Benepass is growing quickly and we’re looking for a stellar Head of Engineering to help us execute against our product and technical vision while still adapting quickly to a changing environment.

In this role, you’ll work with our CTO as well as with our PM, to lead our backend and frontend engineering efforts. You’ll help decide what we should build and when, what the technical milestones should be, and how best to handle dependencies. In addition, you’ll be responsible for making sure we meet our goals around code quality, security, and development velocity. Most importantly, you’ll keep us on the right course over time, as timelines shift and new challenges arise.

While you’ll primarily manage and work on strategy in this role, you should expect to spend some of your time on “in the weeds” engineering work, so that you’re close to the ground truth of what we’re building.


  • Have a degree in Computer Science or equivalent experience
  • Have 3+ years of experience as a software engineer, ideally at a fast growing startup
  • Have 3+ years of experience as an engineering manager, ideally at a fast growing startup
  • Have experience working with PMs/TPMs and translating product goals into engineering goals
  • Have experience building and running a hiring pipeline for engineers
  • Be ruthlessly pragmatic about what to build and (just as importantly) what not to build
  • Know how to write clean, testable, and maintainable code and ensure that the team does the same
  • Have a strong working knowledge of our stack, as well as all of the following:
    • Terraform
    • DevOps
    • Security & Secure Coding Practices
    • Software Architecture
  • Have broad technical knowledge and learn new topics quickly
  • Be comfortable diving into the weeds of our business to inform what we build
  • Be highly organized
  • Thrive in fast-paced environments with a high degree of autonomy
  • Be fluent in English, both verbal and written.

Bonus points if you have experience with payments or FinTech, security and compliance work, and/or writing software in a regulated industry.

That said, we’re ultimately looking for people who’ll be awesome to work with rather than strictly hewing to the above, so if you’re not an exact match but still think you might be good at the job, please do apply.


Python, Django, Django Rest Framework, Javascript, React, Tailwind CSS, React Native (plus a bit of Objective-C and Java when it’s called for), AWS, Docker


  • Competitive compensation + equity
  • 95% coverage of medical, dental, and vision
  • Fantastic benefits (of course 😃), including:
    • $500 WFH setup
    • $150/month cell phone + internet
    • $100/month Wellness
  • Flexible PTO
  • Work from anywhere (during standard US business hours)