Software Engineer

The Role

Pilot is hiring a Software Engineer to join our Bookkeeping Automation team.

This team builds the systems and tooling that power high-quality bookkeeping including secure and reliable agentic workflows integrations with third-party systems and the infrastructure needed to operate them effectively in production. We focus on improving the accuracy efficiency and reliability of bookkeeping at scale.

As a Software Engineer on the team youll build product and platform capabilities that help transform financial data into dependable bookkeeping outcomes. Youll work closely with engineers product managers designers and operational experts to ship systems that are practical measurable and robust.

This is a strong fit for someone who enjoys building real-world automation systems and is excited about the engineering challenges that come with agentic workflows including orchestration security evaluation and observability.

Pilots backend is written in fully typed Python and our frontend stack includes JavaScript TypeScript and . 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
• 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
• 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 PMs 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 dont have experience with every part of our stack wed still love to talk.

Were looking for someone who has:

• 3 years of experience as a software engineer
• 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
• A thoughtful approach to building systems that are trustworthy practical and effective in production

Nice to Have

• Experience with Python 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

Why This Role Matters

The Bookkeeping Automation team is building systems that expand what Pilot can automate while preserving quality trust and control. Agentic workflows are only valuable when they are observable secure measurable and reliable in production. This role is an opportunity to shape those foundations and help define how modern automation can improve financial operations at scale.

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 3000 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 Fintechs 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 $138000 - $186000 in San Francisco CA. Final offer amounts depend on multiple factors such as candidate experience and expertise geographic location total compensation and market 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 Pilots 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.