Lead Engineer (Ruby/Rails)

Published on January 31, 2023

A bit about who we are
Pilot helps companies to handle payroll, benefits, and compliance for their remote teams. We believe that your opportunities in life 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 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 7.0 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 are also a lot of opportunities to work autonomously. You can find more information about our tech stack and the way we work here.
  • 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 don't have to be proficient in complex JavaScript architectures, but you need to have proper intuition in the front-end subjects to be efficient as a tech lead
  • 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

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 practical experience implementing microservices
  • You have domain knowledge in HR tools, payroll, or fintech

In the first month, you’ll:
  • Complete onboarding and get familiar with our vision, strategy, and current objectives
  • Be a part of our buddy system and work with a dedicated person that can help you whenever you need
  • Learn Pilot’s architecture and the problem domain from other leads, engineers, and our Head of Product
  • Start off as an individual contributor: implement your first pull request and push code to all of Pilot users
  • Get familiar with all ongoing major product initiatives at the company

Within the first three months, you’ll:
  • Lead your own team
  • Create and structure documentation for large code projects concisely and consistently
  • Work with the architecture team regularly to define and refine architectural approaches with extensive experience and sharing
  • Establish strong relationships with product and business stakeholders across the organization
  • Help refine roadmaps across teams based on technical strategy and constraints
  • Define and create new product abilities by changing technical strategy or constraints
  • Have made a visible impact on all of our customers
  • Discuss improvements to our engineering processes during the weekly company-wide engineering meetings

Within 6+ months, you’ll:
  • Proactively seek out gaps in technical understanding, especially cross-functional, and work with a variety of teammates to fill the gaps
  • Successfully manage cross-team commitments and work realization
  • Improve productivity of teammates across multiple teams
  • Articulate a coherent future vision for systems that span teams, or many systems across teams
  • Regularly influence multiple teams to align around a company goal
  • Mentor other engineers on your team
  • Competitive salary and stock packages: $101,000-$112,000/y, equity: 0.05% - 0.125%
  • Flexible working hours
  • Unlimited vacation policy
  • Health insurance coverage
  • Parental leave
  • Company hardware (Computer + other equipment)
  • Ability to work remotely from anywhere in the world
  • Opportunity to join an early-stage startup with high growth potential

We try to hold most of our team meetings between 7 am–9 am PST / 4 pm–6 pm CET / 11 pm–1 am JST to accommodate as many time zones as possible.

Even if you don't check all the boxes but think this role might be a good fit for you, please get in touch. We’d love to hear from you! At Pilot, we hire great people with various backgrounds from all over the world. We celebrate diversity and are committed to creating an inclusive environment for everybody. If you'd like to learn more about us and the company's culture, head to our Careers page. 👋