Head of AI Engineering

This is a fully remote position, open to applicants in United States.

📋 Description

• Develop the AIOS Agent SDK as the core foundation for top-tier agents throughout the organization.

• Distinguish the reusable elements of the existing customer-support framework from its customer-support logic, transforming them into a structured internal platform.

• Oversee agent architecture, model strategy, evaluations, AI reliability, technical safety, provider relationships, and the shared runtime environment.

• Ensure the Agent SDK operates in production while delivering context, tools, safety measures, evaluation, and observability infrastructure.

• Evolve Jesse’s harness into the platform that powers Jesse, Aegis, and upcoming AIOS agents.

• Direct the technical trajectory of Jesse and collaborate with engineers and the Clinical Product team working on Aegis.

• Create benchmarks utilizing deterministic checks, simulations, model-based graders, human judgment, and production outcomes.

• Transform production traces, incidents, tool failures, escalations, and outcomes into enhancements in evaluations, architecture, models, and platform capabilities.

• Implement authorization, validation, idempotency, auditability, recovery, human handoff, compliance, privacy, security, and regional requirements.

• Manage model selection, routing, fallbacks, caching, fine-tuning, deployment, and approximately $200k monthly model expenditure.

• Ensure production runtime reliability, tracing, observability, testing, provider resilience, capacity, and incident response.

• Establish AI architecture and strategy, make significant technical decisions, guide engineers, write production code, and develop essential foundations.

• Inherit one engineer and expand the Applied AI team to around five members within the first year.

• Cultivate technical relationships with leading model providers and represent AIOS in external engagements.

⛳️ Requirements

• Over 8 years of experience in software engineering with active contributions to production.

• A minimum of a bachelor’s degree in Computer Science, Machine Learning, or a closely related technical discipline.

• Have personally designed and launched an outstanding agentic system utilized by real customers.

• Profound understanding of harnesses, orchestration, context construction, retrieval, memory, state, tool design, structured workflows, and error recovery.

• Experience in building or significantly owning evaluation systems for probabilistic products.

• Strong fundamentals in systems engineering, including APIs, distributed systems, concurrency, queues, databases, observability, failure modes, and production reliability.

• Sound judgment concerning authorization, validation, idempotency, state transitions, auditability, recovery, and escalation for pivotal agent actions.

• Awareness of current frontier and open-weight model capabilities and their limitations.

• Technical expertise to oversee fine-tuning and AIOS-controlled deployment of open-weight models.

• Proven experience in leading and managing a small technical engineering team.

• Aptitude for making challenging technical decisions, articulating trade-offs, and questioning unsound methodologies.

• Ability to convey complex technical concepts to engineers, product leaders, clinicians, and executives.

• Capability to operate independently in ambiguous environments.

• Proficiency in writing production code and leading by example.

• Accountability for outcomes in instances of quality decline, cost increases, tool failures, or provider degradation.

• Nice to have: experience with agent platforms, customer agents, high-stakes systems, model adaptation, long-term memory, real-time systems, provider relationships, talent development, research translation, and production debugging.

🏝️ Benefits

• Early stage equity.

• Comprehensive medical insurance (if applicable).

• PTO with a yearly minimum (≥2 weeks/year + local national holidays).

• Fully remote work arrangement.

• Personal development budget for books, courses, coaching ($1200/year).

• Personal wellness budget for gym memberships and health apps ($1200/year).

• Complimentary biweekly health coaching.

• MacBook and work-from-home equipment provided as necessary.

• Opportunity to influence the company culture.