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Salary: USD 200,000 - 240,000 / annual
Pilot is a fintech company providing modern bookkeeping and financial management services to small businesses. The company has raised over $170M from top-tier investors including Sequoia, Index Ventures, and Stripe, and recently achieved unicorn status at $1.2B valuation.
The Takeoff team owns core accounting systems that power Pilot's bookkeeping platform—specifically transaction categorization, revenue recognition across platforms like Stripe and Shopify, and financial reporting accuracy. This Staff Engineer role focuses on the largest, most ambiguous technical challenges in this domain.
Key responsibilities include:
- Leading high-ambiguity projects from problem definition through delivery
- Setting technical strategy and making architectural decisions for systems spanning multiple teams
- Identifying cross-team gaps and driving strategy to address them
- Building, testing, and deploying software continuously (daily or more)
- Creating and reviewing technical specs; maintaining high engineering quality standards
- Collaborating with PMs, designers, internal customers, and stakeholders
- Mentoring and sponsoring engineers across the organization
- Investigating production issues and improving system reliability
Tech stack: Python (backend, fully typed), JavaScript/TypeScript/Vue.js (frontend), Terraform (infrastructure), AWS (containerized services), Postgres, modern observability tooling.
Required qualifications:
- 7+ years software engineering experience
- Production Python experience
- Track record leading complex, multi-team technical projects
- Ability to set technical direction and gain cross-functional buy-in
- Strong coding fundamentals and clean code practices
- Product and systems judgment in ambiguous problem spaces
- Excellent communication and cross-functional collaboration skills
- Remote-team experience with strong async/written communication
- Demonstrated mentoring and engineering leadership
- US remote eligibility: CA, GA, NY, NC, TN, TX, WA only
Nice-to-haves: Vue production experience, accounting/bookkeeping/revenue recognition expertise, agentic/AI systems in production, third-party API integration experience.
Pilot offers flexible PTO, competitive benefits, 12-week parental leave at 100% pay, 401(k), and wellness benefits. Founded in 2017, the company serves 3,000+ customers with a blend of custom software and expert bookkeepers.
