Founding Applied AI Lead

Pear VC•Toronto, ON

1d•CA$110,000 - CA$200,000•Hybrid

About The Position

Paxos Health is seeking a hands-on Founding Applied AI Lead to design and manage the AI agents and workflows crucial for their mission of helping patients access prescribed medical technologies. This role involves translating complex manual processes into reliable AI systems, focusing on prompt chains, structured-output schemas, evaluations, workflow specifications, and implementation logic. It's a technical workflow-building position where the candidate will prototype, test, and debug AI workflows, with opportunities for role expansion as the company grows. The position is based in Toronto.

Requirements

Minimum 2+ years of work experience in technical implementation, AI operations, software technical writing, software engineering, technical customer success, or related work.
Actively experiments with LLMs and believes in AI's potential to reshape operations.
Strong English written and verbal communication skills.
Extreme detail-orientation, with the ability to notice 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.
This is an in-person / hybrid (minimum 3 days per week in the office) role.

Nice To Haves

Experience building LLM agents, automations, prompt chains, or AI workflows.
Experience writing technical specs, implementation docs, workflow documentation, test plans, or customer-facing technical materials.
Experience with structured data, JSON, APIs, low-code tools, workflow builders, or lightweight scripting.
Experience designing or maintaining evals, QA processes, test cases, or other systems for improving AI reliability.
Experience at an early-stage startup, starting a company/project, or operating in a high-ownership environment with lightweight structure.
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.
Document system functionality through workflow specs, test plans, prompt/eval documentation, and implementation notes.