IT Systems Lead: AI-Driven Ops & Security

Pilot.com, Inc.; San Francisco, Northern (CA, KY); Hybrid; USD 115,000 - 156,000; Full time

Benefits offered by this job

Flexible vacation/time-off policy

All federal holidays observed

Competitive benefits package including

Parental leave – 100% pay for 12 weeks

401(k) plan

Job summary

Pilot is hiring an IT Operations specialist based in San Francisco to own day‑to‑day IT for the SF office and support a hybrid workforce.

You will manage Okta, MDM (Kandji/Iru, Intune), Google Workspace and a growing AI stack, work with Security, Legal and People, and help scale our AI‑forward operations.

This hands‑on role requires collaborating with teammates on AV, networking, incident response and SOC 2 / ISO27001 compliance.

Qualifications

• 5+ years in IT with lead or sole admin at a SaaS or similar tech company with a hybrid workforce.
• Deep hands-on Okta experience, including Workflows and MFA policies.
• Experience managing Macs with MDM; working knowledge of Windows.
• Familiar with SOC 2 and ISO27001 controls and a compliance platform like Drata, Vanta.
• Comfortable collaborating with Security, Legal, People and executives.

Responsibilities

• Run day-to-day IT for the SF office and provide remote support for the team: onboarding/offboarding, hardware, access requests, and helpdesk tickets
• Administer Okta: app integrations, sign-on/MFA policies, and lifecycle automation
• Manage Mac and Windows fleets through MDM (Kandji/Iru and Intune), including zero-touch deployment and compliance, and asset lifecycle
• Administer Google Workspace and a wide range of SaaS tools (Slack, Zoom, GitHub, Dropbox, etc.)
• Own conference room and AV support: Zoom Rooms, scheduling displays, and some event setup
• Support the development of the InfoSec program, including SOC2 and similar certifications: evidence gathering, IT related remediation, and internal audits
• Administer and support an enterprise AI stack: Manage permissions, connectors, and capabilities for tools like ChatGPT or Claude for Enterprise
• Support office networking: Wi-Fi, firewall/VPN, some DNS and troubleshooting
• Maintain documentation, runbooks, and asset inventory

Skills

Okta

MDM Kandji/Iru

Intune

Networking & AV

SOC 2 / ISO27001

AI-enabled operations

Tools

Okta Workflows

Kandji

Intune

Google Workspace

Slack

Zoom

GitHub

Claude for Enterprise

ChatGPT for Enterprise

Job description

Pilot is hiring an IT Operations specialist based in San Francisco to own day‑to‑day IT for the SF office and support a hybrid workforce.

You will manage Okta, MDM (Kandji/Iru, Intune), Google Workspace and a growing AI stack, work with Security, Legal and People, and help scale our AI‑forward operations.

This hands‑on role requires collaborating with teammates on AV, networking, incident response and SOC 2 / ISO27001 compliance.