Full-Time
Posted on 8/18/2026
Outsourced bookkeeping, tax, and CFO services
$163k - $196k/yr
San Francisco, CA, USA
Hybrid
Three days on-site per week required: Mondays, Tuesdays, and Thursdays.
Bachelor's
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Pilot provides outsourced financial management for startups and small businesses. It handles core back-office tasks—bookkeeping, tax preparation, and CFO-level financial guidance—through a subscription-based service, giving clients ongoing access to a team of finance experts who manage their numbers and strategic planning. The product works by offering tiered service levels tied to client size, with recurring fees for ongoing support rather than one-off projects. Pilot differentiates itself by specializing in early-stage and small companies, delivering a dedicated finance function with scalable expertise, backed by substantial funding from investors such as Sequoia, Index Ventures, Stripe, Bezos Expeditions, and Whale Rock. The company’s goal is to let business owners focus on growth by providing professional, reliable financial management and predictable costs through a repeatable service model.
Company Size
201-500
Company Stage
Series C
Total Funding
$158.3M
Headquarters
San Francisco, California
Founded
2016
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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 wellness benefits such as Modern Health, Headscape, One Medical, Aaptiv and Rightway
Parental leave for birthing or non-birthing parents – 100% pay for 12 weeks
401(k) plan
Pilot touts Meridian, says AI comparable to seasoned accountant. Published June 16, 2026, 4:30 p.m. EDT Updated June 16, 2026, 5:06 p.m. EDT Bookkeeping, tax and outsourced CFO services company Pilot announced the launch of Meridian, which is said to be able to perform the full scope of bookkeeping and financial reporting. Get expert analysis, industry news and practical guidance for modern accounting professionals. Accounting Today Technology Editor Chris Gaetano is the technology editor for Accounting Today. He brings with him more than a decade of experience covering the accounting profession... Read full bio
Pilot has launched Meridian, an AI accounting platform that fully automates the month-end close process for accounting firms. The system, which Pilot has used internally since 2017, has closed over 187,000 months of books for more than 8,000 businesses. Meridian handles the entire close process end-to-end, from client onboarding to producing review-ready financial statements, according to each firm's accounting policies. The platform writes completed output directly into general ledgers and includes built-in controls and audit trails. "Three out of four accounting firms are turning away clients they don't have the capacity to serve," said Jessica McKellar, founder and CEO of Pilot. The system currently has advanced support for QuickBooks Online and also works with Xero and NetSuite, with additional ledgers coming soon.
Agentic AI now does your accounting - how to get started. Your bookkeeper just became obsolete - And that's a good thing. In February 2026, Pilot announced the world's first fully autonomous "AI Accountant" for SMBs - a system that runs the entire bookkeeping process from onboarding through monthly close with zero human intervention. Two months later, Xero unveiled Xero OS, an AI-native operating system designed to power end-to-end autonomous finance for small businesses and their accountants. This isn't another incremental upgrade. It's a fundamental shift in who - or what - handles your books. Welcome to the era of agentic AI in accounting, and if you're still manually categorizing transactions or waiting until month-end to understand your financial position, you're already falling behind. What is Agentic AI (and why should you care)? Beyond chatbots and copilots. You've probably used AI tools that answer questions or generate text. That's "assistive AI" - it waits for your input and responds. Agentic AI is different. It takes autonomous action on your behalf, making decisions and executing multi-step workflows without waiting for you to tell it what to do next. In accounting terms, here's the distinction: | Capability | Traditional AI (Copilot) | Agentic AI (Autonomous) | | Invoice processing | Suggests a category when you upload | Detects invoice in email, validates against PO, auto-approves, codes to GL, schedules payment | | Bank reconciliation | Flags potential matches for review | Reconciles automatically, resolves discrepancies, escalates only true exceptions | | Cash flow forecasting | Generates a report when you ask | Continuously updates projections, alerts you to risks before they materialize | | Month-end close | Prepares a checklist for you | Executes the close process, generates reports, flags anomalies | | Expense categorization | Suggests categories | Learns your patterns, categorizes in real time, corrects errors proactively | According to Accounting Today's analysis of the three trends shaping accounting technology in 2026, the industry is shifting from "AI experimentation" to "AI accountability." Firms and businesses alike are demanding measurable results - faster closes, cleaner forecasts, and real cost savings - not just flashy demos. The numbers are hard to ignore. The adoption curve for agentic AI is accelerating fast: * 58% of small businesses already use some form of AI, with 89% reporting positive impact * Gartner predicts over 40% of enterprise applications will embed role-specific AI agents by the end of 2026 * Benchmark studies show agentic AI deployments driving 3-5x productivity gains in finance operations * Operational costs drop by as much as 38% across core business functions using autonomous AI These aren't projections from a distant future. This is happening right now, in 2026, in businesses the same size as yours. What Agentic AI actually does for your business. The end-to-end workflow. Imagine this: a vendor sends you an invoice via email on Tuesday morning. Here's what happens without you lifting a finger: * Detection - The AI agent identifies the invoice in your inbox * Validation - It cross-references the invoice against the original purchase order * Approval - If everything matches (amount, vendor, terms), it auto-approves within your predefined rules * Coding - The expense is coded to the correct general ledger account based on learned patterns * Scheduling - Payment is scheduled according to your cash flow rules (pay early for discounts, or on the due date to preserve cash) * Forecasting - Your cash flow projection updates automatically to reflect the upcoming payment That's six steps that traditionally require a bookkeeper's time, attention, and judgment - handled autonomously in seconds. Multiply that across every invoice, every bank transaction, every recurring expense, and you're looking at dozens of hours reclaimed every month. Where human judgment still matters. Agentic AI isn't about eliminating humans from finance entirely. It's about eliminating the routine so humans can focus on judgment. The things that still require a human brain: * Strategic decisions - Should you take on that new client? Expand to a new market? * Complex tax planning - Navigating multi-state nexus or entity restructuring * Relationship management - Negotiating terms with vendors or resolving disputes * Exception handling - Unusual transactions that don't fit established patterns This is exactly why platforms like Profit Leap's CFO bot pair AI automation with a CPA backstop. The AI handles the 90% of financial tasks that are routine and predictable. When something genuinely complex arises - a tax question that requires professional judgment, an anomaly that needs human interpretation - a real CPA is available to step in. How to get started with Agentic AI accounting. Step 1: audit your current workflow. Before adopting any autonomous system, understand where your time actually goes. Most small-business owners dramatically underestimate how much time they spend on financial administration. Track one month of: * Hours spent categorizing transactions * Time between receiving invoices and paying them * Hours compiling financial reports or spreadsheets * Time spent answering "what's our cash position?" questions If the total exceeds 10 hours per month, you have a strong business case for automation. Step 2: connect your financial stack. Agentic AI is only as good as the data it can access. The minimum viable setup: * Accounting platform - QuickBooks, Xero, or equivalent * Bank feeds - Direct connections to your business accounts * Payment processor - Stripe, PayPal, or your merchant services * Invoicing system - Whatever you use to bill customers The best platforms handle these integrations natively. Profit Leap connects to QuickBooks, Xero, and Stripe out of the box, meaning your AI CFO can see the full picture from day one - no CSV exports or manual data entry required. Step 3: define your rules and thresholds. Agentic AI operates within boundaries you set. Before going autonomous, decide: * Auto-approval limits - What dollar amount requires human sign-off? * Payment timing rules - Pay immediately for early-pay discounts, or hold until due? * Alert thresholds - When should the system wake you up? (Cash below $X, expense over $Y) * Escalation criteria - What types of transactions always need human review? Step 4: start with low-risk automation. Don't flip the switch on everything at once. A sensible rollout: Week 1-2: Automated transaction categorization and bank reconciliation Week 3-4: Invoice processing and payment scheduling Month 2: Cash flow forecasting and anomaly alerts Month 3: Full autonomous close process with human review This graduated approach builds trust in the system while catching any edge cases early. Step 5: monitor and refine. Agentic AI learns from your corrections. The more you interact with it during the early weeks, the more accurately it operates long-term. Check in weekly during the first month: * Are transactions being categorized correctly? * Are the cash flow projections matching reality? * Are alerts firing at the right times? * Is anything being auto-approved that shouldn't be? The cost of waiting. Every month you delay adopting autonomous accounting, you're paying an invisible tax: | Hidden Cost | Monthly Impact | | Bookkeeper or admin hours on routine tasks | $1,500 - $4,000 | | Late payment fees from missed invoices | $200 - $800 | | Lost early-pay discounts | $300 - $1,200 | | Decisions made without current data | Unquantifiable but significant | | Stress and cognitive load on the owner | Priceless (and not in a good way) | Meanwhile, an AI CFO like Profit Leap costs a fraction of a single bookkeeper's salary, operates 24/7, and gets more accurate over time - not less. The 2026 reality check. Profit Leap, Inc. is at an inflection point. The tools for autonomous accounting exist today. They're affordable for small businesses. And they're being adopted by your competitors at an accelerating rate. The question isn't whether agentic AI will handle your accounting eventually - it's whether you'll adopt it proactively (and reap the competitive advantage) or reactively (after falling behind businesses that moved first). National Small Business Week 2026 kicks off today. If there's one investment worth making this week, it's the financial infrastructure that lets you stop doing your books and start using them to grow.
Pilot, an AI-powered accounting solutions provider, has launched a $250,000 Small Business Growth Fund in partnership with Hello Alice to support 18 small business owners. The fund will distribute one $50,000 grant, two $25,000 grants and 15 $10,000 grants to businesses investing in operations, expansion or financial infrastructure. Recipients will also receive one year of free Pilot bookkeeping services, including access to its AI Accountant, which autonomously handles the entire bookkeeping process from onboarding to final financial statements. The initiative addresses a structural gap in financing access, as many profitable small businesses struggle to secure capital despite strong performance. Applications are open from 24 February to 31 March 2026, with recipients to be announced on 5 May 2026. The programme aims to support SMBs facing tightened credit standards and rising interest rates.
Pilot launches Local Partner Program to empower bookkeepers and strengthen small businesses nationwide. New Initiative Provides Bookkeepers with the AI-powered Technology and Personalized Services to Serve Clients More Efficiently, Supporting SMBs and Local Communities Across the United States SAN FRANCISCO, Dec. 09, 2025 (GLOBE NEWSWIRE) - Pilot, the leader in AI-powered bookkeeping and advisory solutions for SMBs and startups, today announced the launch of the Pilot Local Partner Program. The new program provides independent bookkeepers and accounting firms with access to cutting-edge software and automation capabilities, personalized advisory services and sales enablement tools to scale their organizations and support small businesses within their communities. "Small businesses make up more than half of the private sector, yet many struggle in their first five years because they lack the financial visibility and support needed to make the decisions that help them thrive," said Jessica McKellar, founder and CEO of Pilot. "Local accounting and bookkeeping firms are the partners who show up, who understand the stakes, and who help entrepreneurs turn hard work into lasting progress. They're the quiet champions of small businesses everywhere. With the Pilot Local Partner Program, our goal is to equip these advisors with the tools and services they need so they can lift up the businesses in their own backyards and build lasting relationships with the talented, passionate, and caring business owners who make up the fabric of their communities." The Local Partner Program extends Pilot's proven AI-powered platform to independent bookkeepers and accountants nationwide, enabling them to deliver automated bookkeeping and personalized advisory services to their clients. In addition to access to its platform and processes, Pilot empowers its local partners by connecting them directly with pre-qualified prospects to grow their business and establish new revenue streams. Leveraging its existing sales and marketing channels, Pilot manages the lead generation process and matches bookkeepers with customers based on specialties and location. This allows Pilot partners to operate more efficiently, increase productivity and dedicate more time to servicing their clients strategically. "Our relationship with Pilot is a true partnership, and they are committed to our team's success as well as that of our clients," said Abel Castaneda, Founder and CEO at Apex Advantage Bookkeeping. "This new program allows us to utilize an industry-standard platform and collaborate with a team of experts to scale our business, better serve our customers and strengthen our relationships within the community. With the combination of our expertise and Pilot's best-in-class technology, we are a stronger business that delivers more value to our customers." Pilot provides its customers and partners with a scalable platform and high-quality accounting and advisory services. The company's advanced technology automates most bookkeeping tasks, from onboarding to generating real-time, tax- or-loan ready financials, based on each customer's unique business model and preferences with minimal human intervention. Pilot's AI capabilities, including its 24/7 financial chat advisor, are underpinned by the industry's most comprehensive transaction-level dataset, which is verified by its team of U.S.-based accounting experts. The unmatched volume and accuracy of Pilot's proprietary data enable enhanced automation for real-time financial insights and allows independent accountants and bookkeepers to focus on higher-value advisory services. The Local Partner Program is now available to accounting firms across select cities, with plans for nationwide expansion in the coming year. For more information on the Pilot Local Partner Program or to join, visit: https://pilot.com/local-partners About Pilot Pilot transforms bookkeeping and advisory for SMBs and startups by combining advanced AI automation with human expertise. The Pilot platform leverages a massive, high-quality, human-tagged dataset of financial transactions to deliver unmatched automation, benchmarking, and actionable insights at scale - all verified by US-based bookkeeping experts and customers. With headquarters in San Francisco and Nashville, and backed by leading investors including Sequoia, Index Ventures, Stripe, and Bezos Expeditions, Pilot is building the future of accounting - empowering both customers and local partners. Learn more at https://pilot.com. Media Contact: Geoff Lopes Marketbridge for Pilot [email protected]