Sr. Software Engineer, Bookkeeping Automation

The Role Pilot is hiring a Senior Software Engineer to join our Bookkeeping Automation team. The team builds systems that transform financial data into accurate, reviewable bookkeeping at scale. Our work includes reconciliation tools, integrations with third-party financial systems, and the platform capabilities needed to operate deterministic automation and agent-assisted workflows safely and reliably in production. As a Senior Software Engineer on the team, you'll own projects end to end – from shaping ambiguous problems and writing technical designs through implementation and rollout. You'll partner closely with engineers, product managers, designers, and bookkeeping experts to deliver systems that improve the accuracy, efficiency, and reliability of Pilot's bookkeeping workflows. This is a strong fit for someone who enjoys solving complex automation problems. The work spans data matching and reconciliation, evaluation, auditability, and production observability. 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. Location: San Francisco, CA (3 days/week in office—Mondays, Tuesdays, and Thursdays). #LI-Hybrid Key Responsibilities Own projects end to end, from problem definition and technical design through implementation, rollout, and measurement Build, test, and deploy well-structured, well-tested software continuously Design reliable workflows across services, internal tools, and human operational processes Build observability and evaluation into automation systems so teams can measure quality, investigate failures, and improve performance over time Contribute to the security, auditability, and reliability of systems that handle sensitive financial data Partner with Product Managers, Designers, and bookkeeping and operations experts to turn ambiguous problems into practical solutions Investigate production issues, support the services you own, and address systemic reliability problems Mentor and sponsor teammates and contribute to engineering standards through technical designs and thoughtful code reviews 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: 4+ years of experience as a software engineer Strong software-engineering fundamentals and the ability to write clean, maintainable, well-tested code Experience with Python in production A track record of owning and shipping customer-facing or business-critical systems end to end Experience designing, operating, and debugging reliable production systems Strong product and systems judgment, especially in ambiguous or evolving problem spaces Strong written, verbal, and technical communication skills and comfort working cross-functionally Demonstrated ability to mentor and teach others Nice to Have Experience with fintech, accounting, or financial operations tooling Experience integrating with third-party APIs and external systems Experience with system security, permissions, or handling sensitive data 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, incl