Pilot Fiber
Procurement partnerAbout
Pilot provides bookkeeping, tax preparation, and CFO services for startups and small businesses, combining AI-powered software with a US-based team of finance experts. The company handles the full financial back office including monthly close, financial reporting, and strategic advisory, serving over 3,500 growth-driven businesses. Pilot has raised over $150M in financing from investors including Sequoia, Index Ventures, and Stripe.
Details
VenSearch Intelligence
Ideal Customer
- Pilot's sweet spot is venture-backed or high-growth startups from pre-revenue through approximately $20M in annual revenue, particularly those in SaaS, AI, and technology sectors that require investor-grade, GAAP-compliant accrual-basis financials.
- Their SMB Booster ($10/month) targets businesses started within the last 12 months, while core bookkeeping tiers scale up to custom enterprise plans for multi-entity or complex business structures.
Key Differentiators
- Pilot's core differentiator is its hybrid model combining proprietary AI automation (the 'AI Accountant') with a 100% U.S.-based dedicated human bookkeeping team, which it contrasts against lower-cost offshore alternatives and DIY software.
- It is rated #1 on G2 for bookkeeping services and won Comparably awards for Best Company Culture, Best Company for Women, and Best Company for Diversity in 2021.
Industries Served
- Pilot primarily targets venture-backed technology startups and small-to-mid-sized businesses, with stated industry specializations including SaaS, AI startups (with dedicated GPU/cloud cost tracking), health and medtech, professional services (consulting firms, law firms, MSPs, and advertising agencies), creative agencies, consumer goods and retail (including e-commerce via Shopify and Amazon integrations), and franchises.
- It also serves pre-revenue startups through programs like Startup Booster and SMB Booster.
Service Coverage
- Pilot (pilot.com) operates as a fully remote, nationwide U.S.-based service and works with businesses across all 50 states, not limited to specific regions.
- The company maintains two physical office locations — its San Francisco, CA headquarters and a secondary office in Nashville, TN — but explicitly states on its locations page that it works with businesses across the entire U.S. regardless of where they are based.
Partnerships
- Pilot's most prominent technology integration partnerships are with QuickBooks Online — which serves as the underlying accounting ledger for all client books — and a broad ecosystem of financial tools including Stripe, Gusto, Ramp, Brex, Mercury, Shopify, Square, Rippling, Expensify, Recurly, Chargebee, PayPal, Deel, and Amazon.
- Pilot connects to 10,000+ banks, payment processors, payroll systems, and business tools via secure API connections.
Company Size & Ownership
- Pilot was founded in 2017 by Waseem Daher, Jessica McKellar, and Jeff Arnold — all MIT alumni and serial founders.
- The company employs approximately 397–425 people as of 2025–2026 depending on the source, with GetLatka reporting 416 employees as of December 2025.
Compliance & Certifications
- Pilot.com holds a SOC 2 Type II report per its public trust center documentation, representing its primary publicly referenced security certification.
- However, Pilot does not publicly document ISO 27001, HIPAA, PCI-DSS, FedRAMP, GDPR, or CSA STAR certifications, and its Client Services Agreement explicitly states it does not warrant HIPAA compliance.
Compiled from public sources by VenSearch · Last researched October 14, 2026
Offerings
18 offeringsAccounting and Bookkeeping for Professional Services
Pilot provides bookkeeping, tax, and CFO services tailored for professional services firms including consulting firms, advertising and marketing agencies, law firms, and MSPs. The service includes outsourced accounting, employee utilization reporting, project profitability tracking, and CFO advisory designed for the specific invoicing and staffing dynamics of professional services businesses.
Accounting Services for AI Startups
Pilot offers a specialized accounting and CFO service package for AI startups that includes tracking GPU and cloud compute costs, GAAP-compliant financials, revenue recognition automation, board-ready metrics such as MRR, CAC, churn, and runway, and fundraising or M&A support. Pricing tiers start at $599/month for bookkeeping and scale to $4,000/month for investor-ready CFO services.
AI Accountant
Pilot's AI Accountant is a software platform feature that handles the full bookkeeping cycle including transaction categorization, account reconciliation, vendor identification, and monthly close with minimal client input. It connects to 10,000+ financial tools via secure APIs, learns from transaction history across thousands of businesses, and flags unusual items for human review.
AP & Payroll Services
Pilot offers accounts payable management and payroll administration as part of its small business financial services suite, allowing business owners to offload vendor payments and payroll processing. This is listed as a distinct service on the small business solutions page.
Bookkeeping
Pilot provides outsourced bookkeeping services for startups and small businesses, delivering triple-checked monthly financial statements using a combination of AI automation and a dedicated US-based bookkeeping team. The service handles transaction categorization, account reconciliation, and monthly close, with results delivered through the Pilot Portal.
CFO Services
Pilot offers fractional CFO support provided by former CFOs and operators who help clients with cash flow management, financial modeling, budgeting, hiring plans, fundraising preparation, and strategic guidance. The service is designed to give businesses expert financial leadership without the cost of a full-time CFO.
Communication Portal
Pilot's Portal provides a unified workspace where clients can message their dedicated Pilot bookkeeping team, track open requests such as missing receipts or unclear transactions, and view financials all in one place. Conversations are threaded to specific line items or reports, and team members, advisors, or investors can be given access with appropriate permissions.
Creative Agency Bookkeeping and CFO Services
Pilot provides specialized bookkeeping, tax preparation, and CFO services for creative agencies in brand, digital marketing, content, and social media. The service includes client profitability tracking, invoice collection improvement, cash flow forecasting, and pricing strategy support from a dedicated CFO familiar with agency-specific staffing and invoicing challenges.
Dashboards and Insights
Pilot's live financial dashboards display cash balances across all bank accounts and credit cards, cash flow trends, burn rate, runway estimates, revenue and expense trends by category, and top vendor spend, all updated in real time as transactions come in. The AI Accountant surfaces summaries of what changed since last month, flagging category spikes or unusual vendor activity for early investigation.
Financial Reports
Pilot generates stakeholder-ready financial statements including Profit and Loss, Balance Sheet, and Statement of Cash Flows from AI-prepared, reconciled books through the Pilot Portal. Reports can be filtered by period, vendor, or category, allow drill-down into underlying transactions, and can be downloaded in common formats for investors, lenders, or board meetings.
Integrations
Pilot connects to 10,000+ banks, payment processors, payroll systems, and business tools including Stripe, Gusto, Mercury, Ramp, Shopify, and more via secure API connections. Data syncs automatically into the client's QuickBooks Online file so that transaction data, reconciliation, and bookkeeping happen without the client manually moving data between systems.
Meridian
Meridian is described on the Pilot website as an AI operating system for accounting firms. It is presented as a distinct product from Pilot's direct client-facing services, targeted at accounting firms rather than end-business clients.
Outsourced Operations
Pilot provides outsourced back-office operations support including accounts payable management and payroll administration, allowing business owners to offload time-consuming operational finance tasks. This service functions as an extension of the client's internal team.
R&D Credit
Pilot helps eligible businesses identify and claim Research and Development (R&D) tax credits. This service is listed as a distinct offering within Pilot's suite of financial back-office services.
SMB Booster
SMB Booster is a low-cost program for businesses started in the last 12 months, priced at $10/month, that includes bookkeeping, help opening a bank account, payroll setup, and answers to critical early business questions. It is designed to give new small business owners foundational financial support as they get started.
Startup Booster
Startup Booster is a program offered by Pilot specifically tailored to newly incorporated startups, providing bookkeeping and financial foundation services designed to get early-stage companies investor-ready quickly. It is listed as a distinct service offering on Pilot's site.
Stock Admin
Stock Admin is listed as a distinct service offering within Pilot's suite of back-office services. Based on the site listing it alongside bookkeeping, tax, and CFO services, it covers stock administration support for startups.
Tax
Pilot prepares and files federal, state, and local corporate income taxes for startups and small businesses. The service includes live reminders and status updates about filings to keep clients compliant and up-to-date.
Considering Pilot Fiber?
Our team will work with you to determine if Pilot Fiber is the right fit for your organization. From research and assessment through procurement negotiation and ongoing vendor management — we handle the entire process at no cost to you.