IT Systems Lead

The Role

IT Operations at Pilot is a small team that supports our employees across our San Francisco and Nashville offices and a hybrid workforce. The IT team owns the systems that keep the company running and secure: identity, devices, email, conference rooms, and the SaaS stack. This is an individual contributor role reporting into Director of Security & IT operations, working closely with Security, Legal, People, and executive teams.

This role is the day-to-day owner of IT for the SF office and the primary point of contact for employees who need help. That includes our IT ticket queue and also running the systems behind them:
Okta, our MDM (Kandji/Iru), Google Workspace, and the automations that provision and deprovision access. Pilot is moving quickly toward AI-assisted operations, and a growing part of this job is administering those tools and fostering an AI forward culture.

The role requires hands‑on experience with our tech stack, real comfort with AV and networking, familiarity with SOC 2 controls and evidence, and the aptitude to grow. It also requires someone who works well with people. This person is on the front lines every day, sitting alongside coworkers to solve problems and provide the support and tools to allow everyone to perform their best.

This is a full‑time in‑office role based in our San Francisco office.

• 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, Git Hub, Dropbox, etc.)
• Own conference room and AV support:
  Zoom Rooms, scheduling displays, and some event setup
• Support the development of the Info Sec 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

• 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 ISO
  27001 controls and a compliance platform like Drata, Vanta
• Personable, patient, and methodical; people like asking you for help
• [SF Office requirement]

• Direct experience with Info Sec related initiatives such as SOC2, ISO
  27001, NIST, FedRAMP
• Hands‑on experience deploying AI agents for IT or Operational workflows, familiarity with MCP connectors and permissions, agent identity management and governance
• Git Hub 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+)

Pilot launched in 2017 to bring the back office into the modern era. Pilot provides small businesses with dedicated finance experts - which Pilot hires as full‑time, U.S.

-based employees - who learn the ins-and-outs of their business. Pilot integrates directly with the billing,…