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Sr. Staff Applied AI Engineer (Tech Lead)

OpenLoop Health
Toronto, CAN
Full-time
Senior
Hybrid
Discovered 3 weeks ago
AI agent runtime and orchestrationLLM systems in productionAI evaluation systemsRegression testingModel routing and provider operationsAI observability and tracing

Full Job Posting

About the role

Serve as OpenLoop’s first technical leader for AI and an early hire in the AI Platform pod.

Establish foundational decisions for AI agents, evaluation, safety, affordability, and platform capabilities used by other teams.

The pod is expected to split into AI Infrastructure and AI Tools teams; the role requires depth in at least two core AI engineering disciplines and credibility across the stack.

Until an AI Principal Engineer is hired, carry long-range technical direction for AI across the company.

This is a hands-on role involving coding and design review, with responsibility for architecture and technical quality in partnership with the AI Engineering Manager.

What you’ll do

  • Set technical direction for agent runtime and orchestration, including tool use, context management, handoffs, and build-versus-adopt decisions.
  • Build evaluation systems that measure AI quality, including regression tests and AI-graded evaluations.
  • Decide how to route models across providers, manage version upgrades, and plan for provider outages.
  • Own observability and cost attribution by tracing agent actions and tracking AI spend.
  • Build retrieval and grounding over company data so agents answer with facts.
  • Work with business and operations teams to translate human workflows into agent workflows and identify work that must remain human-led.
  • Protect patient data in every AI system.
  • Make cloud and data infrastructure decisions; the company runs on GCP, and the role partners with the Data Platform team.
  • Raise quality through code and design reviews and mentor engineers new to AI.
  • Explain AI trade-offs to product, operations, and clinical stakeholders, including when AI is not ready for a use case.

Who you are

  • 12 or more years of software engineering experience and real technical leadership experience at tech lead, staff, or principal-level scope.
  • Two or more years building and running LLM-based systems in production, rather than only demos or personal projects.
  • Deep hands-on expertise in agent runtime or evaluation, plus working knowledge across the rest of the AI engineering stack.
  • A track record of measuring AI quality with real evaluation methods and data.
  • Experience leading a small team’s technical direction from zero or close to it.

Preferred experience

  • Healthcare or other regulated-industry experience, including PHI or HIPAA.
  • GCP experience.
  • Experience building an internal platform used by other engineering teams.
  • Background in classic machine learning as well as LLMs.
  • Experience scaling a team from a single pod into multiple teams.

Workplace

  • The company describes flexible hybrid-work flexibility.

Benefits

  • Competitive compensation.
  • Medical, dental, and vision coverage; flexible spending and health savings accounts.
  • Generous paid time off and 401(k) with company match.
  • Life insurance, pet insurance, and other benefits.

About OpenLoop

OpenLoop provides telehealth support solutions intended to streamline care delivery for companies offering virtual patient support across multiple specialties and all 50 U.S. states.

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