Sr. Software Engineer, Bookkeeping Automation

About the role

Pilot is looking for a Senior Software Engineer to join its Bookkeeping Automation team in San Francisco. The team builds large‑scale systems that turn raw financial data into accurate, reviewable bookkeeping, including reconciliation tools and integrations with third‑party financial platforms. You will own projects from problem definition through design, implementation, rollout and measurement.

Key responsibilities

• Define ambiguous problems, create technical designs and deliver end‑to‑end solutions.
• Write, test and continuously deploy well‑structured, well‑tested code.
• Design reliable workflows that span services, internal tools and human operational processes.
• Embed observability and evaluation into automation systems to monitor quality and investigate failures.
• Contribute to security, auditability and reliability of systems handling sensitive financial data.
• Partner with product managers, designers and bookkeeping experts to turn vague requirements into practical implementations.
• Investigate production issues, support owned services and address systemic reliability problems.
• Mentor teammates and help raise engineering standards through design reviews.

Required profile

• 4+ years of professional software engineering experience.
• Strong fundamentals and a track record of shipping customer‑facing or business‑critical systems.
• Experience operating and debugging reliable production services.
• Excellent written and verbal communication and ability to work cross‑functionally.
• Comfort with ambiguous, evolving problem spaces and strong product and systems judgment.

Required skills

• Python (fully typed) in production.
• JavaScript, TypeScript and Vue.js for frontend work.
• Terraform for infrastructure as code.
• AWS for containerized service deployment.
• PostgreSQL for data storage.