Senior Ruby Rails Jobs in Kentucky (NOW HIRING)

We are a highly profitable, fast-growing healthcare startup—a small and mighty team of 230 helping people find and enroll in individual health coverage. To date, we’ve helped over 20 million people enroll in health coverage. We're a mission-driven team that advocates for and cares deeply about the people we serve.

We're a double bottom-line company: revenues and enrollments. The ACA brings high-quality, comprehensive, affordable health coverage within reach for low-income Americans, and we exist to make that promise a reality. Your contribution will help millions of people navigate the complex and confusing health insurance industry and enable them to access health care when needed.

We are committed to building a team that is well-balanced in representation to best serve the people who use our products. We believe in creating inclusive and equitable spaces that build trust and respect and foster a sense of belonging. These values are at the core of our culture and will continue to lead our organization to successful outcomes.

HealthSherpa is a fully remote company and was recognized as a 2026 Best Remote Place to Work by Built In, reflecting our commitment to building a people-first culture rooted in trust, flexibility, and impact.

We are looking for a Senior Product Engineer with 8+ years of experience to improve how technology can transform healthcare.At HealthSherpa, you'll work on a small team charged with exploring, building, and scaling demand-side product experiences in the health insurance marketplace.

You'll work across the Ruby on Rails and ReactJS stack, while also shaping API-first, developer-friendly platforms that can grow with our business. You move fast without sacrificing maintainability, and you excel in environments where data, analysis, and customer obsession shapes decisions.

You'll work in a collaborative pod alongside engineers, product managers, and designers. Together, you'll invent and deliver systems that improve the lives of millions of Americans. You will report to an Engineering Manager.

The base salary range is $174,000 – $210,000 + equity + benefits. Within the range, individual pay is determined by factors including job-related skills and experience.

• Own the design, delivery, and operation of high-quality features and systems across the full stack, with an emphasis on scalable APIs

• Help define and deliver the next generation of health insurance technology by building robust platforms and applying AI/ML to enhance processes and decision-making

• Promote innovation by iterating, and shipping quickly-- treating each release as an opportunity to learn

• Build and evolve tools for carriers, agents, and consumers-- including enrollment, CRM, and tracking systems

• Create meaningful roadmap items and platform commitments that promote new business opportunities

• Collaborate with engineering, product, and design teammates in a high-trust, high-accountability environment

• Improve code quality, scalability, and agility across the codebase

• Operate in a DevOps culture where teams deliver value multiple times per day

• Proactively address security, observability, and telemetry in everything you build

• Learn fast, solve hard problems, and navigate evolving priorities

• Experience with the full software development lifecycle, supporting features post-launch in agile/lean environments

• Experience with Ruby on Rails (or similar backend frameworks) and ReactJS (or similar frontend frameworks)

• Experience with SQL and designing relational data models and reusable components

• Experience building distributed systems at scale, with an understanding of infrastructure as code

• Expertise in building developer-friendly APIs that power product ecosystems

• Knowledge of observability and telemetry, ensuring systems are reliable and measurable

• A product-minded approach, always thinking through problems and solutions from the user's perspective

• The ability to adapt to new technologies and apply them effectively

• Remote-first company (US-based remote only)

• Great compensation package at a high-growth, profitable company

• Excellent benefits package that includes health, vision, and dental coverage for you, your spouse, and dependents

• HSA/FSA options with corresponding contribution limits

• Monthly grocery stipend and home internet reimbursement

• 401K w/ a match after a grace period

• Life and AD&D coverage

• Disability insurance (Short and Long Term)

• Parental leave

• Four (4) weeks of paid vacation in addition to paid holidays

• Home office budget for remote team members

• Mental health and other wellbeing support programs through a partner network
  

As an organization, we value creating an inclusive and accessible experience. If you require reasonable accommodations during the application or interview process, please let your recruiter know.

We welcome and encourage people of diverse backgrounds, experiences, identities, abilities, and perspectives to apply. We are an equal-opportunity employer and a fun place to work. Come join the team at HealthSherpa!