Sr. Software Engineer, Bookkeeping Automation

The Role

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.

Location: San Francisco, CA (3 days/week in office—Mondays, Tuesdays, and Thursdays).

Key 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

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
• 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 Have

• 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

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-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 - $200,000in 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 recruiting notices here, 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 here.