Staff Product Manager

The Role

At Pilot, we're on a mission to grow the small business economy — and we're at an inflection point. AI is fundamentally reshaping what's possible in financial services, and this role sits at the center of that transformation.

We're looking for a Staff Product Manager to lead Pilot's Agent driven bookkeeping automation platform. This is one of the highest-impact, highest-visibility roles at Pilot. The future of our business, and frankly, the future of bookkeeping as an industry, will be shaped by what this team builds. We're talking about the kind of foundational work that sets a company up for double and triple-digit growth, and positions Pilot as the definitive AI-native back office for small businesses.

The foundation of financial insights is banking data. This team owns the core automation, including agent pipelines, that ensures bank transaction data is accurate, timely, and actionable. You'll drive Pilot's AI transformation from the product layer, architecting how we apply agentic workflows to achieve near-fully autonomous bookkeeping, and setting the standard for how great agent driven products get built and shipped.

This is a generalist PM role at its core, but one that requires deep fluency in AI, not just familiarity. You'll work shoulder-to-shoulder with our engineering and technical teams, speak their language, and make hard technical and product tradeoffs with confidence.

Key Responsibilities 

• Own and drive Pilot's AI transformation for a critical product area, defining the roadmap for how agent orchestration becomes the engine of automated bookkeeping
• Ship outstanding features to drive Pilot’s product feature set, and be responsible for that product delivering substantial impact for both our customers and our business
• Partner deeply with technical teams software engineers to design, build, and ship AI-powered features at high quality
• Audit and evaluate system system quality: assess product quality, pipeline reliability, output performance, and data fidelity; push the bar on what "production-ready" means
• Set the strategic vision for how agent-native bookkeeping evolves at Pilot, influencing company-level decisions about technology investment, product direction, and competitive positioning
• Talk to customers, understand their pain points, and translate those insights into customer solutions they didn't know were possible
• Make smart prioritization decisions informed by customer feedback, data, and a clear-eyed view of technical feasibility and business impact
• Serve as the internal and external ambassador for your product, keeping leadership, cross-functional partners, and customers excited and aligned on what's being built and why

About You

• A proven track record of shipping AI, financial, or data-driven products that have moved meaningful business metrics, not just launched, but delivered
• 7+ years building products, ideally with significant time in B2B and/or data-intensive domains
• Deep familiarity with the agent toolchains, model evaluation frameworks, evaluation/orchestration tools (e.g., Arize, LangChain, Prefect, Airflow)
• Outstanding analytical and problem-solving skills: you can break down complex systems, identify failure modes, and make high-quality decisions with incomplete information
• Exceptional ability to learn complex domains quickly and communicate them simply to customers, executives, and the board

Bonus Points

• Experience as a founder or operator running a business yourself
• A background in finance, accounting, or fintech
• Hands-on experience building or deploying AI, agentic, or LLM based products

Why This Role Matters

Pilot is at a once-in-a-generation moment. AI is enabling us to reimagine what bookkeeping looks like, moving from human-heavy workflows to intelligent automation that gives small business owners real-time, accurate financial clarity with minimal friction. The PM who leads this area will have direct influence on our growth trajectory, our technical architecture, and our positioning in the market.

This is not a supporting role. It's a defining one, for Pilot, and for the category.

About Pilot

Pilot launched in 2017 to bring the back office into the modern era. Pilot provides small businesses with dedicated finance experts - which Pilot hires as full-time, U.S.-based employees - who learn the ins-and-outs of their business. Pilot integrates directly with the billing, banking, expense, and payroll systems customers already use. With a special blend of custom software and expert bookkeepers, Pilot delivers accurate, consistent bookkeeping and financial management and tax services that give entrepreneurs the freedom to focus on their business.

Pilot has over 3,000 customers and has raised over $170 million in financing from Sequoia, Index Ventures, Stripe, Bezos Expeditions, and Whale Rock.  Our investors also include a long list of world-class entrepreneurs, including Patrick and John Collison, Drew Houston, and Diane Greene.  Our most recent funding round doubled our valuation to $1.2 billion – Meet Fintech’s Newest Unicorn.

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 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 $197,000 - $313,000 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.