Pilot.com, Inc.
Headquarters
San Francisco, CAFounded
2017CEO / Founder
Waseem DaherEmployees
201-500Funding
Series C — $222MProducts
1 product listedAvg. AI Score
8.0/10Website
pilot.com/
Profile updated
About Pilot.com, Inc.
Pilot.com, Inc. operates an outsourced financial back office for startups and small businesses, delivering bookkeeping, tax preparation, and CFO advisory services that pair dedicated human accountants with proprietary software for real-time reporting. The company was founded in 2017 by Waseem Daher, Jessica McKellar, and Jeff Arnold, three MIT-trained engineers who had previously built and sold two companies together. It is headquartered in San Francisco, with a second office in Nashville, Tennessee.
Pilot's platform automates transaction categorization and monthly close while assigning each client a finance team, targeting venture-backed technology companies, ecommerce sellers, and professional-services firms that outgrow entry-level tools. The founders previously created Ksplice, a Linux software-updating firm acquired by Oracle in 2011, and Zulip, a workplace chat product acquired by Dropbox in 2014; that track record helped Pilot attract early startup clients. The company has since expanded into R&D tax-credit filing and added AI-assisted bookkeeping features.
Pilot has raised roughly $222 million across six rounds from investors including Sequoia Capital, Index Ventures, Bezos Expeditions, Stripe, and Whale Rock Capital, alongside founders such as Patrick and John Collison and Drew Houston. A $100 million Series C in March 2021 valued the company at $1.2 billion. Pilot employs approximately 420 people as of 2026 and remains privately held.
Specialties
Financials
Dated, source-cited figures. Estimates are marked.
Products by Pilot.com, Inc.
All products by Pilot.com, Inc. reviewed by our AI panel of experts.
How Our Review Panel Scores Pilot.com, Inc.
Six independent reviewer personalities assessed Pilot.com, Inc.'s product on their own terms. They landed within 0.8 points of each other, an unusually strong consensus.
Averaged across 1 reviewed product in our catalog. Scores are out of 10.
Competitive Landscape
Who Pilot.com, Inc. competes with, and how they differ.
QuickBooks Live is a cheaper, self-serve alternative — customers do their own transaction categorization in QuickBooks Online with light bookkeeper support, versus Pilot's dedicated bookkeeper, tax, and CFO bundle aimed at venture-backed startups; Pilot itself keeps its clients' books in QuickBooks Online under the hood.
1 product reviewed on TopReviewedZeni bundles AI-driven daily bookkeeping with AP/AR and CFO services for the same venture-backed tech-startup buyer, priced from roughly $549/month versus Pilot's $99+/month tiers, leaning harder on AI automation with less dedicated human bookkeeper time.
Company Timeline
Key milestones in Pilot.com, Inc.'s history, with sources.
- Launch
Launches Meridian, an AI platform that closes the books for accounting firms
Pilot launched Meridian, a B2B AI platform that runs the month-end close for outside accounting firms and returns review-ready financials, trained on more than 187,000 months of books across over 8,000 businesses.
globenewswire.com - Launch
Unveils Pilot AI Accountant, a fully autonomous AI bookkeeper
Pilot launched an AI Accountant designed to run the entire bookkeeping and financial-reporting cycle without human intervention, built on a decade of bookkeeping data from thousands of customers.
globenewswire.com - Milestone
Leadership transition — Jessica McKellar becomes CEO; Waseem Daher moves to executive chair
By April 2025, co-founder Jessica McKellar (formerly CTO) held the CEO title and co-founder Waseem Daher had moved to co-founder & executive chair, per a company press release; Daher was still described as CEO in press as of mid-2024, so the exact handover date is not publicly disclosed.
menafn.com - Launch
Launches Pilot GPT, built on OpenAI's generative AI
Pilot integrated OpenAI generative AI into its bookkeeping workflow as "Pilot GPT," aiming to improve the accuracy of the books it produced for its then more than 1,700 customers.
businesswire.com - Funding
Series C extended to $100M at $1.2B valuation — Bezos Expeditions, Whale Rock Capital join
An initial $60 million Series C led by Sequoia Capital (announced Jan. 26, 2021) was extended with a further $40 million from Bezos Expeditions and Whale Rock Capital, taking the round to $100 million total and doubling Pilot's valuation to $1.2 billion.
techcrunch.com - Launch
Launches three new products: R&D Tax Credit, CFO Services, Extended Services
Pilot expanded beyond core bookkeeping with three new offerings — an R&D tax credit service, CFO Services, and Extended Services — to cover more of a startup's back office.
businesswire.com - Funding
Series B — $40M led by Index Ventures, with Stripe; Pilot Tax launches
Pilot raised a $40 million Series B led by Index Ventures with Stripe as a strategic investor, and simultaneously launched Pilot Tax, its tax-filing service for customers.
techcrunch.com - Funding
Series A — $15M led by Index Ventures
Pilot raised a $15 million Series A led by Index Ventures to expand its software-plus-human bookkeeping service, then serving more than 150 businesses.
techcrunch.com - Founded
Pilot founded by Waseem Daher, Jessica McKellar and Jeff Arnold
The three MIT graduates founded Pilot in San Francisco after two prior companies together — Ksplice (acquired by Oracle, 2011) and Zulip (acquired by Dropbox, 2014).
techcrunch.com - Funding
Seed round — $3.3M from roughly 40 investors
Pilot raised a $3.3 million seed round in early 2017 from about 40 investors as the founders built the initial bookkeeping product.
blog.foundersuite.com
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