Software Engineer

Pilot.com•San Francisco, CA

13h•Hybrid

About The Position

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, 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. 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. 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.

Requirements

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 Haves

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

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