Staff Software Engineer, Takeoff

The Role Pilot is hiring a Staff Software Engineer to join our Takeoff team. The Takeoff team owns core accounting systems behind Pilot's bookkeeping: how transactions get categorized, how revenue from platforms like Stripe and Shopify gets recognized over the right periods, and how it all ties back to accurate financials. What we ship shows up directly in our customers' books. As a Staff Engineer, you'll take on the largest and most ambiguous problems in this space: setting technical direction for systems that sit at the core of Pilot's product, and driving outcomes that span multiple teams. Pilot's backend is written in fully typed Python, and our frontend stack includes JavaScript, TypeScript, and Vue.js. We use Terraform to manage infrastructure, deploy containerized services on AWS, and rely on Postgres and modern observability tooling in production. Key Responsibilities Lead projects with high levels of ambiguity from problem definition through delivery Set technical strategy and make architectural decisions for systems that span teams and surface areas Identify cross-team gaps and missed opportunities, and drive the strategy to address them Build, test, and deploy software in a continuous manner (we deploy daily or more often) Create and review technical specs, and hold Engineering to high quality standards Work with PMs, Designers, internal customers, and stakeholders to ensure we're solving the right problems Mentor and sponsor engineers across the organization Investigate production issues, improve system reliability, and support services as needed About You Even if you don't have experience with every part of our stack, we'd still love to talk. We're looking for someone who has: 7+ years of experience as a software engineer Experience with Python in production A track record of leading complex, multi-team technical projects to successful outcomes The ability to set technical direction and get buy-in across teams and functions Strong coding fundamentals and the ability to write clean, maintainable, well-tested code Good product and systems judgment, especially in ambiguous or evolving problem spaces Strong communication skills and comfort working cross-functionally Experience working effectively on a remote team, including strong async and written communication habits Demonstrated ability to mentor, sponsor, and uplevel other engineers This position is only available for remote employment in the United States in the following states: CA, GA, NY, NC, TN, TX, and WA Additionally, we're interested in engineers with specialties or backgrounds in accounting as well as fintech and related fields. Nice to Have Experience with Vue in production Experience with accounting systems, double-entry bookkeeping, or revenue recognition Familiarity with agentic or AI-assisted systems in production environments Experience integrating with third-party APIs and external systems (e.g. payment processors) 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 th