AI Engineer, Nava
Employee benefits brokerage
Be an early applicant
Employee benefits brokerage
101-200 employees
Be an early applicant
101-200 employees
Company mission
To bring high-quality, affordable healthcare to every American.
Role
Who you are
- Hands-on ownership of the infrastructure under an LLM-based product that other engineers or users depended on: an agent runtime, context or state management, orchestration, or evaluation and tracing. Internal users and inherited systems count
- Shipping LLM features to production and living with them: imperfect model behavior, latency, cost and the tradeoffs between them
- Modern full-stack development in TypeScript and/or Python, integrating foundation-model APIs, tool calling and human review into an application
- Practical evaluation and tracing habits: you check what the model did and learn from real use
- Explaining your decisions to product, design and domain experts, and turning their problems into reusable capabilities
- No specific framework, model provider or minimum audience size is required. We assess comparable work and your reasoning
- We understand that your experience is more than just a list of requirements, so we encourage you to apply even if you don't meet all of the bullet points
What the job involves
- We’re hiring an AI Engineer to build and harden the platform underneath Nava’s LLM-based products. Nava sits at the bleeding edge of AI-driven products, and building there has taught us something: what comes out of the box for LLM applications is not enough
- Agents run long-running tasks, which changes how we deploy software and manage state. Context has to be shipped into zero-trust sandboxes on different platforms, then retrieved and refreshed on our own terms
- Different models need to serve different jobs at a cost we can sustain as usage grows quickly. To ship our products, we built first versions of all of this ourselves, each for the use case in front of us
- What makes this opportunity unique: you take those first versions and harden them into a platform that every Nava AI team builds on. This is protected work, not a ticket queue
- It exists to reduce the unplanned platform work landing on the product engineers at the tip of the spear, and to create the magic that lets the rest of the company move faster with AI
- It is LLM-based product engineering at the frontier of current practice, focused on the patterns for building and maintaining an AI ecosystem, with real employers, employees and Nava teams on the other end
- What You’ll Accomplish in Your First Year:
- Harden the platform for reuse: Take the first-version capabilities built for one product (context management, agent state, sandboxed execution, model routing) and make each reusable across use cases beyond the one it was built for, so new AI features start from the platform instead of rebuilding it
- Make long-running agents safe to run: Design the state management and deployment patterns so an in-flight agent task survives deploys, restarts and retries, and can be resumed, inspected and replayed
- Own context in and out of the sandbox: Build one thoughtful mechanism for packaging context into zero-trust execution environments across platforms, and for ejecting and retrieving new context as an agent works
- Bring cost per task down as we scale: Route the right model to the right job, orchestrate subagents so expensive models do only expensive work, and make token usage measurable and optimized as volume grows
- Give product engineers their time back: Measurably reduce the unplanned platform work interrupting the AI product teams, so their sprints go to features rather than plumbing
- Make the ecosystem maintainable: Document, test, trace and evaluate the shared patterns so a new engineer can adopt them in days and regressions are caught before users notice
- Our Stack:
- React, Node, TypeScript, Python, Postgres and AWS; multiple foundation-model providers; sandboxed execution environments for agents; Langfuse for tracing and evaluation. Coding agents are part of daily work here, and encouraged but not required in the interview
Application process
- A 15-minute introduction with our recruiter, then an approximately 15-minute AI conversation about your most notable LLM-based work, who used it and what you learned from them (voice or typing, camera off)
- Then two interview days booked together: a 60-minute live coding session on Day 1, in your usual environment with any coding agent you like; a 60-minute design conversation and a 60-minute accomplishment discussion on Day 2
- Day 2 depends on the Day 1 outcome
- We send preparation notes ahead of each step
- Same questions for every candidate; we score evidence of comparable work, not polish
Our take
Nava is changing the benefits brokerage space by bringing the perks of big company playbooks to small and medium-sized businesses. Its platform acts as a powerful search engine, giving employers access to over 600 providers and helping them discover the best plan for their teams.
While traditional brokers earn commissions through complex deals with Fortune 500 companies, Nava takes a different approach. It uses technology to craft personalized benefits plans for smaller employers and make it easy for employees to navigate their benefits. From understanding their options and booking appointments to interpreting claims and solving billing issues, Nava simplifies the entire process.
One of Nava's challenges will be staying ahead of the curve by continuously adopting the latest innovations in healthcare benefits. To strengthen its position, the company has acquired i2, a healthcare benefits consulting firm, adding valuable expertise to its team. Additionally, Nava launched AI Benefits HQ off the back of a $30 million fundraise, which will utilise machine learning to streamline benefits admin for HR teams, ensuring a smoother and more transparent benefits journey for employees.
Freddie
Company Specialist at Welcome to the Jungle
Insights
24% employee growth in 12 months
Company
Funding (last 2 of 3 rounds)
Oct 2025
$30m
SERIES C
Jun 2022
$40m
SERIES B
Total funding: $90m
Company benefits
- Medical, Dental And Vision
- HSA & FSA Options
- Mental health support
- Personal healthcare advocacy
- Gynecology and fertility care
- Flexible paid time off
- Parental leave
- Phone and internet stipends
- Home office funding
- Disability and Life insurance
Company HQ
Civic Center, New York, NY
Leadership
Brandon Weber
(Co-Founder & CEO)Prior to Nava, Brandon co-founded VTS, a company that set out to modernize the commercial real estate marketplace. Previously founded Hightower which then merged with VTS. Also held senior positions at CBRE, Zillow and Microsoft.
Donald DeSantis
(Co-Founder & CPO)Co-founded VTS and Hightower which disrupted the real estate industry. Also trained as a UX Designer and co-founded a boutique consultancy called LIFFFT.
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