Staff Software Engineer, Takeoff

The Role

Pilot is hiring a Staff Software Engineer to join our Takeoff team.

The Takeoff team owns core accounting systems behind Pilot's bookkeeping: how transactions get categorized, how revenue from platforms like Stripe and Shopify gets recognized over the right periods, and how it all ties back to accurate financials. What we ship shows up directly in our customers' books.

As a Staff Engineer, you'll take on the largest and most ambiguous problems in this space: setting technical direction for systems that sit at the core of Pilot's product, and driving outcomes that span multiple teams.

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.

Key Responsibilities

• Lead projects with high levels of ambiguity from problem definition through delivery
• Set technical strategy and make architectural decisions for systems that span teams and surface areas
• Identify cross-team gaps and missed opportunities, and drive the strategy to address them
• Build, test, and deploy software in a continuous manner (we deploy daily or more often)
• Create and review technical specs, and hold Engineering to high quality standards
• Work with PMs, Designers, internal customers, and stakeholders to ensure we're solving the right problems
• Mentor and sponsor engineers across the organization
• Investigate production issues, improve system reliability, and support services as needed

About You

Even if you don't have experience with every part of our stack, we'd still love to talk.

We're looking for someone who has:

• 7+ years of experience as a software engineer
• Experience with Python in production
• A track record of leading complex, multi-team technical projects to successful outcomes
• The ability to set technical direction and get buy-in across teams and functions
• 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

• 1. Dismissing manual accounting tasks as beneath you rather than systems to be fixed
• 2. Failing to provide exact numbers or financial impact metrics in past projects
• 3. Lack of familiarity with modern SaaS financial stacks and integrations

I build automated financial engines that give founders their time back while eliminating human error at scale.