Senior Software Engineer, Takeoff

The Role Pilot is hiring a Senior Software Engineer to join our Takeoff team. The Takeoff team owns core accounting systems behind Pilot's bookkeeping: how transactions get categorized, how revenue from platforms like Stripe and Shopify gets recognized over the right periods, and how it all ties back to accurate financials. What we ship shows up directly in our customers' books. As a Senior Software Engineer on the team, you'll own projects end to end, from design through rollout. You'll work closely with engineers, product managers, designers, and accounting experts to ship changes that are safe, well-tested, and easy to reason about. 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. Key Responsibilities Build, test, and deploy software in a continuous manner (we deploy daily or more often) Work with PMs and Product Designers, and participate in product and design reviews Create and contribute to technical specs and testing/rollout plans Write clear technical designs, contribute thoughtful code reviews, and maintain high engineering standards Work with internal customers and stakeholders to ensure we're solving the right problems Mentor and sponsor your teammates to help them grow Investigate production issues, improve system reliability, and support services as needed About You Even if you don't have experience with every part of our stack, we'd still love to talk. We're looking for someone who has: 5+ years of experience as a software engineer Experience with Python or Vue (or other Javascript frameworks) in production Strong coding fundamentals and the ability to write clean, maintainable, well-tested code Good product and systems judgment, especially in ambiguous or evolving problem spaces Strong communication skills and comfort working cross-functionally Experience working effectively on a remote team, including strong async and written communication habits Demonstrated ability to mentor and teach others This position is only available for remote employment in the United States in the following states: CA, GA, NY, NC, TN, TX, and WA Additionally, we're interested in engineers with specialties or backgrounds in accounting as well as fintech and related fields. Nice to Have Experience with Vue in production Experience with accounting systems, double-entry bookkeeping, or revenue recognition Familiarity with agentic or AI-assisted systems in production environments Experience integrating with third-party APIs and external systems (e.g. payment processors) About Pilot Pilot launched in 2017 to bring the back office into the modern era. Pilot provides small businesses with dedicated finance experts - which Pilot hires as full-time, U.S.-based employees - who learn the ins-and-outs of their business. Pilot integrates directly with the billing, banking, expense, and payroll systems customers already use. With a special blend of custom software and expert bookkeepers, Pilot delivers accurate, consistent bookkeeping and financial management and tax services that give entrepreneurs the freedom to focus on their business. Pilot has over 3,000 customers and has raised over $170 million in financing from Sequoia, Index Ventures, Stripe, Bezos Expeditions, and Whale Rock. Our investors also include a long list of world-class entrepreneurs, including Patrick and John Collison, Drew Houston, and Diane Greene. Our most recent funding round doubled our valuation to $1.2 billion – Meet Fintech’s Newest Unicorn . Why Pilot? We invest in our employees’ development and happiness because our employees are the keys to our success and ensuring happy customers The opportunity to join a seasoned founding team that has led companies through two prior successful startups and acquisitions (by Oracle and Dropbox). Flexible vacation/time-