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Salary: USD 133,000 - 192,000 / annual
Pilot is a fintech company providing modern bookkeeping and financial management services to small businesses. The Takeoff team owns core accounting systems that power Pilot's bookkeeping platform, including transaction categorization, revenue recognition across platforms like Stripe and Shopify, and financial reporting.
As a Senior Software Engineer on Takeoff, you will own projects end-to-end from design through production rollout. You'll collaborate with engineers, product managers, designers, and accounting experts to ship reliable, well-tested changes that directly impact customer financial records.
Key responsibilities include building and deploying software in a continuous deployment model (daily or more frequent releases), working cross-functionally with product and design teams, creating technical specifications and rollout plans, writing clear technical designs and thoughtful code reviews, maintaining high engineering standards, working with internal stakeholders to solve the right problems, mentoring teammates, investigating production issues, and improving system reliability.
Pilot's backend is written in fully typed Python; the frontend uses JavaScript, TypeScript, and Vue.js. Infrastructure is managed with Terraform, services are containerized on AWS, and the stack includes Postgres and modern observability tooling.
You should have 5+ years of software engineering experience, production experience with Python or Vue (or other JavaScript frameworks), strong coding fundamentals, good product and systems judgment in ambiguous problem spaces, strong cross-functional communication skills, demonstrated ability to work effectively on remote teams with async/written communication habits, and a track record of mentoring others. Experience with accounting systems, double-entry bookkeeping, revenue recognition, agentic/AI systems, or third-party API integrations is a plus.
Pilot was founded in 2017 and has grown to serve over 3,000 customers. The company has raised $170M+ from top-tier investors including Sequoia, Index Ventures, Stripe, and Bezos Expeditions, and recently achieved unicorn status at a $1.2B valuation.
