Layoff
Sep 2022Third-party layoff reporting says Pilot conducted a round affecting approximately 25 employees.
SourceCompany research
Public company, workplace, funding, and market signals
Updated Aug 2, 2026
Overview
Pilot.com is a privately held, San Francisco-based fintech/accounting-services company that provides an outsourced financial back office for startups and small businesses. It combines proprietary software and AI with U.S.-based finance professionals to deliver bookkeeping, tax preparation, financial reporting, and fractional CFO/advisory services. Founded in 2017 by three MIT computer-science friends, it later expanded its technology into AI Accountant and Meridian for accounting firms.
Primary product
Tech-enabled outsourced bookkeeping and financial-back-office services, supplemented by tax preparation, CFO/advisory services, dashboards, financial reports, and AI accounting products.
Founded
2017
Headquarters
San Francisco, California, United States
Team size
Approximately 300–416; third-party estimates vary and are not an official company disclosure.
Work style
Flexible
Industry
Financial services / fintech
Sub-industry
Tech-enabled accounting, bookkeeping, tax, CFO services, and AI accounting software
Offices
San Francisco, California (353 Sacramento St., Suite 1900; FIDI)
Nashville, Tennessee (818 18th Ave, Suite 102; Music Row)
Funding
Stage
Late-stage venture-backed private company / fintech unicorn
Total raised
$218.3M
Latest round
Series C extension · Mar 2021
Latest amount
$100M
Jan 2022
Mar 2021 · Bezos Expeditions; Whale Rock Capital Management
People & investors
Leadership
Jessica McKellar
Co-founder and CEO
Co-founder and Executive Chair
Jeff Arnold
Co-founder and COO (historically reported; current title not independently confirmed)
Investors
Adam D'Angelo
Adam D’Angelo
Akkadian Ventures
Authentic Ventures
Work & culture
Pilot emphasizes ownership, focus, quality, impact, trust, teamwork, collaboration, and justice. Its stated operating model combines software with a human touch and U.S.-based finance expertise. Public employee-review sources are mixed and mention management concerns and multiple layoff rounds; those reviews are anecdotal rather than company-wide measures.
Work style
Flexible
Compensation
Public engineering postings showed target base compensation of approximately $133,000–$240,000 in most remote locations and $166,000–$267,000 in San Francisco/New York, plus potential equity, 401(k), health benefits, and other benefits. Sponsorship policy was not established from the available evidence.
Benefits
Flexible vacation/time-off policy
Federal holidays observed
Health benefits
401(k) plan
Product & market
Pricing
Published subscription and retainer pricing. Bookkeeping includes Essentials at $99/month and a Core plan starting at $0/month billed annually for zero monthly expenses, with pricing scaling by expense volume and complexity. Tax is generally an annual add-on; CFO services are monthly retainers starting at approximately $1,750/month. Custom plans are quoted.
Differentiators
- —Combination of proprietary software/AI and dedicated human finance professionals rather than self-serve software alone
- —Startup-focused accrual bookkeeping and investor-ready financial reporting
- —Integrated bookkeeping, tax, CFO/advisory, and back-office services
- —U.S.-based finance/advisory team
- —Operational data from thousands of businesses and more than 187,000 months of books used to develop Meridian
- —Meridian aims to complete the accounting close end-to-end and return review-ready financials to accounting firms
- —Reportedly more than 80% of business historically came from referrals and organic interest
Scale & contact
Estimated revenue
Approximately $43M–$65M annually, based on third-party estimates; Pilot does not publicly disclose audited revenue.
Estimated monthly visits
170K
Signals & risks
Layoff
Jun 2023Third-party reporting says Pilot laid off approximately 45 employees, or 13% of its workforce; it described this as a difficult economic environment and reported severance support.
SourceLatest news
GlobeNewswire / Pilot · Jun 2026
Pilot launched Meridian, an AI platform for accounting firms that completes month-end close end-to-end and produces review-ready financials; it supports QuickBooks Online and also works with Xero and NetSuite.
Accounting Today · Jun 2026
Independent trade coverage described Meridian's automation of onboarding, transaction processing, reconciliation, reporting, and close controls, while noting Pilot's claim that the system performs like a seasoned staff accountant.
GlobeNewswire / Pilot · Feb 2026
Pilot announced a $250,000 grant fund for 18 small-business owners, including one $50,000 grant, two $25,000 grants, and fifteen $10,000 grants, plus one year of free Pilot bookkeeping for recipients.
Pilot Blog · Feb 2026
Pilot introduced a free trial that shows businesses income, expenses, profit, loss, and cash flow in one place, and lets users connect bank and card accounts.
Open Positions
4 jobs at Pilot.com
Sr. Software Engineer
On-siteEngineeringSan Francisco, CA4d ago
On-site