Senior Software Engineer (Bookkeeping Automation)

• 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
• 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

Benefits

• Flexible vacation/time-off policy
• All federal holidays are observed
• Parental leave for birthing or non-birthing parents – 100% pay for 12 weeks
• 401(k) plan
• Development opportunities & employee happiness initiatives
• Seasoned founding team that has led companies through two prior successful startups and acquisitions (by Oracle and Dropbox)
• Wellness benefits such as Modern Health, Headscape, One Medical, Aaptiv and Rightway

• Even if you don’t have experience with every part of our stack, we’d still love to talk
• Strong product and systems judgment, especially in ambiguous or evolving problem spaces
• Demonstrated ability to mentor and teach others
• A track record of owning and shipping customer-facing or business-critical systems end to end
• Strong written, verbal, and technical communication skills and comfort working cross-functionally
• Experience designing, operating, and debugging reliable production systems
• Strong software-engineering fundamentals and the ability to write clean, maintainable, well-tested code
• Experience with Python in production
• 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
• 4+ years of experience as a software engineer