Software Engineer

The Role Pilot is hiring a Software Engineer to join our Bookkeeping Automation team. This team builds the systems and tooling that power high-quality bookkeeping, including secure and reliable agentic workflows, integrations with third-party systems, and the infrastructure needed to operate them effectively in production. We focus on improving the accuracy, efficiency, and reliability of bookkeeping at scale. As a Software Engineer on the team, you’ll build product and platform capabilities that help transform financial data into dependable bookkeeping outcomes. You’ll work closely with engineers, product managers, designers, and operational experts to ship systems that are practical, measurable, and robust. This is a strong fit for someone who enjoys building real-world automation systems and is excited about the engineering challenges that come with agentic workflows, including orchestration, security, evaluation and 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). Key Responsibilities Build, test, and deploy software in a continuous manner Develop systems that power bookkeeping automation, including agentic workflows and integrations with third-party platforms Design and implement reliable workflow orchestration across services, tools, and operational processes Build observability into automation systems so teams can understand performance, investigate failures, and improve quality over time Contribute to the security and reliability of systems that handle sensitive financial data and operational decisions Help design and improve evaluation frameworks that measure workflow quality, correctness, and business impact Partner with PMs, designers, and cross-functional stakeholders to turn ambiguous problems into practical solutions Write clear technical designs, contribute thoughtful code reviews, and maintain high engineering standards Investigate production issues, improve system reliability, and support services as needed Ability to work in our San Francisco office Mondays, Tuesdays, and Thursdays 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: 3+ years of experience as a software engineer Experience building production software and shipping customer-facing or business-critical systems 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 Interest in building automation systems that are reliable, observable, and secure A thoughtful approach to building systems that are trustworthy, practical, and effective in production Nice to Have Experience with Python in production Experience with workflow orchestration, automation platforms, or distributed systems Familiarity with agentic or AI-assisted systems in production environments Experience building observability, alerting, or operational debugging tools Experience with system security, permissions, or handling sensitive data Experience building evaluation or quality measurement frameworks Experience with fintech, accounting, or financial operations tooling Experience integrating with third-party APIs and external systems Why This Role Matters The Bookkeeping Automation team is building systems that expand what Pilot can automate while preserving quality, trust, and control. Agentic workflows are only valuable when they are observable, secure, measurable, and reliable in production. This role is an opportunity to shape those foundations and help define how modern automation can improve financi