Founding Applied AI Lead

Pear VC•New York, NY

1d•$110,000 - $175,000•Hybrid

About The Position

Paxos Health is seeking a hands-on Founding Applied AI Lead to design and own the AI agents and workflows that enable patients to access the medical technologies their doctors prescribe. This role sits at the intersection of product, engineering, AI, and customer implementation, focusing on translating messy manual workflows into reliable AI systems. The ideal candidate will be comfortable with technical building blocks like JSON, structured outputs, low-code workflow tools, and lightweight scripting, with the ability to prototype, test, and debug AI workflows. As an early employee, there is a significant opportunity for growth and to shape the scope of the role as the company expands.

Requirements

Minimum 2+ years of work experience in technical implementation, AI operations, software technical writing, software engineering, technical customer success, or related work.
Actively experiment with LLMs and believe in AI's potential to reshape operations.
Strong English written and verbal communication skills.
Extreme detail-orientation, with the ability to identify edge cases, inconsistencies, and quality issues.
Comfortable interacting directly with enterprise customers.
High ownership mentality, comfortable operating in a fast-moving startup environment.
Based near New York City or Toronto, or willing to relocate.
Ability to work in-person/hybrid (minimum 3 days per week in the office).

Nice To Haves

Experience building LLM agents, automations, prompt chains, or AI workflows.
Experience writing technical specs, implementation docs, workflow documentation, or test plans.
Experience with structured data, JSON, APIs, low-code tools, workflow builders, or lightweight scripting.
Experience designing or maintaining evals, QA processes, or test cases for AI reliability.
Experience at an early-stage startup or in a high-ownership environment.
Experience in complex, document-heavy workflows in regulated domains like healthcare, legal, fintech, insurance, or compliance.
Experience in healthcare, healthcare operations, reimbursement, prior authorizations, appeals, RCM, insurance, or clinical documentation.

Responsibilities

Design and improve Paxos’s AI workflows, owning prompt chains, agent patterns, structured-output schemas, evals, and test cases.
Translate reimbursement complexity into testable workflow logic, including payer rules, document requirements, clinical evidence standards, and operational edge cases.
Own AI quality and reliability by analyzing failures, improving prompts and schemas, and building evals.
Work directly with customers during implementation to clarify requirements, understand edge cases, and translate learnings into workflows and reusable capabilities.
Document system functionality through workflow specs, test plans, prompt/eval documentation, and implementation notes.