SlipstreamJobs tracks this role from the company's public career site. Apply directly on the employer's site.
Pilot is a fintech company providing bookkeeping automation and financial management services to small businesses. Founded in 2017, Pilot has raised over $170M from top-tier investors including Sequoia, Index Ventures, and Stripe, and recently achieved unicorn status at $1.2B valuation.
You'll join the Bookkeeping Automation team as a Senior Software Engineer, owning projects end-to-end from problem definition through technical design, implementation, rollout, and measurement. The team builds systems that transform financial data into accurate, reviewable bookkeeping at scale, including reconciliation tools, third-party financial system integrations, and deterministic automation with agent-assisted workflows.
Key responsibilities include:
- Owning full-stack projects from ambiguous problem spaces to production deployment
- Building well-tested, maintainable software with continuous deployment
- Designing reliable workflows across services, internal tools, and human operational processes
- Implementing observability and evaluation systems to measure quality and improve performance
- Contributing to security, auditability, and reliability of systems handling sensitive financial data
- Partnering cross-functionally with product managers, designers, and domain experts
- Investigating production issues and addressing systemic reliability problems
- Mentoring teammates and establishing engineering standards through technical leadership
The tech stack includes fully typed Python backend, JavaScript/TypeScript/Vue.js frontend, Terraform for infrastructure, containerized services on AWS, Postgres, and modern observability tooling.
You'll work 3 days/week in the San Francisco office (Monday, Tuesday, Thursday). The role requires 5+ years of software engineering experience, strong fundamentals, production Python experience, and a track record of shipping customer-facing or business-critical systems. Experience with fintech, accounting, third-party API integrations, and handling sensitive data is a plus.
