[Hiring] Head of AI Engineering @AIOS (YC W20/S21)

Role Description

As Head of AI Engineering at AIOS, your fundamental role is to build the AIOS Agent SDK and make it the foundation for world-class agents across the company. You are not joining to discover our first AI use case or build another chatbot.

• Our customer-facing agent gathers context from across our product and customer history, retrieves the right knowledge, reasons through multi-step cases, and decides when to act, respond, escalate, or stand down.
• This existing harness will become the nucleus of the AIOS Agent SDK.
• You’ll separate its reusable foundations from its customer-support logic and turn them into a strongly opinionated internal platform.
• We’re also building an AI clinical decision-support system to help clinicians evaluate patient eligibility, contraindications, dosing, and risk.
• You’ll be the DRI for agent architecture, model strategy, evals, AI reliability, technical safety, provider relationships, and the shared runtime.
• This is a technical leadership role where you’ll lead by example as you grow the team.

Qualifications

• 8+ years of software engineering experience and remain an active production contributor.
• Bachelor’s degree in Computer Science, Machine Learning, or a closely related technical field.
• Experience building and shipping an exceptional agentic system used by real customers.
• Ability to reason deeply about harnesses, orchestration, context construction, retrieval, memory, state, tool design, structured workflows, and error recovery.
• Experience building or meaningfully owning evaluation systems for probabilistic products.
• Strong systems-engineering fundamentals.
• Knowledge of how to let an agent act safely.
• Understanding of the capabilities and limitations of current frontier and open-weight models.
• Experience leading and managing a small technical engineering team.
• Strong communication skills to explain difficult technical ideas to various stakeholders.
• Ability to create clarity in ambiguous environments and make high-quality decisions.
• Experience writing production code and leading from inside the work.
• Ownership mentality in addressing quality drops, cost spikes, and tool failures.

Requirements

• Experience with agent platforms, customer agents, and high-stakes systems.
• Experience with model adaptation, long-term memory, and real-time systems.
• Experience working directly with frontier model providers.
• Ability to identify and nurture exceptional AI engineers.
• Fluency in translating relevant research into reliable production systems.
• Ability to navigate from debugging to redesigning and handling incidents.

Benefits

• Compensation: $200k-$400k/yr, + equity.
• Healthcare: comprehensive medical insurance (if appropriate).
• Vacation: PTO with a yearly minimum (≥2wks/yr + local national holidays).
• Remote: fully distributed team functioning remotely.
• Personal development: budget for books, courses, coaching ($1200/yr).
• Personal wellness: budget for gym, health apps ($1200/yr).
• Coaching: free biweekly health coaching.
• Equipment: Macbook & work-from-home equipment provided as needed.