Pilot

Pilot operates the financial back office for startups and small businesses, offering bookkeeping, tax preparation and CFO/advisory services delivered through a combination of software and human experts. The company describes its model as "50/50 people and software": tooling provides dashboards, real-time expense tracking and cash-flow scenario modeling, while US-based accountants, fractional CFOs and former operators provide strategic guidance on questions such as hiring capacity, cost reduction and profitability. Advisory staff highlighted on the site come from investment banking, venture capital, corporate strategy and startup finance/operations backgrounds.

The service set has expanded over time. At launch Pilot performed bookkeeping only; by the January 2021 Series C announcement it had added guidance on business metrics and R&D tax credit documentation and claims, positioning itself as making capabilities previously limited to enterprises with dedicated finance teams — such as CFO-level financial strategy and monthly spending variance analysis — available to startups and SMBs. A 2025 company blog post lists bookkeeping, accounting, tax, CFO advisory and capital management as its offerings. Pilot also publishes content marketing assets such as a Founder Salary Report and a free burn-rate calculator, and its blog references a Pilot AI Accountant and a Local Partner Program for bookkeepers.

Customer work described publicly includes converting a fast-growing services firm from cash to accrual accounting and clearing a $1M invoice backlog, building financial models and data rooms used to close financing rounds, setting up books and investor-ready financials for a pre-seed company within four weeks including multi-state hiring compliance, and preparing audit-ready books for Passage AI ahead of its acquisition by ServiceNow.

Founding story

Waseem Daher, Jessica McKellar and Jeff Arnold met at MIT's computer club and had previously founded Ksplice (started June 2008, bootstrapped, sold to Oracle in July 2011) and Zulip, a pre-Slack group chat app acquired by Dropbox in March 2014. After time at Dropbox they decided in late 2016 to start a third company, targeting a business rather than consumer problem, aimed at startups and small businesses. Customer discovery interviews across SMB and mid-market finance, accounting, legal and HR teams identified finance and accounting as the most pressing unsolved pain point — a problem they had experienced themselves in 2009 when they used QuickBooks for Dummies to do Ksplice's books. They chose bookkeeping because of pain-point prevalence, market size, high average sales price and low competition. In January 2017, with no engineers, software or bookkeepers, they asked founder friends to pay $100 for bookkeeping; Arnold and Daher did the books manually while McKellar wrote code.

Business model

Pilot sells outsourced financial back-office services to businesses, combining proprietary software with staffed accounting and advisory teams. The original product was described as a monthly subscription bookkeeping service for startups; the current site markets bookkeeping, tax and advisory work, with a free trial entry point and a sales-assisted motion ("Contact Sales").

Service subscription: the founders' first customers were signed at $100 to have their bookkeeping handled, and the initial offering is described as a monthly subscription bookkeeping service; the sources note the segment's high average sales price was one reason the founders chose it.

Traction

Over 1,000 companies served as of January 2021, 1,500+ startups from pre-seed to Series D as of the Office Hours page, and 3,500+ startups and small businesses cited on the current homepage. Total funding disclosed grew from $120M at the Series C to over $150M per the About page, and the company was described as valued at $1.2 billion.

Latest developments

The company's site promotes a 2026 Founder Salary Report, states it is trusted by 3,500+ startups and small businesses, and lists San Francisco and Nashville offices. Blog headlines reference the unveiling of a Pilot AI Accountant and the launch of a Local Partner Program for bookkeepers. In January 2025 Pilot published an analysis of competitor Bench's shutdown and acquisition, framed around cash flow and burn-rate management.