Staff Software Engineer, Takeoff

Pilot Company; United States; Remote; USD 140,000 - 210,000; Full time

Benefits offered by this job

Flexible vacation/time-off policy

All federal holidays observed

Competitive benefits package including

wellness benefits

Parental leave for birthing or non-工作

Job summary

Pilot Company is seeking a senior software engineer to lead high-ambiguity projects, defining problem scope and delivering scalable solutions. You will set architectural direction for cross-team systems and drive collaborations with PMs, designers, and stakeholders.

You will mentor engineers, improve system reliability, and contribute to a culture of clean, well-tested code. Strong async communication and remote collaboration are valued.

Qualifications

• 7+ years of experience as a software engineer.
• Experience with Python in production.
• Proven track record leading multi-team tech projects.
• Ability to set technical direction and gain buy-in across teams.

Responsibilities

• Lead projects with high ambiguity from problem definition through delivery.
• Set technical strategy and make architectural decisions for cross-team systems.
• Identify gaps across teams and drive strategic improvements.
• Build, test, and deploy software in a continuous manner.
• Create and review technical specs and demand high quality from Engineering.
• Collaborate with PMs, Designers, internal customers, and stakeholders to solve the right problems.
• Mentor and sponsor engineers across the organization.
• Investigate production issues, improve reliability, and support services.

Skills

Python

Technical leadership

Communication

Mentorship

Async/written communication

Clean code

Remote collaboration

Tools

Vue.js

APIs

Accounting systems

Job description

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
• 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

Requirements

• 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
• Experience working effectively on a remote team, including strong async and written communication habits
• Demonstrated ability to mentor, sponsor, and uplevel other engineers

Preferred Qualifications

• Experience with Vue in production
• Experience with accounting systems, double-entry bookkeeping, or revenue recognition
• Familiarity with agentic or AI-assisted systems in production environments
• Experience integrating with third-party APIs and external systems

Benefits

• Flexible vacation/time-off policy
• All federal holidays are observed
• Competitive benefits package including additional wellness benefits
• Parental leave for birthing or non-working parents
• 401(k) plan
• Equity eligibility
• Health benefits