Roundtrip Senior Software Engineer (Remote) Remote, MD · Remote, PA · Remote, VA · Remote, FL · Remote, CO · Remote, CA · Remote · Full time Company website

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Founded in 2016, Roundtrip is committed to removing transportation barriers and revolutionizing healthcare access. With a passion for patient care, we harness cutting-edge technology to provide unrivaled scheduling and coordination of non-emergency medical transportation. Our clients include some of the most prestigious healthcare providers and forward-thinking Medicare Advantage health plans, all benefiting from our innovative SaaS platform and Navigation Center services. By leveraging our solution, our clients have successfully reduced patient no-shows, expedited the patient discharge process, improved patient and staff satisfaction, and decreased healthcare expenditures on patient rides.

Position Summary:

This role will join our Technology team, reporting to the CTO and working alongside a small group of multi-disciplinary engineers and designers. You’ll own complex problems end-to-end: from understanding the “why” behind a feature to designing and shipping the solution, and everything in between. 

 As a Senior Software Engineer, you will be responsible for: 

• Designing and delivering complex technical solutions independently, from initial scoping through production 
• Elevating the quality of the team through coaching, code review, and engineering best practices 
• Collaborating closely with cross-functional partners to translate business and customer context into well-designed software 

Role Structure & Compensation:

At Roundtrip, we believe engineers do their best work when they understand the problems they're solving, not just the tickets in front of them. We're a small team with real ownership, meaningful impact, and a culture that values curiosity, collaboration, and high standards.

We're a fully remote team that collaborates in real time throughout the day. While this role is open to candidates across the U.S., our team primarily works on Eastern Time (ET), with core collaboration hours from 11:00 AM to 4:00 PM ET. Occasional travel for company-wide meetings is required (about 10%).

This is a full-time U.S.-based role. We're looking for someone who can make Roundtrip their primary professional commitment. If you're seeking part-time or contract work or can't dedicate your full professional focus to this role, it may not be the right fit.

The salary range for this role is $160,000–$190,000, depending on experience with our technology stack and demonstrated ability to work independently. This position is intended for a well-established senior candidate who is on the path to Principal level.

What You’ll Do:

• Design and build features across the full stack, from Rails APIs and Postgres data models on the backend to React and Node on the frontend.
• Take full ownership of solutions from initial design through production and ongoing operation 
• Lead solution design conversations by evaluating trade-offs, surfacing technical considerations, and aligning on approach for large initiatives.
• Write and maintain well-formed unit and end-to-end tests; identify appropriate test coverage for every change 
• Conduct thorough, coaching-oriented code reviews and thoughtfully incorporate feedback on your own work.
• Leverage AI planning, coding, and review tools deliberately, and help the team develop strong habits around how to use them 
• Partner with Product, Design, and Customer Success to deeply understand business problems and translate them into effective technical solutions.
• Actively maintain technical documentation so your solutions are understandable, extensible, and operable by others 

What You’ll Have:

• Proven, production experience with Ruby on Rails (or comparable language) and a strong command of application and relational database design 
• Proficiency with front-end technologies (React, JavaScript, and CSS)
• Experience designing and scaling high-traffic APIs and data-intensive systems
• Strong systems thinking—you consider how individual decisions impact the broader platform, not just the immediate feature.
• Ability to clearly evaluate trade-offs between performance, maintainability, and testability, and explain them to non-technical stakeholders.
• Strong ownership mindset—you work independently, take initiative, and provide clear, constructive, and growth-oriented feedback in code reviews.

What We Offer:

• Comprehensive Medical, Dental, and Vision Coverage: Roundtrip offers competitive benefits designed to meet a variety of needs. We cover 100% of the employees’ premium for our base medical plan, with buy-up options and family coverage available at an additional cost.
• 401(k) with Matching and Immediate Vesting: Roundtrip matches employee contributions up to 3% and all employer contributions are 100% vested from day one.
• Company Stock Options Plan: Option grants to allow each employee to share our success with the opportunity to own a piece of the company.
• Fully Remote Team: Work from anywhere in the U.S. (role dependent). As a remote-first company, we stay connected daily through Slack and Teams, with in-person gatherings to bring the team together.
• Flexible, Unlimited Time Off: We trust our team to take the time they need, for rest, vacation, or personal matters. Minimum of 10 days off per year required, 11 paid company holidays observed annually and Paid Parental Leave.
• Flexible Fridays: We reserve Friday afternoons (after 12pm ET) for focused work and flexibility by limiting internal meetings, helping you close out the week at your own pace.
• Lifestyle Benefits: Twice yearly credits to Fringe, an online marketplace of hundreds of well-being and lifestyle services including Uber Eats, DoorDash, Airbnb, coffee subscriptions, and more.
• Fixed Monthly Remote Work Stipend: To offset any costs you may incur as a remote employee, such as internet, cell phone, or supplies etc. (company laptop provided).

Employment Eligibility & Equal Opportunity Statement:

 At Roundtrip we are not only focused on our mission but also hold ourselves to high standards when it comes to our team. Being part of the Roundtrip team isn't just about showing up and doing your job, it's about living our values every day: Lead with Empathy, Own the Outcome, Innovate Responsibility, Embrace Evolution and Partner for Impact.

 

Diversity & Inclusion is more than initiative at Roundtrip. Our team is committed to creating a diverse environment and is proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or other protected class. If, due to a disability, you need accommodation during the interview or application process, please email [email protected].

 

Due to the nature of our business all applicants must be located in the United States and authorized to work for any employer. Roundtrip is unable to sponsor or take over sponsorship of an employment visa.

 

What happens next:

 Our team will carefully review all applications. Due to the high volume of interest, we’re unable to contact every applicant individually. If your experience aligns with what we’re looking for, a member of our team will reach out to move you into the interview process.

We know there are a lot of scammers out there, so please note that all legitimate communications related to open opportunities will exclusively come from “@roundtriphealth.com” emails addresses. We will also never ask you to download any kind of software as a part of the interview process.

Interview Process:

Our process is designed to be transparent, practical, and reflective of the role. All interviews will take place over Teams. The outline below gives a snapshot of what to expect, though it is subject to change.

• Initial Screen (30 minutes) with People Operations to review your experience and assess alignment with the role requirements.
• CTO interview (45 minutes) focused on systems thinking, collaboration style, and how you approach technical challenges.
• Team Panel Interview (45 minutes) Meet with members of our Technology Team to dive into your architecture, design patterns, and technical knowledge, as well as your systems thinking and collaboration style.