​Skydio, a leader in autonomous flight technology, is seeking an experienced IT Systems Administrator to join the team at its HQ. This position is central to maintaining a reliable IT environment, requiring advanced technical support, infrastructure automation, and collaboration with the network team.

• ​Location: Onsite, 5 days/week at Skydio HQ in San Mateo, CA.
• ​Annual Base Salary: $110,000 – $150,000 + equity + benefits.
• ​Experience: Minimum of 4 years of hands-on technical experience supporting Linux, Windows, and Mac environments.
• ​Focus: Infrastructure-as-Code (IaC) using Terraform, advanced scripting (Python, Bash), Identity Management (Okta), Device Compliance (JumpCloud), and multi-OS support/troubleshooting.

​Key Responsibilities: Automation, Identity, and Networking

​The administrator will drive efficiency through automation while providing hands-on support for core infrastructure and network operations.

• ​Automation & IaC: Use Terraform for infrastructure automation (IaC) to streamline provisioning. Write scripts (Python, Bash) to automate recurrent IT and onboarding tasks.
• ​Identity Management: Administer and improve Okta for access, provisioning, SSO, MFA, and automation workflows. Expertise in configuring Okta Identity, including RBAC and federation protocols (SAML/OAuth).
• ​Device Management: Manage JumpCloud for device compliance, policy enforcement, and scripting across all operating systems.
• ​Support & Mentorship: Provide escalated support for complex IT issues. Provide hands-on support for hardware diagnostics, system provisioning, and patch management. Act as a technical mentor to junior staff.
• ​Networking Support: Provide support to the network engineer, assisting with tasks like configuring switches and wireless networks. Utilize network troubleshooting tools (Wireshark, tcpdump) to diagnose and resolve network performance issues.
• ​Documentation: Document processes, configurations, and troubleshooting procedures to maintain clear technical records.

​Required Skills and Knowledge

• ​Multi-OS Experience: Minimum 4 years supporting Linux, Windows, and Mac environments.
• ​Identity Expertise (Mandatory): Expertise in Okta administration (SSO, MFA, RBAC, SAML/OAuth) and strong knowledge of JumpCloud.
• ​Automation Expertise (Mandatory): Expertise in scripting (Python or Bash) and hands-on experience with Terraform for infrastructure management.
• ​Networking Fundamentals: Knowledge of network infrastructure fundamentals (TCP/IP, DNS, DHCP, VLANs) and the ability to troubleshoot using advanced tools.
• ​Certifications (Plus): Industry certifications such as CompTIA A+, Network+, Linux+.