Senior Software Engineer

Requirements

• Even if you don’t have experience with every part of our stack, we’d still love to talk
• 5+ years of experience as a software engineer
• Experience with Python in production
• 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
• Demonstrated ability to mentor and teach others
• (Desirable) Experience with Vue in production
• (Desirable) Experience with workflow orchestration, automation platforms, or distributed systems
• (Desirable) Familiarity with agentic or AI-assisted systems in production environments
• (Desirable) Experience building observability, alerting, or operational debugging tools
• (Desirable) Experience with system security, permissions, or handling sensitive data
• (Desirable) Experience building evaluation or quality measurement frameworks
• (Desirable) Experience with fintech, accounting, or financial operations tooling
• (Desirable) Experience integrating with third-party APIs and external systems

• Pilot is hiring a Senior Software Engineer to join our Empowerment team
• This team removes friction and creates self-service workflows to improve customer experience and time to value
• We build the customer-facing experiences that turn prospects into self-sufficient Pilot customers. We own the trial funnel, onboarding, and the bank sync and access workflows underneath them
• As a Senior 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
• Pilot’s backend is written in fully typed Python, and our frontend stack includes JavaScript, Type Script, and Vue.js
• We use Terraform to manage infrastructure, deploy containerized services on AWS, and rely on Postgres and modern observability tooling in production
• 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
• Mentor and sponsor your teammates to help them grow
• 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 Product Managers, 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