Sr. Product Engineer

Pilot.com; San Francisco (CA); Hybrid; USD 166,000 - 200,000; Full time

Job summary

Pilot is seeking a Senior Software Engineer to join our Bookkeeping Automation team in San Francisco. You will own projects end to end, from problem definition and design through implementation and rollout, partnering with product, design, and bookkeeping experts to improve accuracy and reliability of Pilot's workflows.

This role focuses on building automated, auditable, and scalable bookkeeping systems, spanning data reconciliation, third-party integrations, and production observability.

Qualifications

• 4+ 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.

Responsibilities

• Own projects end to end, from problem definition and technical design through implementation, rollout, and measurement.
• 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.

Skills

End-to-end ownership

Python production

Shipping systems

Mentoring

Job description

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 productio

n.
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 workflo

ws.
This is a strong fit for someone who enjoys solving complex automation problems. The work spans data matching and reconciliation, evaluation, auditability, and production observabil

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

Key Responsib

• ilities
  Own projects end to end, from problem definition and technical design through implementation, rollout, and measurementBuild, test, and deploy well-structured, well-tested software cont
• inuouslyDesign reliable workflows across services, internal tools, and human operational p
• rocessesBuild observability and evaluation into automation systems so teams can measure quality, investigate failures, and improve performance o
• ver timeContribute to the security, auditability, and reliability of systems that handle sensitive financ
• ial dataPartner with Product Managers, Designers, and bookkeeping and operations experts to turn ambiguous problems into practical s
• olutionsInvestigate production issues, support the services you own, and address systemic reliability
• problemsMentor 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 lov

e to talk.
We're looking for someo

• ne who has:
  4+ years of experience as a softw
• are engineerStrong software-engineering fundamentals and the ability to write clean, maintainable, well
• -tested codeExperience with Python i
• n productionA track record of owning and shipping customer-facing or business-critical system
• s end to endExperience designing, operating, and debugging reliable produc
• tion systemsStrong product and systems judgment, especially in ambiguous or evolving pr
• oblem spacesStrong written, verbal, and technical communication skills and comfort working cross-
• functionallyDemonstrated ability to mentor and

teach others

• Nice to Have
  Experience with fintech, accounting, or financial oper
• ations toolingExperience integrating with third-party APIs and ex
• ternal systemsExperience with system security, permissions, or handling
• ata

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 U

• nicorn.
  Why Pilot?
  We invest in our employees’ development and happiness because our employees are the keys to our success and ensur
• ing happy customersThe opportunity to join a seasoned founding team that has led companies through two prior successful startups and acquisitions (by O
• racle and Dropbox).Flexible vacat
• ion/time-off policyAll federal ho
• lidays are observedCompetitive benefits package including additiona
• l wellness benefitsParental leave for birthing or non-birthing parents – 10
• 0% pay for
• 12 weeks401(k) plan
  The base pay range target for the role seniority described in this job description is $166,000 - $200,000 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 order, 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.