Founding Engineer

Recruiting From Scratch•San Francisco, NY

3d•Onsite

About The Position

Our client is building an AI-native health insurance platform designed to transform how small businesses access and manage employee health benefits. The company is replacing the traditional health insurance brokerage model with AI-powered workflows that automate complex brokerage and servicing processes while enabling human brokers to provide higher-quality, consultative guidance. The platform uses AI agents to automate labor-intensive workflows including plan research, quoting, enrollment, and ongoing benefits servicing. Backed by leading venture capital investors, the company operates as a small, talent-dense organization with a highly experienced founding team and a rapidly expanding engineering function. As a Founding Engineer, you'll join a small engineering team and have significant ownership over product architecture, AI systems, user experience, and engineering culture. This is an opportunity for a strong full-stack or backend-focused engineer who wants to build AI-native products from 0-to-1 while solving high-impact problems in healthcare and insurance.

Requirements

2–8 years of experience in software engineering or related technical roles
Experience owning products or major projects end-to-end
Experience in full-stack or backend-focused engineering roles
Strong experience building and shipping production software
Experience taking products from ideation through production
Strong Python proficiency
Strong TypeScript proficiency
Strong backend engineering fundamentals
Strong full-stack engineering capabilities
Experience building production APIs
Experience building user-facing applications
Strong React experience
Experience working with LLMs and AI APIs
Strong software architecture fundamentals
Strong API design and integration skills
Experience working with databases and data models
Strong debugging and troubleshooting skills
Experience building production-grade software
Ability to rapidly learn emerging AI technologies
Ability to evaluate and integrate new AI tooling
Ability to build reliable applications on top of modern AI infrastructure
Strong understanding of application architecture
Ability to work across frontend, backend, and AI systems
Strong systems design and engineering fundamentals
Strong computer science fundamentals
Exceptional ownership and execution ability
Highly hands-on engineering mindset
Strong builder mentality
Comfortable operating in ambiguous environments
Strong first-principles problem-solving ability
Excellent technical communication skills
Strong product intuition
Strong customer empathy
Comfortable working directly with brokers and service operators
Strong curiosity around AI and emerging technologies
Comfortable learning rapidly
Strong bias toward action
Comfortable taking ownership without heavy direction
Strong architectural judgment
Comfortable making decisions with incomplete information
Strong ability to prioritize competing technical and product needs
Low-ego working style
Strong collaboration skills
Comfortable working closely with founders
Strong sense of urgency
Comfortable working in a small, talent-dense engineering team
Strong interest in healthcare and insurance technology
Strong interest in AI agents and AI-native products
Comfortable working across the full product stack
Comfortable building from 0-to-1
Strong communication with technical and non-technical stakeholders
High slope and learning velocity
Strong engineering quality instincts
Comfortable working on-site in San Francisco or New York 5 days/week

Nice To Haves

Experience working in startup or high-growth environments preferred
Experience building AI-powered products preferred
Experience with LLMs, AI agents, or modern AI tooling preferred
Experience building or integrating AI agents preferred
Experience with agentic AI systems preferred
Experience with AI evaluation systems preferred
Experience designing AI guardrails and reliability systems preferred
Experience with MCP or MCP-connected systems preferred
Experience with distributed or scalable systems preferred
Bachelor's degree in Computer Science, Engineering, Mathematics, or related technical field preferred
Strong computer science fundamentals
Equivalent practical engineering experience accepted
Candidates with strong technical pedigree through high-growth startups, leading technology companies, trading firms, or top-tier universities preferred

Responsibilities

Build and iterate on agentic AI systems that automate complex health insurance brokerage workflows
Develop AI agents that support broker analysis and operational workflows
Build systems that help service operators serve significantly more clients at higher quality
Own full-stack product development from initial concept through production
Design backend services and APIs using Python
Build frontend applications and user experiences using TypeScript and React
Integrate LLMs into production applications
Build and maintain AI agent orchestration systems
Design evaluation systems for AI agents
Develop guardrails and reliability infrastructure for high-stakes AI workflows
Build systems that monitor and evaluate AI agent performance
Develop tools and workflows using MCP and modern AI infrastructure
Translate complex insurance workflows into scalable software systems
Work directly with brokers and internal service operators to understand operational pain points
Build tools that improve broker productivity and customer experience
Design systems capable of handling complex and messy real-world insurance data
Build AI-powered workflows for plan research and comparison
Develop systems supporting quoting and enrollment workflows
Build automation for ongoing customer servicing
Work across the product stack based on the highest-priority company needs
Make architecture and technology decisions in a rapidly evolving environment
Own technical projects from ideation through production deployment
Build reusable infrastructure and engineering patterns as the company scales
Help define the technical architecture for a rapidly growing AI-native product
Establish engineering standards and development practices
Contribute to engineering culture as the team scales
Collaborate closely with the founding team and engineering leadership
Balance rapid iteration with reliability and quality
Solve ambiguous technical problems using first-principles thinking
Work closely with internal stakeholders to rapidly validate and improve products
Build products that directly impact how small businesses and employees access healthcare benefits
Help shape the long-term engineering and AI strategy of the company

Benefits

Competitive founding equity package
Opportunity to join an early-stage AI-native healthcare company
Founding-level ownership over product and engineering decisions
Opportunity to shape engineering culture and architecture
Direct collaboration with founders and senior technical leadership
Opportunity to build AI agent systems from 0-to-1
Exposure to LLMs, MCP, AI agents, and modern AI infrastructure
Opportunity to solve complex healthcare and insurance workflows
High autonomy and significant technical ownership
Opportunity to build products directly impacting access to healthcare benefits
Small, highly talented engineering organization
Strong mission-driven culture
Opportunity to influence the company's technical direction as the engineering team scales
H-1B, OPT, TN, and other visa support