Controller

About the role

Pilot just shipped Meridian , the AI platform that closes the books end to end. We built it and ran it across 8,000+ businesses and 187,000+ months of close before we sold it to anyone. As our Controller, you'll run accounting at the company defining what AI-native finance & accounting looks like. AI handles the number-crunching now. Your domain is the plumbing underneath it: the registers, the syncs between systems, the close process itself. AI is only as good as the process it runs on, and you'll own that process. With a small team, this is a player-coach role. You'll own accounting operations and develop the team, designing the close, controls, and systems a modern finance org runs on, and you'll be hands-on in the close itself, down to completing reconciliations and posting journal entries if necessary, while you set the direction. You're the accounting expert leadership trusts to make the call, and the partner other teams come to when they need finance to move with them. You will report to the CFO.

Responsibilities

• Own the monthly close, compliance, audit, revenue, AP/AR, treasury, and payroll. You are accountable for getting it right and on time.
• Lead the existing accounting team and grow it. You'll develop the people here, shape who we hire and how the team works. You're in the details: completing reconciliations, posting journal entries, and managing the close itself, alongside the people you lead.
• As tools automate the manual work, you'll rethink what your team does and how it's structured, and move their time toward judgment and strategy.
• Build the controls and policies that let us scale, then automate them. You'll be an early internal power user of Meridian and set the bar for AI-assisted close at a high-growth company.
• Lead major projects: ERP and billing system implementation, running Pilot's own finance stack on Pilot, and supporting the executive team through fundraising and diligence.
• Translate complex accounting into plain language so people understand the reasoning behind the numbers.
• Be the accounting partner the rest of the company wants in the room. FP&A, RevOps, and department leaders should leave your conversations unblocked and better informed.
• Default to "how might we" over "no." Find the path that protects the books and unblocks the business. You're energized by changing how things have always been done.
• Take a proactive, roll-up-your-sleeves approach to problem solving and execution.
• About You
• 10+ years of accounting experience, including time as a Controller or equivalent scope.
• Startup experience required. You've built and operated in a resource-constrained, fast-moving environment.
• A builder with a bias for improving over preserving. You treat manual or outdated processes as a problem to solve, and you rally the team around the solution.
• Deep US GAAP knowledge with hands-on ASC 606, ideally in SaaS or subscription businesses.
• Fluency with modern accounting tools (QuickBooks, NetSuite, or similar ERP) and real enthusiasm for adopting AI in the accounting function.
• Strong communicator who builds relationships and gets people aligned in a remote or hybrid setting.

Requirements

• Big 4 or public accounting background.
• CPA certification
• ASC 718 stock based compensation accounting.
• ASC 842 lease accounting.
• Fintech, bookkeeping, or B2B SaaS experience.
• ERP / financial system implementation experience.
• Fundraise or investor diligence support.
• About Pilot
• Pilot launched in 2017 to bring the back office into the modern era.
• A few more reasons people join and stay:
• A seasoned founding team that has built and exited two prior startups (acquired by Oracle and Dropbox).
• 3,500+ customers and $170M+ raised from Sequoia, Index Ventures, Stripe, Bezos Expeditions, and Whale Rock; our most recent round doubled our valuation to $1.2B ( "Meet Fintech's Newest Unicorn" ).
• Investors who are world-class operators: Patrick and John Collison, Drew Houston, and Diane Greene.
• Flexible time off, all federal holidays observed, competitive benefits with added wellness perks, 401(k), and 12 weeks of fully paid parental leave for birthing and non-birthing parents.
• Why Pilot?
• 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 vaca

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