Pilot.com Inc.
Pilot provides intelligent bookkeeping, tax, and CFO services for startups and small businesses, combining software automation with expert human guidance to handle the financial back-office.
At a Glance
- Tech Startups
- E-commerce
- D2C Brands
- High-growth SMBs
AI Tools by Pilot.com Inc.
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Pilot
AI Bookkeeping for Startups
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Latest News
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Pilot.com Announces Inaugural Small Business Networking Event in Nashville
Pilot Launches Local Partner Program for Independent Bookkeepers
Products & Services
Automated bookkeeping service integrated with QuickBooks Online, supported by dedicated account managers.
Tax preparation and filing services for federal and state compliance, including R&D tax credit support.
Fractional CFO services providing strategic financial guidance, budgeting, forecasting, and fundraising support.
Autonomous AI system that performs bookkeeping tasks with minimal human intervention.
Market Position
Positions itself as a premium, tech-enabled alternative to traditional bookkeeping services like Bench or manual CPAs, emphasizing accuracy and strategic partnership through its 'Software + Human' model.
Leadership
Founders
Waseem Daher
MIT graduate. Previously co-founded Ksplice (acquired by Oracle) and Zulip (acquired by Dropbox). Group Product Manager at Dropbox and Senior Director at Oracle.
Jeff Arnold
MIT graduate. Previously co-founded Ksplice and Zulip. Former Senior Director at Oracle and Engineering Manager at Dropbox. Serves as COO and Board Chairman.
Jessica McKellar
MIT graduate. Previously co-founded Ksplice and Zulip. Director of Engineering at Dropbox. Prominent figure in the Python community and former Director of the Python Software Foundation.
Executive Team
Waseem Daher
Chief Executive Officer
Three-time founder (Ksplice, Zulip, Pilot). Previously at Oracle and Dropbox.
Jeff Arnold
Chief Operating Officer
Three-time founder. Expert in operations and financial systems for startups.
Board of Directors
Founding Story
Founded by three MIT friends after selling their two previous startups (Ksplice and Zulip) to Oracle and Dropbox. The idea was born when Oracle's finance team noted the high quality of the internal bookkeeping tools the trio had built for their previous company.
Business Model
Revenue Model
Subscription-based service (SaaS + Services model)
Pricing Tiers
Basic bookkeeping for early-stage startups; includes $200/mo discount for pre-revenue companies.
Standard bookkeeping for growing companies needing accrual accounting and more complex reports.
Billed annually. Basic fractional CFO support.
Billed annually. Comprehensive strategic financial planning.
Simple tax filing for early-stage startups.
Target Markets
- Tech Startups
- E-commerce
- D2C Brands
- High-growth SMBs
- Venture-backed startups scaling from seed to Series C+
- E-commerce businesses needing inventory and cash flow tracking
- Professional services firms requiring fractional CFO input
- Companies preparing for fundraising or M&A
- Element5
- Ladris
- Optimal AI
- Various venture-backed startups