Lead Systems and Network Administrator
9 hours ago
Chicago
Lead Systems and Network Administrator Job Description: We’re seeking a proactive, adaptable Lead Systems Administrator who combines deep technical expertise with strong systems thinking. This individual must be equally comfortable troubleshooting a complex network issue, implementing security controls, designing identity and access management systems, and developing long-term infrastructure strategy. This is a multi-disciplinary role encompassing IT infrastructure management, networking, identity management, and security operations. While this position remains highly hands-on, we are looking for someone who can think beyond day-to-day operations and help shape the future state of our technology environment. The ideal candidate will bring a balance of technical execution, architectural thinking, operational excellence, and strategic planning. You will work alongside another Senior Systems Administrator to jointly manage our infrastructure, networking, identity management, and security operations. Both administrators share responsibility for critical systems, operational planning, security improvements, and technology decision-making. The team also includes a junior IT support technician who assists with day-to-day support operations. Key Responsibilities: Strategic Planning & Architecture • Help define and execute the long-term roadmap for infrastructure, identity management, endpoint management, networking, and security systems, • Evaluate technologies, platforms, and architectural approaches to improve scalability, security, reliability, and operational efficiency, • Develop standards, processes, and best practices that reduce operational complexity and support organizational growth, • Partner with leadership and stakeholders to align technology initiatives with business objectives, • Assess technical tradeoffs and make recommendations that balance security, user experience, operational overhead, and cost, • Lead or contribute to infrastructure modernization and continuous improvement initiatives Identity & Access Management • Improve our Single Sign-On (SSO) configuration and provisioning processes, • Manage and evolve our Identity and Access Management (IAM) systems to meet security and compliance needs, • Administer and optimize MDM platforms and endpoint management solutions, • Implement and maintain role-based access controls and access management best practices, • Collaborate on IT policy development and security governance initiatives, • Design scalable identity and access management processes that support organizational growth and changing business needs Infrastructure & Networking • Design, implement, and maintain enterprise networking infrastructure including switches, firewalls, wireless networks, VPNs, and related systems, • Manage office network equipment including switches, firewalls, access points, and physical wiring to ensure stable and secure connectivity, • Configure and maintain firewall policies, VLANs, DNS, DHCP, and network security controls, • Monitor network performance, troubleshoot complex connectivity issues, and plan for future capacity needs, • Implement and maintain local servers and cloud-based infrastructure to support evolving operational and scalability requirements, • Participate in backup, disaster recovery, and business continuity planning, • Maintain infrastructure documentation including network diagrams, asset inventories, and operational runbooks, • Identify opportunities to improve infrastructure resiliency, standardization, automation, and operational maturity User Support & Systems Operations • Provide escalation-level support and technical expertise for Mac and Windows environments, • Partner with a junior IT support technician to ensure effective issue resolution and a high-quality employee experience, • Help define tooling, processes, standards, and best practices for IT operations and end-user support, • Step in to diagnose and resolve high-priority or complex issues when necessary, • Maintain and optimize onboarding and offboarding workflows, including hardware, licensing, and access management, • Evaluate and implement technologies that improve operational efficiency, reliability, and security, • Mentor junior team members and help elevate technical capabilities across the IT organization Security & Compliance • Partner with leadership to ensure security policies are enforced, documented, and continuously improved, • Conduct security audits, vulnerability assessments, and remediation efforts, • Support patch management, endpoint security, and system hardening initiatives, • Monitor and respond to security events and operational risks, • Help prepare for compliance with relevant standards and frameworks such as SOC 2 and ISO 27001, • Evaluate security technologies and recommend improvements to strengthen the organization’s security posture, • Contribute to security strategy, risk management, and long-term security planning Team & Collaboration • Work closely with a fellow Senior Systems Administrator to share operational responsibilities across infrastructure, networking, identity management, and security systems, • Participate in infrastructure planning, architecture discussions, and technology evaluations, • Maintain documentation and operational procedures to ensure continuity and effective knowledge sharing across the team, • Collaborate with engineering, security, and business stakeholders to align technology solutions with organizational needs, • Serve as a trusted technical advisor on infrastructure, security, and operational initiatives Required Qualifications • 5+ years of relevant experience in systems administration, network administration, infrastructure engineering, security engineering, or related IT roles, • Strong familiarity with both Apple macOS and Windows environments, • Hands-on experience with SSO solutions (JumpCloud, Okta, Microsoft Entra ID, or similar), • Proficiency managing IAM tools, MDM platforms (Apple Business Manager, JumpCloud, Okta, Intune, Jamf, Kandji, or similar), and endpoint management systems, • Strong understanding of TCP/IP networking, routing, switching, DNS, DHCP, VPNs, VLANs, firewalls, and wireless networking, • Experience administering networking infrastructure such as UniFi, Fortinet, Cisco, Meraki, Palo Alto, or similar technologies, • Experience managing hosted infrastructure platforms such as Microsoft 365, Exchange Online, Google Workspace, or similar services, • Experience designing, implementing, or evolving infrastructure, security, or identity architectures, • Ability to evaluate technical tradeoffs and make recommendations that balance business, security, and operational requirements, • Strong written and verbal communication skills with the ability to communicate effectively with both technical and non-technical stakeholders Preferred Qualifications • Experience leading infrastructure modernization, cloud migration, security improvement, or operational maturity initiatives, • Experience supporting compliance frameworks such as SOC 2, ISO 27001, HIPAA, or similar standards, • Experience with infrastructure automation, scripting, or configuration management tools, • Previous experience serving as a technical lead, infrastructure architect, or security-focused engineering lead while remaining hands-on with implementation
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