Senior IT Systems Engineer, LeoLabs

• The right candidate combines deep hands-on systems administration experience with the ability to lead cross-functional projects, manage technical risk, communicate with executives, and deliver measurable improvements in reliability, security, onboarding speed, and support efficiency
• Must be eligible to obtain and maintain a U.S. personnel security clearance
• 7+ years of IT systems administration, systems engineering, endpoint engineering, or infrastructure operations experience
• 3+ years leading or materially owning IT infrastructure, endpoint, automation, or workplace technology projects
• Advanced troubleshooting experience across Windows, macOS, Microsoft 365, endpoint management, identity, networking fundamentals, and collaboration systems
• Advanced PowerShell scripting experience, including automation for provisioning, device configuration, reporting, remediation, or administrative workflows
• Hands-on experience with Microsoft 365 administration, Entra ID, Office applications, Teams, SharePoint, Exchange, and licensing/group management
• Advanced experience with Microsoft Defender and Microsoft Sentinel or comparable endpoint security/SIEM tooling
• Strong experience supporting macOS and Windows endpoints in a managed enterprise environment
• Experience with Intune, Jamf Pro, endpoint deployment automation, patching, compliance policies, and software packaging
• Working knowledge of Wi-Fi, VLANs, DNS, DHCP, VPN, certificates, 802.1X, RADIUS, and NAC concepts
• Experience using Jira and Confluence or comparable systems for project tracking, documentation, and operational knowledge management
• Experience building out and maintaining ITSM/ESM systems
• Excellent customer service, communication, documentation, stakeholder management, and cross-functional collaboration skills

Desirable

• This is a senior, project-oriented IT systems engineering role focused on building scalable, secure, and automated IT capabilities for LeoLabs
• Rather than operating only as a ticket-queue administrator, this role owns IT projects from discovery and design through implementation, documentation, adoption, and operational handoff
• The Senior IT Systems Engineer – Infrastructure & Automation will partner with the Head of IT, Security Team, Network Team, SRE, and business stakeholders to modernize endpoint management, collaboration systems, identity workflows, Wi-Fi/NAC, and IT support automation
• This position will also mentor our Jr staff as they mature into more senior roles
• Within 1 Month
• Complete onboarding and gain a strong understanding of LeoLabs business context, IT systems, team structure, current support model, and active modernization initiatives
• Review current onboarding, offboarding, endpoint deployment, Microsoft 365, Defender, Sentinel, Jamf, Intune, Wi-Fi, and Jira/Confluence processes
• Create an initial project inventory covering quick wins, risks, dependencies, owners, and proposed sequencing
• Establish working relationships with IT, Security, Network, Cloud, SRE, SOC, and executive stakeholder groups
• Within 3 Months
• Own and actively drive two to three priority IT infrastructure or automation projects with documented scopes, milestones, risks, and acceptance criteria
• Deliver improvements to new-hire onboarding and endpoint deployment workflows, including automation opportunities and measurable baseline metrics
• Begin Wi-Fi modernization or secure access planning, including current-state assessment, target design input, vendor coordination, and pilot approach
• Improve ticket triage, documentation quality, escalation paths, and recurring-issue analysis for IT support operations
• Within 6 Months
• Deliver a more automated and standardized onboarding and device provisioning experience for new employees
• Implement improved Intune/Jamf baselines for endpoint compliance, software deployment, patching, EDR health, and reporting
• Advance Wi-Fi, 802.1X/RADIUS, NAC, or VLAN-related work from assessment into pilot or implementation
• Partner with Software and Security teams to streamline vulnerability management workflows and improve remediation visibility
• Onboard or improve key Defender/Sentinel telemetry sources and create repeatable documentation for operations and audit support
• Within 12 Months
• Deliver a mature endpoint and account lifecycle program with automation across onboarding, offboarding, device deployment, access assignment, compliance reporting, and support handoff
• Complete or materially advance the Wi-Fi/security upgrade path with improved authentication, segmentation, documentation, and operational support procedures
• Demonstrate measurable reductions in provisioning time, recurring tickets, manual support steps, endpoint drift, and unresolved vulnerability backlog
• Create a documented IT infrastructure improvement roadmap for the next planning cycle, including project backlog, control gaps, automation candidates, and staffing or tooling recommendations
• Establish a deep operational understanding of the IT environment and serve as a trusted project owner for future modernization efforts