Senior Software Engineer, Bookkeeping Automation – Hybrid SF

Pilot.com; San Francisco (CA); Hybrid; USD 166,000 - 200,000; Full time

Job summary

Pilot is seeking a Senior Software Engineer to join our Bookkeeping Automation team in San Francisco. You will own projects end to end, from problem definition and design through implementation and rollout, partnering with product, design, and bookkeeping experts to improve accuracy and reliability of Pilot's workflows.

This role focuses on building automated, auditable, and scalable bookkeeping systems, spanning data reconciliation, third-party integrations, and production observability.

Qualifications

• 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.

Responsibilities

• Own projects end to end, from problem definition and technical design through implementation, rollout, and measurement.
• 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.

Skills

End-to-end ownership

Python production

Shipping systems

Mentoring

Job description

Pilot is seeking a Senior Software Engineer to join our Bookkeeping Automation team in San Francisco. You will own projects end to end, from problem definition and design through implementation and rollout, partnering with product, design, and bookkeeping experts to improve accuracy and reliability of Pilot's workflows.

This role focuses on building automated, auditable, and scalable bookkeeping systems, spanning data reconciliation, third-party integrations, and production observability.