Remote Second In Command Pilot Jobs in California

• 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.

• 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 You treat manual or outdated processes as a problem to solve, and you rally the team around the solution.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.

• 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.

Pilot launched in 2017 to bring the back office into the modern era.

You'd join at a real inflection point. On June 16, 2026, Pilot launched Meridian - an AI platform that fully closes the books and produces review-ready financials for accounting firms. We built it inside our own accounting operation and refined it across 8,000+ businesses and 187,000+ months of books before offering it to the market. As Controller, you'll run a finance function that uses this technology first and helps shape where it goes next. Few accounting leaders get to operate at this edge.

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.

• 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 additional wellness benefits
• Parental leave for birthing or non-birthing parents - 100% pay for 12 weeks
• 401(k) plan

The base pay range target for the role seniority described in this job description is between $210,000 - $300,000 in San Francisco, CA. Final offer amounts depend on multiple factors such as candidate experience and expertise, geographic location, total compensation, and market data. In addition to cash pay, full-time regular positions are eligible for equity, 401(k), health benefits, and other benefits; some of these benefits may be available for part-time or temporary positions.

Pilot commits to provide a work environment free of discrimination and harassment, as well as equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. You may view all of Pilot's recruiting notices here, including our EEO policy, information about requesting a reasonable accommodation in the job application process, recruitment agency policy, recruitment scam notice, and important E-Verify information. You may view our job candidate privacy policy here.