AI Technical Leader

Location: Remote in the United States or Toronto, Canada

Company

hirify.global provides telehealth support solutions that help companies deliver virtual care across multiple specialties and all 50 U.S. states.

What you will do

• Set the technical direction for AI agent runtime, orchestration, tool use, context management, and handoffs.
• Build evaluation systems, regression tests, and AI-graded evaluations to measure production quality.
• Design model access and operations, including provider routing, version upgrades, and outage planning.
• Own AI observability, tracing, cost attribution, retrieval, and grounding over company data.
• Translate human workflows into agent workflows while defining which decisions must remain with people.
• Guide cloud and data infrastructure on GCP, review code and designs, mentor engineers, and communicate AI trade-offs to product, operations, and clinical stakeholders.

Requirements

• 12+ years of software engineering experience with technical leadership at tech lead, staff, or principal scope.
• 2+ years building and operating production LLM-based systems.
• Deep hands-on expertise in agent runtime or AI evaluation, with working knowledge across the broader AI engineering stack.
• Experience measuring AI quality using real evaluation methods and data.
• Experience setting the technical direction for a small team from its early stages.
• Ability to work remotely from the United States or Toronto, Canada.

Nice to have

• Healthcare or other regulated-industry experience, including PHI and HIPAA.
• GCP experience.
• Experience building an internal platform used by other engineering teams.
• Classic machine learning experience alongside LLM expertise.
• Experience scaling a team from one pod into multiple teams.

Culture & Benefits

• Competitive compensation.
• Medical, dental, and vision coverage.
• Flexible Spending and Health Savings Accounts.
• Generous paid time off and hybrid-work flexibility.
• 401(k) with company match, life insurance, pet insurance, and other benefits.
• Flat organizational structure centered on autonomy, competence, and belonging.