Senior Software Engineer, FinTech Bookkeeping Automation

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

Benefits offered by this job

Flexible vacation policy

All federal holidays observed

Wellness benefits

Parental leave (100% pay for 12 weeks)

401(k) plan

Equity eligibility

Job summary

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, including reconciliation tools and integrations with third‑party financial systems.

Based in San Francisco with a hybrid office schedule (3 days a week in the office), you will own projects end to end—from problems to design, implementation, rollout, and measurement—collaborating with product managers, designers,

Qualifications

• 4+ years of experience as a software engineer.
• Strong software‑engineering fundamentals and clean, well‑tested code.
• Experience with Python in production.
• Track record 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 in ambiguous problem spaces.
• Excellent written and verbal communication; comfortable cross‑functional collaboration.
• Demonstrated ability to mentor and teach others.

Responsibilities

• Own projects end to end from problem definition to rollout and measurement.
• Build, test, and deploy well‑structured, well‑tested software continuously.
• Design reliable workflows across services, internal tools, and human processes.
• Build observability and evaluation into automation systems to measure quality and performance.
• Contribute to security, auditability, and reliability of systems handling financial data.
• Collaborate with PMs, Designers, and bookkeeping experts to turn ambiguous problems into practical solutions.
• Investigate production issues and mentor teammates while improving engineering standards.

Skills

Python production

End-to-end ownership

System design

Observability

Mentoring

Cross-functional collaboration

Clean code

Communication

Tools

Terraform

AWS

Postgres

Vue.js

TypeScript

JavaScript

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, including reconciliation tools and integrations with third‑party financial systems.

Based in San Francisco with a hybrid office schedule (3 days a week in the office), you will own projects end to end—from problems to design, implementation, rollout, and measurement—collaborating with product managers, designers,