Sr. AI Engineer

Sr. AI Engineer

Remote

About The Role:

Rightway helps members get the right care at the right time and price. Hundreds of thousands of the requests we handle every year involve questions like: What is the status of my prior authorization? What will this drug cost? How does my benefit apply?

Answering these questions well requires getting the right data from the right systems, understanding the context, and communicating the answer clearly. Today, much of that work is done manually.

We are building Agent OS, our platform for creating and operating AI-powered workflows across Rightway. It provides the foundation for connecting AI to our systems, evaluating its performance, and running it safely and reliably in production.

This is an early, foundational platform build. You will be one of a small number of engineers shaping the architecture and engineering patterns behind how AI operates across Rightway.

The hard problems here are not just about model or prompt quality. They are about building systems whose correctness can be measured, whose access to sensitive data can be controlled, and whose architecture can support many workflows without becoming fragile or overly specialized.

What You'll Do:

• Build the core platform for running AI-powered workflows reliably in production.
• Create safe, well-defined ways for AI systems to interact with Rightway's existing services and data.
• Design the authorization and data-access patterns required to operate AI in a healthcare environment.
• Build evaluation infrastructure that helps us measure quality, compare changes, catch regressions, and make informed decisions about what is ready for production.
• Develop the observability, tracing, and auditability needed to understand how AI systems behave in production.
• Design operational controls that allow us to deploy AI workflows safely and evolve them over time.
• Establish reusable platform patterns that other engineers can use to build AI-powered capabilities.
• Make thoughtful build-versus-buy decisions as the ecosystem around agents, models, tools, and evaluation continues to evolve.
• Partner closely with product, security, compliance, data, and engineering teams to turn new AI capabilities into production systems.
• Help shape the technical direction of Rightway's broader AI platform as both the technology and our use cases evolve.

Who You Are:

• 5+ years of experience building and operating production backend, infrastructure, or platform systems.
• Experience shipping LLM-based or AI-powered systems to production, beyond prototypes and demos.
• Strong backend and distributed systems fundamentals, including APIs, typed service contracts, service boundaries, failure handling, schema evolution, scalability, and operating against systems you do not fully control.
• A strong understanding of authorization, data boundaries, and the engineering controls required when AI systems operate on sensitive information.
• Exercises good judgment about where models should be used, where deterministic software is the better choice, and where additional safeguards or human intervention are required.
• Experience designing abstractions and platform capabilities that can support multiple use cases without overfitting to the first one.
• Comfort working in ambiguity and turning emerging problems into clear technical decisions, documented patterns, and working systems.
• Strong written and verbal communication across engineering, product, security, compliance, and data teams.
• A bias toward pragmatism - shipping useful systems, learning from real-world usage, and iterating.

We Also Expect Depth In Several Of The Following:

• Agent-based systems, including agent orchestration, tool/function calling, MCP, structured outputs, context management, or similar patterns for connecting models to external systems and data.
• AI evaluation systems, including offline evals, regression testing, version comparison, and measuring whether changes improve or degrade system behavior.
• AI observability and tracing, including understanding model calls, tool calls, agent execution paths, failures, latency, and production behavior. Experience with platforms or standards such as LangSmith, Braintrust, Arize Phoenix, OpenTelemetry, or similar is valuable.

Extra Credit:

• Experience with gRPC, protobuf, GraphQL, or other strongly typed service interfaces.
• Experience with OAuth, delegated authorization, service-to-service authentication, or similar identity and access patterns.
• Production experience with retrieval, structured output, classification, or other common LLM application patterns.
• Experience building developer platforms or internal platform infrastructure.
• Experience in healthcare technology or another highly regulated environment.
• Familiarity with HIPAA, PHI, or other sensitive-data requirements.
• Experience working with identity or data models that span multiple systems and sources of truth.
• Experience with voice AI, such as speech-to-text, text-to-speech, or real-time conversational voice systems.

Our Stack:

Rightway's platform spans TypeScript, Node.js, React, React Native, Ruby, PostgreSQL, Kafka, and Kubernetes, with gRPC and protobuf across a distributed set of internal services.

You do not need experience with every technology in our stack. We care more about strong engineering fundamentals, relevant depth, sound technical judgment, and the ability to learn quickly.

Compensation: $175,000 - $215,000 annually, in addition to bonus and equity

Compensation offered will be determined by geographic location, experience, and qualifications.

Cybersecurity Awareness Notice:

In response to ongoing and industry-wide fraudulent recruitment activities (i.e., job scams), Rightway wants to inform potential candidates that we will only contact them from the @ rightwayhealthcare.com email domain. We will never ask for bank details or deposits of any kind as a condition of employment.

About Rightway:

Rightway is on a mission to harmonize healthcare for everyone, everywhere. Our products guide patients to the best care and medications by inserting clinicians and pharmacists into a patient's care journey through a modern, mobile app. Rightway is a front door to healthcare, giving patients the tools they need along with on-demand access to Rightway health guides, human experts that answer their questions and manage the frustrating parts of healthcare for them.

Since its founding in 2017, Rightway has raised over $200mm from investors including Khosla Ventures, Thrive Capital, and Tiger Global. We're headquartered in New York City, with satellite offices in Denver and Dallas. Our clients rely on us to transform the healthcare experience, improve outcomes for their teams, and decrease their healthcare costs.

How We Live Our Values To Our Teammates:

We're seeking those with passion for healthcare and relentless devotion to our goal. We need team members that embody our core values:

1) We Are Human, First Our humanity binds us together. We bring the same empathetic approach to every individual we engage with, whether it be our members, our clients, or each other. We are all worthy of respect and understanding and we engage in our interactions with care and intention. We honor our stories. We listen to—and hear—each other, we celebrate our differences and similarities, we are present for each other, and we strive for mutual understanding.

2) We Redefine What Is Possible We always look beyond the obstacles in front of us to imagine new solutions. We approach our work with inspiration from other industries, other leaders, and other challenges. We use ingenuity and resourcefulness when faced with tough problems.

3) We Debate Then Commit We believe that a spirit of open discourse is part of a healthy culture. We understand and appreciate different perspectives and we challenge our assumptions. When working toward a decision or a new solution, we actively listen to one another, approach it with a "yes, and" mentality, and assume positive intent. Once a decision is made, we align and champion it as one team.

4) We Cultivate Grit Changing healthcare doesn't happen overnight. We reflect and learn from challenges and approach the future with a determination to strive for better. In the face of daunting situations, we value persistence. We embrace failure as a stepping stone to future success. On this journey, we seek to act with guts, resilience, initiative, and tenacity.

5) We Seek To Delight Healthcare is complicated and personal. We work tirelessly to meet the goals of our clients while also delivering the best experience to our members. We recognize that no matter the role or team, we each play a crucial part in our members' care and take that responsibility seriously. When faced with an obstacle, we