---
title: 'IT Systems Lead at Pilot.com'
canonical: 'https://feeny.ai/job/it-systems-lead-pilot-com-san-francisco-531pbktpkrwq'
type: 'job'
last_seen: '2026-09-15'
---

# IT Systems Lead at Pilot.com

- **Company:** Pilot.com
- **Location:** San Francisco, CA
- **Posted:** 2026-09-11
- **Last confirmed live:** 2026-09-15
- **Apply:** https://job-boards.greenhouse.io/pilothq/jobs/8797055002

## Job description

## 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.

## Key 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

## About You

- 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

## Nice to Have

- 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+)

## About Pilot

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](https://pilot.com/blog/pilot-unicorn-bezos-expeditions-whale-rock/).

Why Pilot?

- 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](https://pilot.com/recruiting-notices), 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](https://pilot.com/terms/privacy-job-candidate).

## About Pilot.com

## Company Overview
- **One-liner**: Pilot provides bookkeeping, tax preparation, CFO, and COO services for startups and small businesses, combining software with a team of US-based finance experts.
- **Entity Type**: Private (Series C; total funding of $212.1M)
- **Headquarters**: San Francisco, California, United States (with a second HQ in Nashville, Tennessee)
- **Founded**: 2016
- **Founders**: Jessica McKellar (Founder & CEO)

## Core Business
- **Primary industry**: Accounting / Financial Services / Fintech
- **Target customers**: B2B – startups and small-to-medium businesses (SMBs) that are growth-oriented (from 2 to 20+ employees through to exit preparation)
- **Mission/purpose**: “Build the future of the financial back office to help small and medium sized businesses grow and flourish.”

## Products & Services
- **Bookkeeping**: Full-service bookkeeping with IRS-ready books, real-time expense tracking, and intelligent dashboards.
- **Tax Services**: Year-round tax compliance and strategy to maximize deductions and minimize liabilities.
- **CFO Services**: Strategic guidance from former CFOs and operators, including cash flow modeling, fundraising support, profitability optimization, and exit planning.
- **COO Services**: Operational advisory for scaling businesses, including financial operations consulting.
- **Meridian (AI Operating System)**: An AI-powered platform that automates book closing and provides analytics, designed to help accounting firms and internal teams work more efficiently.

## Market Standing
- **Valuation**: Not publicly disclosed (private company).
- **Key Metric**: Annual revenue of $20.0M (estimated) and total funding of $212.1M across 6 rounds.
- **Notable Investors**: Sequoia, Index Ventures, Stripe, Bezos Expeditions (Jeff Bezos’s investment company), Whale Rock Capital Management, and Akkadian Ventures. Also includes angel investors Patrick and John Collison, Drew Houston, and Diane Greene.
- **Growth Signals**:
  - Headcount grew 15.3% YoY to ~220 employees.
  - Trusted by 3,000+ growth-driven startups and small businesses.
  - Active job postings increased 167.9% year-over-year (75 open roles as of mid-2026).
  - Expanding into franchise and accounting firm verticals (dedicated marketing leads hired).

## Competitive Advantages
- **Human + Software Model**: Combines automated tools with a dedicated team of US-based CPAs, CFOs, and operators – providing both efficiency and strategic insight.
- **Deep Startup Expertise**: Specializes in complex financial needs like fundraising, cap table management, international expansion, and exit preparation – areas where generic bookkeepers fall short.
- **Meridian AI Platform**: Proprietary AI operating system that automates book closing, giving Pilot a technology moat in the accounting space.
- **Strong Investor Backing**: Backed by top-tier VCs and influential operators, providing credibility and a network effect.

## Strategic Focus
- **Vertical Expansion**: Targeting accounting firms and franchise businesses with dedicated marketing and sales teams.
- **Product Innovation**: Continued development of Meridian AI to serve both internal clients and external accounting firms.
- **Scaling the Team**: Aggressively hiring across engineering, marketing, sales, and operations to support growth.
- **Geographic Reach**: Maintaining dual headquarters (San Francisco and Nashville) while offering remote roles to access broader talent.

## Why Work Here
- **Culture & Values**: Emphasizes ownership, focus, quality, trust, teamwork, collaboration, and justice. Described as a high-performance, respectful environment where “everyone takes personal responsibility to treat each other with respect, fairness, and dignity.”
- **Work Model**: Hybrid – offices in San Francisco (FIDI with Bay views) and Nashville (Music Row). Many roles are listed as remote (e.g., Senior Software Engineer, Infrastructure), and some are location-flexible.
- **Growth Opportunity**: Rapidly growing company with increasing headcount and job postings; opportunity to work on impactful financial products for thousands of businesses.
- **Engineering Culture**: Focus on building resilient systems, root cause analysis, and shipping frequently. “If you like to build things and watch them ship, this is your office.”
- **Diversity & Inclusion**: Committed to equal employment opportunity and building a diverse, inclusive team.

## Sources
1. [pilot.com](https://pilot.com/) – Official website
2. [pilot.com/about](https://pilot.com/about) – About page (investors, locations, mission)
3. [pilot.com/careers](https://pilot.com/careers) – Careers page (values, culture, office locations)
4. [linkedin.com/company/pilothq](https://www.linkedin.com/company/pilothq) – LinkedIn company page (headcount, revenue, funding, employee breakdown)
5. [job-boards.greenhouse.io/pilothq](http://job-boards.greenhouse.io/pilothq) – Greenhouse job board (open roles, departments)

## Other roles at Pilot.com

- [Senior Manager, Revenue Accounting](https://feeny.ai/job/senior-manager-revenue-accounting-pilot-com-san-francisco-1zx15xdteyak) — San Francisco, CA
- [Senior Accountant, General Ledger](https://feeny.ai/job/senior-accountant-general-ledger-pilot-com-san-francisco-wabt8m1mgeb9) — San Francisco, CA
- [Sr. Software Engineer, Takeoff](https://feeny.ai/job/sr-software-engineer-takeoff-pilot-com-remote-kjgqfjfgegeb)
- [Staff Software Engineer, Takeoff](https://feeny.ai/job/staff-software-engineer-takeoff-pilot-com-remote-ewbjnqz9yddw)
- [Engineering Manager, Infrastructure](https://feeny.ai/job/engineering-manager-infrastructure-pilot-com-remote-047nzzw2yzec)
- [Consultant, Payroll Operations](https://feeny.ai/job/consultant-payroll-operations-pilot-com-nashville-a1zzxf81myk9) — Nashville, TN
- [Manager, Business Operations](https://feeny.ai/job/manager-business-operations-pilot-com-san-francisco-nb5ef5kbqw3x) — San Francisco, CA
- [Manager, Business Operations](https://feeny.ai/job/manager-business-operations-pilot-com-nashville-20em5cskwhc6) — Nashville, TN
- [Sr. Software Engineer, Bookkeeping Automation](https://feeny.ai/job/sr-software-engineer-bookkeeping-automation-pilot-com-san-francisco-bxty312j22bm) — San Francisco, CA
- [Sr. Software Engineer, Infrastructure](https://feeny.ai/job/sr-software-engineer-infrastructure-pilot-com-remote-2s8fp7m6bbzr)