Sr. Software Engineer

Pilot.com•San Francisco, CA

15d•Hybrid

About The Position

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.

Requirements

5+ 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 Haves

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

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