Founding Applied AI Lead

Pear VC, Inc.

Job Overview

Location

Toronto

Job Type

Full-time

Full Job Description

📋 Description

• As the Founding Applied AI Lead at Paxos Health, you will design and own the AI agents and workflows that enable healthcare manufacturers to secure insurance coverage for life-saving medical technologies, directly impacting patient access to care.
• You will translate complex reimbursement policies, clinical documentation, and payer rules into reliable AI systems using prompt chains, structured outputs, evals, and workflow logic, working closely with engineering, product, and customers to implement and improve solutions.
• You will join a mission-driven, early-stage team of founders and engineers from Stanford, Medtronic, Meta, and Microsoft, operating in a fast-paced, high-ownership environment where your contributions will shape the company’s technical foundation and growth.
• You will gain deep expertise in applied AI for healthcare operations, build end-to-end workflow ownership experience, and have the opportunity to grow into broader technical or product leadership roles as the company scales.

🎯 Requirements

• Minimum 2+ years of experience in technical implementation, AI operations, software technical writing, software engineering, technical customer support, or related fields.
• Strong passion for AI and hands-on experimentation with LLMs to improve real-world operations.
• Excellent written and verbal communication skills in English.
• Exceptional attention to detail, with the ability to identify edge cases, inconsistencies, and quality gaps in complex systems.
• Comfortable engaging directly with enterprise customers to gather requirements and translate feedback into technical improvements.
• Thrives in ambiguous, fast-moving startup environments with high ownership and minimal process.
• Located in or willing to relocate to Toronto or New York City, with ability to work in-person or hybrid (minimum 3 days/week in office).

🏖️ Benefits

• Competitive salary range of $110,000–$200,000 CAD, adjusted based on experience and level.
• Significant equity package as an early employee in a venture-backed startup.
• Comprehensive benefits through an employer-of-record partner, including supplemental health coverage for Canadian employees.
• Opportunity to work with a highly accomplished founding team from Stanford, Medtronic, Meta, Microsoft, and successful entrepreneurial backgrounds.
• Dynamic, learning-focused culture that values feedback, innovation, and team bonding (e.g., playing Geoguessr after standups).

Skills & Technologies

Senior

Hybrid

$110k-200k

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Pear VC, Inc.

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About Pear VC, Inc.

Pear VC is an early-stage venture capital firm founded in 2013 and based in San Francisco. It invests pre-seed and seed capital in enterprise software, consumer, fintech, healthcare, and deep-tech startups. The firm provides founders with a full-time, in-house product, design, and growth team during the company-building phase. Pear manages over $1.8 billion across multiple funds and has backed companies such as DoorDash, Guardant Health, Gusto, and Branch. The partnership emphasizes hands-on support, data-driven insights, and a tight-knit community to accelerate product-market fit and subsequent fundraising.

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