success in their careers is important to us. You will work alongside some of the brightest professionals in the industry and benefit from the knowledge and strengths of everyone on your team.
EOE/M/F/D/V
Job Type: Full-time
Pay: $65,000.00 - $85,000.00 per year
Work Location: Hybrid remote in Bonita Springs, FL 34134
