IT Systems Lead

Pilot.com•San Francisco, CA

7d•$115,000 - $156,000•Onsite

About The Position

Pilot's IT Operations team is a small group supporting employees across San Francisco and Nashville offices, as well as a hybrid workforce. The team manages critical systems including identity, devices, email, conference rooms, and the SaaS stack. This is an individual contributor role reporting to the Director of Security & IT Operations, with close collaboration with Security, Legal, People, and executive teams. The role is the primary day-to-day owner of IT for the San Francisco office and the main point of contact for employee support needs. This includes managing the IT ticket queue and the systems behind it, such as Okta, MDM (Kandji/Iru), Google Workspace, and automation for provisioning/deprovisioning access. A growing aspect of this role involves administering AI tools and promoting an AI-forward culture, aligning with Pilot's move towards AI-assisted operations. The position requires hands-on experience with the existing tech stack, proficiency in AV and networking, familiarity with SOC 2 controls and evidence, and a strong aptitude for growth. Excellent interpersonal skills are essential, as the person in this role will be on the front lines, assisting coworkers and providing the necessary support and tools for optimal performance. This is a full-time, in-office position based in San Francisco.

Requirements

5+ years in IT, with at least 2 as a lead or sole admin at a SaaS or similar technology company with a hybrid workforce
Deep hands-on Okta experience, including Workflows, complex Authentication flows, and other automations
AI enabled and agile, utilizing the frontier AI tools to increase efficiency for the team and company
Experience managing Macs with an MDM; working knowledge of Windows
Comfortable owning AV, conference rooms, and events end to end
Familiar with SOC 2 and ISO27001 controls and a compliance platform like Drata, Vanta
Personable, patient, and methodical; people like asking you for help
[SF Office requirement]

Nice To Haves

Direct experience with InfoSec related initiatives such as SOC2, ISO27001, NIST, FedRAMP
Hands-on experience deploying AI agents for IT or Operational workflows, familiarity with MCP connectors and permissions, agent identity management and governance
GitHub Enterprise, developer tooling administration, Cloud IAM experience, or similar developer support experience
Prior fintech or regulated-industry experience
Relevant certs (Okta, Jamf/Kandji, Network+/Security+)

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