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Salary: USD 115,000 - 156,000 / annual
Pilot is a fintech company providing modern back-office solutions for small businesses, with over 3,000 customers and $1.2B valuation (backed by Sequoia, Index Ventures, Stripe, Bezos Expeditions, Whale Rock).
You will be the day-to-day IT owner for Pilot's San Francisco office and primary support contact for employees across SF and Nashville offices plus hybrid workforce. This is a hands-on individual contributor role reporting to the Director of Security & IT Operations, working closely with Security, Legal, People, and executive teams.
Key responsibilities include:
- Running day-to-day IT operations: onboarding/offboarding, hardware provisioning, access requests, and helpdesk ticket management
- Administering Okta (app integrations, sign-on/MFA policies, lifecycle automation, Workflows)
- Managing Mac and Windows device fleets via MDM (Kandji/Iru, Intune) including zero-touch deployment, compliance, and asset lifecycle
- Administering Google Workspace and SaaS tools (Slack, Zoom, GitHub, Dropbox, etc.)
- Owning conference room and AV support: Zoom Rooms, scheduling displays, event setup
- Supporting InfoSec program development: SOC 2 and similar certifications, evidence gathering, IT remediation, internal audits
- Administering enterprise AI stack: managing permissions, connectors, and capabilities for tools like ChatGPT or Claude for Enterprise
- Supporting office networking: Wi-Fi, firewall/VPN, DNS, troubleshooting
- Maintaining documentation, runbooks, and asset inventory
Pilot is moving quickly toward AI-assisted operations; a growing part of this role involves administering those tools and fostering an AI-forward culture. You will sit alongside coworkers daily, solving problems and providing support to enable everyone to perform their best.
Requirements:
- 5+ years in IT, with at least 2 years as a lead or sole admin at a SaaS or similar technology company with hybrid workforce
- Deep hands-on Okta experience, including Workflows, complex Authentication flows, and automations
- AI-enabled and agile; comfortable utilizing frontier AI tools to increase team and company efficiency
- Experience managing Macs with MDM; working knowledge of Windows
- Comfortable owning AV, conference rooms, and events end-to-end
- Familiarity with SOC 2 and ISO27001 controls and compliance platforms (Drata, Vanta)
- Personable, patient, methodical; people enjoy asking you for help
- Must be based in/willing to work from SF office
Nice to have:
- Direct experience with InfoSec initiatives (SOC2, ISO27001, NIST, FedRAMP)
- Hands-on experience deploying AI agents for IT/operational workflows, MCP connectors, agent identity management
- GitHub Enterprise, developer tooling administration, Cloud IAM, or developer support experience
- Prior fintech or regulated-industry experience
- Relevant certifications (Okta, Jamf/Kandji, Network+/Security+)
