Lead Ruby on Rails Engineer

✨ Featured
Remote - EU Remote - Poland Contract Lead

Published on May 08, 2026

Benefitbay is the chosen platform for brokers, employers, and employees that supports secure SOC II Type II end-to-end ICHRA deployment for companies of all sizes.


First available in January of 2020, ICHRA (pronounced ICK-RA), stands for Individual Coverage Health Reimbursement Arrangement. With ICHRA, employers can provide an allowance of tax free dollars to their employees who then use those dollars to shop for a health plan that meets their own specific needs. No more one-size-fits-all group package. Employers can provide wonderful health plans for their team, individually tailored to each person’s needs, with a fixed, predictable cost.

Experts anticipate a seismic shift in the benefits industry from group to individual as ICHRA plans will become a critical company feature when recruiting top talent. The best candidates will expect the freedom and portability that ICHRA allows. They will expect to be able to change jobs without having to change doctors. And benefitbay is touted as the solution that will finally set this shift in motion by solving the inefficiencies that have slowed ICHRA adoption thus far.

Benefitbay is the first-of its-kind, end-to-end solution that enables employers to easily model, deploy and oversee their ICHRA plans, in full compliance with regulation and with full confidence that their employees will have tools and support to select and enroll in the plan that’s right for them.

Company Description
Benefitbay is a leading platform designed for brokers, employers, and employees, offering secure SOC II Type II end-to-end ICHRA (Individual Coverage Health Reimbursement Arrangement) deployment for companies of all sizes. ICHRA allows employers to provide tax-free allowances for employees to choose personalized health plans, replacing the traditional one-size-fits-all group packages. This innovative solution ensures fixed, predictable costs for employers while empowering employees with flexibility and portability in their healthcare options. As the benefits industry transitions from group to individual plans, Benefitbay is at the forefront, solving inefficiencies and driving the adoption of ICHRA. Employers use Benefitbay to confidently model, deploy, and manage their ICHRA plans while ensuring compliance and employee support.

Role Description
We're looking for a Lead Software Engineer to join a strong team of leads and seniors who set a high engineering bar. This is a hands-on IC role - you won't manage a team, but you'll work directly with our product team and external partners/vendors to own and deliver projects within our monolith. You'll collaborate with other engineers on architectural decisions, tackle the hardest problems in the codebase, and raise the bar on code quality and engineering practices. We need someone who can take a requirement from product or a vendor spec and drive it to production independently.

What You'll Do
  • Drive architectural decisions across a Rails 8+ monolith
  • Own the most complex features and integrations end-to-end - insurance carriers, payroll providers (SOAP, REST APIs)
  • Identify and resolve systemic issues - performance bottlenecks, tech debt, reliability gaps - proactively, not just when assigned
  • Design and implement background job architectures (Sidekiq Pro) for enrollment processing, premium calculations, compliance reporting, and carrier file exchanges
  • Collaborate on setting technical direction on testing strategy, code quality standards, and CI/CD improvements
  • Mentor our senior engineers through code review, pairing, and technical guidance - leading by example, not by title.
  • Collaborate with a distributed team across US and Eastern European time zones

Requirements
  • Bachelor's degree in Computer Science, Software Engineering, or a related field
  • Deep Ruby on Rails expertise (6+ years) - you should be able to navigate a large Rails codebase confidently and make sound architectural trade-offs
  • 10+ years of professional web software engineering experience
  • The role is full-stack - we don't separate backend and frontend. You'll build and maintain UI with Hotwire alongside your backend work.
  • Strong understanding of relational databases (MySQL or PostgreSQL) - query optimization, indexing, schema design, migrations at scale
  • Extensive experience with background job processing (Sidekiq or ActiveJob) - designing job architectures, handling failures, managing queues
  • Track record of building and maintaining third-party integrations (APIs, file-based exchanges, webhooks)
  • Experience improving engineering practices in a team - testing, code review, CI/CD, observability
  • Ability to work autonomously - you identify what needs to be done and do it without waiting for direction
  • Profficiency with Git and CI/CD pipelines
  • Professional English proficiency (written and verbal) - daily sync and async communication with EU and US-based team
  • Overlap with US Eastern Time for at least 3-4 hours daily

Nice to Have
  • Experience with AWS services (ECS, RDS, S3, ElastiCache, CodePipeline)
  • Terraform or other infrastructure-as-code experience
  • Healthcare, insurance, or payroll domain experience
  • Experience with HIPAA, HITRUST, or SOC 2 compliance requirements
  • Familiarity with Tailwind CSS
  • Experience working in a large codebase with a lot of legacy code (project age 13+ years).

What We Offer
  • Long-term full-time engagement
  • Competitive compensation in USD/EUR
  • Fully remote position within Eastern Europe
  • Work on a production system that directly impacts healthcare access for thousands of employees
  • Modern tech stack - we run the latest Ruby and Rails versions and upgrade aggressively
  • High autonomy - own features from design to deployment
  • Collaborative team with lightweight process (Jira tickets, automated PR pipelines, AI-assisted code review)
  • B2B contract arrangement
  • Software and AI tools subscriptions covered
  • Company-provided hardware: MacBook of your choice, external display, and accessories

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