IT Systems Lead

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, 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

• 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

• 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+)

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, banking, expense, and payroll systems customers already use. With a special blend of custom software and expert bookkeepers, Pilot delivers accurate, consistent bookkeeping and financial management and tax services that give entrepreneurs the freedom to focus on their business.

Pilot has over 3,000 customers and has raised over $170 million in financing from Sequoia, Index Ventures, Stripe, Bezos Expeditions, and Whale Rock.  Our investors also include a long list of world-class entrepreneurs, including Patrick and John Collison, Drew Houston, and Diane Greene.  Our most recent funding round doubled our valuation to $1.2 billion – Meet Fintech’s Newest Unicorn.

• We invest in our employees’ development and happiness because our employees are the keys to our success and ensuring happy customers
• The opportunity to join a seasoned founding team that has led companies through two prior successful startups and acquisitions (by Oracle and Dropbox).
• Flexible vacation/time-off policy
• All federal holidays are observed
• Competitive benefits package including additional wellness benefits
• Parental leave for birthing or non-birthing parents – 100% pay for 12 weeks
• 401(k) plan

The base pay range target for the role seniority described in this job description is $115,000 - $156,000 in San Francisco, CA. Final offer amounts depend on multiple factors such as candidate experience and expertise, geographic location, total compensation, and market data. In addition to cash pay, full-time regular positions are eligible for equity, 401(k), health benefits, and other benefits; some of these benefits may be available for part-time or temporary positions.
Pilot commits to provide a work environment free of discrimination and harassment, as well as equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. You may view all of Pilot’s recruiting notices here, including our EEO policy, information about requesting a reasonable accommodation in the job application process, recruitment agency policy, recruitment scam notice, and important E-Verify information. You may view our job candidate privacy policy here.