Payroll, benefits and compliance for remote teams.

Lead Engineer

Job Type
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About the role

A bit about who we are

Pilot helps companies handle payroll, benefits and compliance for their remote teams. We believe that your opportunities in live shouldn’t be dictated by where you’re from or where you happen to live, and we’re helping our customers live by that too. We’re a team of 15 backed by Sam Altman, Y Combinator, Credo Ventures, Automattic, Kyle Vogt and many other amazing investors.

What you will be working on

You’ll lead a group of 2-3 developers inside our product team oriented towards a specific feature set (such as international payments, employee benefits, technical infrastructure) and report directly to one of our founders. We’ll expect both technical leadership (designing software architecture, ensuring high code quality) and a bit of management (one-on-ones with your direct reports, managing scope of features, planning).This role is not a strictly management role. We want you to be able to build our product, make decisions about the software architecture, and utilize your technical leadership skills to ensure successful deliveries made by your team.

Most of our code is in Ruby—we use Rails 6.1 with bits of React on the front-end. Our primary database is PostgreSQL with Redis as a worker backend and RabbitMQ as a message queue broker.

We have a distributed data model with multiple applications communicating with each other using both asynchronous(events) and synchronous means. We deploy our apps to Heroku.

We have a pretty lightweight process: 1-week sprints, weekly planning sessions and asynchronous progress updates. We use Slack, Linear, Tandem, and Zoom to communicate and plan our work. We enjoy working together as a team, but there’s also a lot of opportunity to work autonomously.


  • Experience leading engineering teams.
  • Experience in building complex enterprise products at a startup pace.
  • Proficiency with Ruby and Ruby on Rails.
  • Understanding of modern JavaScript ecosystem
  • You have practical experience implementing microservices
  • Working understanding of React (nice to have: TypeScript). You don’t have to be a front-end expert as we use them sparingly.
  • Excellent oral and written communication skills. You’ll be working with a distributed team, so first-class communication is a must.
  • Experience and desire to work in distributed teams. Expect your teammates to be all over the world.

We’d especially like to talk to you if

  • You have a demonstrated history of tech leadership
  • You’re interested in software architecture and distributed systems
  • You enjoy working on internal libraries/frameworks
  • You have domain knowledge in HR tools, payroll or fintech.


  • Competitive salary and stock packages: $91,400/y, equity: 0.05% - 0.125%
  • Unlimited vacation policy
  • Ability to work remotely from anywhere in the world

We try to hold all most of our team meetings between 7am–9am PST / 3pm–5pm BST / 11pm–1am JST to accommodate as many time zones as possible.

Why you should join Pilot

We are Pilot, a Y Combinator-backed startup after a successful seed funding round, with a small distributed team working remotely from Poland and San Francisco. Our mission is to create a more open worldwide job market. Today, we’re doing that by helping companies hire and pay remote international staff.

Team Size:32
Location:San Francisco
Matt Drozdzynski
Matt Drozdzynski
Staszek Kolarzowski
Staszek Kolarzowski