IT Systems Lead

About the role

Pilot is looking for an IT Systems Lead to own day‑to‑day IT operations for its San Francisco office and support a hybrid workforce. You will manage identity, devices, email, conference rooms and the SaaS stack while collaborating closely with Security, Legal, People and executive teams.

Key responsibilities

• Run day‑to‑day IT for the San Francisco office and provide remote support (onboarding, off‑boarding, hardware, access requests, help‑desk tickets).
• Administer Okta, including app integrations, sign‑on/MFA policies and lifecycle automation.
• Manage Mac and Windows fleets via MDM (Kandji/Iru and Intune), handling zero‑touch deployment, compliance and asset lifecycle.
• Administer Google Workspace and a suite of SaaS tools such as Slack, Zoom, GitHub and Dropbox.
• Own conference‑room AV support, including Zoom Rooms, scheduling displays and event setup.
• Support InfoSec initiatives, gathering evidence for SOC 2/ISO 27001 and handling internal audits.
• Maintain the enterprise AI stack (ChatGPT, Claude), managing permissions and connectors.
• Maintain office networking (Wi‑Fi, firewall/VPN, DNS) and keep documentation, runbooks and asset inventory up to date.

Required profile

• 5+ years in IT with at least 2 years leading or being the sole admin for a SaaS‑focused, hybrid workforce.
• Deep hands‑on experience with Okta, including Workflows and complex authentication automations.
• Proven ability to manage Mac fleets with an MDM and solid knowledge of Windows administration.
• Comfortable owning AV equipment, conference‑room setups and event support.
• Familiarity with SOC 2 and ISO 27001 controls and compliance platforms such as Drata or Vanta.
• Personable, patient and methodical – colleagues regularly seek your help.

Required skills

• Okta (including Workflows)
• Kandji / Intune MDM
• Mac and Windows fleet management
• Google Workspace
• Slack, Zoom, GitHub, Dropbox
• Zoom Rooms and AV support
• SOC 2 and ISO 27001 compliance tooling (Drata, Vanta)
• Enterprise AI tools (ChatGPT, Claude)
• Wi‑Fi, firewall/VPN and DNS networking

What we offer

• Competitive base salary $115k‑$156k (San Francisco) plus equity.
• Flexible vacation / time‑off policy and observation of all federal holidays.
• Comprehensive health, wellness and parental‑leave benefits (100 % pay for 12 weeks).
• 401(k) plan.
• Opportunity to work with a fast‑growing fintech unicorn and a supportive founding team.