Systems Administrator

At Flagship Financial Group, we strive to make a positive impact on our customers’ lives through responsible auto financing and on our employees’ careers through continuous learning and advancement opportunities. Following our recent acquisition and the appointment of a new CEO, we are entering an exciting period of transformation, shifting toward a high-growth, tech-forward, and operationally excellent future.

We are seeking a Systems Administrator to manage, support, and continuously improve the technology infrastructure that powers our business operations. This role is responsible for the administration, security, performance, and reliability of enterprise systems, servers, cloud platforms, network services, and end-user technologies. Reporting to the Director of Infrastructure & Technology Operations, this position plays a key role in ensuring a secure, scalable, and highly available technology environment that supports our employees, customers, and business objectives.

• Administer and maintain enterprise infrastructure, including Windows servers, Active Directory, Microsoft 365, cloud environments, storage solutions, and virtualization platforms.
• Monitor system performance, availability, and security to ensure optimal operation and minimize downtime.
• Manage user accounts, permissions, group policies, and access controls across corporate systems and applications.
• Support and maintain endpoint management solutions, software deployment processes, and device compliance standards.
• Configure, troubleshoot, and support network services, including DNS, DHCP, VPN, wireless, and connectivity solutions.
• Lead infrastructure upgrades, migrations, patch management activities, and system enhancement projects.
• Respond to and resolve escalated technical issues, providing advanced troubleshooting and root cause analysis.
• Partner with cybersecurity, application, and business teams to implement and maintain secure technology solutions.
• Develop and maintain system documentation, technical procedures, disaster recovery plans, and operational standards.
• Support business continuity efforts through backup management, recovery testing, and high availability planning.
• Evaluate emerging technologies and recommend improvements that enhance efficiency, security, and scalability.
• Participate in on-call support rotations and provide after-hours support as needed for critical business operations.

You possess a deep understanding of enterprise systems and technology environments and are committed to maintaining stable, secure, and efficient operations.

You enjoy diagnosing complex technical issues, identifying root causes, and implementing long-term solutions that prevent future disruptions.

You prioritize security in every aspect of system administration and proactively identify and mitigate technology risks.

You communicate effectively with both technical and non-technical stakeholders and build strong partnerships across the organization.

• 2+ years of progressive experience in Systems Administration, Infrastructure Support, or Information Technology.
• Experience administering Windows Server environments, Active Directory, Microsoft 365, and cloud-based technologies.
• Proven experience supporting virtualized environments such as VMware or Hyper‑V.
• Experience managing endpoint devices, patching processes, and enterprise software deployments.
• Strong troubleshooting experience across servers, operating systems, networks, and infrastructure services.
• Experience supporting cybersecurity initiatives, access management, and technology compliance requirements.
• Experience working within a regulated…