Sr. Software Engineer

The Role Pilot is hiring a Senior Software Engineer to join our Empowerment team. This team removes friction and creates self-service workflows to improve customer experience and time to value. We build the customer-facing experiences that turn prospects into self-sufficient Pilot customers. We own the trial funnel, onboarding, and the bank sync and access workflows underneath them. As a Senior Software Engineer on the team, you’ll build product and platform capabilities that help transform financial data into dependable bookkeeping outcomes. You’ll work closely with engineers, product managers, designers, and operational experts to ship systems that are practical, measurable, and robust. 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.Location: San Francisco, CA (3 days/week in office - Mondays, Tuesdays, and Thursdays). Key Responsibilities Build, test, and deploy software in a continuous manner Develop systems that power bookkeeping automation, including agentic workflows and integrations with third-party platforms Design and implement reliable workflow orchestration across services, tools, and operational processes Build observability into automation systems so teams can understand performance, investigate failures, and improve quality over time Mentor and sponsor your teammates to help them grow Contribute to the security and reliability of systems that handle sensitive financial data and operational decisions Help design and improve evaluation frameworks that measure workflow quality, correctness, and business impact Partner with Product Managers, Designers, and cross-functional stakeholders to turn ambiguous problems into practical solutions  Write clear technical designs, contribute thoughtful code reviews, and maintain high engineering standards Investigate production issues, improve system reliability, and support services as needed Ability to work in our San Francisco office Mondays, Tuesdays, and Thursdays 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 in production Experience building production software and shipping customer-facing or business-critical systems 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 Interest in building automation systems that are reliable, observable, and secure Demonstrated ability to mentor and teach others Nice to Have Experience with Vue in production Experience with workflow orchestration, automation platforms, or distributed systems Familiarity with agentic or AI-assisted systems in production environments Experience building observability, alerting, or operational debugging tools Experience with system security, permissions, or handling sensitive data Experience building evaluation or quality measurement frameworks Experience with fintech, accounting, or financial operations tooling Experience integrating with third-party APIs and external systems 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 – https://pilot.com/blog/pilot-unicorn-bezos-expeditions-whale-rock/. 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-off policy All federal holidays are observed Competitive benefits package including additional wellness benefits Parental leave for birthing or non-birthing parents – 100% pay for 12 weeks 401(k) plan The base pay range target for the role seniority described in this job description is $166,000 - $267,000 in San Francisco, CA. Final offer amounts depend on multiple factors such as candidate experience and expertise, geographic location, total compensation, and market data. In addition to cash pay, full-time regular positions are eligible for equity, 401(k), health benefits, and other benefits; some of these benefits may be available for part-time or temporary positions. Pilot commits to provide a work environment free of discrimination and harassment, as well as equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. You may view all of Pilot’s https://pilot.com/recruiting-notices, including our EEO policy, information about requesting a reasonable accommodation in the job application process, recruitment agency policy, recruitment scam notice, and important E-Verify information. You may view our job candidate privacy policy https://pilot.com/terms/privacy-job-candidate. Offices: San Francisco, California, United States (San Francisco);