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AI Engineering Lead at AIOS — Remote, $200-$400k/yr + equity

Fella & Delilah· Engineering
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Remote$200k - $400kFull-timePosted 2mo ago

About the role

Senior technical leadership role focused on building the AIOS Agent SDK and two major systems (agent platform and AI clinical decision-support) to enable autonomous AI-powered workflows across the company. Fully remote with collaboration in Pacific Time hours.

Responsibilities

  • `Agent SDK`: You’ll turn Jesse’s (customer support tool) existing harness into the strongly opinionated internal platform powering Jesse, Aegis (clinical support tool), and future AIOS agents. You’ll own its architecture, reusable primitives, supported extension points, developer experience, and integration with our existing infrastructure.
  • `Jesse & Aegis`: You’ll become the senior technical owner of Jesse and work closely with the engineers and Clinical Product team building Aegis. You’ll improve both systems while extracting the shared foundations they need across context, retrieval, memory, orchestration, tools, state, and escalation.
  • `Evals & Experimentation`: You’ll build trustworthy benchmarks using deterministic checks, simulations, model-based graders, human judgment, and production outcomes. You’ll establish the path from offline evaluation to controlled production experiments so major changes ship with evidence.
  • `Production Learning Loop`: You’ll turn traces, poor resolutions, escalations, incidents, tool failures, and successful outcomes into better evals, stronger architecture, improved models, and permanent platform capabilities.
  • `Safety & Compliance`: You’ll make consequential agent actions safe through authorization, validation, idempotency, auditability, recovery, and human handoff. You’ll encode compliance, privacy, security, and regional requirements into the platform wherever possible.
  • `Models & Economics`: You’ll own model selection, routing, fallbacks, caching, and our ~$200k monthly model spend. When the evidence supports it, you’ll lead the data preparation, fine-tuning, evaluation, and AIOS-controlled deployment of specialized open-weight models.
  • `Reliability`: You’ll own the shared runtime in production, including tracing, observability, testing, provider resilience, capacity, and incident response. You’ll be the senior engineering DRI when an AI system behaves unsafely, quality regresses, or the platform fails.
  • `Technical Leadership`: You’ll set AIOS’s AI architecture and strategy in close partnership with the VP of Engineering. You’ll make the final call on major technical decisions, guide engineers across product pods, and remain hands-on by writing production code and personally building the most important foundations.
  • `Build the Team`: You’ll inherit one engineer and build the Applied AI team to approximately five exceptional people during your first year. You’ll own our technical relationships with leading model providers and represent AIOS externally where doing so strengthens our work.

Qualifications

  • 8+ years of software engineering experience and active production contributor
  • Bachelor’s degree in Computer Science, Machine Learning, or a closely related technical field
  • Personally built and shipped an exceptional agentic system used by real customers that reasoned across multiple steps, used tools, changed state, and operated under real production constraints
  • Ability to reason deeply about harnesses, orchestration, context construction, retrieval, memory, state, tool design, structured workflows, and error recovery
  • Experience with evaluation systems for probabilistic products, including dataset construction, evaluator design, simulations, regression detection, noisy metrics, and production outcomes
  • Strong systems-engineering fundamentals (APIs, distributed systems, concurrency, queues, databases, observability, failure modes, production reliability)
  • Judgment around authorization, validation, idempotency, state transitions, auditability, recovery, and escalation for safe agent actions
  • Understanding of frontier/open-weight models and when to deploy open-weight models; experience with fine-tuning and deployment is a plus
  • Demonstrated leadership of a small technical engineering team; ability to set direction and develop engineers
  • Technical authority to make difficult, well-reasoned decisions and communicate trade-offs clearly
  • Excellent communication skills to explain complex technical ideas to engineers, product leaders, clinicians, and executives
  • Independence to make high-quality decisions in ambiguous environments without hand-holding
  • Hands-on builder mentality; will write production code and lead from inside the work
  • Ownership mindset to take responsibility for outcomes when quality or reliability dips

Skills

Required:Agent SDK architecture and toolingAgent safety, governance, and complianceEval design and production experimentationReliability and observability

Benefits

  • Healthcare: comprehensive medical insurance (if appropriate)
  • Vacation: PTO with a yearly minimum (≥2 weeks/yr + holidays)
  • Personal development: budget for books, courses, coaching
  • Personal wellness: budget for gym, health apps
  • GLP-1s: free membership with a clinic offering GLP-1s
  • Equipment: Macbook & home-office equipment provided as needed
  • Opportunity to shape company culture
Last updated Oct 21, 2026. Interested? Apply on the company site.
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About Fella & Delilah

Fella & Delilah is the direct-to-patient clinic for busy families to…

Fella is optimized for busy bigger guys who want a no-nonsense solution to getting healthier. Delilah is built for strong women in their prime who want a sustainable solution to feel their best. We use affordable, effective weight loss medication to solve our customers’ most pressing healthcare need, then aim to remain their core healthcare provider for the rest of their life — expanding to hormonal health, mental health, longevity, and primary care. **We’ve grown >1000x since Aug 2021, >100x since Aug 2022, >10x since Aug 2023**. We’re >$50M ARR. We’ve been cashflow positive for the last 24mo. We’re >10,000 customers with high NPS. Almost all of this has so far been through Fella. Delilah is still very new. We’re a young startup and we’re just getting started. This is still Day 1 and all our work is ahead of us. You can read more about working at Fella & Delilah here: https://www.notion.so/Working-at-Fella-Delilah-14a2ac8575d34d148d009bb410387af4?pvs=21

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